On the surface, they seemed about as well suited to…

On the surface, they seemed about as well suited to each other as two people could possibly be. Both were young, tall, athletic, and toothsomely attractive. They exuded a confidence that bordered on cockiness. They were witty, direct, scrupulously well mannered, and hardworking. They were devoted to their families and unerringly loyal to their friends. They were both products of the Ivy League (he earned his bachelor’s degree at Columbia University, she earned hers at Princeton) and even went to the same law school—Harvard.

Yet their backgrounds could scarcely have been more different. Where Michelle Robinson and her older brother, Craig, grew up in the same South Side Chicago apartment their mother lived in for over thirty years, biracial Barack experienced a rootless childhood that left him wondering who he really was—and where he really belonged. It was precisely that thirst for stability that led Barack to the supremely grounded Michelle.

The restlessness that defined Barack’s early life stretched back at least two generations—to his white grandfather, Stanley Armour Dunham, the man he would affectionately call “Gramps.” The son of a roustabout who worked the oil rigs in and around El Dorado, Kansas, eight-year-old Stanley came home from school one day to discover his mother’s body hanging from a shower rod—a suicide that everyone in town chalked up to her husband’s rampant infidelity.

Whether it was the shock of finding his mother’s body or the mere fact that he had inherited his father’s wild streak, Stanley was soon branded incorrigible. Expelled from high school after striking the principal, Dunham spent the late 1930s as a self-styled hobo, riding the rails from Detroit to San Francisco.

It was back on home turf in the oil boomtown of Augusta, Kansas, that Stanley, then twenty-two, met eighteen-year-old Madelyn Payne, the restless, fresh-faced daughter of a Standard Oil office manager and a former schoolteacher. Madelyn’s parents were straitlaced Methodists who disapproved of drinking, smoking, card-playing, and dancing. Not that that kept Madelyn from sneaking off whenever she could to hear Benny Goodman, Glenn Miller, and Tommy Dorsey play at Wichita’s Blue Moon Dance Hall. “All the big bands came,” recalled Madelyn’s classmate Nina Parry. “It was wonderful—and nobody had more fun than Madelyn.”

Madelyn, who boasted to anyone who would listen that she counted a full-blooded Cherokee among her ancestors (not to mention several slave owners as well as Confederate President Jefferson Davis), was instantly smitten with the lanky young drifter from the proverbial wrong side of the tracks. Her parents, understandably, felt otherwise.

A few weeks before she graduated from Augusta High School, Madelyn and Stanley sneaked off during the spring weekend of the annual junior-senior banquet and secretly married. Madelyn continued to live at home. On the day she was handed her diploma, she sprang the news on her unsuspecting parents.

For the next eighteen months, the newlyweds managed to scrape by until the Japanese invasion of Pearl Harbor led Stanley, like most of his male contemporaries, to enlist. Before Stanley shipped out to the European theater, he was stationed at Fort Leavenworth. It was there, on November 29, 1942, that Madelyn gave birth to a baby girl.

The new father made no effort to conceal his profound disappointment. He had wanted a son, and was convinced right up until the end of his wife’s pregnancy that a son was what he was getting. Clearly unwilling to concede defeat, he persuaded Madelyn to go ahead with plans to name the newest member of the Dunham family after him. The name on her birth certificate: Stanley Ann Dunham.

While Stanley was stationed overseas, Madelyn took a job on the production line at Boeing’s B-29 plant in Wichita. As soon as he was discharged from the service in 1945, Stanley did what millions of other veterans did at the time: he decided to enroll in college on the GI Bill. The Dunhams headed to the West Coast, where Stanley attended the University of California at Berkeley for six months before dropping out. Guided by Stanley’s insatiable wanderlust, the Dunhams returned to Kansas. There he found a job managing a furniture store on El Dorado’s dusty Main Street, while Madelyn helped make ends meet by working as a cashier in a local restaurant. Soon they were on the move again—first to Texas, where they bounced from one dusty hamlet to another.

It was in one of those Texas towns that Stanley Ann experienced racial hatred firsthand. One afternoon, she and a young black girl were playing in the Dunhams’ backyard when a mob of local schoolchildren approached, hurling rocks and racial epithets. Madelyn chased them off, and when her husband called the children’s parents the next day to protest, he came to the sobering realization that the rock-throwing youngsters were just aping their parents’ prejudices. Black children and white children, he was told pointedly, were not to play together.

The Dunhams returned to Kansas, where—despite the markedly less racist atmosphere—little Stanley still had to withstand the inevitable teasing over her name as she moved from one school to the next. The Dunhams’ only child was studious and—perhaps because the constant relocating made her feel like a perennial outsider—something of a loner. More apt to spend her time reading than seeking new friends, Stanley Ann withdrew into her own solitary world. Whatever anxieties she may have been experiencing manifested themselves in a childhood case of asthma.

Stanley Ann had not yet turned thirteen when, in 1955, the Dunhams packed up and moved again—this time to Seattle, where the Boeing-dominated local economy was in the midst of a postwar boom. As soon as they arrived, Stanley landed a job as a salesman at Standard-Grunbaum Furniture at the corner of Second Avenue and Pine Street. The store’s groan-producing slogan: “First in Furniture, Second at Pine.”

The Dunhams moved into an apartment in Seattle’s Columbia City neighborhood and enrolled Stanley Ann in Eckstein Junior High School. The next year they moved to Mercer Island, situated in the middle of Lake Washington just opposite Seattle. On Mercer Island, they rented Unit 219 of Shorewood Apartments, a sprawling new complex for upwardly mobile families. Determined to stay in the workforce, Madelyn started commuting to nearby Bellevue to work as an escrow officer at a small bank.

Even before she boarded a school bus on the first day of school, Stanley Ann made an impression on her fellow Mercer Island High students. “I know, I know,” she told classmate Elaine Johnson after they met while waiting for the bus. “It’s a boy’s name, and no, I don’t like it. I mean, would you like to be called Stanley? But my dad wanted a boy and he got me. And the name Stanley made him feel better, I guess.”

In fact, Stanley Ann made no secret about the resentment she harbored toward her overbearing father. Stanley senior could be scathing in his criticism of his daughter; he berated her for being too timid, for not excelling at sports, for getting a single B on her report card even when the rest of her grades were all As. “He was hard on her,” remembered Stanley Ann’s friend Maxine Box. “He picked on her.” As a result, she developed a nervous habit that set her apart from the other girls: Stanley Ann “cracked her knuckles,” recalled Box, “and I mean constantly.”

Stanley Dunham, whose temper was described by friends and family members alike as “explosive” and “violent,” did more than merely pick on his daughter. Given to explosive outbursts, he was “a door slammer, a yeller, and a thrower,” a neighbor said. Worse, “there were bruises on Stanley Ann’s arm from where he grabbed her. He would slap her when she talked back. But a lot of us kids got punished that way back then, well into our teens.”

Whenever she could, Madelyn, who had turned quiet and serious as she shouldered more of the financial responsibilities for the household, protected her daughter from Dunham’s stinging words. Still, Stanley Ann learned to defend herself—at least from the verbal abuse her father routinely dished out. “He had a sarcastic sense of humor,” recalled Box, “and she could give it right back—and then some.”

“Stannie,” as she soon became known to her tight circle of friends, soon gained a reputation as a superb student. “She was very intellectual and above all of us,” said Box, “not just thinking about boys and clothes.” She also possessed a cutting wit. “She had a really ironic sense of humor—sort of downbeat—and she was a great observer,” remembered another classmate, Iona Stenhouse. “There was an arched eyebrow or a smile on her face about the immaturity of us all. I felt at times that Stanley thought we were a bit of a provincial group.”

Not that Stannie’s high school years weren’t filled with the sleepovers, sock hops, poodle sweaters, and football games that were staples of an adolescence lived in 1950s America. She listened to the Kingston Trio and Ricky Nelson and watched American Bandstand, but she also discussed jazz and beat poetry with like-minded friends at Seattle coffeehouses like the Encore and Cafe Allegro, and caught foreign films at the city’s only art house, the Ridgemont.

Stanley Ann “never dated the crew-cut white boys,” said her friend Susan Blake. “She had a worldview, even as a young girl.” Another pal, Chip Wall, agreed that Stanley Ann “was not a standard-issue girl. You don’t start out life as a girl with a name like Stanley without some sense you are not ordinary.”

Mercer Island High School itself was anything but ordinary. The year before Stanley Ann enrolled there, John Stenhouse, then chairman of the Mercer Island School Board, testified before the House Un-American Activities Committee that he had been a member of the Communist Party. At the same time, teachers Jim Wichterman and Val Foubert routinely ruffled feathers by challenging their students to question authority and societal norms. While English teacher Foubert assigned such controversial texts as Ayn Rand’s Atlas Shrugged, William Golding’s Lord of the Flies, J. D. Salinger’s Catcher in the Rye, and Margaret Mead’s writings on homosexuality, philosophy teacher Wichterman led classroom discussions on Camus, Sartre, Kierkegaard, and Karl Marx. The hallway connecting Foubert’s and Wichterman’s classrooms was dubbed “Anarchy Alley.”

“I had them read The Communist Manifesto,” Wichterman recalled, “and the parents went nuts. They didn’t want any discussions about sex, religion, or politics.” As for Stanley Ann, Wichterman remembered that “she’d question anything: What’s so good about democracy? What’s so good about capitalism? What’s wrong with communism? She had an inquiring mind.” Fellow student Jill Burton-Dascher agreed: “Stannie was intellectually way more mature than we were and a little bit ahead of her time, in an off-center way.”

The Dunhams were not part of the inevitable campaign to have Wichterman and Foubert fired. At a time when the overwhelming majority of their neighbors supported Dwight Eisenhower’s election to a second presidential term in 1956, they backed Democrat Adlai Stevenson. “If you were concerned about something going wrong in the world, Stanley would know about it first,” Chip Wall said. “She was a fellow traveler…. We were liberals before we knew what liberals were.” Box agreed: “We were all questioners. It was the feeling of the whole school. We were on the debate team. We knew about current events.”

The chain-smoking, whiskey-drinking, bridge-playing Dunhams also turned their backs on their midwestern Methodist and Baptist upbringings. By the time Stanley Ann was sixteen, the family was attending Sunday services at the East Shore Unitarian Church in Bellevue. At the height of the McCarthy era, its congregation was so outspokenly left-leaning that East Shore Unitarian soon became known throughout the region as “the Little Red Church on the Hill.”

Although Stanley Ann and her father both delighted in ruffling establishment feathers, they were not close. “He was always welcoming to the kids,” Box said, “but he embarrassed Stanley because he tried too hard” to impress her friends. Indeed, Stanley Dunham was more than faintly reminiscent of the Willy Loman character in Death of a Salesman, and while his brand of backslapping affability—replete with knowing winks and off-color jokes—may have seemed merely entertaining to strangers, it left his daughter feeling nothing less than mortified.

Stanley senior “always tried to get a rise out of people,” agreed schoolmate Susan Blake. “It seemed like every time her father opened his mouth, she would roll her eyes.”

The tensions between the two Stanleys often erupted into full-blown arguments in front of her friends. “He would belittle her with incredibly sarcastic remarks, and she would snap back right on the spot—she always stood up for herself,” said Box. “But it was awkward for the rest of us to have to watch. Stannie’s mother was very no-nonsense and would tell them both to grow up and stop being silly—she was sort of the mediator—but there was a lot of tension in that family. I wouldn’t have wanted to grow up dealing with a father who was as egocentric as Stannie’s was.”

When she was sixteen, Stannie managed to escape for two months to Chicago, where family friends hired her to take care of their children during summer vacation. Flush with her newfound feeling of independence, she went to a downtown art house to see the film Black Orpheus, a 1959 retelling of the Greek myth of Orpheus and Eurydice.

Set among the crowded, cliff-hugging favelas of modern-day Rio during Carnaval, Black Orpheus was written, produced, and directed by a white Frenchman. The Portuguese-speaking, all-black cast portrayed characters who were exotically beautiful, sensual, and childlike in their naïveté. The film, which she would revisit many times over the years, might seem condescendingly racist by later standards, but at the time it offered Stanley Ann an enticing first glimpse of a culture vastly different from her own, and would have a profound influence on the way Stanley viewed both the Third World and people of color.

Stanley Ann’s Chicago sojourn opened her eyes to a world of new possibilities. As expected, nearly all of her friends had applied to the University of Washington. She did not. One afternoon several months before graduation, she opened an official-looking envelope, carefully unfolded the letter inside, then read it and reread it before squealing with delight. She had received early acceptance at the University of Chicago—her ticket out of Seattle and away from her domineering dad.

Stanley senior had other ideas. Stanley Ann was too young to be on her own, he insisted. Besides, he was packing up his family and moving again—this time to take a higher-paying job selling furniture at a store in Honolulu.

Stanley senior made the announcement over dinner one night, and with his customary flair. “Hawaii!” he proclaimed. After five rain-soaked years in the Pacific Northwest, Stannie’s father argued, it was “high time we all get some sun.” Besides, Hawaii was far more than America’s newest state—a status it had achieved just the year before—it was the new frontier. “It’s paradise, for Christ’s sake!” he bellowed in the face of his daughter’s reluctance to pull up stakes and relocate yet again. “Everyone wants to live in Hawaii!”

Everyone but Stannie. She told Maxine Box that she wanted to stay put—if she couldn’t go to the University of Chicago, then at the very least she wanted to join her friends at the University of Washington in Seattle. There were loud arguments between father and daughter—fights that sometimes turned violent—but ultimately Stanley Ann had no choice but to resign herself to yet another move as her father pursued an elusive dream of success. “Remember me,” Stannie wrote wistfully in Maxine’s high school yearbook, “when you are old and gray.”

The Dunhams’ only child went along to Hawaii, but not without making it clear that she was no longer willing to live in her father’s looming shadow. From now on, she declared, there would be only one Stanley in the family. Henceforth, she was to be called simply Ann.

The Dunhams arrived in Honolulu in the summer of 1960 and rented a roomy, three-bedroom house near the University of Hawaii’s Manoa campus. Ann enrolled there in the fall of that year and, as one of the few undergraduates who didn’t seem to have roots in the islands, kept mostly to herself. “She was the shy, timid girl in the corner,” a fellow student said. Another student, Neil Abercrombie, recalled that Ann “was scarcely out of high school. She was mostly kind of an observer.”

In her Russian class, Ann was soon observing a dynamic young graduate student from Kenya named Barack Obama. The first African to enroll at the University of Hawaii, Barack—he pronounced his first name with the emphasis on the first syllable, as in barracks—Obama was already a campus celebrity of sorts. He gave newspaper interviews and spoke at local schools and churches about his upbringing on the shores of Lake Victoria as a member of the Luo tribe. “He had this magnetic personality,” Abercrombie said. “Everything was oratory for him, even the most commonplace observation.”

Audiences were fascinated to hear that Obama’s father, Onyango Obama, had enlisted in the British colonial forces and traveled to Europe, India, and Zanzibar, where he converted from Christianity to Islam, tacked “Hussein” to the front of his name, and enthusiastically embraced polygamy. Barack Obama, who was the biological son of Onyango’s second wife but was actually raised by Onyango’s third wife, told rapt listeners that he had been raised a Muslim but now considered himself an atheist. He also described how he had attended village schools and herded goats for his father before being accepted to an exclusive Christian boarding school run by the Anglican Church. As part of the “educational airlift” program started by Kenyan nationalist leader Tom Mboya and designed to provide Western educational opportunities to young Africans, twenty-three-year-old Barack received a scholarship to study global economics at the University of Hawaii.

One fascinating tidbit that Barack Obama chose not to share with his audiences—and certainly not with his fellow students—was that he had been married at the age of eighteen in a tribal ceremony to a woman named Kezia. When he left to attend school in Hawaii, Obama left a pregnant Kezia behind with their infant son.

Ann—Obama called her “Anna”—was soon smitten with the engaging young African, and it became clear that he was attracted to her. “I think she was attracted to his powerful personality,” Abercrombie mused, “and he was attracted to her beauty and her calmness.”

Before long, Ann brought her African boyfriend home for dinner with her parents. Both Stanley and Madelyn could not help but be impressed by the affable, articulate, supremely confident young economics student, who smoked a pipe and vowed he would return to his country to help “shape the destiny of Africa.” But the obvious physical affection between Ann and their guest clearly rattled Madelyn. “I was feeling protective, I guess,” she later recalled of that first meeting. Ann “was so young,” she went on. “I just didn’t want to see her get hurt. People can be so cruel.”

If there was any place in America where interracial dating seemed unlikely to raise hackles, it was Hawaii. Here native Hawaiians mingled with Chinese, Japanese, Portuguese, Filipino, European, and mainland American immigrants—and one in five white women married Asian men. Yet one ingredient was conspicuously absent from Hawaii’s fabled melting pot. In 1960, less than 1 percent of the state’s population was black.

At the time, interracial marriage was still illegal in twenty-three states. Hawaii, Ann pointed out to her concerned parents, was not one of them. However open-minded they might have considered themselves, the Dunhams were not happy when Ann told them she intended to marry the charming young man from Africa.

If the Dunhams were distressed at the news, the prospective groom’s father, Hussein Onyango Obama, was downright livid. In a lengthy letter to Stanley and Madelyn, the most senior Obama railed against the idea of a biracial union. He did not, he stated flatly, want the Obama blood “sullied” by a white woman.

Ann, who had actually started sleeping with Barack just a couple of weeks after their first meeting in September 1960, made the case for marrying him more compelling when she announced in late October that she was pregnant. Whatever the Dunhams’ feelings about the perils of interracial marriage, these were trumped by a desire not to see their only child become an unwed mother.

On February 21, 1961—a Thursday—Barack Obama and Ann Dunham were reportedly married in a civil ceremony on the island of Maui, although there are no official records showing that a legal ceremony ever took place. There were certainly no witnesses—no family members were present, and none of their friends at the university had the slightest inkling that they were even engaged. “Nobody was invited to the wedding,” Neil Abercrombie said. “Nobody.” (Their only son, also named Barack, would later concede that the circumstances of his parents’ marriage were “murky,” “fragile,” “haphazard”—a “bill of particulars that I’ve never quite had the courage to explore.”)

When Ann wrote to her friends back in Seattle with the news that she had dropped out of college after a single semester, married an African man, and was expecting a baby, they were understandably surprised. “Shocked—very shocked—is more like it,” said Maxine Box. “I can’t think of anything she said or did that would lead to such a radical thing. We could see Stanley, with her good grades and intelligence, going to college—but not marrying and having a baby right away.” As for marrying a black man: “At that time, you practically crossed the street if you saw a black man and a white woman,” Box explained. “Black and white didn’t go together at that time.”

Certainly it would have complicated matters even further if Ann and her parents had been made aware of Barack’s still-extant marriage to Kezia, or the two young children they shared. For now, Stanley in particular took pride in the fact that his new son-in-law was a highly educated man of the world who could speak authoritatively on a wide range of subjects, from the global economy to his own experiences traveling throughout Africa and Europe.

Even a born storyteller like Stanley could not help but be struck by Obama’s thundering voice. “It was a deep, resonant bass with a timbre you could not forget,” Richard Hook said of his friend’s voice. “Barack would walk into a room and say, ‘My name is Barack Obama’…and everyone in the room would instantly look up. Everyone wanted to know who he was.”

Pake Zane, who had also known the senior Obama in Hawaii and later visited him in Kenya twice, agreed that Obama’s voice was “startling and at the same time incredibly seductive. He had the same sort of deep tone in his voice that the actor James Earl Jones has, only much louder. He also had a hint of a British accent, very Oxford-sounding.” As for his appearance, Zane recalled that Obama was “not a large man, but he carried himself like a king. And he was one of the blackest people I’ve ever met—almost this beautiful shade of purple.”

Even friends had to concede that Barack’s cocksure manner “rubbed a lot of people the wrong way at first,” Abercrombie said. “He did not lack for self-importance. He was a self-involved, egotistical, vivid person…. But we forgave him that because he was so genuine. People always liked him. They just thought, ‘Well, that’s Barack.’”

Although he had been known to thoroughly disarm hate-spewing bigots with soothing calm—one bar patron who started out calling Barack a “nigger” wound up feeling so guilty after Barack gently lectured him on the evils of intolerance that he gave Barack a hundred dollars in cash on the spot—Obama could also be impulsive. On one occasion, Barack drove a visiting fellow African up the road that wound through Oahu’s windward peaks to the Nuuanu Pali Lookout, site of a fierce battle won by King Kamehameha I. It was while standing on the edge of the precipice and marveling at the canyon stretched out before them that the visitor asked to take a puff from Barack’s favorite pipe—and accidentally dropped it over the side.

Mortified, the visitor apologized and promptly offered to buy Obama a new pipe. But that wouldn’t do. Obama wanted his pipe, and when the visitor refused to climb over the railing and climb down the face of the cliff to get it, Barack grabbed him by the waist and lifted him over the railing. It was only after a frantic Ann interceded that Barack put the terrified man down.

Barack’s driving proved equally terrifying. An unrepentant speed demon who often absentmindedly reverted to driving on the left-hand side of the road, Obama racked up more than his share of traffic tickets and fender benders. “You really took your life in your hands,” Pake Zane said, “when you drove with him.”

Obama’s recklessness aside, Stanley, like nearly everyone else, could not help but be impressed by his larger-than-life persona. Madelyn was more circumspect. She did not entirely trust her son-in-law when he claimed to have Ann’s best interests at heart. “I am a little dubious,” she later said, “of the things people from foreign countries tell me.” Nevertheless, she suggested that Ann and her husband move into the Dunhams’ roomy house so that they could all await the new baby’s arrival together.

On the afternoon of August 4, 1961, Barack drove his pregnant wife the eight miles from their bungalow at 6085 Kalani-anaole Highway due east to Honolulu’s Kapiolani Hospital for Women and Children. Founded in 1890 by Queen Kapiolani, known as “the Queen who loved children,” the hospital was originally called the Kapiolani Maternity Home and was intended strictly for native Hawaiian mothers.

After just two hours in labor, Ann gave birth to an eight-pound two-ounce boy. In keeping with the tradition established by Stanley’s father, Stanley, they named the baby Barack Hussein Obama.

While her new husband went back to the University of Hawaii to finish up his studies, Ann devoted herself entirely to the care of little Barack. From the very beginning Stanley and Madelyn called their grandson “Barry”—ostensibly to distinguish him from his father, Barack, but also to ease the path toward social acceptance by Americanizing the child’s name. “It was hard enough to have to deal with the obviously charged issue of having a black grandson back in the early 1960s,” said one of their Kansas relatives. “To have to constantly explain his African name—that was too much. Besides, ‘Barry’ just sounds so nice and friendly. It was a very popular name back then…. ‘Barack’ always seemed harsh—kind of threatening, even.”

The following June, Barack graduated from the University of Hawaii with a degree in economics. He intended to eventually return to Kenya and lead his generation in building a new, modern Africa. On graduation day, he was interviewed by the Honolulu Star-Bulletin. Barack contrasted the more accepting behavior of whites in the islands with that of whites in other parts of the world, and praised Hawaii as a model for promoting harmony among various ethnic groups. He said nothing of his wife and son.

Before he could return to his homeland, however, Obama needed to earn his PhD in economics in the United States. The prestigious New School in New York City offered him a full scholarship—enough money to make it possible to bring both Ann and their infant son with him. Harvard also offered Obama a scholarship, although one that would not afford him the luxury of bringing his young family along.

Ann was thrilled about the New School offer and was excited about the prospect of moving to New York. Her hopes were dashed when Obama decided instead to accept the Harvard offer. “How,” he asked her, “can I refuse the best education?”

Yet there were others who agreed with Ann, most notably Kenyan nationalist Tom Mboya, who had become something of a mentor to Barack. Although Obama never mentioned his wife and child to Mboya in his letters, Mboya had been told of their existence and chastised Barack for abandoning them.

No matter. Late that July of 1962, Obama departed for Harvard—alone. He did not even stay to celebrate his son’s first birthday. “I know he loved Ann,” Abercrombie insisted. “But I think he didn’t want the impediment of being responsible for a family. He expected great things of himself and he was going off to achieve them.”

At Harvard, Obama rented an apartment just off Central Square and quickly made his presence known. Regardless of his avowed feelings for Ann and little Barry, Barack soon began dating Ruth Nidesand, a tall, blond American teacher from an affluent New England family. Nidesand’s money enabled Barack to move in certain social circles in Cambridge and to indulge his growing fondness for expensive suits, silk ascots, and Johnnie Walker Black Label scotch. “He would shout in that big, deep voice, “Waiter, another double!’” recalled his friend Leo Odera Omolo. Soon Barack was known to his drinking buddies as “Mr. Double Double.” Later, Barack would actually take to calling himself “Dr. Obama.” In fact, while he did earn a master’s in economics from Harvard, he never pursued a doctorate.

Ann continued to write Barack and to send him photos of their son. Even Obama called his son “Barry” when he showed those photos to his new friends and fellow graduate students at Harvard. Although she was blissfully unaware of her husband’s infidelity, Ann made the decision not to follow him to Massachusetts. “She was under no illusions,” Abercrombie observed. “He was a man of his time, from a very patriarchal society.”

At her mother’s urging, Ann filed for divorce in January of 1964, charging “grievous mental suffering.” Barack did not contest the action; by that time, he was planning to return to Africa with his new love, Ruth Nidesand. The following year, he and Nidesand would marry and go on to have two sons. But the relationship would not be without its tense moments, since Barack senior was still married to his first wife, Kezia. However open-minded Ruth may have been, she was not about to allow Kezia and her two children by Barack to move in. So Barack, a willing polygamist, merely visited his first wife periodically. The inevitable result: two additional children with Kezia.

Back in Hawaii, Ann had plans of her own. A full year before starting divorce proceedings, she had resumed her studies at the University of Hawaii. While she attended classes—and made ends meet with the help of food stamps—her parents took care of little Barry. One of his earliest words would be toot—short for tutu, the Hawaiian word meaning “grandparent”—and the name by which Madelyn Dunham would be known by her adoring grandchildren. Barry bestowed a somewhat less imaginative nickname on Stanley. To Barry, Stanley senior would always be, simply, Gramps.

To help offset some of the family’s mounting bills, Toot went back to work—this time as a secretary at the Bank of Hawaii. She was soon promoted to teller and then to assistant loan officer, bringing in enough extra cash to easily support both Ann and her baby.

Barry’s early childhood—spent primarily in the company of his doting grandparents—was nothing short of idyllic. He learned to snorkle at Hanauma Bay on Oahu’s southeast coast, tagged along when Gramps went spearfishing with his Portuguese sailor friends in Kailua Bay, enjoyed the lomi-lomi salmon and roast pig served at neighborhood luaus, and cooled off on sweltering summer days by downing “shave ice”—Hawaii’s answer to the snow cone.

Mom, meanwhile, had fallen in love with yet another foreign student—this time an Indonesian man named Lolo Soetoro. The fact that lolo was Hawaiian slang for “crazy” meant raised eyebrows whenever Soetoro was introduced to anyone on the islands, but he took it in stride. In fact, the compact, dark-haired Soetoro was as soft-spoken and unflappable as Barack senior had been flamboyantly self-assured. Lolo was not above engaging in a little horseplay with Ann’s young son on the Dunhams’ living room floor or laughing at Gramps’s cringe-making jokes over endless games of chess.

Barry was an outgoing, slightly pudgy six-year-old when his mother sat him down and told him she was going to marry Lolo and that they were going to move sixty-seven hundred miles away to Indonesia. It would be their first journey outside the country, and Ann, clearly wondering if this was the right thing to do, wept as she broke the news to her son. As far as Barry was concerned, it was perfectly fine as long as his mother loved Lolo. “Do you love him, Mom?” he asked point-blank. She did, she told Barry tearfully as she swept him up in her arms.

Lolo returned to Indonesia earlier than he had expected—summoned, as were all Indonesian students studying abroad, by the new military government that had toppled Indonesia’s longtime dictator, Sukarno. Many of these students, viewed as a potential threat by the new right-wing regime, were imprisoned or executed. Unbeknownst to Ann, Lolo was immediately drafted by the Indonesian army and sent to fight guerrillas in the jungles of New Guinea.

It would be nearly a year before Ann and Barry finally joined Lolo in Indonesia—a year during which the once easygoing Lolo seemed to have undergone a dramatic change. Now stuck in a low-paying job surveying roads for the Indonesian army, he was prone to binge drinking and long, sullen silences.

For the moment, however, it was enough just to cope with their exotic new surroundings. Barry and Ann moved into Lolo’s small, flat-roofed bungalow on a dirt road just outside Jakarta at 16 Haji Ramli Street, where cockatoos, dogs, chickens, ducks, baby crocodiles, and even a pet monkey named Tata roamed the backyard. The absence of paved roads, electricity, and indoor plumbing scarcely fazed the boy, who viewed everything as an adventure.

When the children in his neighborhood viewed the foreigners in their midst suspiciously, Barry climbed atop a wall that separated his house from his neighbors’, where he cawed and flapped his arms like a giant bird. “That got the kids laughing,” recalled Kay Ikranagara, a friend from that period, “and then they all played together.”

At first, he was teased about his weight—the other kids called him “Fatty” in Indonesian—and about his color. The only black many of these children had ever seen, he was also routinely referred to simply as “Negro”—an appellation that, according to another friend, Bambang Sukoco, did not seem to bother him.

He even became accustomed to the periodic lashings he received at the hands of the nuns at Franciscus Assisi Primary School. He was the school’s only non-Indonesian student; the children of most foreigners went to Jakarta’s International School, but Ann and Lolo lacked the money for tuition.

Ann’s son was enrolled at Franciscus Assisi as “Barry Soetero”—using his stepfather’s surname—and his nationality was listed on official school documents as Indonesian. Since the Catholic school had been in operation for less than a year and needed local children to fill its classes, it made a point of opening up the student body to all faiths. “At that time,” explained his teacher Israella Darmawan, “Barry was registered as a Muslim because his father, Lolo Soetoro, was Muslim.” Former vice principal Tine Hahiyari and third-grade teacher Effendi also recalled that Barry was registered as a Muslim, which determined what weekly religion class he attended. “Muslim students were taught that religion class by a Muslim teacher, and Christian students were taught by a Christian teacher,” Effendi said. “Barry was definitely Muslim. He studied the Koran.”

Occasionally, Barry went with his stepfather and his friends to Friday-night prayers at the local mosque. “We prayed a lot but not really seriously—just following actions done by older people in the mosque. But as kids, we loved to meet our friends and went to the mosque together and played,” said one of Barry’s close friends at the time, Zulfin Adi. According to Adi, Barry often wore a sarong to the mosque.

Barry quickly discovered that he liked to tell people what to do. His first day at school, he commanded his fellow students, “Baris!” (“Make a line!”), then “Siap grap” (“Get ready”), and finally “Tegap!” (“Stand straight!”). Barry then reviewed the line and, once he was satisfied it was straight, allowed the students to march into the classroom. “Sometimes I had to tell him to let the other kids do it,” said Israella Darmawan. Her nickname for Barry: “Little Curly-Haired One.”

Because he was a full head taller than any of the other children in class, Barry also helped Darmawan clean the blackboards. Although he was one of her brightest students—“especially at mathematics”—it was Barry’s instinct for leadership that most impressed his teachers at the time. “He always wanted to be number one, to be at the front. Psychologically, he wants to be in charge.” Nor was he above informing on his fellow students. “Whenever they misbehaved,” third-grade teacher Cecelia Sugini said, “Barry would tell me to make them stop.”

This sense of righteous indignation extended to the playground. Whenever the other children tried to cheat during games of marbles, Barry would stand up and yell, “Kamu curang, kamu curang!” (“You cheat! You cheat!”), recalled Zulfin Adi. “We could never cheat him. We did try, but he always found out.” Adi described his friend as “resolute.” Barry, he said, “never hesitated to stand up to defend his rights.”

Given Barry’s take-charge personality, Darmawan was not surprised at his response when he was asked to write an essay on the theme “What I Want to Be When I Grow Up.” “I,” Barry wrote in the opening line, “will become President.” At the time, Darawan said, it was hard to tell from the essay if he intended to become President of the United States or Indonesia. “His father was Indonesian,” she recalled. “His sister was Indonesian. He spoke Indonesian. There was no reason to think that he meant anything other than becoming President of Indonesia.”

It had taken less than a year for Barry to essentially master Indonesia’s language and customs. What he found more daunting—even frightening—were his countless encounters with human misery. Beggars, some disfigured by leprosy, others missing limbs, accosted him on the street or came to the house pleading for money or food.

Understandably, Ann, who had a penchant for bursting into tears at the slightest provocation, found herself weeping on a daily basis. Initially unable to turn down any of the beggars who appeared on the doorstep—“Your mother has a soft heart,” Lolo observed—Ann eventually learned to be more selective.

Ann soon began teaching English to Indonesian business executives at the U.S. embassy in Jakarta. The yawning chasm between this tiny elite and the rest of the country’s vast population was a fact of Indonesian life Ann was unwilling to accept. When Lolo joined that elite—landing a job at an American oil company and quickly advancing through its ranks—Ann grew even more indignant. Proud of his attractive American wife, he insisted that she accompany him to cocktail parties and other company functions, but she refused.

With the birth of Barry’s half sister Maya in August of 1970, Lolo hoped that Ann would become less restless and more resigned to her role as a wife in Indonesian society. Certainly she had no quarrel with Lolo’s attitude toward her son; in every way possible, he treated Barry as his own.

Still, Ann felt isolated and alone. Moreover, she knew that this was neither the childhood nor the future she had in mind for her son. “You are not an Indonesian,” she reminded Barry frequently. “You are an American. You have American values. Don’t ever forget that.” Accordingly, during these years abroad she went to great lengths to ensure that Barry never lost his command of the English language and the American idiom. Each day before dawn she woke him up to drill him with lessons from an English correspondence course, then headed off to her job at the American embassy. “She would be totally exhausted,” he recalled. “But it was very important to her that I never lose sight of who I was, and where I fit in in the scheme of things.”

That also meant reinforcing Barry’s black heritage by having him read books about civil rights leaders like Martin Luther King and listen to recordings ranging from Harry Belafonte and Maha-lia Jackson to Sam Cooke, Aretha Franklin, and Stevie Wonder. “Every black man was Thurgood Marshall or Sidney Poitier, every black woman Fannie Lou Hamer or Lena Horne,” Barry would later recall. “To be black was to be the beneficiary of a great inheritance, a special destiny.”

To Ann, it was also important for Barry to view his absent father as a role model. She preferred to overlook the fact that Barack senior would go on to father numerous other children (for a grand total of eight) with his various wives and lovers in Kenya. Instead, she stressed Barack senior’s intellect, his idealism, and his commitment to bettering the lives of his fellow Africans. “Your brains, your character,” Ann told her son, “you got from your father.”

In fact, Barack senior seldom even bothered to inquire about his American family, much less seek to have direct contact with his son. No matter. The boy was willing to accept whatever his mother told him about his father as gospel—for now.

Barry’s mother had done such an effective job of building up Barry’s self-esteem that he was nine before it ever occurred to him that being black was anything but a blessing. It was then that he came across a magazine article about a black man who had tried to chemically lighten the color of his skin and wound up horribly scarred. In one life-altering moment, the young boy realized for the first time that there might be something wrong with being black—that it was a condition that some people found so onerous that they would go through painful, expensive treatments to turn themselves white. Seeing the photos was “violent for me,” he later wrote. “My stomach knotted. Did my mother know about this?”

Barry said nothing to his mother or to anyone at the time. But he would remember that this was the moment when he began to harbor serious doubts about where he really fit in as a biracial child.

After two years at Assisi, Barry transferred to a public school; this one, like all public schools in Indonesia, was Muslim and incorporated in its regular curriculum teachings from the Koran. “At the Catholic school, when it came time to pray,” Barry later said, “I would close my eyes, then peek around the room. Nothing happened. No angels descended. Just a parched old nun and thirty brown children, muttering words.” At “Muslim School,” as he later referred to the public school he attended, the teacher sent a note home to Ann complaining that Barry misbehaved by making faces during Koranic studies. Ann took Barry aside and admonished him to “be respectful,” but declined to punish him as the teacher requested.

“My whole family was Muslim,” Barry’s sister Maya later said, “and most of the people I knew were Muslim.” It was a situation that did not sit entirely well with Ann. Barry’s mother, whose own deep spirituality belied a distrust of all organized religion, did what she could to drum Western ideals of equality, democracy, and fairness into her son’s brain. She also tried to imbue both her children with a sense of the spiritual. “Our mother was fascinated by all things lunar,” Maya recalled. “She called herself a ‘Lunatic,’ and would take us out in the middle of the night to gaze at the moon if it was particularly full or bright.”

The lessons Barry learned from his stepfather were of a more practical nature. When a schoolmate tossed a rock at Barry and left him with a goose egg on the side of his head, Lolo produced two sets of boxing gloves and taught his stepson how to defend himself. “Men,” Lolo told Barry, “take advantage of weakness in other men.”

Yet Ann’s son preferred the role of peacemaker. Once again, he accomplished this simply by telling his peers how to behave. They invariably complied. “If his friends were having arguments, he’d become a mediator,” recalled Harmon Askiar, one of Barry’s Jakarta neighborhood playmates. “He would grab one friend’s hand and grab the other friend’s hand and force them to shake and be friends again.”

After three years in Indonesia, Ann told her ten-year-old son that his time there was about to come to an end. The owner of the furniture store that employed Stanley Dunham in Honolulu was an alumnus of Hawaii’s elite Punahou prep school, and Gramps had asked if he couldn’t pull some strings to get Barry accepted.

Founded in 1841 by American missionaries, Punahou (Hawaiian for “new spring”) was more than just the islands’ answer to such tony mainland schools as Andover, Exeter, Groton, and Hotchkiss. Punahou actually offered a first-class private school education from kindergarten straight through high school. By 2009, it would grow to include more than thirty-seven hundred students, making Punahou the largest independent school in the United States.

Not surprisingly, competition to get into the middle school and high school classes was especially fierce. Even children from some of Hawaii’s wealthiest and best-connected families had to settle for being wait-listed. Somehow Gramps not only got Barry bumped to the head of the line, but he also managed to wrangle young Obama a full scholarship.

Race also played a significant role in Barry’s selection. Out of a student body that included Caucasians, Asians, Hispanics, and numerous combinations of these groups, there were only four blacks at Punahou when Barry enrolled there. “The school had essentially been all-white until the 1960s and had always had this elitist reputation,” said a former teacher at Punahou. “By the 1970s there was a lot of pressure to be more inclusive. Barry was biracial, but he was also someone who had spent years in Indonesia. Not that it mattered that much back then, but we were told he was a Muslim. It was all very exotic and appealing to the powers-that-be at the school.”

Exotic was something Barry desperately did not want to be. On the first day of school, teacher Eric Kusunoki struggled with Obama’s first name while calling the roll. “Is Bar-ack here?” he asked. When the new student said to him, “Just call me Barry,” Kusunoki nodded. “He didn’t say it like he was exasperated or anything,” Kusunoki said. “He just corrected me.”

Despite the fact that it was Gramps’s influence that managed to pave the way for Barry’s entrance into prep school, the economic power in the Dunham family had shifted to Toot. While Gramps had given up the furniture business to sell life insurance over the phone—an inherently frustrating and at times demeaning job he soon discovered he was not particularly well suited to—Toot had gradually climbed up the corporate ladder to become the first female vice president of the Bank of Hawaii.

It was an opportunity for her son that Ann could not pass up—not even if it meant that she would be separated from him. On a hot day in August, she and Maya waved good-bye from the gate as an airline employee took Barry’s hand and led him toward the plane that would take him home to live with his grandparents. He turned to see his mother’s lower lip tremble as it so often did when she fought back tears, although even at this young age he suspected that such displays were primarily for public consumption. Barack’s sister believed their mother’s emotional outbursts were genuine enough. “She cried a lot,” Maya said. “If she saw animals being treated cruelly or children in the news or a sad movie—or if she felt like she wasn’t being understood in a conversation.”

Ann was, in fact, capable of keeping an emotional distance from those around her—including her own children. “She kept a certain part of herself aloof or removed,” observed one of Ann’s close friends in Indonesia, Mary Zurbuchen. “Maybe in some way this was how she managed to cross so many boundaries.”

At this point, Toot and Gramps would pick up where Ann left off when it came to shoring up Barry’s self-confidence. When one of his fellow students at Punahou asked if his African father was a cannibal and others asked to touch his hair—he refused—Barry’s grandparents urged him to simply shrug it off. Unlike their daughter, they were less interested in stressing Barry’s ties to Africa than they were in seeing him blend in. Although Toot declared more than once that she considered Harry Belafonte “the handsomest man in the world,” her mantra was “what color you are just doesn’t matter.”

Increasingly, it did matter to Barry. When he befriended the only other black student in his grade—a girl named Coretta—on the playground, the other kids gathered around to tease them for being boyfriend and girlfriend. Embarrassed, Barry shouted for Coretta to stay away from him and even gave her a shove. Bewildered and upset, she sprinted away in tears.

In part, Barry, like any ten-year-old boy, objected to being thought of as anyone’s boyfriend. But he was also distancing himself from the only other person in class who shared his skin color. There was a part of him that did not want to be classified simply as black—a lingering result, he would later conclude, of that magazine article about the man trying to bleach his skin. In shoving Coretta, he felt guilty for having committed an act of betrayal.

Barry quickly realized that the often insensitive questions from his peers were not about to abate. Soon he was embellishing the truth. His grandfather, he told his wide-eyed classmates, was a chief, his father a prince, and the family name Obama meant “burning spear.” (Actually, Kenyatta means “burning spear.” Unfortunately, the surname Obama is from the Luo word bam, meaning “crooked” or “bent.” Barack means “blessed.”)

That first December back in Hawaii, Barry’s parents both visited—first Ann from Indonesia and, two weeks later, Barack senior from Kenya. For Barry’s father, who had just been released from the hospital after being injured in an auto accident and now walked with the aid of a cane, this visit was intended to provide some much-needed rest and relaxation.

On a stiflingly hot July weekend just two years earlier, Barack senior was shopping in Nairobi when he bumped into his old mentor Tom Mboya. “You are parked on a yellow line,” Barack senior joked with Mboya. “You’ll get a ticket.” Minutes later, Mboya was gunned down on the street.

Barack, who worked in Kenya’s Ministry of Economic Planning and Development, had already infuriated his superiors by publicly criticizing his government’s economic policies and for complaining that he was working for men less capable than he was. Now he risked angering powerful forces in the Kenyan government by testifying at the trial of Mboya’s accused assassin.

On the basis of Barack senior’s testimony and that of nine other eyewitnesses, Mboya’s killer was tried and hanged. But from that point on, Obama’s career—and life—began to spiral out of control. On a visit to Nairobi’s Ministry of Economic Planning and Development, American international development expert Clive Gray noticed Obama lurching down a hallway.

“What’s the matter with that guy?” Clive asked a ministry staff member. Obama had changed so dramatically that Clive hadn’t recognized him at first.

“He is always very intoxicated,” the staffer replied, “and unable to do his job.”

Although the senior Obama had impressed Gray as “kind of a loudmouth” when he first encountered him at Harvard, he remembered how much promise the young Kenyan had shown back then. Looking at him now, Gray could hardly believe that this was the man who had vowed to save his country from economic ruin. “It was,” Gray said, “very sad.”

Although he did not share the details with either the Dunhams or his son, Barack senior had been driving drunk when he slammed into a tree and badly fractured his leg. It was only the latest in a series of accidents involving alcohol that left Barry’s dad with a permanent limp.

Barry was understandably horrified when he learned that his father had accepted an invitation from his fifth-grade homeroom teacher, Mabel Hefty, to speak to her pupils. But by the time Barack senior had finished telling Barry’s class about the wonders, challenges, and mysteries of life in Africa—about tribal customs, wildlife, and Kenya’s own struggle against the British for independence—his son was beaming with pride.

It was, Barry would recall, a “tortured moment” that ended with “tremendous relief” that his father had managed to impress teachers and students alike. “That he’s different, but is somehow able to communicate with great confidence a sense of common humanity was actually a great object lesson for me.”

At home, however, Barack senior’s humanity was somewhat less evident. Barry had eagerly anticipated watching Dr. Seuss’s How the Grinch Stole Christmas on television—a holiday tradition in the Dunham household—but instead was ordered by his father to do his homework. “I tell you, Barry, you do not work as hard as you should,” he said. “Go now, before I get angry at you.” From that point on, Barry could not wait for his father to leave.

That Christmas visit would last scarcely four weeks. Despite the tensions with Barack senior and the fact that both his parents were married to other people, Barry would treasure this as the only time he could recall being together with his father, mother, and grandparents as a family unit.

What Barry did not know at the time was that his father had pleaded with his mother to return with him to Africa—and to bring Barry and Maya with her. Ann, who was aware that Barack senior already had at least two wives and a half-dozen children waiting for him back home, declined.

When his father and mother both left—he bound for Kenya, she for Indonesia—Barry tried to accept the separation as “just the way things were.” But later, he would confess, “I suspect it had more of an impact than I know.”

Ann promised her son that she would return to live with him in Hawaii the following year. In the meantime, his character would continue to be molded and shaped to a large extent by Toot and Gramps.

Now occupying a modest two-bedroom apartment just ten minutes away from Waikiki, on Beretania Street in Honolulu’s Makiki neighborhood, the Dunhams were going through some trying times of their own. Without the ability to literally pump someone’s hand or look that person in the eye as he told one of his over-the-top stories, Gramps quickly discovered that he just wasn’t cut out for life as a telemarketer. “Of course, people were hanging up on him all the time, or making excuses for why they were too busy to see him,” said a family friend. “It was really killing him slowly inside, making him very resentful—especially toward Madelyn.”

The Dunhams were secure financially—thanks to Toot’s steady rise at the Bank of Hawaii. She now earned far more than her husband, despite the fact that the male executives she was training were often promoted ahead of her and invariably paid fatter salaries. It was a commonly seen brand of overt corporate sexism that infuriated her daughter. “How can you stand it, Mom?” Anne would demand. “It’s not right. It’s totally unfair. You should stand up and do something about it.”

Not that Toot could ever be described as a shrinking violet. “I was afraid of her,” said Alton Kuioka, who was a young trainee in the Bank of Hawaii’s loan department in 1969. Kuioka would eventually become the bank’s vice chairman. “She definitely intimidated me. If you were new and learning she was like a drill sergeant.” Another trainee at the time, Dennis Ching, also confessed to being “totally scared” of Barack’s grandmother. “She was like the grande dame of escrow…. She gave me a file and said, “You’re a college grad. Here, close this.’ You don’t know how to swim, and she throws you in, and you either sink or swim.”

Barry was sensitive to the new dynamic in the Dunham household and to the simmering tensions between his grandparents. Fortunately for Barry, his mother left Lolo and returned with Maya to Honolulu, determined to pursue her master’s in anthropology at the University of Hawaii. Ann found a small apartment just off the Punahou campus and moved into it with her two children.

To all outward appearances, Punahou was not unlike any small New England college. There were arched windows, broad lawns, indoor and outdoor tennis courts, ivy-covered lecture halls of neo-Romanesque design, state-of-the-art laboratories, an Olympic-size pool, and—to maintain it all—a $180 million endowment. Barry would flourish here academically. “Barry could whip out a paper that was due the next day the night before,” recalled Suzanne Maurer, whose son, Darin, was a classmate of Barry’s. “The other kids spent weeks writing the same paper.”

Losing the baby fat that had made him the butt of jokes as a boy back in Jakarta, Barry became one of the lesser stars on Punahou’s basketball team—its sole left-handed player.

One of Barry’s closest friends at Punahou, Bobby Titcomb, remembered Barack “dribbling his ball, running down the sidewalk on Punahou Street to his apartment, passing the ball between his legs. I mean, he was into it.”

If he was not the most talented player, he was, said teammate Alan Lum, “a leader on the court” in part because of his penchant for enforcing the rules. “He would call people on it if they were doing something wrong,” Lum said. “He would question coaches. He was strong and confident enough to ask those questions. I respected him for that.”

Barack’s knack for “calling people out” did not make him any less popular with his fellow students. “He was the kind of guy,” said classmate Dan Hale, “who could walk into a room and navigate the cliques.” Although never regarded as a big man on campus, he made friends easily, went to school dances, and, like all adolescents, made his first few awkward attempts at dating. Weekends were spent bodysurfing at Sandy Beach in East Honolulu or picnicking at Puu Ualakaa State Park on Mount Tantalus, with its sweeping views of Diamond Head, Punchbowl Crater, and downtown Honolulu.

Occasionally, Barack would take off hiking with one of his friends. “We’d go hike up Peacock Flats and camp, just the two of us,” recalled Bobby Titcomb. “We’d try to get away from everything. We’d basically live on nuts and whatever we could eat on the trail for two or three days. And we’d talk about how the world could be.”

Notwithstanding these periodic soul-searching treks into the wilderness à la Henry David Thoreau, Barack was never regarded as a loner. “He fit in as much as, if not more than, any other student,” Darin Maurer said. “He wasn’t the most popular kid in school, but he was certainly well liked. I never really saw that he was suffering.” Neither did Alan Lum. “To always have had that smile on his face…and yet to be going through that internal struggle,” Lum said. “I feel I lost an opportunity to connect with him.”

But Barry was suffering. Beginning with those first embarrassing questions from the other kids and their attempts to touch his hair or rub his head, Barry became increasingly sensitive to the fact that others viewed him as different. “I began to think,” he later conceded, “that as a black man being raised by white people, I should belong to both worlds—and yet I couldn’t help feeling that I really belonged to neither.”

In the small apartment he shared with his mother and sister, Barry watched Soul Train on television and sang along with the Temptations and Stevie Wonder—all a conscious effort, he would later admit, to shore up his sense of self as a young black American. His mother had always been his staunchest ally in that endeavor, but when Barry turned fourteen she made a stunning announcement: She was returning to Indonesia to do fieldwork for her PhD. She was taking Maya with her, but Barry would be allowed to decide for himself whether he was going to accompany his mother or remain in Hawaii.

Barry chose to stay behind with his grandparents. He had had enough of starting over. As difficult as it was being one of the few blacks at Punahou, he had made friends and was thriving academically. Moreover, Gramps and Toot had always stood by Barry while at the same time giving him considerable control over his own life—actually more autonomy than he had enjoyed while living with his mother. “We have total confidence,” they liked to tell him when he was faced with a decision, “that you will do the right thing.”

For Barry, the “right thing” meant confronting prejudice wherever it reared its ugly head. While growing up in the racial and ethnic hodgepodge that was Hawaii, Barry still encountered the kind of discrimination inflicted on blacks in less exotic locales. He demanded but never got an apology from a woman in the Dunhams’ apartment building who bolted out of the elevator when he stepped into it. At Punahou, Barry reacted to being called a “coon” by punching a classmate in the face. After he overheard a basketball coach dismiss members of an opposing team as just “a bunch of niggers,” Barry angrily informed the coach that he was “an ignorant white motherfucker.”

One of his closest friends at Punahou, Keith “Ray” Kakugawa, believed Barry was perhaps too sensitive to perceived slights. “He made everything look like it was all racial,” claimed Kakugawa, who was half black, half Japanese, and two years older than Barry. During one basketball game being coached by Kakugawa’s father, Barry complained that he was frequently benched just because he was black. “No, Barry, it’s not because you’re black,” the senior Kakugawa told him. “It’s because you missed two shots in a row.”

“Barry’s biggest struggles then,” Keith said, “were about missing his parents. His biggest struggles were his feelings of abandonment. That idea that his biggest struggle was race is bull.”

In truth, Barry did not have to venture outside his own family to encounter evidence of the barriers that still existed between blacks and whites. One morning, as she stood waiting for the bus that would take her to work, Toot was approached by a homeless man asking for money. She tried to ignore him, but the man persisted. So Toot dug around in her purse, pulled out a dollar bill, and, with a wan smile, gingerly handed it to him.

Toot had hoped the man would move on to the next victim, but instead he kept his outstretched hand palm-up and asked for more. He was, she later said, “insistent” and “menacing.” It was at this moment that the bus pulled up and Toot quickly hopped aboard. As she settled into her seat, she looked back at the homeless man. He never stopped smiling.

Now Toot wanted Stanley to give her a ride to work each morning. The idea of being accosted once again at the bus stop was too much for her. But Gramps knew the real reason behind his wife’s anxiety—which he shared with Barack—and he was anything but sympathetic. She would never say anything of the sort to her grandson, but Toot confided to her husband that the homeless man “was, well, you know…. He was black.

The sudden realization that even his beloved grandmother harbored a deep-seated fear of black men pushed Barry over the edge. Toot and Gramps and his mother had always loved him unconditionally, and yet they did not have the answers he needed as a biracial man. He was growing up in a white household, and now, Keith Kakugawa said, Barry “felt he was not getting a part of who he was.”

Barry got some of the answers he needed from Frank Marshall Davis, a leading black activist and writer of the 1930s and 1940s who eventually settled in Hawaii. Gramps had introduced Davis to Barry in hopes that the older gentleman might give him some insight into what it meant to be a black American.

Barry would later write that he was “intrigued by old Frank, with his books and whiskey breath and the hint of hard-earned knowledge behind the hooded eyes.” When he told Frank about the panhandler who accosted Toot, Barry was surprised at the old man’s answer. Frank told him she was right to be scared because “black people have a reason to hate.” It was at that moment that Barry felt he might never have really known his family at all. “The earth shook under my feet…” he recalled. “I stopped, trying to steady myself, and knew for the first time that I was utterly alone.”

Barry continued his journey of self-discovery by plunging into the works of Langston Hughes, James Baldwin, W. E. B. Du Bois, and Ralph Ellison. When Barry checked The Autobiography of Malcolm X out of the Punahou school library, Kakugawa was taken aback. “Hold on, man,” he said. “What you gonna do? Change your name to something Muslim?”

“Well,” Barry replied with a shrug, “my name is Barack Obama.”

Kakugawa looked at his friend quizzically. “No it isn’t,” he insisted.

“Yes, my name is Barack. Actually, it’s Barack Hussein Obama.”

“Get off it!” Kakugawa shot back before the librarian threatened to throw them out.

What upset Kakugawa most was the fact that, for all his friend’s railing against racism, Barry “seemed about as solidly middle-class American as you can get,” he recalled. “I knew his dad was African and had taken off when Barry was small, but I had no idea that he had left Barry with an African name. I felt that he had obviously gone out of his way to hide that from me and from the rest of his buddies at the time.”

Indeed, Barry was not yet ready to fully embrace his African heritage by insisting that he be called Barack. But he did find a kindred spirit in assassinated Black Muslim leader Malcolm X, whose unambiguous hatred of “blue-eyed devils” softened after he visited Mecca and saw whites praying to Allah alongside blacks. Already exposed to its teachings during his four formative years in Indonesia, Barry now wondered if Islam did not provide an orderly framework for racial harmony—and a way for him to reconcile conflicts over his own biracial background.

Barry returned to the Koran for answers and told friends at the time that he was seriously considering joining the Nation of Islam. “For a while he talked a lot back then about what a great man Malcolm was,” Keith Kakugawa said. “But the rest of us were just interested in basketball and beer and sex, so he kind of gave up.”

Unable to reconcile his own growing resentment of “white folks” with his abiding affection for his white mother and grandparents, Barry stopped talking race altogether. “I learned,” he later explained of this period in his life, “not to care.”

Barry turned instead to alcohol—and to drugs. At sixteen, he began sneaking off to drink, smoke pot, or snort cocaine (“a little blow when you could afford it,” as Barry later put it) with his new friends. He financed his marijuana and cocaine purchases with money he earned working summers at the Baskin-Robbins ice-cream parlor on Honolulu’s South King Street.

Despite the fact that he played on Punahou’s basketball team, he was not welcome at the Senior Bench, the stone bench where the jocks, cheerleaders, and other “popular” kids hung out. Nor did he spend time with the theater people, the nerds, or student-leader types like classmate Steve Case, who went on to cofound America Online.

“Barry hung out with the stoners,” said another classmate, who remembered that Obama was among the school’s fifteen or so “druggies.” Barry’s new group of friends were known to both faculty and students as the “Bingham Benchers” because they gathered each day on benches outside Punahou’s Bingham Hall (named after one of the first Christian missionaries in Hawaii, Hiram Bingham).

“Junkie. Pothead. That’s where I was headed,” Barry would later say, admitting that in high school he made plenty of “bad decisions.” There were several Bingham Benchers who paid a heavy price for those decisions. One was severely injured in a car crash while driving under the influence, one was committed to a mental institution after taking LSD, another barely survived an overdose, and yet another was arrested after police pulled him over and found drugs in the trunk of his car.

Keith Kakugawa’s plight may have hit closest to home. A track star with Olympic potential, Kakugawa slid into a life of drugs after graduation from Punahou and would wind up spending years behind bars.

Barry, who had wisely resisted the persistent efforts of one of his Bingham Bench buddies to get him to try heroin, somehow managed to emerge relatively unscathed. “You’ve been very lucky,” his mother said after confronting him about his unsavory band of pals. “But your luck won’t hold out forever. Don’t waste your life.”

Barry remained unconvinced. On more than one occasion, he drove drunk—speeding down a highway with gin clouding my head,” he recalled. There was, he would also admit, more than one occasion when he found himself bloodied in a booze-fueled fight. Through it all, there were the furtive meetings with drug dealers in public parks and alleyways—encounters during which he risked losing everything if one of those dealers turned out to be what he, like his friends, derisively called a “narc.”

Conversely, Obama continued to do well on Punahou’s basketball team, earning the nickname “Barry O’Bomber” for his driving jump shot. Over the years, he worked his way up the ranks until, in his senior year, he made the varsity team. “It was rare for someone to make the team in the last year,” said varsity coach Chris McLachlin. “It’s a testament to Barry’s perseverance that he practiced and practiced and perfected his game until he was finally given a spot on the varsity team.” Unfortunately, the team was so top-heavy with talent that he often found himself sitting on the bench. At one point, he approached McLachlin as the appointed representative of several benched players. “He wanted to know what they could do to get in the game, how they could improve,” McLachlin said. “He was very respectful, much more mature than other kids his age.”

Still, that final year his grades slipped noticeably—though not enough to keep him from being accepted to several major universities in Hawaii and on the U.S. mainland. His final choice—Occidental College in Los Angeles—was unexpected, but Barry had his reasons: he had struck up a friendship with an attractive young coed from the affluent L.A. suburb of Brentwood who was vacationing with her family on Oahu, and he was hoping to hook up with her once he got to Los Angeles.

The yearbook entry for “Barry Obama,” which featured a photo of him in a short-cropped Afro, reflected those things he considered important at the time: basketball, family, and his fellow pot smokers. Included was a snapshot of “Barry O’Bomber” on the basketball court with the Pidgin English caption “We go play hoop,” a photo of his paper-strewn dorm room desk showing a beer bottle, turntable, telephone, and tennis trophy as well as Zig-Zag rolling paper and a book of matches under the title “Still Life”—and, most revealing, a nod to those who mattered most to Barry at the time. He thanked Toot, Gramps, “Ray” (Keith Kakugawa), and “Choom Gang” for “all the good times.” Choom is the act of smoking pakalolo, the Hawaiian word for marijuana. Barry signed off with “LATERS”—slang for “see you later.”

At his Punahou graduation ceremonies in June 1979, Barry, beaming in his navy blue blazer and blue and gold rep tie, bounded onstage to accept his diploma to loud cheers from his mother and grandparents. No one was more moved than Toot, who sobbed as she rushed up to Barry after the ceremony and draped an orchid lei around his neck.

Conspicuously absent that day was Barack senior. It had been eight years since they had seen each other, and four years since Barry, weary of trying to forge a bond with his father, had stopped corresponding with him.

It was around this time that Neil Abercrombie was vacationing in Kenya and decided to look up his old University of Hawaii buddy. By this point Barack senior, who had been sidelined in the Ministry of Tourism, was depressed and drinking even more heavily than usual.

Barack senior had always been a menace behind the wheel—drunk or sober. “He was a terrible driver,” said his friend Philip Ochieng. “He would get very excited and zoom like Mr. Toad.” Now, driving under the influence on a more or less daily basis, he caused a series of serious accidents. One of these resulted in the death of another motorist. Inexplicably, Barack was never charged in the case.

On another occasion, Obama himself was struck by a hit-and-run driver and left for dead. “They tried to kill me,” he told his old friend Pake Zane when Zane and his wife, Julie, visited him in Kenya in the 1970s. Obama went on to tell them he had been marked for death by forces within the Kenyan government because, despite the testimony he had given years earlier as a prosecution witness in the trial of nationalist leader Tom Mboya’s accused killer, he still knew who was really behind Mboya’s assassination.

“It all made him a very angry man,” Zane said. “He was limping badly, and he would go out every night and get really drunk and really abusive. He yelled at everyone in that booming voice. It was overwhelming—just way too heavy to take. Even his friends couldn’t stand to be around him anymore.”

“He was a very bitter man,” Abercrombie said of Barack when he last saw him in 1979. Obama felt he had “not been given the chance to fulfill his destiny and play a major role in the running of his country…. He was drinking too much. His frustration was apparent.”

The two men talked for hours. Most of that time, Abercrombie sat quietly while a well-lubricated Barack railed against his bosses in government. The only thing that was memorable was what Barack Obama Sr. did not say. Not once, Abercrombie marveled, did Barack Obama ask about his ex-wife or the son who was graduating from high school that year. “Even for a man as self-absorbed as Barack was,” Abercrombie said, “I was shocked. How sad for his son…”

She was a slight, graying Mexican woman of indeterminate age, and she smiled wanly at Barry and his friends as she trudged down the hallway toward their dorm room at eight o’clock. Monday morning. The students were sitting on the floor, propped up against the wall with beer cans in hand, oblivious to the woman’s presence. They had been partying for two days straight and were far too busy praising their own stamina as they passed around yet another joint.

Jackets and shoes were heaped against the front door, making it difficult for the cleaning lady to push her way into Barry’s dorm room. Once she did, she wished she hadn’t.

“My God!” she cried in Spanish as she surveyed the wreckage—a mind-spinning blur of bottles, cans, pizza cartons, half-eaten hamburgers, styrofoam cups, Chinese food take-out containers, discarded wrappers, cigarette butts, and overturned bowls of potato chips and popcorn. The kitchen sink brimmed with dirty dishes, and the towel-heaped bathrooms, where many a porcelain bus had been driven, were simply indescribable.

Wading through the debris, she held a rag up to her nose and mouth to protect against the overpowering stench—a rank blend of cigarette and marijuana smoke, incense, rotting food, urine, and vomit. Since she had worked for a decade as a maid assigned to clean up the dormitories at Occidental College, the Mexican woman had no illusions about what awaited her each Monday morning. But there were limits. She wept as she stepped back into the hallway to fetch her mop and pail. Standing there was another maid who, after surveying the scene, offered to help.

As the two women, neither of whom spoke English, gathered up their cleaning supplies for the assault on Barry’s room, they glanced down the hall. They shook their heads in disgust at the sight of Barry and his pals convulsed with laughter.

Just as he had identified with some of the most unsavory elements in his high school class, Barry wasted no time seeking out the hardest partyers once he arrived at Occidental. For the next two years, he would be unapologetic in his pursuit of getting high.

Toward that end, Obama cast himself during this period as, in the words of his classmate and friend Eric Moore, “a definite surfer-type.” Barry’s carefully chosen uniform of flip-flops, Hawaiian shirts, and board shorts—finished off with wraparound sunglasses, a puka shell necklace, and an ever-present cigarette—was designed to convey the sort of familiar, laid-back persona that Occidental’s overwhelmingly white student body would find least threatening.

Rounding out the image of a well-heeled surfer dude cum college man was Barry’s used red Fiat—a gift from his grandparents. It also helped that he played intramural sports, including tennis, flag football, and water polo. (Barry tried out for but did not quite make Occidental’s basketball team.) “He was an athletic guy,” recalled his freshman roommate Paul Carpenter. “He was gifted in that regard.” Barry was also “superbright,” Carpenter said. “He could get through the course work in a fraction of the time it took me.”

Classmate Margot Mifflin remembered him as “an unpretentious, down-to-earth, solidly middle-class guy who seemed somewhat more sophisticated than the average college student. He was slightly reserved and deliberate in a way that [she] sometimes thought betrayed an uncertainty.”

There were those, however, who saw Barry’s “reserved and deliberate” demeanor as a sign of something else. “He definitely had a cocky, sometimes arrogant way about him,” recalled another classmate, Robert McCrary. “He was not open to others.”

Eric Moore agreed with Margot Mifflin that Barry “was already very polished” by the time he arrived at Occidental. Being biracial, having grown up in Hawaii and lived for a time in Indonesia, Barry was “more worldly than the average kid in California,” Moore said. “But he still wanted to fit in.”

When they first met, Moore, an African American from the mostly white Colorado college community of Boulder, was taken aback by Obama’s first name. “What kind of name is Barry Obama for a brother?” he kidded.

“Actually, my name is Barack Obama,” he replied.

“That’s a very strong name,” Moore said. “Why don’t you use it?”

Barry sighed and shook his head. “It’s just too much of a hassle,” he said. “I don’t want to have to explain it every five seconds.”

“Well, screw that Barry shit,” Moore said. “From now on I’m calling you Barack.”

Obama was grateful that Moore called him Barack, although Paul Carpenter was among many students who never heard him called Barack at all. “It was always Barry,” Carpenter said. “And if someone asked him what he preferred, he didn’t hesitate to say Barry.” Anne Howells, who taught literary theory at Occidental in the winter of 1980, concurred: “I asked him if Barack was a Hawaiian name, and he told me it was African. But when I went around the room asking each student what he or she wanted to be called, the only African American in the class did not hesitate to answer. ‘Barry,’ he said.”

In truth, this part of sunny Southern California, with its tile-roofed, Spanish-style houses, palm-lined streets, and sweeping views of the Pacific, seemed comfortably familiar to Barry. Back at Punahou, he was never exposed to anything resembling a slum or a ghetto. At “Oxy,” he was just as shielded from the grim realities of life for blacks in communities like Watts, Compton, and South Central L.A.

Still, he did set out to build relationships with other African Americans on campus. Soon he was spending most of his time with a handful of other black undergraduates. Unlike the white students and faculty members who called him Barry, his African American friends addressed him as “Obama.” Wahid Hamid, a wealthy Pakistani who became one of Barack’s closest friends at Occidental, was “not surprised that he decided to embrace that identity because ‘Barry’ could be perceived as trying to run away from something and trying to fit in, rather than embracing his own identity, in many ways, kind of opening himself to who he is.”

Hamid was just one of the many foreign students that Barry went out of his way to befriend during his freshman year. His inner circle at that time included another well-to-do Pakistani named Mohammed Hasan Chandoo as well as Vinai Thummalapally, a native of Hyderabad, India. Thummalapally, who roomed with Barry and Paul Carpenter that first year at Oxy and was six years older than Barry, did a three-mile run with him every morning before classes. As they ran, Thummalapally invariably shared his dreams of opening a successful business back home in India. Barry made it clear that he had no interest in the private sector. “I want to get into public service,” he told Thummalapally, pausing after each run to reward himself with another cigarette. “I want to write and I want to help people who are disadvantaged.”

Obama quickly impressed his professors with his newfound social conscience. “He hung out with the other young men and women who were most serious about issues of social justice,” said Roger Boesche, one of Barry’s political science professors.

Boesche was also impressed with Barry’s fearlessness when it came to questioning his teachers—a self-confidence that bordered on cockiness. The professor was having lunch at a local restaurant called The Cooler when he looked up to see Barry standing by his table. “I really think I deserved a better grade than the one you gave me,” he told Boesche point-blank.

“You are really smart, Barry,” Boesche replied. “But I’m afraid you just aren’t working hard enough.”

“I disagree,” Barry pressed on. “You’re holding me up to a higher standard than everybody else in class and that’s unfair. I’m being graded on a different curve than everybody else and I’d like to know why.”

Clearly taken aback, Boesche squirmed in his seat for a moment. “You are capable of so much better, but no, Barry, I gave you the grade you deserved.”

Barry shook his head and walked off, never saying anything to his professor that might be construed as rude or inappropriate. He told Moore, Hamid, and his other friends, however, that he was “really pissed off” about his grade. “If he thought he was being treated unfairly,” said an Occidental classmate, “he just wouldn’t let go of it. He was a man obsessed. But he never really became outwardly agitated, either.”

However “pissed off” he may have been, Barry still seemed congenitally incapable of losing his temper. Even when everyone else in the room seemed to be shouting to make a point, Vinai Thummalapally said, Obama “wouldn’t get worked up. Other people would be standing, waving their arms around, and Barack wouldn’t even change his position on the sofa—and still he could make his point. Everybody would just suddenly shut up and listen when he talked.” According to Thummalapally, his roommate never swore: “Not once can I ever remember him using a cussword. Imagine it: an eighteen-year-old who never used profanity.” By the same token, Thummalapally insisted, Barry “was not a nerd. He was not a bore. People were drawn to him.”

Even though as a biracial man he could still easily move from one social circle to another (“He had the benefit of knowing both cultures firsthand,” Eric Moore observed), Barry felt at his most comfortable in the company of other African American students. They understood completely, for example, when Barry said he suspected his professors were holding him to a different standard because of his color. In turn, he nodded sympathetically whenever the others griped about the slights and insults they endured on any given day.

It was no small irony that these conversations were the exception rather than the rule. Obama quickly discovered that he and his black friends banded together precisely so they wouldn’t have to think about race all the time. The question of race always hung in the air whenever they were in the company of whites. “To constantly think about race,” he said, “it’s so damned exhausting.” Most of the time, Barry later said, he and his friends talked about the same things their white counterparts talked about: “Surviving classes. Finding a well-paying gig after graduation. Trying to get laid.”

As “progressive” as he and his friends claimed to be, they showed no remorse when the Mexican maids came to clean up their mess after yet another nonstop weekend of partying. That unfortunate disregard for others continued into Barry’s sophomore year, even as he and other members of Occidental’s Black Student Alliance planned a demonstration demanding that Occidental divest itself of its interests in apartheid South Africa.

The rally, staged opposite the president’s office, marked Barry’s public speaking debut. Haltingly at first, he managed to seize the attention of the lunchtime crowd with a speech that scarcely lasted one minute. For the first time he realized that the timbre of his voice was not unlike his father’s. “He had this booming voice,” Eric Moore said. “It helped that people knew who he was because he was so popular on campus, but he also had this commanding presence.”

When that lunchtime crowd cheered and applauded his speech (albeit fleetingly), no one was more surprised than Barry. It was heady stuff for a nineteen-year-old still in the throes of an identity crisis. “I knew I had them,” he later wrote. “The connection had been made.”

No romantic connection, however, had been made with anyone. His infamous parties notwithstanding, Barry did not come close to forging a serious relationship with any female during his first two years at college. According to one Oxy colleague, “Barry dated girls, but there was no one who came close to being his girlfriend or anything like that. Barry wasn’t at all shy, and women liked him, but he seemed too focused on himself to really get involved with someone romantically.”

After two years at Occidental, Barry was floundering. He had no idea of what he wanted to do with his life, or where he wanted to settle down. Neither Hawaii nor California—at least the affluent parts of California he had been exposed to—offered him the sort of life experience he longed for. Barry wanted to live in a city—the sort of multinational, multicultural, polyglot urban environment that would stimulate him intellectually and ground him at the same time.

As soon as he learned that Occidental had begun a transfer program with New York’s Columbia University, he signed up. Barry’s friend Eric Moore pleaded with him to remain at Oxy, but Barry argued that he needed to make a clean break from his past—and that meant leaving his friends behind. “I think there was a lot of stuff going on in me,” Obama later said. “I was starting to work it through. It’s hard to remake yourself around people who have known you for a long time.”

Before he made the trip to New York, Barry made another voyage that would, he later said, shape his view of the world. Traveling to Pakistan with his friend Wahid Hamid, Barry spent three weeks touring the countryside around Karachi. He had already witnessed grinding Southeast Asian poverty during his childhood years in Indonesia, but he was still shocked by what he saw in Pakistan—particularly the power that wealthy landowners had over the lives of the peasants who worked their fields. As the landowners drove by in their Land Rovers and Mercedeses, the workers—men, women, and children alike—would literally bow down until they passed. “It was straight out of the Middle Ages,” Barry would later recall. “The serfs bowing to their lord and master.”

Barry’s Pakistan connection would continue even after he arrived in New York. Unable to get into the cold-water flat he had arranged to rent on 109th Street in Spanish Harlem—he would spend his first night in Manhattan huddled with his belongings in an alley—Barry called up the only person he knew in the city for help.

Barry had met Pakistani Sohale “Hal” Siddiqi a year earlier, when Siddiqi was visiting his friends Hamid and Chandoo in Los Angeles. Now Siddiqi was making ends meet working as a salesman at a boutique during the daytime and as a waiter at night.

“He arrived disheveled and without a place to stay,” Siddiqi said. Instantly, Siddiqi recognized something of himself in the homeless African American. “We were both very lost,” he said. “We were both alienated.”

Siddiqi took Obama in, helped him move into the Spanish Harlem apartment a few days later, and then helped him move out when it turned out the apartment had no heat. Together, they found a sixth-floor walk-up on East Ninety-fourth Street between First and Second Avenues—but there was a catch. In order to secure the lease, they would both have to show they were financially stable. Obama refused to lie on the application—he put down that he was a Columbia University student with no income—leaving it to Siddiqi to falsely claim that he earned a substantial salary working for a high-end catering firm.

Barry, despite his refusal to participate, was fully aware of the subterfuge. “We didn’t have a chance in hell of getting this apartment unless we fabricated the lease,” Siddiqi said. “So I was the one who had to do it.”

A Park Avenue penthouse it wasn’t. Drugs were sold on the stoops of neighboring buildings in broad daylight, and gunshots punctuated the night. The apartment itself was a dark, cramped, postage-stamp-sized one-bedroom with leaky pipes, noisy radiators, and paint peeling from the ceiling. There was no money for furniture. The two men slept on mattresses on the floor; the living room couch and chairs were picked up off the street. There were no tables at all. They and anyone who happened to visit them ate from paper plates balanced on their laps.

This spartan existence was all in keeping with Barry’s plan. He had actually begun reinventing himself the minute he arrived in Manhattan. Relocating to New York, he said later, “was a really significant break. It’s when I left a lot of stuff behind.” His name, for instance. From this point on, if anyone asked how he wished to be addressed, the answer was always the same: “Call me Barack.”

This change was not, he later insisted, “some assertion of my African roots—not a racial assertion. It was much more of an assertion that I was coming of age. An assertion of being comfortable with the fact that I was different and that I didn’t need to try to fit in in a certain way.”

Most important, Barack now eschewed the alcohol and drugs that had threatened to derail his life—“the final, fatal role,” he wrote, “of the young would-be black man.” There would be no more weekend bacchanals, no more Mexican maids throwing up their hands in despair.

For the next two years, Barack embarked on a lifestyle that bordered on the monastic. He fasted on Sundays, and for the rest of the week adhered steadfastly to Dick Gregory’s vegetarian diet. Gone were the blazers and neatly pressed khakis of his prep school days, now replaced by a navy surplus peacoat worn with Levi’s and a turtleneck picked up at the Salvation Army for five dollars. “I think self-deprivation was his shtick,” Siddiqi recalled, “denying himself pleasure, good food and all of that.”

Siddiqi made up for his roommate’s self-imposed asceticism. He drank, smoked pot, and did lines of cocaine with friends in their apartment. He continually offered Barack drugs, and every time, according to Siddiqi, he refused.

For the most part Barack was, by his own admission, leading “a pretty grim and humorless” life. His routine consisted of getting up and running three miles, attending classes at Columbia, then coming home to spend hours reading. Any free time was spent aimlessly wandering the streets. His exploration of the city—from the stately limestone mansions and brick town houses of the Upper East Side to Chinatown and the Financial District to the slums of Harlem and the South Bronx—served only to underscore the inequities of American life and fuel his growing despair. He now began to keep detailed journals, which he filled with his observations and his poetry. “Strange,” he wrote after yet another cabdriver drove past him to pick up someone else. “Don’t they see my white relatives?”

When Barack did bother to venture outside the little world he had created for himself, it was to lecture Siddiqi and anyone else he came in contact with about the plight of the world’s poor and the failure of Western societies to do anything about it. Predictably, Siddiqi, whose own goal in life at the time “was to make a lot of money to buy stuff,” grew tired of Barack’s sermonizing.

“Who do you think you are, Barack? A saint?” Siddiqi asked. “Why are you so serious all the time?” Then he delivered the coup de grâce. “Barack,” Siddiqi said with a sigh, “you are becoming a bore.”

Perhaps. But Barack wasn’t, Siddiqi hastened to add, “entirely a hermit” during this period. He would invite friends over to the apartment and relax on the floor listening to Van Morrison, Ella Fitzgerald, Bob Dylan, Stevie Wonder, and his new favorite, Billie Holiday. Nor had he given up his principal vice: smoking. “He’d be sprawled out on the couch,” Siddiqi recalled, “listening to his music and blowing smoke rings in the air.”

There was something else Barack was not entirely willing to give up. He would join friends for a night out every now and then, and even went cruising some of the East Side’s more notorious singles bars with Siddiqi. “We were always competing,” recalled Siddiqi, who claimed that several of his female friends told him they considered Barack “a hunk.” Although Barack still abstained from alcohol, he and his roommate would, said Siddiqi, “go to bars and try hitting on the girls. He had a lot more success. I wouldn’t outcompete him in picking up girls, that’s for sure.”

Years later, Barack would write that during this time he had a yearlong affair with a wealthy young white woman who had “dark hair, specks of green in her eyes. Her voice sounded like a wind chime.” The romance ended, he claimed, after he visited the young lady’s stately country home, looked around at the photographs of Presidents, Senators, and industrialists that hung on the walls, and decided he could never be a part of her world. The actual breakup, as Barack would describe it years later in his book Dreams from My Father, supposedly took place in the street after he had taken her to see a new play by an angry young black playwright. “She couldn’t be black, she said,” Barack wrote. “She would if she could, but she couldn’t. She could only be herself, and wasn’t that enough?”

Barack then observed that even if she’d been black it wouldn’t have worked out. “I mean,” he wrote, “there are several black ladies out there who’ve broken my heart just as good.”

No one, including his roommate and closest friend at the time, Siddiqi, knew of this mysterious lover’s existence—or could recall Obama’s heart ever being broken by a woman regardless of her race. Not that Barack had taken a vow of celibacy—far from it. “One-night stands,” a barhopping friend remembers. “That seemed to be pretty much it.”

Neither his mother, Ann, nor his sister Maya encountered any of Barack’s women friends when they visited him that first summer in New York. Thanks in part to Ann’s enduring fascination with all things Third World, they hit it off instantly with Barack’s free-spirited Pakistani roommate.

The same could not be said for Siddiqi’s mother when it was her turn to visit from Pakistan. Having never known a black person, she treated Barack with contempt. “My mother was terribly rude to him,” Siddiqi admitted. Barack reacted by being “so polite and kind to her.”

Accordingly, Siddiqi was there for Barack in November 1982 when the call came from Africa that would change Obama’s life forever. As he so often did, Barack senior had been out carousing with friends in the honky-tonk town of Kaloleni, this time celebrating rumors that he was soon to be given a big promotion. Having already lost both his legs in another one of his accidents and now walking on crude prosthetic limbs, he was driving himself home but never made it. Veering off the road, he crashed into the six-foot-high stump of a giant gum tree and died instantly. He was forty-six.

Barack was frying eggs in the tiny kitchen of his apartment when his Aunt Jane, a woman he had never met, phoned with the news. “Listen, Barry, your father is dead,” Aunt Jane said. “He is killed in a car accident. Hello? Can you hear me?”

Barack scarcely knew how to react. His father remained a myth to him—“both more and less than a man”—and because of that he would later say he felt “no pain, only the vague sense of an opportunity lost.” When he called his mother to tell her Barack senior had been killed, she cried out in anguish.

Barack senior was buried in the village where he was raised, Nyang’oma Kogelo. Attending the funeral were several top government ministers, as well as more than forty members of Obama’s extended family. His American son was not among them.

Siddiqi, meanwhile, continued his wanton ways. “I was partying all the time,” he said. “I was disturbing his studies.” Barack needed to be free from unnecessary distractions; he had settled on a major—political science, specializing in international relations—and was now heading down the home stretch toward his degree.

Frustrated that Barack would not loosen up, Siddiqi accused him of kowtowing to his white professors. “Look at you,” Siddiqi sniped. “You’re nothing but an Uncle Tom.” He would deliver this particular zinger on several occasions, and each time his target reacted the same way—with benign indifference.

Indeed, Barack’s fabled unflappability was already very much in evidence. One morning he and Siddiqi were walking Siddiqi’s pug, Charlie, on Broadway when a hulking street person approached them and began stomping on the pavement next to Charlie’s head. Siddiqi angrily confronted the homeless man, and as the two men squared off, Barack suddenly stepped between them. “Hey, hey, hey!” Barack said, shoving his face right into the stranger’s. The man looked into Obama’s eyes and backed down. “It was an incredible scene,” Siddiqi said. “Barack could be pretty fearless. He always stood up for what he thought was right.”

Still, Barack could not put up with his friend’s undisciplined behavior indefinitely. By the start of his senior year, he had moved out of the East Ninety-fourth Street apartment and in with a new roommate. “Barack was really patient,” Siddiqi later said. “I’m surprised he suffered me as long as he did.”

Barack could not always count on friends. But he knew that the people he considered at the time to be his only real family—his mother, Maya, Gramps, and Toot—would be there for him when, in June of 1983, he graduated from Columbia University with a degree in political science.

During his waning days at Columbia, he had nurtured dreams of becoming a community organizer—although he was not precisely sure what a community organizer actually was or what the job entailed. “I’ll organize black folks,” he told himself. “At the grass roots. For change.”

For Barack, organizing would be no less than “an act of redemption”—a chance to earn, through shared sacrifice, “full membership” in the black community. He thought back to the “sit-ins, the marches, the jailhouse songs” of the civil rights era and imagined himself there—only this time fighting for the social, economic, and political rights of a new generation.

In the spring of 1983, Barack fired off scores of letters to black politicians, civil rights organizations, and neighborhood, tenants’ rights, and community action groups around the country. He was a young black progressive-minded Ivy League graduate, he told them, and he was eager to do whatever he could for the cause.

He received not a single reply. Undaunted, he decided instead to take a job that would pay the bills while he waited for some discerning activist group to take him up on his offer. He promptly landed a job as a research associate at Business International Corporation, a small publisher of newsletters tracking the activities of corporations operating overseas (a few years later the firm would be acquired by Britain’s The Economist Group).

Barack would later describe Business International as a leading consulting house where, in order to fit in, he wore a power suit and carried a briefcase. Not so, according to those who worked with him. “It was a bit like a sweatshop,” said one of his BI coworkers, Dan Armstrong. “I’m sure we all wished that we were high-priced consultants to multinational corporations. But we also enjoyed coming in at ten, wearing jeans to work, flirting with our coworkers, partying when we stayed late, and bonding over the low salaries and heavy workload…. Barack never wore a tie, much less a suit. Nobody did.”

Like others who worked alongside Barack then, Armstrong found him to be “aloof—reserved and distant with his coworkers.” Another BI coworker, Bill Millar, went a step further. “I worked next to Barack nearly every day he was at Business International,” said Millar, who had a degree in finance and Wall Street experience. “I found him arrogant and condescending. He just sort of rolled his eyes if you tried to explain something to him. I’ll never forget it.”

Nevertheless, within a few months Barack was promoted to financial writer, contributing articles to one of the firm’s key newsletters, Business International Money Report. He was also put in charge of editing the company’s global reference service, Financing Foreign Operations, and given a substantial raise. (He was not assigned his own secretary, however, as Barack would later claim. “The idea that Barack had a secretary is laughable,” Armstrong said. “Only the company president had a secretary.”)

BI’s informal atmosphere aside—a former top executive of the firm called it “high school with ashtrays”—the fact remained that twenty-two-year-old Barack was the firm’s only black executive. All the other African Americans he encountered at Business International were secretaries, receptionists, mail-room clerks, and security guards—the men and women who were indispensable to the entire operation but seldom given the opportunity to rise above their station.

Barack felt more than a little self-conscious about his management position, but he could not afford the luxury of feeling guilty. The women in the secretarial pool and the other black staffers were all rooting for him to succeed. Whether he liked the work or not, he was, for the time being at least, determined not to disappoint them.

Barack kept toiling away at his Wang computer terminal until he received yet another wake-up call from Africa. This time it was his half sister Auma, Barack senior’s daughter by his first wife, choking back tears as she delivered more bad news. Their half brother David, Barack senior’s son by his third wife, Ruth Nidesand, had been killed in a motorcycle accident.

Barack had never met David, but news of his brother’s sudden and shocking death rekindled his desire for “redemption” through community organizing. After a little more than a year laying the foundation for a climb up the corporate ladder, Barack quit his job at Business International.

For the next three months, he worked as a community organizer for Ralph Nader’s New York Public Interest Research Group out of the Harlem campus of the City College of New York. He quickly discovered that students—even minority students—were less interested in protesting against the Establishment than they were in joining it. “A good job in corporate America, a fat paycheck, and nice things—that’s what they all want,” he told a fellow activist. “Can you blame them?”

Of course, Barack had willingly given up all those things, and by the late summer of 1985 he was broke. It was then, while perusing a publication called Community Jobs, that he spotted a want ad offering a position as a community organizer trainee in Chicago. Barack answered the ad immediately, sending along his résumé. Within a week he found himself sitting in a Lexington Avenue coffee shop on the Upper East Side with the man who had placed the ad, Jerry Kellman.

The ad had been an act of desperation for Kellman, a stocky, not quite middle-aged man who looked like he had spent the night on tumble dry. Beginning with the campus antiwar movement in the 1960s, Kellman had spearheaded one social protest after another, and in the process built a reputation as one of the Midwest’s most effective community organizers.

Now Kellman faced his most daunting challenge yet. Chicago was hemorrhaging manufacturing jobs, driving more of the city’s urban working class into unemployment and poverty. Unions no longer had the clout they once had, so now Kellman was trying to convince Chicago’s powerful black churches to stand up to the corporations on the workers’ behalf.

Trouble was, Kellman and his colleagues were white and, for the most part, Jewish. Black pastors on Chicago’s South Side were suspicious of their motives. “Here we were trying to organize in Chicago’s African American community,” Kellman said, “and we didn’t have any African Americans on our staff. It did not look good, obviously.”

Before their meeting in the coffee shop, Kellman had interviewed Barack on the phone for nearly two hours. “He was clearly very bright,” Kellman remembered. “But there are a lot of very bright young people out there. But he was also mature, confident, articulate.”

Kellman was particularly intrigued by Barack’s upbringing. “His father had left the family, his mother wasn’t around a lot, he moved from one culture to another—and it all left him feeling like an outsider,” Kellman said. “Outsiders can do one of two things: they can try to join the mainstream or they can identify with the other outsiders. Barack identified with the other outsiders. That was important.”

Satisfied that Barack was the right person for the job, Kellman came right to the point during their face-to-face meeting. “I can’t break through,” Kellman admitted to Barack. “So that’s why I need someone like you.”

Barack, Kellman later said, “was looking for the civil rights movement, but it was over. Organizing was the closest thing he could find to it.” Barack was also looking to avoid the mistakes made by his father. “My father was a brilliant man, an intellectual,” Barack told Kellman. “He returned to Kenya bursting with ambition to do things for his native country, but he didn’t know how to turn his ideals into reality. So he ended up just another bitter, broken bureaucrat with a drinking problem. I am not,” Barack vowed, “going to end up like my father.”

It remained to be seen whether Barack was different from so many other young college graduates who had come to Kellman seeking to make a difference. “The pattern was that people Barack’s age who had done well in school, who were Phi Beta Kappa and Rhodes Scholars, would volunteer in the inner city and quickly unravel. They’d burn out in a matter of months. I hoped that his motivation was strong enough so that wouldn’t happen to him.”

The pay Kellman was offering—ten thousand dollars for the first year—amounted to less than a quarter of what Barack had been earning as a junior financial writer. No matter. It was the opportunity he had been waiting for. By working shoulder to shoulder with his fellow African Americans in this most American of cities, he would finally lay claim to that elusive sense of self that he had been so desperately seeking.

Barack would also find something else in Chicago—something that had proved equally precious, equally elusive. He would find the love of his life.

I always tease her she had sort of the South Side version of Ozzie and Harriet. Or Leave It to Beaver.


I was just a typical South Side little black girl.


We knew you would do this 15 years ago when we could never make you shut up.

—Michelle’s parents, in their 1988 Harvard Law School yearbook ad congratulating her

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