Prologue

That little Kennedy . . . he thought he was a god.”

The words were sharp and wrong, like a curse shattering the civility of the soft evening air. They seemed particularly strange coming from the genial older gentleman strolling by Willie Morris’s side. In fact, they were the only strident remarks that Morris had heard him utter in the past few days, as the graying spymaster regaled his young visitor with a lifetime of covert adventures.

And then the storm passed. The man was himself again—the chatty and amiable Allen Welsh Dulles, a man whose conviviality masked a world of dark secrets. The two men continued their walk on that Indian summer evening in 1965, ambling along the rust-colored brick sidewalks as the lampposts began casting their yellow light on picturesque Georgetown—home of Washington hostesses, martini-loving spies, influential newspapermen, and the assorted insiders who fed off the fizz and sizzle of the nation’s capital. Turning the corner from the unassuming, two-story brick mansion on Q Street that Dulles rented, they now found themselves on R Street, straddling the vast greenery of the Dumbarton Oaks estate.

Dulles, the creator of America’s sprawling intelligence empire, had summoned Morris—a rising young editor at Harper’s magazine—to help him set the record straight on the most cutting humiliation of his career. He wanted to write his side of the story about the Bay of Pigs. The words alone still brought a spasm of pain and rage to Dulles’s face. It was just a spit of sand and scrubby palms along Cuba’s southern coast. But it was the scene, in April 1961, of the biggest disaster in the CIA’s history—a motley invasion that fell ignominiously short of toppling Cuba’s dangerously charismatic leader, Fidel Castro. The failed invasion, Dulles said, was “the blackest day of my life.”

In public, the newly minted president, John F. Kennedy, took responsibility for the fiasco and made gracious remarks about Dulles as he prepared to usher the aging spy out the door, after a half century of public service encompassing eight different presidencies. But in private, a vicious war had begun between the Kennedy and Dulles camps, with the two men and their advocates working the press and arguing not just the botched mechanics of the invasion, but the past and future of U.S. foreign policy.

The Bay of Pigs came after a long string of Dulles victories. Given free rein by President Eisenhower to police the world against any insurgent threat to U.S. dominion, Dulles’s CIA overthrew nationalist governments in Africa, Latin America, and the Middle East, and even targeted troublesome leaders in allied European countries. Dulles called himself “the secretary of state for unfriendly countries”—which had an ominous ring when one took note of what happened to unfriendly countries in the American Century. Meanwhile, his brother John Foster Dulles—Eisenhower’s official secretary of state—brought the gloom of a doomsday-obsessed vicar to his job, with his frequent sermons on Communist perfidy and his constant threats of nuclear annihilation. John Foster Dulles needed Communism the way that Puritans needed sin, the infamous British double agent Kim Philby once remarked. With his long, dour face topped by his ever-present banker’s homburg, the elder Dulles always seemed to be on the brink of foreclosing on all human hope and happiness.

By 1959, John Foster Dulles was rapidly succumbing to stomach cancer. It was as if the bile building up inside him all those years over the fallen state of the world had finally devoured him. And by then Eisenhower himself was heart-troubled and weary of his job. Only Allen Dulles still stood firmly at the top, past retirement age at sixty-six, but still determined that the ancient regime must continue.

When President Kennedy began his vigorous new reign in 1961, he decided to keep Allen Dulles as CIA chief, despite the obvious differences in their world outlooks. With his brush mustache, wire-rim glasses, tweed suits, and beloved pipe, Dulles could have been one of the elderly dons that young Jack Kennedy had studied under at Harvard. As a young senator, JFK had broken from the Eisenhower-Dulles regime over the older men’s nuclear brinksmanship—a game that Kennedy felt courted the abyss. Kennedy had also signaled an eagerness to dramatically change America’s hostile relationship to the developing world, expressing a sympathy for the national liberation movements in Algeria, the Congo, Vietnam, and elsewhere that he saw as historically inevitable. While President Eisenhower viewed the onrush of anticolonial independence in the Third World as a “destructive hurricane,” Kennedy recognized it as the future.

Though their visions for how the United States should navigate the globe were profoundly far apart, Kennedy was loath to completely overturn the old ruling order that had been presided over by a popular World War II hero. Keeping Eisenhower men like Dulles and other Republican pillars of power like Wall Street banker and statesman C. Douglas Dillon, whom JFK named his Treasury secretary, was the new president’s way of assuring the nation that he would be leading an orderly transition to the New Frontier. But Kennedy soon realized that when it came to men like Dulles, his political calculation was a grave mistake.

Allen Dulles was one of the wiliest masters of secret power ever produced by America. And his most ambitious clandestine efforts were directed not against hostile governments but against his own. While serving in multiple presidential administrations, he learned to manipulate them and sometimes subvert them.

In the view of the Dulles brothers, democracy was an enterprise that had to be carefully managed by the right men, not simply left to elected officials as a public trust. From their earliest days on Wall Street—where they ran Sullivan and Cromwell, the most powerful corporate law firm in the nation—their overriding commitment was always to the circle of accomplished, privileged men whom they saw as the true seat of power in America. Although Foster and Allen did not come from the same wealthy families who dominated this elite club, the brothers’ shrewd talents, missionary drive, and powerful connections firmly established them as top executives in this rarefied world.

As younger men, the Dulles brothers were obsessive chess players. When they faced each other over a chessboard, everything else faded away. Even during his whirlwind courtship of Martha Clover Todd, a free-spirited beauty from a prominent family to whom he proposed after a three-day siege, Allen could not be distracted from a lengthy joust with his brother. The Dulleses would bring the same strategic fixation to the game of global politics.

John Foster Dulles would rise to become the chief counsel for American power, a man destined to quietly confer with kings, prime ministers, and despots. He liked to think of himself as chess master of the free world. His younger brother would become something more powerful still—the knight-errant who enforced America’s imperial will. As director of the CIA, Allen Dulles liked to think he was the hand of the king, but if so, he was the left hand—the sinister hand. He was master of the dark deeds that empires require.

The Dulles brothers were not intimidated by mere presidents. When President Franklin Roosevelt pushed through New Deal legislation to restrain the rampant greed and speculation that had brought the country to economic ruin, John Foster Dulles simply gathered his corporate clients in his Wall Street law office and urged them to defy the president. “Do not comply,” he told them. “Resist the law with all your might, and soon everything will be all right.”

Later, when Allen Dulles served as the United States’ top spy in continental Europe during World War II, he blatantly ignored Roosevelt’s policy of unconditional surrender and pursued his own strategy of secret negotiations with Nazi leaders. The staggering sacrifice made by the Russian people in the war against Hitler meant little to Dulles. He was more interested in salvaging the Third Reich’s security apparatus and turning it against the Soviet Union—which he had always regarded as America’s true enemy. After the war, Dulles helped a number of notorious war criminals escape via the “Nazi ratlines” that ran from Germany, down through Italy, to sanctuary in Latin America, the Middle East, and even the United States.

Allen Dulles outmaneuvered and outlived Franklin Roosevelt. He stunned Harry Truman, who signed the CIA into existence in 1947, by turning the agency into a Cold War colossus far more powerful and lethal than anything Truman had imagined. Eisenhower gave Dulles immense license to fight the administration’s shadow war against Communism, but at the end of his presidency, Ike concluded that Dulles had robbed him of his place in history as a peacemaker and left him nothing but “a legacy of ashes.” Dulles undermined or betrayed every president he served in high office.

Dulles would serve John F. Kennedy for less than a year, but their briefly entwined stories would have monumental consequences. Clearly outmatched in the beginning by the savvy spymaster, who beguiled Kennedy into the Bay of Pigs disaster, JFK proved a quick learner in the Washington power games. He became the first and only president who dared to strip Dulles of his formidable authority. But Dulles’s forced retirement did not last long after Kennedy jettisoned him from the CIA in November 1961. Instead of easing into his twilight years, Dulles continued to operate as if he were still America’s intelligence chief, targeting the president who had ended his illustrious career. The underground struggle between these two icons of power is nothing less than the story of the battle for American democracy.

Walking through Georgetown on that warm September evening, Willie Morris was perplexed to hear Dulles erupt with such scorn at the mere mention of Kennedy’s name. But there was a reason that—nearly two years after JFK’s bloody end—Kennedy’s hold on the public’s imagination still disturbed Dulles. He knew who the real “god” was—and it was not Jack Kennedy.

After their stroll, the two men returned to Dulles’s home for drinks and dinner, and then more work on his article, which was to be titled “My Answer to the Bay of Pigs.” There was a sad stillness to the Dulles residence: Clover was away, at the family’s summer retreat on Lake Ontario; their son, Allen Jr., a brilliant young man who had suffered a grievous head wound in the Korean War, was in and out of sanitariums; their grown daughters Joan and Toddie had their own worries and misfortunes. There was nothing to distract Morris and Dulles besides the fleeting presence of one or two servants. Morris proved a good companion, a son of Mississippi who knew how to keep up his end when the bourbon and conversation began flowing. And he was the most touted magazine editor of his generation, on his way to becoming the youngest editor of the venerable Harper’s at age thirty-two. Under his leadership in the late ’60s, Harper’s would glow with the vibrant writing of Norman Mailer, William Styron, and David Halberstam.

But, in the end, even with Morris’s expert hand, Dulles could not wrestle his manuscript into shape, and the old spook withdrew it from publication. By the time Dulles finally gave up, after months of toil, the article had gone through multiple drafts, adding up to several hundred coffee-stained pages. The drafts, now stuffed into boxes at a Princeton library where the Dulles papers are housed, are a window into Allen Dulles’s tortured relationship with the young president. In finally abandoning the massive project, which one historian later called “The ‘Confessions’ of Allen Dulles,” the old spymaster seemed to conclude that he was saying both too much and too little about what he had been through with Kennedy.

By writing the article, Dulles had set out to rebut charges made by JFK loyalists Theodore Sorensen and Arthur Schlesinger Jr. that Kennedy had been tricked by his intelligence advisers into the disastrous Cuban adventure. But instead, the spymaster’s scribblings—in between angry eruptions at Kennedy and his White House circle of “doubting Thomases” and “Castro admirers”—revealed the myriad ways that Dulles’s CIA had indeed contrived to lure the young president into the Cuban sand trap.

When the Bay of Pigs operation was under way and “the chips were down,” Dulles wrote, he was confident that JFK would be compelled to do the right thing and send in the awesome power of the U.S. military to rescue the invasion. That’s the way the CIA game was played: there was a certain amount of hoodwinking and massaging of White House anxieties, and then the president fell in line. But this time, the president, despite his youth and the collective browbeating of his gray-haired national security ministers, stood his ground. Kennedy said no to expanding an operation that he had felt all along was sordid. And the long reign of Allen Dulles came crashing down.

At least, that’s the way Dulles’s story is told in biographies and CIA histories. The truth is that Dulles’s reign went on, deeply cloaked, toward an even more catastrophic conclusion.

In the first days and weeks after his ouster, Dulles’s world caved in. Suddenly unmoored from the daily routines of power he had known ever since he was a budding young spy in the service of Woodrow Wilson, Dulles seemed “a very tragic man,” in the words of one CIA colleague. He shuffled around his Georgetown home, with his gout-ridden feet softly coffined in bedroom slippers. But Dulles’s “tragic” period did not last long. He soon began meeting with a surprising range of CIA officers—men from the top rungs of the agency, as well as agents from the field. They paraded in and out of the brick manor on Q Street, huddling with him in his book-lined study and on sunny days quietly chatting on his walled-in terrace. His day calendar was filled with yet more meetings at his favorite Washington retreats, the Alibi Club and the Metropolitan Club, where he dined with the same generals and national security wise men with whom he had done business at the CIA. It was, in fact, as if he had never left the spy agency.

Dulles would turn his Georgetown home into the center of an anti-Kennedy government in exile. As time went by, the Dulles circle became ever more disenchanted with JFK’s foreign policy, which they considered appeasement of the Communist enemy. Dulles grew bolder in his opposition. He met with a controversial Cuban exile leader named Paulino Sierra Martinez, a former henchman for the deposed dictator Fulgencio Batista. Sierra, whose anti-Castro activities were underwritten by the Mafia and U.S. corporations with a stake in Cuba, later fell under Secret Service suspicion in a conspiracy against President Kennedy. The topic of Sierra’s meeting with Dulles in April 1963 remains a mystery.

By October 1963, Dulles felt confident enough to speak out against Kennedy’s foreign policy in public, ignoring the Washington etiquette that deemed it bad form to criticize a president whom you recently had served. Dulles declared that the Kennedy presidency suffered from a “yearning to be loved by the rest of the world.” This “weakness” was not the mark of a global power, insisted Dulles. “I should much prefer to have people respect us than to try to make them love us.”

In the weeks leading up to the assassination of President Kennedy on November 22, 1963, the flurry of meetings at Dulles’s home intensified. Among the CIA men coming in and out of Q Street were several who later came under investigation by the House Select Committee on Assassinations and other probes for their possible connection to the president’s murder. And on the weekend of the assassination, Dulles hunkered down for unexplained reasons at a secret CIA facility in northern Virginia known as “the Farm,” despite the fact that he had been removed from the agency two years earlier. Such was the odd swirl of activity around the “retired” Dulles.

After Kennedy’s assassination, Dulles would again push himself into the Washington spotlight, lobbying President Lyndon Johnson to appoint him to the Warren Commission. Dulles was so actively involved in the official investigation of Kennedy’s murder that one observer remarked it should have been called the Dulles Commission. He worked carefully behind the scenes with his former CIA colleagues to steer the inquiry away from the agency itself and toward “lone gunman” Lee Harvey Oswald.

How did a bitter political enemy of President Kennedy wind up playing a lead role in the official investigation into his death? It was just one more mystery in a lifetime full of enigmatic twists and turns. Just as puzzling is why the American press never troubled itself to explore this intriguing question.

Over half a century later, many questions about JFK’s violent end remain “unspeakable,” in the words of Kennedy biographer James W. Douglass—at least in the carefully controlled arena of media discourse. It is even more unthinkable in these circles to explore the suspicion that Allen Dulles himself—a towering pillar of the U.S. establishment—might have played a role in the epic crime against U.S. democracy that took place in Dallas. But this is just one of many taboo and top secret areas of Dulles’s life explored in this book.

The Allen Dulles story continues to haunt the country. Many of the practices that still provoke bouts of American soul-searching originated during Dulles’s formative rule at the CIA. Mind control experimentation, torture, political assassination, extraordinary rendition, massive surveillance of U.S. citizens and foreign allies—these were all widely used tools of the Dulles reign.

Dulles was capable of great personal cruelty, to his intimates as well as his enemies. Underneath his twinkly-eyed personality was an icy amorality. “Our faults did not often give us a sense of guilt,” remarked Eleanor Dulles, who followed her two brothers into the Washington arena. Allen was less troubled by guilt or self-doubt than any of his siblings. He liked to tell people—and it was almost a boast—that he was one of the few men in Washington who could send people to their deaths.

But Dulles was not a rash man; he was coldly calculating. As the chairman of cloak-and-dagger America, he would never initiate a high-stakes operation unless he felt he had the support of the principal members of his “board”—the Washington and Wall Street men of influence who quietly dominated the nation’s decision-making.

What follows is an espionage adventure that is far more action-packed and momentous than any spy tale with which readers are familiar. This is a history of secret power in America.

We often forget how fragile a creation democracy is—a delicate eggshell in the rough-and-tumble of history. Even in the cradle of democracy, ancient Athens, rule by the people could barely survive for a couple of centuries. And throughout its brief history, Athenian democracy was besieged from within by the forces of oligarchy and tyranny. There were plots led by generals to impose military rule. There were secret clubs of aristocrats who hired squads of assassins to kill popular leaders. Terror reigned during these convulsions, and civil society was too intimidated to bring the assassins to justice. Democracy, Thucydides tells us, was “cowed in mind.”

Our country’s cheerleaders are wedded to the notion of American exceptionalism. But when it comes to the machinations of power, we are all too similar to other societies and ones that have come before us. There is an implacable brutality to power that is familiar throughout the world and throughout history. And no matter where power rules, there is the same determination by those in high places to keep their activities hidden.

The Devil’s Chessboard seeks to shine a torch down the well of “deep politics,” as Peter Dale Scott—an important scholar of American power—has termed this underworld of unaccountable authority. Until we have a full reckoning of the Dulles era and its high crimes, the country cannot find its way forward.

In the course of researching this book, I came to know Joan Talley, one of the three children of Allen Dulles. When we met in her Santa Fe cottage, in a room cluttered with books and artifacts, Joan was nearing ninety and, after a long career as a Jungian therapist, devoting herself to editing the searingly intimate diaries of her mother. Our conversations at times took on a therapeutic character, as we wrestled with the painful legacy of her father and, more broadly, the American soul. In an effort to understand her family, and her own life, Joan had delved deeply into the historical literature on the Cold War and the CIA. She had read all about the coups and trench coat mayhem. “It seems we just went wild,” she told me. “And the CIA was leading the way.”

But as she pored through her mother’s diaries, Joan also was seeking a deeper understanding of her father than mere history can provide. One afternoon, she invoked Jung’s Red Book, the master’s night journey into his own tortured soul. “Jung says you must embrace the dark, as well as the light, to understand life,” remarked Joan, sitting in the passenger seat as I drove her dusty Prius through New Mexico’s high-desert chaparral.

The next morning, we spoke again over the phone. Joan was still agitated by our conversations about her father the previous day. She was trying to make sense of how she could have been so oblivious to this violent rush of history as a younger woman, even when it roared right through her own living room.

“Life sweeps you along—you see people floating by. Everyone is so busy and in the moment. It’s only later that you realize what happened and how alarming it all was. You read books and you finally try to put it all together, and you don’t know what to believe.

“But it’s very important to understand it all—the dark and the light.”

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