Biographies & Memoirs


Courted by Old Joe Kennedy: The Outfit Arrives

His papa bought him the presidency.

-Lee Oswald, speaking with his wife,

Marina, about President Kennedy

It consumed our lives that year.

-Jeanne Humphreys, speaking of

Curly’s work on Jack Kennedy’s behalf

The decade that ushered in a sociological revolution of youth and sexual liberation began fittingly enough: On January 20, 1960, Joe Kennedy’s forty-two-year-old son, Jack, declared for the presidency, one year after then thirty-four-year-old Fidel Castro had seized America’s Cuban playground; on the sexual front, February 29 saw Playboy magazine mogul Hugh Hefner, then just thirty-three years old, open his first Playboy Club in the vortex of the Outfit’s power structure at 116 East Walton Street in downtown Chicago. These seemingly disparate, but seminal, occurrences held more commonalties than the youthfulness of their standard-bearers: They could not ignore the power and influence of the middle-aged men who composed Chicago’s Outfit.

The Second City bosses wasted little time in sinking their claws into Hefner’s new “key club” venture. As with most other Near North businesses, the Playboy Club had to make accommodations with the countless semilegit enterprises within the all-encompassing grasp of the Outfit. The intersections started with Hef’s liquor license, which had to be approved by the Outfit-controlled First Ward headquarters, where John D’Arco and Pat Marcy reigned supreme.

Much of the club’s cutlery was said to be supplied by businesses owned by Al Capone’s brother Ralph, while other furnishings had their origin in the gang’s distribution warehouses. In addition to the army of Outfit soldiers who were seen cavorting at the new jazz-inflected boite, Accardo’s boys (via Humphreys’ union stranglehold) controlled the numerous concessions - bartenders, waiters, coat checkers, parking valets, jukeboxes - so vital to the new enterprise. Local bands that supplied the requisite cool-jazz backdrop were booked by the Outfit’s musicians’ union. Coordinating the gang’s feeding frenzy was the club’s general manager, Tony Roma (of later restaurant fame), who was married to Josephine Costello, daughter of Capone bootlegger Joseph Costello.1

Outfit bosses were bestowed exclusive Number One Keys, which allowed them to date the otherwise off-limits “bunnies” and drink on a free tab. Slot king, and Humphreys crony, Eddie Vogel, dated “Bunny Mother” Peg Strak, who later became Roma’s executive secretary when Roma was promoted to operations manager of Playboy Clubs International, Inc., which oversaw the empire of sixty-three thousand international key holders. Although Hefner himself has never been tainted by his club’s unavoidable contact with the Outfit, it is interesting to note that in 1977, when he fought a copyright infringement lawsuit filed by Universal Studios, Hefner employed the services of Sidney Korshak. For a $50,000 fee, Korshak attempted in vain to settle the case with the studio, which was run by his old friend Lew Wasserman.

On the night of the gala Playboy Club opening, the top Outfit men, Joe Accardo, Mooney Giancana, Curly Humphreys, and Johnny Rosselli, were not in attendance. Now at the peak of their influence, the Chicago bosses had been invited to a power summit in New York City.2 However, this time their host was not another Commission boss coping with internal strife, but was none other than Ambassador Joe Kennedy.

Details of the meeting first surfaced fifteen years later, when Manhattan lawyer Mario Brod gave a series of interviews to historian Richard Mahoney. Brod had been a liaison between the Central Intelligence Agency and the New York crime bosses since World War II, when the CIA’s precursor, the Office of Strategic Services (OSS), had kicked off the U.S. government’s long, mutually beneficial relationship with the underworld. The partnership had its known origins in 1942, when the OSS enlisted Meyer Lansky and the imprisoned Charles “Lucky” Luciano in its effort to deter wartime sabotage in the New York harbor. The government also utilized Luciano’s Italian contacts to gain intelligence in anticipation of the invasion of Sicily. For his efforts, detailed in Rodney Campbell’s book The Luciano Project, Lucky Luciano was allowed to leave prison in exchange for permanent exile in Italy. At the time, Brod was an OSS captain in Italy under future CIA counterintelligence chief James Angleton. In that theater, Angleton and Brod coordinated the information received from Luciano.3 After the war, Brod maintained his contacts with both the underworld and the U.S. intelligence community from his Park Avenue law office. According to Angleton’s biographer, Tom Mangold, “[Brod] helped the CIA, on a regular, salaried, contract basis, with all those awkward jobs in the intelligence business that need an untraceable intermediary.” Leonard McCoy, a longtime CIA analyst who became the deputy chief for counterintelligence, described the Angleton-Brod relationship thus: “Angleton used Brod anytime he needed to go around normal channels. Brod was involved with organized labor officials, and certain unsavory characters. Whenever Angleton needed to keep the world from knowing the CIA was involved in an operation, he used Brod.”

When Bobby Kennedy announced he was going to subpoena Brod in 1963 to ask about his Teamster friends, Angleton personally called Kennedy and advised him to drop the initiative. Angleton came to Brod’s rescue again in 1975, when he convinced a Senate committee to drop Brod from its interview list, lest he suffer retaliation at the hands of mobsters who had no inkling of his cozy history with the U.S. government.

Although Brod had no recollection as to which of his mob friends invited him to Felix Young’s Restaurant in Manhattan on February 29,1960, he had a clear memory of who showed up and what was discussed. Rosselli told Brod that Joe Kennedy, whom Johnny had known since both their early Hollywood days in the 1920s, had asked Rosselli to set up the confab. Brod told Mahoney that the New York and Boston crime bosses, whom Kennedy had also asked Rosselli to invite, failed to show up. Once the attendees were in place, Joe Kennedy quickly got to the point: He wanted a large contribution to Jack’s campaign, and more important, the Outfit’s labor support for the election push. According to Brod, Curly Humphreys objected, noting that Joe’s other son Bobby was on an adrenaline-fueled mob-chasing crusade. Mahoney, who finally wrote of Brod’s account in 2000, noted, “The elder Kennedy replied that it was Jack who was running for president, not Bobby, and that this was ’business, not politics.’” After that weak argument, Kennedy left the restaurant and his unimpressed guests. However, Rosselli told the group that it was significant that Joe Kennedy had come to them. He asked his associates to at least consider the Kennedy alliance. Little did the bosses know, but Joe Kennedy was used to getting his way, and he would continue to arrange sit-downs with the Outfit in hopes of winning them over.

In 1988, ignorant of Mahoney’s unpublished interview with Brod, Irish journalist Anthony Summers spoke with Edna Daulyton, the hostess at Felix Young’s Restaurant in 1960. She also remembered the February powwow, telling Summers, “I took the reservations.” Daulyton recalled an even larger roster than did Brod, informing Summers, “It was as though every gangster chief in the United States was there. I don’t

remember all the names now, but Johnny Rosselli was there . . . They were all top people. I was amazed Joe Kennedy would take the risk.”4

But Joe Kennedy believed that he had to take the risk if his son was to stand any chance of prevailing in the upcoming national contest. On the Republican side, Vice President Richard Nixon had allied with Outfit connected Teamster boss Jimmy Hoffa.5 (When Nixon was defeated, his part of the deal could not be delivered, but his debt to the Teamster leader would be more than nullified when Nixon eventually became president.)

Papa Joe knew, however, that an arrangement with the Chicago Outfit would trump any alliances formed by the opposition. Joe had had firsthand knowledge of the power of the Chicago gang since his purchase of the world’s largest office building, the Chicago Merchandise Mart, in 1945, a virtual impossibility without making concessions to the gang.6 As to why Joe Kennedy would “take such a risk” in meeting personally with hoods, a clue is offered by an associate of Joe’s son-in-law Steve Smith, who overheard Joe telling Smith that the other candidates “didn’t have the balls to go straight to the mob themselves.” Joe did. But then again, Joe Kennedy had been dealing with the underworld for years, and among Kennedy’s earliest shady acquaintances was the gang from Chicago.

Joe Kennedy and the Outfit

Joe Kennedy was Meyer Lansky with a Harvard degree.

-A member of the Chicago Outfit

Few doubt that Old Joe Kennedy had the “balls” to deal directly with gangsters. And historians agree that since the days preceding the 1929 stock market crash, when Kennedy had sold short on his stocks, driving the Depression even deeper while he profited from the nation’s misery, Joe Kennedy’s empire had come first, with patriotism and ethics distant runners-up. As for Kennedy’s ability to make deals with the underworld, the story likely begins during Volstead, when many immigrants seized the brass ring known as bootlegging.

It is all but universally accepted as historical fact that in the 1920s Joe Kennedy was up to his eyes in illegal alcohol. Leading underworld bootleggers from Frank Costello to Doc Stacher to Owney Madden to Joe Bonanno to Meyer Lansky to Lucky Luciano have all recalled for their biographers or for news journalists how they had bought booze that had been shipped into the country by Joseph Kennedy.7 On the receiving side of the booze business, everyone from Joe’s Hyannis Port chums to the eastern Long Island townsfolk who survived the Depression by uncrating booze off the bootleggers’ boats tells tales of Joe Kennedy’s involvement in the illegal trade.

Overlooked by most was the 1996 discovery of a written record that described Kennedy’s illegal alcohol trafficking. While researching a television documentary based on Edward Behr’s book Prohibition, the A&E Network producers uncovered the records of a 1926 Canadian government investigation into Canadian alcohol exported to America during prohibition. At the time the report by the Royal Commission on Customs and Excise was compiled, Canadian authorities were attempting to discern how much export tax they were owed by the American bootleggers. The commission’s paperwork, displayed on the show that aired, showed that the one American purchaser’s name that appeared time and time again was Joseph Kennedy. The files showed that Kennedy had been buying up liquor from Canada’s Hiram Walker facility, which had upped its production by 400 percent to meet the demand of Kennedy and the other U.S. “importers.” In the same Hiram Walker address book that contained the name Joseph Kennedy were the names of other American bootleggers, among them Al Capone and his “financial director” Jake Guzik. It was the earliest hint of an intersection between Kennedy and the Chicago underworld.

The inclusion of Kennedy’s and Capone’s names in the same Canadian government bootlegging file may not be coincidence. Rumors have long been rife in Chicago that one of the many hoods Kennedy had cut sales deals with was none other than Al Capone. The core of the allegations is that Kennedy made arrangements with Capone regarding transshipment of booze across Lake Michigan from Canada - a route controlled by Capone’s Syndicate. Recently, a fascinating corroboration for those stories has surfaced.

In 1994, John Kohlert, a master piano tuner and retired plant supervisor for Wurlitzer Pianos, gave a videotaped oral history just prior to his death at age ninety-three.8 In his recitation, Kohlert pointed out that he had obtained two master’s degrees, one in acoustical engineering from Johns Hopkins University. But he had got his start as a young piano tuner in the speakeasies owned by the man who paid for his college education, Al Capone. On the tape, Kohlert tells his story of Al Capone merely as an unremarkable aside to the history of his life.

One night in 1926, while tuning the home piano of Capone (who had become like a father figure), young Kohlert was invited to stay for a spaghetti dinner. “We’re having a special guest,” Big Al informed the young man. At the dinner, Joe Kennedy showed up, and Kohlert watched as Capone and Kennedy struck a deal wherein Capone traded his whiskey (from his Canadian distillery) for a shipment of Kennedy’s Seagram’s brand. The exchanges were to be made in Lake Michigan, off Mackinac Island.

Years later, when Kohlert was arrested in Britain (on stowaway charges - he had escaped Nazi Germany, but had no passport), he got a message out to the now ambassador to Great Britain, Joseph Kennedy. The note said: “I hope you remember me from that spaghetti dinner in Cicero . . . “ The next day, Kennedy came to the prison and saw to Kohlert’s release. In 1944, when Joe introduced Haig & Haig whiskey to Chicago, his agent was, according to FBI files, Tom Cassara, a Miami gangster who was shot dead soon after arranging the deal with an operative from the Outfit.

Curly Humphreys also remembered Joe Kennedy from the Volstead era. Years later, Curly Humphreys’ daughter, Llewella, recalled her father speaking of his distrust of Kennedy, explaining that one of Curly’s hijacked booze trucks was hit by bombs tossed by Kennedy’s bootleggers, an apparent double cross by Kennedy, the details of which were not clarified for the family. Jeanne Humphreys also has vague memories of Curly speaking about a booze theft by Joe Kennedy’s forces. Kennedy’s interest in Al Capone’s liquor business was buttressed by Washington Postreporter and Joe Kennedy biographer Ronald Kessler, whose sources indicated that Joe promised a Chicago friend that “if he got Al Capone’s business, he would give him 25 percent. The man got the business, but Joe then fired him and hounded him so he could not find another job.”

Curly Humphreys was also said by his family to have connected with Kennedy when the Irish patriarch moved in on the film business and eventually plundered the stocks of operations such as the Pathe newsreel company. Kennedy was a major player in Tinseltown in the 1920s when he purchased Film Booking Office (FBO) and Radio-Keith-Orpheum (RKO). While his family stayed on the East Coast, Joe lived in Beverly Hills for three and a half years producing seventy-six mostly forgettable films for FBO, and conducting a much publicized affair with actress Gloria Swanson. After his 1931 appointment by President Roosevelt to be the first chairman of the Securities and Exchange Commission, Kennedy intermittently returned to Hollywood, most notably to mediate a dispute in the boardrooms of Paramount Pictures, an uproar referred to as a corporate “civil war.” This was during the same period that the Outfit, through Johnny Rosselli, controlled most of the craft unions and received kickbacks, or extortion, from most of the major studios.

Still other Outfit leaders crossed paths with Joe Kennedy. Johnny Rosselli told the Church Committee years later that he, like Curly Humphreys, remembered Joe Kennedy from his robber-baron, bootlegging, stock-plundering days. Rosselli testified that he knew Joe as far back as his 1930s Hollywood era, when the two used to golf and play cards together. According to Dade County (Florida) police files, Rosselli maintained his acquaintance with the elder Kennedy for the rest of Kennedy’s life, and that in a 1960 golfing chat, Papa Joe expressed his concern to Rosselli about his sons’ problems with women. Rosselli gave a similar recounting to D.C. police detective and mob expert Joe Shimon.

Joe Takes Charge of the Backrooms

Joe Kennedy had coveted the Oval Office for three decades, first for himself and then for his namesake son, Joe, Jr., who was killed in World War II. All those who met his second son, Jack, however, readily saw that he had the requisite charm, charisma, and intellect to succeed where the father had failed. It is now clear that Joe Kennedy concluded that for Jack to gain the Oval Office, the cooperation of all was necessary - and Joe meant all. As the patriarch himself said, “There are no accidents in politics.” He thus informed Jack, “I will work out the plans to elect you president.” Joe Kennedy biographer Richard Whalen summed up the ensuing electoral atmosphere: “Jack’s campaign had two separate and distinct sides. On display before the voters was the candidate, surrounded by clean-cut, youthful volunteer workers, the total effect being one of wholesome amateurism. At work on the hidden side of the campaign were the professional politicians whom Joe had quietly recruited. In his hotel suite and other private meeting places, they sat with their hats on and cigars aglow, a hard-eyed, cynical band, brainstorming strategy.’

Early on, Joe set his sights on the massive labor vote. Likely unaware of the deal already cut between Nixon and Hoffa, Joe Kennedy attempted to forge a Kennedy alliance with the very man his son Robert was railing against in the McClellan hearings. The senior Kennedy called old family friend Frank Sinatra, asking him to first arrange a meeting with liberal Teamster leader Harold Gibbons. Gibbons met with Joe at the Kennedy compound in Palm Beach, whereupon Joe assured him that Bobby’s anti-Teamster vendetta had been put aside. ’Well, Mr. Gibbons,” Kennedy advised, “I don’t think there’s much of a war going on between the Kennedys and Hoffa. I hardly hear the name Hoffa in our house anymore.” Although the Hoffa-baiting Bobby was certainly not on the same page as Papa Joe regarding the Teamster overture, there is evidence that his more accomrnodating brother Jack was indeed. Jimmy Hoffa’s strong-arm Joe Franco was present when John Kennedy phoned Hoffa to offer a truce. Hoffa was entertaining the idea when Kennedy then had the temerity to ask Hoffa for a campaign contribution. According to Franco, this sent Hoffa into a screaming tirade against the brother of his nemesis, Bobby Kennedy. Joe Kennedy, however, would continue to assuage the fears of other Teamster leaders throughout the 1960 election year. He became fast friends with Gibbons, often sharing a table at Miami Beach’s Eden Roc Hotel, according to Gibbons’ secretary and PR director, Jake McCarthy.

Even before the 1960 primary season commenced, Joe Kennedy began his plan to undo the damage caused by his firebrand son, Bobby. John L. Lewis, head of the United Mine Workers Union, related a story to the Chicago Tribune’s Walter Trohan. According to Lewis, Joe Kennedy flew in to see him soon after Jack’s announcement, asking for help in the important primary in West Virginia - a state overflowing with mine workers. Lewis told Kennedy to relax - he already had the state won. Lewis was well aware of the agents Joe Kennedy had dispensed throughout the state, dispersing cash to county assessors, judges, party chairmen, etc. The average payoff was said to be $4,000 to $5,000. It was understood that much of this was undertaken without Jack Kennedy’s knowledge. Lewis recalled, “His agents would say, ’Joe Kennedy is very interested in this state and he would like to help you out.’ He never mentioned Jack.”

By the time Senator John Fitzgerald “Jack” Kennedy declared his candidacy for the 1960 presidential nomination, his father had determined that the electoral-rich state of Illinois had to be guaranteed. However, many experts feel that, given the strong Irish Catholic labor tradition in that city, support for Jack Kennedy was already a lock. Nonetheless, in his desire to acquire the state’s twenty-seven electors, Joe decided he couldn’t leave anything to chance, his own knowledge of the inner workings of that city having come from his long history as a businessman who had to keep Chicago’s local pols, unions, and hoods happy. As early as 1952, according to numerous accounts, Joe Kennedy had sent Kenny O’Donnell, a Harvard friend of Bobby Kennedy’s and an early member of the “Kennedy machine,” to Chicago to sow the seeds for young Jack’s eventual campaign for the presidency. O’Donnell would become the patriarch’s liaison to Chicago mayor Richard Daley. Joe Kennedy and Richard Daley were longtime political cronies, who lunched together often at Joe’s Merchandise Mart. So close was their relationship that Daley was seemingly cleared to spend Joe’s money as he saw fit. On one occasion, when candidate Kennedy was speaking in Chicago, Daley wanted the event televised nationally, at a cost of $125,000. The mayor instructed an aide: “Go over to Mr. [foe] Kennedy at the Merchandise Mart, and he’ll give you the check.” Which is exactly what happened.

In truth, Richard Daley had a selfish motive in getting out (or inventing) Chicago’s Democratic vote. Within the last year, Republican Ben Adamowski, the state’s attorney who was on the Republican slate, had announced major indictments against members of Daley’s infrastructure.9 Most disconcerting for Daley and the Outfit was the rumor that the recent charges would be the tip of the iceberg should Adamowski, who was personally protecting Morrison, win another four-year term. Among other looming problems was Adamowski’s investigation of Daley’s city commissioner of investigations, Irving “Sweep It Under the Rug” Cohen. According to Adamowski’s chief investigator, Paul Newey, “It was Cohen’s purpose to keep all the book joints going, but under wraps so that the media wouldn’t make an issue of it during an election year. Daley knew it was wide-open.”

“Gee, the mayor is fit to be tied, Curly,” Pat Marcy informed Humphreys one day at Celano’s. “He’s letting the Polack, Adamowski, rib him, and he shouldn’t do that,” Humphreys replied. Humphreys then suggested that the “boys” should attempt to have a more friendly police commissioner installed to take the heat off of Daley. But all Humphreys’ local politicking was soon to be dwarfed by a new assignment emanating from Hyannis Port, Massachusetts.

With the pundits predicting a virtual toss-up in the November election, the Kennedy patriarch had decided he needed the support of the Chicago Outfit, which was legendary for its ability to marshal foot soldiers to get out the vote locally and was known to be in control of many of the labor unions across the country. Papa Joe, knowing that Jimmy Hoffa would never endorse Bobby Kennedy’s brother, concluded that the key players would also have to include the non-Teamster labor unions so often infiltrated by the likes of Curly Humphreys. Kennedy intimates make it clear that Joe intended to embark on his own to run the election show, dealing with these less savory elements, hopefully in ways that would not become public knowledge. Those who knew Joe could hardly be surprised at just how low the Old Man would go to fulfill his dream. Jack’s aide-de-camp Kenny O’Donnell later acknowledged, “If Jack had known about some of the telephone calls his father made on his behalf to Tammany Hall-type bosses during the 1960 campaign, Jack’s hair would have turned white.” “You know, the old man is hurting you,” a friend warned Jack. To which Kennedy responded, “My father is working for his son. Do you want me to tell my father to stop working for his son?” Former Speaker of the U.S. House of Representatives from Massachusetts, and longtime Kennedy family friend, Thomas P. “Tip” O’Neill recalled, “These things happened, although Jack didn’t always know about them. But the Old Man made his own arrangements over and above the campaign staff. Jack certainly knew that his father was spending a lot of money.” A stock joke of Kennedy’s on the campaign trail had candidate Kennedy quipping, “I have just received a wire from my father. It says, ’Don’t buy one more vote than is necessary - I’ll be damned if I’ll pay for a landslide.’”

Clearly, the candidate was not always aware of the details, but those very details, just now emerging, would later force the Kennedy family to play coy when the investigators into Jack’s murder, three years hence, were desperate for a motive.

The decision reached, Joe began his secret liaisons with the Outfit, and many believe it was not a new occurrence. Joe Kennedy’s alleged dealings with Capone notwithstanding, the patriarch had surely reached accommodations with Chicago’s gangster element on other occasions. Chicago, after all, was the scene of one of Kennedy’s greatest financial triumphs, the purchase of the enormously undervalued Merchandise Mart for $12.5 million, of which he was rumored to have put up none of his own money. (It was reputed to be worth five times that much, and by 1969 it was valued at $75 million.10) With the Mart located in the heart of Chicago’s business district, it is virtually inconceivable that the Outfit-controlled unions did not have a vise grip on most if not all of the service and concession contracts that supported the behemoth. Joe Longmeyer, a veteran independent Chicago labor organizer, remembers one day when Curly Humphreys came into the furniture store where Longmeyer was working. “Humphreys arranged for the store owner to have entree at the Mart,” Longmeyer says. Such an opening allowed merchants to purchase wholesale goods in the Mart. “Since Humphreys had some kind of relationship with the management of the Mart, he got my boss in,” Longmeyer added. Few old-time Chicagoans doubt that Kennedy, either by choice or necessity, formed some sort of alliance with the Outfit to guarantee the Mart’s smooth running. As one of Giancana’s drivers recently remarked, “Nobody does real business in Chicago without knowing Mooney. Joe [Kennedy] knew where the power was.”

Joe Kennedy’s first known election overture to Capone’s heirs was the luncheon at Felix Young’s, which Joe had had Johnny Rosselli arrange. However, when that summit produced no agreement, Joe Kennedy decided to approach the day-to-day boss, Mooney Giancana, separately. After all, they shared a mutual friendship with Frank Sinatra, whom Joe could use to press his case with Mooney.11 One other commonality practically defied belief: Mooney Giancana, Johnny Rosselli, and Joe’s candidate son all shared a girlfriend, Judy Campbell.

Joe and Mooney

In 1997, Meyer Lansky’s best friend and close associate, Vincent “Jimmy Blue Eyes” Alo, consented to a first-ever interview in which he recalled his knowledge of Joe Kennedy’s efforts to approach Mooney Giancana on behalf of his son:

Joe came to me very early. Joe Kennedy and I had a mutual friend, Phil Regan, the actor and singer from Brooklyn. Joe sent Phil to see me.12 We met at the Sea View in Bal Harbour [Floridaj. Phil told me that they had it [the electoral vore] figured out to the last detail. Even that early they knew that Chicago would make all the difference. I don’t know how they knew it - this was before computers. The point is that they knew I knew Sam Giancana. Joe Kennedy wanted me talk to him about helping Jack in Chicago. I turned him down. I wasn’t in the habit of interfering in elections. The next thing I hear is that they went to Sinatra.13

Although the Lansky faction, according to Jimmy Alo, had declined to serve as Joe’s liaison to the Outfit, Joe had far from given up. As Alo later heard through the mob grapevine, Joe Kennedy indeed called on Frank Sinatra, one of the best friends of Joe’s son-in-law actor Peter Lawford.

When Lawford wed Jack Kennedy’s sister Patricia in 1954, he introduced the rakish Kennedy to the world of his fellow Rat Packers, which included Frank Sinatra, Dean Martin, Sammy Davis, Jr., Joey Bishop, and Lawford. Throughout the fifties, young Senator Kennedy trysted with his new pals in Hollywood and Las Vegas. Not long after his announcement to run, Jack Kennedy celebrated at the Sands in Las Vegas with Sinatra and the Rat Pack, who were there filming Ocean s Eleven. An FBI airtel memo from local agents to Director Hoover noted, “Showgirls from all over town were running in and out of the Senator’s suite.”

Joe Kennedy knew that Sinatra had a special kinship with Mooney Giancana, an influence that might now be used to convince the Outfit to support the Kennedy master plan. Sinatra had been chummy with Mooney at least as far back as the early fifties, when Rosselli and the Outfit had given a push to the singer’s stalled movie career. The two exchanged pinkie rings, and Sinatra often closed his shows by singing “My Kind of Town (Chicago Is)” as a tribute to Mooney. Fellow crooner and friend Eddie Fisher remarked, “Frank wanted to be a hood. He once said, T’d rather be a don of the Mafia than president of the United States.’ I don’t think he was fooling.” However, in real mob circles, Sinatra was often derided as a “wanna-be.”

In 1997, the author undertook new research for an ABC News film project that coincided with the release of the Seymour Hersh book The Dark Side of Camelot. One key task was to attempt to learn more about Joe Kennedy’s election appeal to the Outfit. What was learned added much detail to the long-rumored Sinatra contact. Although Frank Sinatra had previously refused all interview requests concerning his contacts with members of the underworld, that silence would be broken in 1997. After speaking with her father, Tina Sinatra was authorized to relay the following account:

A meeting was called [between Joe and Frank]. Dad was more than willing to go. It was a private meeting. I remember it was over lunch. I believe it was at Hyannis. Dad said he was ushered in. He hadn’t been to the house before. Over lunch Joe said, “I believe that you can help me in Virginia and Illinois with our friends. I can’t approach them, but you can.” Joe wanted Frank to approach the union leader with the most influence, which was Sam Giancana. Sam could rally his people - to make certain that neighborhoods were encouraged to get out and vote.

It gave Dad pause. I know that it did that because he said that it did that. But it still wasn’t anything he felt he shouldn’t do. So off to Sam Giancana he went. Dad calls Sam Giancana to make a golf game and told Sam of his belief and support of Jack Kennedy. And I believe that Sam felt the same way.

Apparently, Joe Kennedy decided that communicating with Mooney Giancana via Sinatra was unsatisfactory. Perhaps not trusting the crooner to make the case for Jack as strong as he could, Joe pressed to meet Mooney face-to-face. For years the talk of such a meeting has persisted in Chicago. Veteran Chicago Tribune Washington bureau chief Walter Trohan recently recalled what he had been hearing from ace police reporter (and two-time Pulitzer Prize winner) George Bliss: “He told me that in the course of seeking the presidency against Nixon, Joe Kennedy was dealing with Giancana. I couldn’t believe it at the time.” Former sports promoter and bookie Harry Hall, who knew Joe Kennedy, Mooney Giancana, and other luminaries, has a similar memory: “I spent a lot of time with the Kennedys in the Biltmore Hotel. Joe knew all the racketeers. I had heard he made a lot of promises to the Outfit for their support.” Recent interviews seem to, at long last, put some teeth into the reports Bliss and Hall were receiving.

One of Joe Kennedy’s oldest Chicago friends (and political allies) was the revered circuit court judge of Chicago William J. Tuohy, whom Kennedy had met in 1945. According to one well-placed source, when Joe needed to meet with Mooney Giancana, he asked Tuohy who might arrange it. Tuohy contacted the source, a close personal friend, who had served as an assistant state’s attorney in his office in previous years and was now well-known to represent members of the Outfit.

Robert J. McDonnell was described by his legal peers as “the rising star” in the state’s attorney’s office in the 1950s. One newsman went so far as to say “McDonnell could’ve been governor one day.” Born into a family (the Healys) that were the landed gentry of Chicago - McDonnell’s father worked with Joe Kennedy on the purchase of the Merchandise Mart, and his uncle was the premier public-works construction contractor in Chicago - McDonnell’s future seemed bright. However, along the way, McDonnell fell prey to the twin demons of booze and gambling. Soon he found himself working off his marker with the Outfit by defending them in court. This being the case in 1960, Tuohy knew McDonnell would know how to contact Giancana.

Although McDonnell knew many key mob players, at the time he had only a fleeting acquaintance with Mooney Giancana (in later years, he would marry the don’s daughter Antoinette). McDonnell told Tuohy that the way to reach Mooney was through his First Ward spokesman, Pat Marcy, who in turn was secretary to First Ward alderman John D’Arco. Tuohy, who indeed knew Marcy, thought the entire business was distasteful and made it clear that he was doing this only at the insistence of Joe Kennedy.

“Pat Marcy came over and talked with Judge Tuohy,” says McDonnell. “A few days later I was told that Mooney [Giancana] wanted to meet with me at the Armory Lounge.” The day he got the call, McDonnell drove to Giancana’s Forest Park headquarters. There Mooney informed him that he would attend the meeting, but only if it was kept secret. Two days later, Judge Tuohy called McDonnell. “The meeting is on for tonight at five o’clock in the judge’s chambers,” said the judge. “I want you there.”

Tuohy and Kennedy were already on-site when McDonnell arrived. Soon, Pat Marcy walked through the courthouse doors escorting Mooney Giancana. After making the introductions, Bob McDonnell left the men to talk in private. “As I was leaving, Judge Tuohy said to me, ’Wait for me, Bob. I’m just going to tell them to shut the doors when they’re finished.’” Tuohy and McDonnell exited, leaving the three men to their business. Exiting, Tuohy remarked to McDonnell, “I’m glad I’m not privy to this.” “He was very dispirited,” says McDonnell. “This was a man of the highest integrity.”

McDonnell is quick to emphasize that he has no firsthand knowledge of what the three men discussed. “But I later heard that Joe Kennedy was asking Mooney and Marcy what help they could bring to the election of his son. He was obsessed with the election of John Kennedy - absolutely obsessed with it., And I don’t know what deals were cut. I don’t know what promises were made.” Mooney’s brother Chuck later wrote, “All Mooney said was that he was too busy meeting with Joe Kennedy, working out the details of their agreement for Jack’s presidential campaign.” McDonnell adds, “This was the biggest secret in Chicago. Everyone was sworn to secrecy. Bill Tuohy was a highly religious, very moral man. I think he felt himself debased by Kennedy’s request. And I think he resented it. He did not discuss it again.”

Although McDonnell had no firsthand knowledge of what deal was struck, Mooney was telling his associates that, as a quid pro quo, he expected a hot line to the White House.

Following form, Mooney Giancana had to seek approval for such an alliance from his puppet masters, Accardo, Humphreys, and Ricca. “Even at that time,” Curly’s widow recalls, “Mooney didn’t make a move without the approval of the boys, you know.” If that approval was granted, then it would be assumed that Curly Humphreys, the gang’s political mastermind, would play a role in carrying out the directive. He did.

The episode is not only recalled by Jeanne Humphreys, but is recorded in her three-hundred-plus-page handwritten journal that details her extraordinary life with Curly. According to Jeanne, the “new business” was broached at one of the Outfit’s Thursday-night business dinners at Accardo’s Palace. She recalled her husband coming home the night the vote was taken to support the Giancana-Sinatra-Kennedy pact. “Mooney’s talking about trying to get that Joe Kennedy’s kid elected president,” Curly informed his wife. “He’s trying to impress Sinatra.” Through her husband, Jeanne picked up bits and pieces of what had transpired at the Palace. “Apparently, Joe had promised that his boys would back off the Outfit, especially in their Las Vegas business,” Jeanne said. “Mooney bragged about the assurances he got from Kennedy.”

The initial vote was two for the deal (Accardo and Giancana), and one opposed (Humphreys). Just as he had at Felix Young’s, Curly refused to fall in line. Jeanne said, “Murray was against it. He remembered Joe Kennedy from the bootlegging days - called him an untrustworthy ’four-flusher’ and a ’potato eater.’ Something to do with a booze delivery that Joe had stolen. He said Joe Kennedy could be trusted as far as he, Murray, could throw a piano.” Of course hijacking hootch during Volstead was considered fair game, and Joe Kennedy may also have been such a victim. Doc Stacher, Meyer Lansky’s boyhood friend and bootlegging partner, remembered an incident in 1927 in which a shipment of Joe’s booze from Ireland was stolen in a Boston gunfight in which nearly all of Kennedy’s men were killed by Bugsy Siegel’s violent troops. When Siegel was upbraided by Lansky, Bugsy explained, “It really wasn’t our fault. Those Irish idiots hire amateurs as guards.”

Perhaps Humphreys had other reasons to be wary of the association: His old chum Lucky Luciano had been double-crossed when he’d made a deal with a previous presidential candidate, Franklin Roosevelt. And then there was Bobby Kennedy. As Humphreys’ grandson George Brady recalled from his many trips to Chicago to visit Humphreys, “There was also trepidation about backing JFK because of Bobby. But, on the positive side, Frank [Sinatra] talked him up.”

All that was needed was the vote of board member Paul Ricca, currently in “college” in Terre Haute. “Murray had to go to see Paul in prison,” Jeanne remembers. “When he got back from seeing Paul, he said, ’They’ve all gone along with it now, that Jack Kennedy thing.’”

“Anyway, the vote was three to one in favor,” Jeanne says. “Murray was stunned that the others voted with Mooney, but he later remarked about how the ’spaghetti-benders’ all stick together.” An entry in Jeanne’s journal reads: “Murray said he thought Mooney was nuts and that he [Murray] was working on Paul’s [Ricca] immigration problems, with no time for screwball ideas. He paced and mumbled.” Regardless of his personal misgivings, Curly deferred to the majority vote. Jeanne asked her husband what this meant for his workload. “Nothing - if I can get away from it,” Curly responded. “I’ve got enough on my hands.” But in his gut, Humphreys knew there was no one else with his particular skills, and sooner or later, the election fix would become just one more piece of gang business on his plate.

The FBI, which had been attempting to follow Humphreys’ every move, could attest to the gangster’s hectic schedule. On May 23, the G followed Humphreys to Washington, where he lobbied the Outfit’s agenda. The FBI followed the gang boss to O’Hare Airport, and one agent later described Humphreys’ appearance, noting, “He was dressed in a very conservative black suit, wearing his glasses as always to conceal his blind eye. He had on a long-sleeved shirt, neatly showing an inch of linen. His shoes were bright polished, every inch of him looked like the CEO of Motorola or some other high profile Chicago company . . . he could have been anything he wanted in this world - an attorney, a congressman, a top legitimate businessman. I believe that.”

On a later trip to Washington, Humphreys met with Congressman Libonati to confer on the Ricca parole. Also on the agenda was Curly’s desire to have Libonati introduce legislation that would outlaw then Attorney General Bobby Kennedy’s surveillance techniques. Libonati had the temerity to tell a Chicago television reporter, “Yes, I know Giancana. [My] bill would cover him.” When Bobby Kennedy heard of the Libonati bill, he ranted, “If Libonati shows up in Congress next year, I’ll have him arrested!”

The Bureau watched as Curly left Washington’s Woodner Hotel, carrying a small package, “believed to be a thick wad of cash,” to Libonati’s 224 C Street home, and leaving without it. From there, Curly proceeded to the Hamilton Hotel, where he met with Congressman Thomas J. O’Brien. Upon returning to the Woodner, the Bureau learned, Humphreys “went to the room of a well-known Washington call girl where he apparently spent the rest of the night.”

Humphreys would return to the nation’s capital two weeks later to meet with prominent mob lawyer H. Clifford Adler.

Back in Chicago, Giancana’s soldiers coordinated the initial phase of the Joe Kennedy deal. The first order of business was to guarantee Jack Kennedy’s victory in the upcoming West Virginia primary on May 10. Although Kennedy had won the recent Wisconsin contest, the margin was far too slim to convince the national power brokers he could win the nation. Tied to the misgivings was the rampant anti-Catholicism in many parts of the country. In Wisconsin, Kennedy had failed to win even one of the four Protestant districts. Thus, the Kennedy team deemed rabidly anti-Catholic West Virginia the make-or-break primary. But the very state that campaign chronicler Theodore White called one of “the most squalid, corrupt, and despicable” states was about to meet its equal, in the form of Joseph Kennedy.

West Virginia state senator John Chernenko recently stated that just prior to the all-important West Virginia primary, he received a call from Dick Wright, the Kennedy chairman of the West Virginia primary, and one of the most powerful Democrats in the state. Wright requested that Chernenko go to Mingo Junction, Ohio, just across the Ohio River from West Virginia, to meet with Frank Sinatra. “The purpose of the meeting was for Sinatra to review the campaign in West Virginia and to see how much financial assistance was needed,” Chernenko said. No fan of Sinatra’s, Chernenko declined the offer. But soon, mob-controlled jukeboxes across the state began featuring Jack Kennedy’s campaign theme song, a reworded version of Sammy Cahn’s current hit “High Hopes,” sung by Frank. A Kennedy aide traversed the state paying tavern owners twenty dollars each to play the song repeatedly.

Nonetheless, as FBI wiretaps would later disclose, Sinatra’s and Giancana’s close friend Paul “Skinny” D’Amato, the manager of Atlantic City’s 500 Club, spent two weeks in the state dispensing over $50,000 for the Kennedy effort. D’Amato clarified to writers Hellerman and Renner that it was not the money that mattered so much - the Kennedys already had plenty of that - but it was the gang’s massaging of the poverty-stricken West Virginia pols. According to D’Amato, his boys’ contribution was in the form of “desks and chairs and supplies for politicians around the state.” The FBI taps also picked up a conversation wherein Giancana reminded Rosselli of “the donation that was made” to the Kennedy effort. What the FBI failed to learn was that, according to D’Amato, Joe Kennedy even paid him a personal visit and, in exchange for Skinny’s aid, promised that, if elected, his son Jack would allow deported New Jersey mobster Joe Adonis to return to the United States. Once again, Joe Kennedy’s zeal to see Jack elected would place his boy in a severely compromised position. (As president, Jack Kennedy refused to go along with the deal.) Corroboration for the direct Joe Kennedy D’Amato contact was obtained in 1988 by historian Dan B. Fleming, who spoke with Skinny’s next-door neighbor, Joseph DelRaso, now an attorney in Ft. Lauderdale, Florida. “Skinny told me Joe Kennedy called him directly to help in the West Virginia campaign,” recalled DelRaso.

Kennedy eventually beat Senator Hubert Humphrey in West Virginia by a 60-40 margin. Humphrey complained, “I can’t afford to run through the state with a little black bag and a checkbook.” (Humphrey spent an estimated $25,000 compared to Joe Kennedy’s $l-$2 million.)

Covert Conclaves at Crystal Bay

The contacts between Joe Kennedy and Mooney Giancana appear to have continued throughout 1960. Jeanne Humphreys remembered, “We went to Mooney’s house in West Palm Beach in Florida, and there was a lot of conversation about it. Mooney was going out to California and meeting with Joe Kennedy, and it just kept evolving and evolving.” When Curly began the laborious task of coordinating his unions behind Kennedy, Jeanne wondered why he had to do all the work; after all, the idea had been Giancana’s. “I said, ’Where’s Mooney?’” Jeanne recalls. “Murray said, ’He’s taking care of his end, Blondie. He’s with Joe Kennedy in California.’ My husband didn’t go into great detail.” Although Jeanne was not privy to the “evolving” meetings in California, details have emerged about where they were likely held.

As one hoodlum friend of Joe’s told writers Denton and Morris, “Joe’s] ties to the underworld intersected at a hundred points,” and if the players in these intersections had a clubhouse where their furtive caucuses could be conducted, it was the Cal-Neva Lodge. Described in ads as “Heaven in the High Sierras,” the Lodge consists of luxury bungalows, a swimming pool, and a casino. This idyllic venue is set on a parcel of land that literally straddles the California-Nevada state line on the north shore of Lake Tahoe, a region known as Crystal Bay. When gambling was illegal in both states, the owners of the Cal-Neva Lodge confounded raiding police by merely pushing the card tables across the room - and the state line - the direction dependant on which locale was conducting the raid. When Open Gambling was approved in Nevada, the gambling paraphernalia found a permanent home on the Nevada side of the casino room. The Lodge had been built in 1926 and purchased two years later by the “Duke of Nevada,” real estate mogul Norman Biltz. In 1930, Biltz married Esther Auchincloss Nash, the aunt of Joe Kennedy’s future daughter-in-law Jacqueline Bouvier. During the 1960 campaign, Biltz canvassed the Vegas Strip, collecting some $15 million for the Kennedy war chest. Jack Kennedy himself had made it clear that he coveted secret Sin City contributors, writing a note to pal Frank Sinatra, “Frank - How much can I count on from the boys in Vegas? JFK.” The note hung in Sinatra’s “Kennedy Room” for four decades.

At about the same time as Biltz’s purchase, Joe Kennedy began frequenting the Lodge, a hunting and fishing escape that would be a lifelong getaway for him and his clan. Wayne Ogle, the longtime maintenance manager at the Lodge, has recalled how for years he would ship two ten-foot Tahoe pine Christmas trees from the Lodge’s property to the Kennedy home in Hyannis.

Joe Kennedy was not the only former bootlegger escaping to the sanctuary of the Cal-Neva. In recent years, Mooney Giancana had been using the bucolic setting to escape the G’s surveillance. According to both Mooney’s people and the G, Giancana had viewed the Lodge as a personal haven from the Bureau. Although agents would tail him as he moved about the Las Vegas casinos, it was later learned that Mooney and his driver would go to a movie matinee, sneak out the back door, and drive to Crystal Bay, where the don could either relax or conduct business.

The Lodge changed hands numerous times, with many of the purchasers underworld dwellers. For a time, Bugsy Siegel’s San Francisco partner, Elmer “Bones” Remer, took the helm; at another juncture, Bill Graham, who fronted for the Outfit at Reno’s Bank Club, owned the Lodge. In 1955, Joe Kennedy’s lifelong friend Bert “Wingy” Grober (so-named due to a shriveled left arm) took over the Cal-Neva. Grober, a sometime associate of Meyer Lansky’s in Florida, had previously operated Miami Beach’s Park Avenue Steak House, where his liquor and steak supplier was his pal Joe Kennedy. During Grober’s five-year tenure, it was commonly believed that he was fronting for the real owner, Joseph Kennedy. As seen in the case of Morton Downey, Joe frequently hid his business interests behind other owners of record. Las Vegas chroniclers Roger Morris and Sally Denton recently located sources who claimed to know of the secret arrangement. “Wingy was old Joe’s man there,” one of the locals recalled, “and he looked after his stake in the joint.” Another candidate for a Kennedy front was Charlie Bloch, Grober’s partner in the Park Avenue Steak House. Bloch, it turns out, was Joe Kennedy’s liquor distributor for the Southern region that included Miami and was believed by some to have been another of the Cal-Neva’s many silent partners.

Two years after the fact, the FBI was told by a former New York-based federal prohibition agent named Byron Rix of a secret election-year liaison at the Lodge between Joe Kennedy and “many gangsters.” Rix, who was personally acquainted with the Kennedy family and later worked in the Las Vegas gambling business, learned from numerous unnamed sources that Joe Kennedy had a nefarious meeting in 1960 at the Cal-Neva. In 1962, the FBI summed up Rix’s information in a memo to then Attorney General Bobby Kennedy, noting that “this memorandum is marked ’Personal’ for the Attorney General and copies are not being sent to any lower echelon officials in the Department in view of Rix’s remarks concerning the Attorney General’s father.” The memo summarized Rix’s story thus:

Before the last presidential election, Joseph P. Kennedy (the father of President John F. Kennedy) had been visited by many gangsters with gambling interests and a deal was made which resulted in Peter Lawford, Frank Sinatra, Dean Martin and others obtaining a lucrative gambling establishment, the Cal-Neva Hotel, at Lake Tahoe. These gangsters reportedly met with Joseph Kennedy at the Cal-Neva, where Kennedy was staying at the time.

The Cal-Neva was uniquely equipped to cater to gangland gatherings, according to a Lodge hairdresser from the 1970s who set up her shop in Sinatra’s old bungalow. When she took over the singer’s gatehouse cabin, the hairdresser discovered that it concealed an extensive tunnel system that interconnected the various cabins and the main lodge, and which had allowed the stars and “underworld” bosses to come and go without being seen.

The Nevada Gaming Commission would later learn that one of the “others” in on the deal was Mooney Giancana. And, as will be seen, the group Rix mentioned would indeed buy the Cal-Neva from Wingy Grober (or the likely actual owner, Joe Kennedy) and install everyone’s buddy, Skinny D’Amato, to run the casino.

By July, with the West Virginia primary behind them, the Outfit, at Mooney’s request, escalated its electioneering efforts on behalf of Sinatra’s friend young Jack Kennedy. Curly Humphreys, already fatigued from his regular duties, undertook the onerous chore of helping the son of the distrusted Joe Kennedy win the presidency. “[Murray] hated having to go along with the Outfit’s vote to back Kennedy,” Jeanne Humphreys recalls. “It was a constant source of aggravation for him.” But, like it or not, Humphreys was a team player and thus once again settled into his role as the gang’s political mastermind.

Luckily for history, Curly Humphreys decided to allow his wife, now the only living witness to the politicking, into the inner sanctums of the Kennedy effort. Jeanne remembers how one day in early July, Curly told her to pack her bags. “I thought perhaps Murray was lamming it again, and we’d be on our way to Key Biscayne, or God knows where.” To Jeanne’s dismay, she was informed that she had a choice: either hole up with Curly in Chicago or go alone to Key Biscayne or Vegas. When she was told that Curly would be in seclusion at the Hilton Hotel on Michigan Avenue for at least two weeks, Jeanne chose to stay with him, writing in her journal: “Realizing he would be alone practically across the street from the 606 Club and a few blocks from all those willing strippers, I opted to stay at the hotel. What I said was, ’I’ll do my time at the hotel.’” The couple abandoned their Marine Drive apartment and found two suites waiting at the Hilton, reserved for Humphreys in the name of “Mr.

Fishman,” a joke since Jeanne had developed an obsession for fishing in the Keys. Curly explained that what he was about to do had to be kept secret from the G-men, who were monitoring the gang’s homes and regular meeting places. “They were looking for us everywhere,” Jeanne recalls. “This was very secret.” Once settled in, Jeanne wondered where the rest - Joe Accardo, Gussie Alex, etc. - were. “Murray said they were busy keeping Roemer and the G looking for them elsewhere, while we were getting things done.” Getting what done? Jeanne wondered. As she quickly learned, her husband’s big secret was the work of fixing Jack Kennedy’s election.

Jeanne soon found herself a virtual prisoner at the swank hotel, which the locals still knew by its previous name, The Stevens, for two weeks, bored to tears while her husband worked himself to exhaustion. From Jeanne’s journal: “I felt like the Prisoner of Zenda, Anne Boleyn in the Tower, Napoleon on Elbe, and Byron at Chillon. Murray said I was more like a bird in a gilded cage.” One of Curly’s gophers, Eddie Ryan, was the first to arrive, running errands for both his boss and Jeanne, who occasionally needed a change of clothes from home.

In 1996, Jeanne recalled for the first time what she witnessed at the Stevens/Hilton, scenes that were corroborated by her own contemporaneous writings. “Lists were everywhere,” she wrote in her journal. “Murray was arranging lists in categories of politicians, unions, lawyers, and contacts . . . I could see that one list had at least thirty to forty names on it.” Once the lists were developed, Humphreys began making contact with the power brokers whom he could order to back Jack. “Murray’s phone rang off the hook - always politicians and Teamsters,” Jeanne says. Soon the contacts began arriving at the Stevens from around the country to receive their marching orders from Humphreys. Among the regular visitors were Murray Olf, the powerful Washington lobbyist, Teamster official John O’Brien, and East St. Louis boss of the Steamfitters Union, Buster Wrort-man. “The people coming to the hotel were Teamsters from all over the country - Kansas, St. Louis, Cleveland, Vegas,” Jeanne recently said. “They were coming in from everywhere, then fanning out again.”

Although Jeanne knew no specifics about how the labor leaders were going to guarantee Kennedy’s election, it is not difficult to deduce what was going on. At the time of the Kennedy-Nixon contest, the millions of unionized American workers tended to follow the dictates and endorsements of their leaderships. Although most Teamsters complied with Hoffa’s endorsement of Nixon, tens of thousands of other non-Teamster unions across the nation were just waiting for the word from above. In a close election, these votes could make all the difference. Jim Strong, the Chicago Tribune’s labor reporter for twenty years, including 1960, recently spoke of the other weapons (besides the members’ votes) that organized labor brought to the table. “With its nationwide links, the Outfit could reach out across the country,” Strong says. “When the various locals endorsed a candidate, their modus operandi would be primarily to set up phone banks, get out the vote by driving voters to the polls, and write checks. That’s how they did it.” Factoring in the immense number of locals controlled by Humphreys, it becomes clear how he would be overworked at the Stevens.

Not allowed to go out due to the FBI’s surveillance, Jeanne Humphreys tried to occupy herself by reading. Her best friend became Phil Itta, the hotel maitre d’, who kept her supplied with crossword puzzles, books, newspapers, and treats from room service. Itta, a trusted friend of Humphreys’, swept the rooms for FBI bugs, handpicked the room-service waiters, and installed new tamper-proof locks on the suites’ chests of drawers.

While Curly was holed up in the Stevens, his upperworld alter ego, Joe Kennedy, was likewise ensconced at Marion Davies’ mansion in Los Angeles, his base of operations for maneuvering the delegates at the Democratic National Convention in the City of Angels. As one of his first moves, Kennedy brought in Chicago “backroom” pol Hy Raskin to deliver the convention delegates for Jack. Raskin was the number two man in the Democratic National Committee, legendary for his extensive Windy City contacts. By now, Joe Kennedy and other Washington insiders knew that Jack Kennedy’s Democratic rival, Senator Lyndon Johnson, had already lined up the support of New Orleans boss Carlos Marcello, much as Nixon had done with Hoffa.14 When the convention convened in L.A., Joe was conspicuously absent on the night of his son’s nomination speech. His non-attendance didn’t go unnoticed by the crowd, many of whom queried, “Where’s Joe?” Randolph Churchill called it “a lovely party, but where’s the host?” The perception was that Joe did not want his personal history to mar this night with controversy. But that was only part of the rationale. As he watched the proceedings from the Los Angeles home of Marion Davies, eleven miles from downtown in Beverly Hills, Joe met with party bosses, and old friends who owed him favors. Besides Raskin, others, such as popular Southern author William Bradford Huie, were enlisted to distribute cash to various influential politicians on Jack’s behalf.15 Longtime family friend Judge Francis X. Morrissey wrote, “It was Ambassador Joseph Kennedy who made sure that the votes for the various delegations in the big key states, like New York, Pennsylvania, Illinois, and New Jersey, all went for Jack.” It may never be known what promises were made by Joe on Jack’s behalf, but it is a matter of record that Joe’s promises to the underworld were among those that would severely handicap his son’s administration.

When Jack successfully snared the nomination, Mort Sahl, the political satirist, attempted to put a humorous spin on the underhanded politicking, wiring the patriarch: “You haven’t lost a son, you’ve gained a country.”

With the nomination commandeered, the Humphreys repaired to their Key Biscayne home for some much needed R St R. To their dismay, however, they found that the G had been harassing Jeanne’s brother’s family, who also lived in the area. Not long after arriving, the Humphreys were attending a family get-together when Jeanne was approached by her seven-year-old niece, Diana. With tears in her eyes, the child said one of her schoolmates had asked her if her aunt and uncle were murderers. It turned out that the G, desperate to draw out Curly and Jeanne from their hiding place, had begun harassing members of Jeanne’s family and friends, displaying Curly’s 1934 mug shot. Diana’s girlfriend’s Cuban family was distraught over the prospect of being sent back to the island if they did not cooperate with the G. Curly had Jeanne’s brother complain to the local FBI office, which claimed to know nothing of the encounter. The Family Pact, apparently, only applied to Roemer’s jurisdiction.

Even as they attempted to unwind in Florida, the “Harts” saw their getaway home visited regularly by reminders of Curly’s other life. In August, the Humphreys entertained Jimmy Hoffa at a time when their Key Biscayne neighborhood was enduring a fetid sewer backup. Still smarting from his treatment in Washington at the hands of Bobby Kennedy, Hoffa told Jeanne that he wondered if Bobby had fallen into Biscayne Bay, the stink was so awful. When the talk turned serious, Jeanne witnessed her husband explaining the Outfit’s work in support of Joe Kennedy’s son to the Teamster boss. “Of course I can’t officially endorse it,” Hoffa said. “But who knows? Maybe the Italians are right. If Jack feels he owes us one . . . “

Another visitor was Mooney Giancana, with whom the Humphreys dined at one of Giancana’s favorite Ft. Lauderdale restaurants. The trio was chauffeured by Mooney’s Florida driver, Dom, the parking valet at the Outfit’s Miami Beach Kennel Club. Although Curly and Jeanne had hoped to escape the campaign, it was all that Mooney wanted to talk about. Jeanne Humphreys described the dinner conversation in her journal:

Besides discussing what politicians had to be “turned around,” what union heads had to be convinced, and how much good it would do in the end, I was amazed to hear that Jackie K. had to be told not to wear slacks anymore when campaigning. Since I wasn’t included in the conversation I almost choked trying to suppress my laughter. There was a lot of “Frank said this” and “Frank said that” and “It’ll all pay off” repetition. Mooney was exuberant. I could read M [Murray] like a book and saw his lack of enthusiasm. When there was a lull in the conversation I told Mooney I should be put on the campaign payroll. His exact words were: “We’ll all get our payoff in the end.” How prophetic!

As if Mooney Giancana had not injected enough drama into the year 1960, he embarked on yet another adventure while waiting for the November election. Apparently, the election fix was not a large enough marker to have over the Oval Office, especially if Joe Kennedy’s kid lost the contest. Thus, Mooney, at Johnny Rosselli’s instigation, concluded that the only sure guarantee of the Outfit’s hold over the next president was its participation in a fanciful White House-CIA scheme to murder Cuban leader Fidel Castro.

1. Chicago historian Ovid Demaris described how Roma operated the club: ’One of Roma’s first acts as general manager of the Chicago Playboy Club was to award the garbage collection to Willie “Potatoes” Daddano’s West Suburban Scavenger Service . . . Attendant Service Corporation, a [Ross] Prio-[Joseph] DiVarco enterprise, was already parking playboy cars, checking playboy hats, and handing playboy towels in the rest room. Other playboys were drinking [Joe] Fusco beers and liquors, eating [James] Allegretti meat, and smoking [Eddie] Vogel cigarets.’

2. An FBI telex of March 10,1960, notes Rosselli’s flight to New York from L.A. The Bureau guessed that Johnny was there on film production business.

3. Confidential government sources reported to Johnny Rosselli’s biographers that “Mr. Smooth” also had a history of cooperation with the federal government. According to officials of the International Cooperation Agency, Rosselli assisted the CIA-backed Standard Fruit Company in the 1957 ouster of Guatemala’s president, Castillo Armas.

4. A third corroboration for the Kennedy luncheon at Young’s is a contemporaneous handwritten record, names included. Regretfully, the material is stored in an off-limits portion of a federal archive. The author was made aware of it through an employee with access. Out of consideration for the well-being of both the employee and the record, the location cannot be disclosed. There is currently an effort to force an opening of the collection that holds the material.

5. Senate investigator Walter Sheridan, and separately, journalist Dan Moldea, have detailed how California congressman Allan Oakley Hunter played the go-between in the Nixon-Hoffa dealing. With assurances from Nixon that he would, if elected, ease Hoffa’s legal harassment, Hoffa saw to it that the Teamsters executive board endorsed Nixon. Close Hoffa aide Ed Partin has stated that he witnessed Hoffa deliver $1 million to the Nixon war chest, half of it collected from New Orleans boss Carlos Marcello, and half from New York/New Jersey mobsters. Marcello rightfully feared deportation in a Kennedy administration.

6. Completed in 1930, the 4,023,400-square-foot Mart was the largest office space in the world until the construction of the Pentagon.

7. According to the late talk-show host Morton Downey Jr., the son of Joe’s closest friend and business partner, Irish tenor Morton Downey Sr., Joe Kennedy and Downey (accompanied by Mort Jr.) would often meet at Frank Costello’s Waldorf-Astoria headquarters, where the foursome regularly went for haircuts.

8. The videotape is in the author’s possession.

9. Adamowski was a strait-laced anticorruption crusader who had broken from the Democratic ranks in protest of Daley’s ties to both the underworld and the party machine’s patronage gravy train. In 1959, Adamowski unearthed a $500,000-per-year traffic-ticket-fixing scheme in the city’s traffic court, with the kickbacks ending up lining the pockets of Daley appointees. At the beginning of 1960, Adamowski had broken the Summerdale Scandal, in which a twenty-year-old burglar admitted that, for two years, twelve Chicago policemen had assisted in his wholesale thievery by acting as lookouts, then using their patrol cars to cart off the goods to be fenced. cont’d overt cont’d When the dust settled, eight cops were imprisoned, and many more suspended. Also caught up in the fallout from the Summerdale Scandal were numerous Outfit-controlled police, who were being summarily reassigned. Concurrent FBI wiretaps disclosed that the thief, Richie Morrison, was the nephew of the mistress Curly Humphreys had taken on the lam with him to Mexico three decades earlier, Billie Jean Morrison. The Bureau also heard that after Morrison was arrested, Curly attempted to funnel money to Billie Jean to silence her talkative nephew. “This is gonna be the biggest thing that ever hit the mayor,” Humphreys predicted. “This kid has got thirty coppers, he has them all set up . . . This will spread like wildfire.” The Genius then pronounced his decree: “Well, boys, I don’t see how the Democrats can win with this scandal. This will whip the hell out of this administration... I hate to do it but we got to watch out for this administration.” As Humphreys told an associate at Celano’s tailor shop, “We can tell [the aunt] to give him five thousand dollars and tell him to claim he was hypnotized.”

10. Years later, Kennedy’s wife, Rose, observed, “Joe had a genius for seeing something and knowing it would be worth something more later on. And with the Mart, he was absolutely right... it skyrocketed in value and became the basis for a whole new Kennedy fortune.”

11. Incredibly, there is evidence that even mob-hating Robert Kennedy may have acknowledged the need to court the crime bosses. Award-winning investigative journalist for Newsday Mike Dorman was told by New Orleans Mafia don Carlos Marcello that RFK traveled to the Crescent City, attempting to convince Marcello to deliver the Louisiana delegation to JFK in the Democratic convention. Marcello turned him down, politely informing him that he was backing Lyndon Johnson. Marcello was convinced that this was the genesis of Bobby’s later obsessive crusade against both him and LBJ.

12. Phil Regan would go on to spend a year in jail for bribing a California zoning commissioner, eventually pardoned by California governor Jerry Brown.

13. Although Alo turned down acting as liaison with Giancana, some evidence suggests that Meyer did his bit to help in the election. In a letter written by a former employee of Las Vegas’ Desert Inn Hotel to its owner, Moe Dalitz, the employee, Annie Patterson, had, in 1966, fallen upon hard times and wrote the former Cleveland-based gambler for financial assistance. In her letter, Patterson firmly links Joe Kennedy to Lansky. In the context of her letter, it is clear that Patterson had gotten to know Joe Kennedy at either the Desert Inn or the Flamingo. It is also clear that Kennedy had wronged Patterson in some way. She alludes to a letter she had written, in retribution, to J. Edgar Hoover that instigated wiretaps that somehow incriminated the Kennedys. She further states that the material was locked away because “apparently none wanted to cross with the Kennedys.” The letter continued: “Meyer Lansky was not the one who I knew. Mr. Kennedy told me about him and all the money that he parlayed from Las Vegas for the presidential campaign . . . I did not feel welcome to write to the Flamingo because Mr. Kennedy went around me and at no time was I paid one penny for my work; nor would I have ever contacted Mr. Lansky because I know (or had been told by Mr. Joseph Kennedy) that they were very close friends; in fact, it was Mr. Lansky that caused wiretapping to start there in the first place. He continued to “needle” Mr. J. Kennedy that Mr. K. was not receiving his full share of the take and why - so the Kennedy clan got together. I sincerely don’t believe that Mr. Lansky had any idea of the damage that he was causing anyone because he wanted to be socially accepted by the Kennedy clan . . . I feel sure that if I contacted the kind-hearted Lansky and requested help, I would receive it but that is against my principals. He is a friend of Mr. Kennedy -I have never met him personally but I saw him from a distance in Miami Beach. (They met me there for an appointment.)” The Lansky election allegations appear to be supported by an FBI memo from a confidential friend of Lansky’s noting that prominent Miami hoodlums “are financially supporting and actively endeavoring to secure the nomination for the Presidency as Democratic candidate, Senator John F. Kennedy.”

14. The key source of the information was Marcello’s bagman Jack Halfen. Marcello had been paying Johnson, and many others to kill legislation that threatened slot-machine and wire-service gambling. For ten years, according to Halfen, Johnson was paid $100,000 per year. Johnson’s voting record reflects that Marcello’s money was well spent. Halfen initially gave many of the details (and proof) to award-winning journalist Mike Dorman in his book Payoff. More details were unearthed in my first book, Live by the Sword. Interestingly, when I obtained Halfen’s list of bribe recipients, near the top of the list was Supreme Court justice Tom Clark, the same Tom Clark who, as attorney general, played such a key role in the early parole of the Outfit’s Hollywood seven.

15. Later, during JFK’s presidency, Joe again called on Huie. This time the author was given a briefcase full of cash by the patriarch to deliver to Governor George Wallace, during his segregationist standoff against the Kennedy brothers. According to Huie’s protege, reporter Mike Dorman, Joe thought he could pay Wallace to “just go away.”

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