Joseph P. Kennedy did more than invest his time and money in his unrelenting drive in 1960 to elect his oldest surviving son president. He risked the family’s reputation—and the political future of his sons Bobby and Teddy—by making a bargain with Sam Giancana and the powerful organized crime syndicate in Chicago. Joe Kennedy’s goal was to ensure victory in Illinois and in other states where the syndicate had influence, and he achieved it, after arranging a dramatic and until now unrevealed summit meeting with Sam Giancana in the chambers of one of Chicago’s most respected judges. The deal included an assurance that Giancana’s men would get out the Kennedy vote among the rank and file in the mob-controlled unions in Chicago and elsewhere, and a commitment for campaign contributions from the corrupt Teamsters Union pension fund.
Jack Kennedy and his brother took office knowing that organized crime and Giancana had helped win the 1960 election. Just what Joe Kennedy promised Giancana in return is not known, but the gangster was convinced he had scored the ultimate coup by backing a presidential winner. The heat would now be off the Chicago syndicate.
The 1960 presidential election was a cliff-hanger in which John Kennedy defeated Richard Nixon by a final plurality of 118,000 out of more than 68 million votes. Since then, journalists and historians have raised questions about Kennedy’s victory—by fewer than 9,400 votes—in Illinois, one of the last states to report and the one that gave Kennedy his dramatic early-morning triumph. The Illinois election was quickly mired in charges of vote fraud, with Republicans accusing Democrats, led by Mayor Richard Daley, of rigging the returns in Chicago. It was widely known that the mayor, since taking office in 1955, had been controlling returns in state and local elections in Chicago, and that in 1960 he had pressured his precinct captains to produce votes for Kennedy. The allegations of vote fraud did not faze Daley, the archetype of the big-city political boss. He stoically dismissed the charges, telling reporters, “This is a Republican conspiracy to deny the presidency to the man who was elected by the people.”
Allegations of vote fraud were eventually filed against Democrats in eleven states. The Republican Party, after a series of high-level meetings in Washington, decided in late November to send officials on troubleshooting missions to seven of the eleven states—New Jersey, Texas, Missouri, New Mexico, Nevada, South Carolina, and Pennsylvania. Kennedy’s margin in some of these states was so minute—he took Nevada and New Mexico by fewer than 2,500 votes—that any significant pattern of vote fraud could have changed victory to defeat. All the missions were futile.
It was the election in Illinois that captured the nation’s attention. The turnout in Chicago was high, as usual: more than 89 percent of the eligible voters voted, or were recorded as having voted. The city’s Democratic machine had turned out more than 80 percent of the voters in the 1952 and 1956 presidential elections. What was unusual in 1960 was Kennedy’s huge plurality in Chicago, which enabled him to offset a wave of downstate Republican votes. He won Chicago by 456,312 votes, a margin nearly four times as great as his final plurality in the nation as a whole.
These statistics have been repeatedly cited in countless articles and books discussing the election in Illinois, with the assertion usually made that the Illinois vote was less essential, and therefore less dramatic, than was initially thought. Kennedy’s narrow victories in Texas, Michigan, New Jersey, and Missouri, the argument goes, gave him 303 electoral college votes—34 more than he needed to claim the White House. But the fact is that Illinois was essential to Kennedy’s victory. Without the state’s 27 electoral votes, Kennedy would have had a plurality of only 7 votes over Nixon in the electoral college, with 26 unpledged Democratic electors in Mississippi, Georgia, and Alabama threatening to bolt unless they received significant concessions on federal civil rights policy from the Democratic Party. A loss in Illinois would have given those unpledged electors—fourteen of whom eventually did choose to cast their votes for Democratic senator Harry F. Byrd, of Virginia—a huge increase in leverage. They had the power, if Kennedy lost Illinois, to throw the election into the House of Representatives for the first time in the twentieth century.
At the time, Kennedy’s huge Chicago margin was widely considered suspect, even by the newly elected president. “Mr. President,” Kennedy quoted Mayor Daley as telling him on election night, “with a little bit of luck and the help of a few close friends, you’re going to carry Illinois.” That reported assurance caused a furor when it was made public in 1977 by the journalist Benjamin Bradlee, a close Kennedy friend who shared dinner with the newly elected president at Hyannis Port on the evening after the election. Bradlee would assert, lamely, in a later memoir that “Me, I don’t know what the hell Daley meant.” Two grand juries were convened in Chicago after the election, but they ended up indicting only five low-level Democratic Party officials for vote buying and vote fraud. The official investigations continued until July 1961, when a downstate Democratic county judge—in what one journalist subsequently described as “a gross display of partisanship”—dismissed the last of 677 contempt charges that alleged that Democratic precinct workers had intentionally erred in tallying votes. The judge ruled that there was “insufficient evidence” to prove that Democratic Party officials in Chicago had intentionally made errors in counting.
Richard Nixon had no illusions about what happened in Illinois, but he chose not to demand a recount, as some Republican leaders urged him to do. Many Americans considered Nixon’s decision not to contest the legitimacy of the election one of his finest hours. In his memoir, RN, Nixon was candid in admitting that his decision was based on self-interest: “And what if I demanded a recount and it turned out that despite the vote fraud Kennedy had still won? Charges of ‘sore loser’ would follow me through history and remove any possibility of a further political career.”
Nixon was right. The recount in Illinois was in the hands of the Democratic Party, and would not have come close to telling the real story of the election.
Joe Kennedy dealt with the mob out of necessity. As the owner of the Merchandise Mart, he understood as well as anyone the extent to which organized crime dominated the major unions in Chicago in the late 1950s. The Chicago “outfit,” headed by Al Capone, had begun expanding into legitimate business and unions before World War II; by the late 1940s more than one hundred unions were controlled by the mob, providing millions of dollars annually in cash and—equally significant to Chicago’s politicians—a huge manpower base that could be mobilized on demand. The outfit’s labor expert was Murray “the Camel” Humphreys, who was credited in one biography with maintaining personal control over sixty-one unions at the height of the Capone empire.
The Kennedy patriarch’s turn to Giancana for help was all the more risky because of Jack and Bobby’s known antagonism to organized crime, stemming from their involvement in the late 1950s with the Senate special investigating committee on labor racketeering, officially known as the Select Committee on Improper Activities in the Labor or Management Field. Robert Kennedy had been especially aggressive and insulting in his first known encounter with Giancana, during the gangster’s testimony before the committee in June 1959. Giancana took the Fifth Amendment and made a point of smiling at each of Kennedy’s questions. “I thought only little girls giggled, Mr. Giancana,” Kennedy remarked at one point. The exchange made huge news.
Joe Kennedy, according to the family biographers, bitterly objected to his sons’ involvement with the Senate Rackets Committee. Senator John Kennedy was one of four Democrats on the committee, whose chairman was John L. McClellan, the Democrat from Arkansas. Robert Kennedy was the committee’s chief counsel, and the driving force behind the high-profile investigations into labor racketeering, which placed special emphasis on the activities of James R. Hoffa, head of the Teamsters Union. In his 1978 biography, Robert Kennedy and His Times, Arthur Schlesinger described Joe Kennedy as being “deeply, emotionally opposed” to his sons’ participation on the committee. Schlesinger described the senior Kennedy as believing that “an investigation … would not produce reform; it would only turn the labor movement against the Kennedys.… Father and son [Robert] had an unprecedentedly furious argument.” Joe Kennedy then asked his good friend Supreme Court Justice William O. Douglas to intervene with Bobby. It didn’t work, according to Schlesinger. Douglas told Joe that Bobby felt that the committee represented “too great an opportunity” to give up.
Joe Kennedy, fearful of losing union support in 1960, understood that labor unions, honest or not, could supply political campaigns with money and foot soldiers—and Jack, so his father believed, would need a great deal of both to win the presidency. Hoffa, as hard-boiled as Bobby Kennedy, was sure to do all he could to stop JFK in 1960. Joe Kennedy was convinced that he had to make a deal in Chicago, and he turned for help to an old friend, William J. Tuohy, chief judge of the Circuit Court of Cook County (Chicago). Tuohy, who died in 1964, was given an assignment: to set up a clandestine meeting between Joe Kennedy and Sam Giancana, known as Mooney to his colleagues. Tuohy, who had served the state’s attorney of Cook County before being elected to the bench in 1950, did not know Giancana. But a former protégé from his days in the state’s attorney’s office, Robert J. McDonnell, was then one of the mob’s leading attorneys.
“Tuohy asked me to come to his chambers,” the seventy-one-year-old McDonnell recalled in an interview for this book. The call came, McDonnell estimated, in the winter of 1959–60. “I went. We chatted. He said, ‘I don’t know how to pose this question. Do you know Mooney Giancana?’ I said yes. He said, ‘How do you suggest that I arrange a meeting between Mr. Giancana and Joseph Kennedy?’” McDonnell gave the judge the name of a local politician with close ties to the syndicate. A few days later, McDonnell was summoned to a meeting with Giancana at the Armory Lounge in suburban Forest Park, and was told that the meeting with Kennedy was going to happen in Tuohy’s courtroom. “Can you guarantee this will be a very, very private meeting?” Giancana asked, according to McDonnell.
The jittery Tuohy invited McDonnell to attend. “So,” McDonnell continued, “I showed up about five o’clock. The courts were just getting out, and darkness was enveloping the courtroom. It’s always melodramatic at that time of day.” McDonnell entered the judge’s chambers and was introduced to Joe Kennedy. After twenty minutes or so, McDonnell said, “we heard footsteps come into the courtroom, and in walked Mooney Giancana” and one of his associates. McDonnell made the introductions. “The three of them sat down. Judge Tuohy and I left the chambers. We went over to the jury box in the courtroom. I remember Judge Tuohy saying to me, ‘I’m glad I’m not privy to this.’ He was very dispirited. This was a man of the highest integrity, and he was asked to do a favor for Joe Kennedy. And I know that it repulsed him.” McDonnell and Tuohy left the courthouse while the meeting between Kennedy and Giancana was still going on.
He later heard from his clients, McDonnell said, that Kennedy “was obsessed with the election of John Kennedy—absolutely obsessed with it. I don’t know what deals were cut; I don’t know what promises were made. But I can tell you, Mooney had so many assets in place. They were capable of putting drivers in every precinct to help out the precinct captains, to get the voters out. And they had the unions absolutely going for Kennedy. I realize that today the unions don’t vote as they’re told to vote, but in the days of 1960 they did. Mooney assisted in all of this.
“There was no ballot stuffing,” McDonnell added. “I’m not suggesting that. They just worked—totally went all out. He [Kennedy] won it squarely, but he got the vote because of what Mooney had done. I’m convinced in my heart of hearts that Mooney carried the day for John F. Kennedy.”
McDonnell, a Notre Dame graduate who was seriously wounded in World War II, was in financial trouble by the time of Tuohy’s call for help. His success as a trial lawyer in the state’s attorney’s office was overwhelmed by his addictions to gambling and alcohol; by the early 1950s, he was constantly in debt and little more than a paid mouthpiece for the outfit. In 1966, he was found guilty of passing forged money orders; his license to practice law was suspended but not revoked. McDonnell renewed his legal practice in the early 1980s but lost his license after a second conviction for the attempted bribery of an electrical workers union official. In 1983 McDonnell married Antoinette Giancana, Sam Giancana’s daughter; they were divorced in 1995.
McDonnell’s account was buttressed by interviews for this book demonstrating that Joe Kennedy did have a long-standing, if little-known, friendship with Judge Tuohy. Tuohy’s two sons, Patrick and John, both lawyers, told me that they knew nothing about a meeting involving their father and Sam Giancana, but they recalled Joe Kennedy—“the Ambassador,” as he liked to be called—at casual dinners in their home after the war. John Tuohy told me that his father and Joe Kennedy attended a Chicago Bears football game together in 1947. Both Tuohys also said they knew McDonnell as a lawyer who, as Patrick put it, had fallen “off the normal track.” Patrick added, “I’m pretty sure my father knew him.”
Another witness to meetings between Kennedy and Tuohy was Thomas V. King, who was general manager of the Merchandise Mart in 1960, and worked directly under Kennedy. King said in an interview for this book that Kennedy and Tuohy “were very, very close.” It was his understanding, King added, that “Joe took care of him, too—helped him out financially.” King witnessed a number of meetings between Kennedy and Tuohy at the Merchandise Mart, he said, but did not hear their discussions. “I was an employee then, in the background,” King explained.
Robert McDonnell’s firsthand testimony is compelling, and evocative of a similar account of Joe Kennedy’s insistence on a meeting with Giancana which appeared on national television in 1992, in a miniseries produced for CBS by Tina Sinatra, Frank’s daughter. In the script for one episode of the dramatized series, the actor playing Joe Kennedy tells the actor playing Sinatra that “the best thing you can do for Jack” is to “go to those people” who “control the [Teamsters] union.” Sinatra, in a subsequent scene, relays the request to Sam Giancana and gets his approval.
In a 1997 interview for this book, Tina Sinatra acknowledged that her father had provided the information for the scenes and had explicitly approved the script. Sinatra, in effect, broke faith with a long-held secret in an effort to provide some pizzazz for his daughter’s show: he publicly admitted for the first time that he played a role in brokering Giancana’s support for Jack Kennedy in 1960.
“What I understood,” Tina Sinatra told me, “was that a meeting was called” late in 1959 at Hyannis Port. “Dad was more than willing to go. He hadn’t been to the house before. Over lunch, Joe said, ‘I think that you can help me in West Virginia and Illinois with our friends. You understand, Frank, I can’t go. They’re my friends, too, but I can’t approach them. But you can.’ I know that it gave Dad pause. But it still wasn’t anything he felt he shouldn’t do. So off to Sam Giancana he went.” Her father arranged to meet Giancana on a golf course, Tina said, away from Giancana’s seemingly constant FBI surveillance. Sinatra told him, Tina said, “I believe in this man and I think he’s going to make us a good president. With your help, I think we can work this out.”
Joe Kennedy’s goal, Tina said, was “to assure the wins in Illinois and West Virginia—you know, getting the numbers out, getting the unions to vote.”
Being a middleman seemed logical to her father, Tina said. “The notion that Joe would go to Sam Giancana was out of the question, for obvious reasons. Frank’s affiliation with Sam Giancana and other mobsters—we all understand that. The Mafia was very smart. They knew that power and control would keep this country together. Now I don’t think that they should have been out shooting each other, but they did. By the thirties and forties, when Dad was in the business, they were controlling the nightclubs. They were controlling the entertainment world. They were a motivated bunch. The power of an entertainer and the power of a mobster—it’s all very much a part of America. They were all from the same neighborhoods. My dad grew up with gangsters next door. He was living with them. They were his personal friends, and he’s not going to cast away a friend. The great vein through Frank Sinatra is loyalty. There is an absolute commitment to friends and family. It’s very Italian and probably gave him a little more in common with the mob types.”
Furthermore, Tina said, “these weren’t people that Joe [Kennedy] didn’t know. He had these relations as well. My grandmother called him ‘that rum-running son of a bitch.’ They did use the underworld to put their Golden Boy over the top—conduit, Frank Sinatra. They [didn’t] hesitate to ask for favors; the Kennedys were very able to ask for anything they needed. And I think they were accustomed to getting it. Everybody was duped,” she added, when Robert Kennedy, as attorney general, targeted organized crime as eagerly as he had done for the Senate Rackets Committee.
Frank Sinatra, Tina said, was enthusiastic about Jack Kennedy. “Dad felt that Jack Kennedy was a breath of fresh air. He said he hadn’t been as excited about an election since Roosevelt, whom he also campaigned for.” What is generally not known about her father, Tina Sinatra told me, is the extent to which politics was always a part of his life. “He was born into a family that was very politically motivated,” she said, especially his mother, Dolly, who was a local Democratic campaign worker in Hoboken, New Jersey. “Dad says that he was carrying placards for candidates when he couldn’t read what was on the signs. Politics were run out of the kitchens” in those days, Tina added. “I remember he taught me” about “potholder campaigns. They’d give gifts to the woman of the house, because she would be the one who would be making certain the voters voted.”
Jack Kennedy was special, Tina said. Her father was strongly attracted to Kennedy’s “lifestyle. And his power. I know they had a lot of fun together.” Both before and after winning the presidency, Kennedy especially enjoyed weekend visits to Sinatra’s home in Palm Springs, with its routine womanizing. “It’s not as though the president and Dad would meet to play golf,” Tina said. “Their small circle of friends would come together and have a good time. It was a place to escape to. I was never, ever there. That was not a weekend you brought the kids into.”
Her father, Tina added, “was a happy bachelor-type guy. He was single. Jack Kennedy wasn’t.”
J. Edgar Hoover’s FBI had picked up some hints of the preelection bargaining between Kennedy and the Chicago outfit, but it could not make them public because of the way the information was gathered. Beginning in the late 1950s, FBI agents had begun installing bugging devices in organized crime hangouts across the nation, without any specific court authorization to do so. Three bugs were put in place in Chicago. One of them produced many conversations—sometimes in Sicilian dialect—both before and after November 1960, in which Sam Giancana talked about an election deal with Joe Kennedy. In his 1989 memoir, Man Against the Mob, William F. Roemer, Jr., who was a special agent in the FBI’s Chicago office in the early 1960s, revealed that Giancana had been overheard on a still-unreleased FBI wiretap discussing a straightforward election deal: mob support in return for a commitment from the Kennedy administration “to back off from the FBI investigation of Giancana.” Transcripts of these conversations, with the source concealed, were circulated, in some cases during the campaign, on a need-to-know basis throughout the Justice Department.
Giancana also bragged, off microphone, about his influence. In My Story, a 1977 memoir by Judith Campbell Exner, the Los Angeles woman who was sexually involved with Kennedy in the early 1960s while also meeting with Giancana, the mob leader is quoted as telling her, “Listen, honey, if it wasn’t for me your boyfriend wouldn’t even be in the White House.”
Giancana was not exaggerating. In a 1997 interview for this book, G. Robert Blakey, a former special prosecutor for the Justice Department, said that the FBI wiretaps, many of which have yet to be made public, confirmed that the Chicago syndicate used all its muscle to support Kennedy. “There has been a problem with vote fraud in Chicago really since the turn of the century,” said Blakey, who obtained access to the wiretaps in the late 1970s while serving as chief counsel to the House Assassinations Committee. The FBI bugs in Chicago, he told me, demonstrated “beyond doubt, in my judgment, that enough votes were stolen—let me repeat that—stolen in Chicago to give Kennedy a sufficient margin that he carried the state of Illinois.” The electronic surveillance also showed that organized crime’s control of the voting was far more extensive than has been previously known, Blakey said: Giancana was overheard before one election discussing the specific number of votes a corrupt Illinois congressman was to receive.
“The surveillance in Chicago also establishes that money generated by the mob was put into the 1960 [national] election,” Blakey told me. The funds traveled from the singer Frank Sinatra, who was a close friend of Sam Giancana’s, “to Joe Kennedy. Can you say mob money made a difference?” Blakey asked. “My judgment is yes.” In return, Giancana and his colleagues were convinced, Blakey told me, that “the Kennedys would do something for them”—reduce FBI pressure on their activities.
No two men could have emerged from backgrounds more different than those of Jack Kennedy of Hyannis Port and Palm Beach and Sam Giancana of Chicago. But the men had much in common. Each was obsessed with women; each was fascinated by Hollywood and was found fascinating in return; each learned how to operate in secrecy; and each could rigorously compartmentalize his life. Giancana was a foul-mouthed Mafia murderer who took on a top-secret mission for the CIA in 1960 and 1961 and never talked publicly about what he did. Kennedy was a brilliant politician who could openly espouse the idealism of a New Frontier and the Peace Corps while being deeply involved in a world of secret escapades that could destroy his career.
Giancana, born in 1908, began his criminal career as a hit man for Al Capone in the area known as Little Italy or The Patch, just west of downtown Chicago. By age twenty, Giancana had reportedly murdered dozens of men on his way to gaining control of the Chicago Mafia. His first conviction, for auto theft, came at the age of seventeen; he was arrested three times in connection with murder investigations by the time he was twenty. In all, Giancana was arrested sixty times during his career. By the late 1950s, his operation was skimming millions of dollars off mob-dominated gambling casinos in Las Vegas and in Havana, Cuba, and it had both political and economic control of at least six heavily populated wards in Chicago. The Chicago Mafia also exercised direct control over mobster and Teamsters Union activities in Cleveland, St. Louis, Kansas City, Las Vegas, and Los Angeles.
“Giancana was just a killer, that’s all,” Sandy Smith, the former chief investigative reporter for Time magazine who spent twenty years covering organized crime in Chicago, recalled in an interview for this book. “And he was proud of it. As a boss, if there was a problem, he’d listen to a very brief description and then say, ‘Hit him! Hit him!’ There were a lot of hits.” The mob boss “couldn’t really talk to you,” Smith told me. “Giancana would curse and scream and howl and try to intimidate you. He was, in almost every respect, a savage.”
Nonetheless, Giancana was immensely popular in Hollywood. His biographers usually date his ties there to the mid-1950s, a time when the Chicago mob was migrating to the West Coast. Yet Giancana’s daughter, Antoinette, in her 1984 memoir, Mafia Princess, told of her 1949 trip to Hollywood as a teenager, during which a major producer fell all over himself giving her a guided tour of the Metro-Goldwyn-Mayer studio. “I was treated with as much respect as if I had been one of the studio’s superstars,” she wrote. By the late 1950s, Giancana, often identifying himself as Sam Flood, was openly socializing in Las Vegas with the entertainers, who were paid enormous sums to perform at hotels whose casinos he controlled. His close friend was Frank Sinatra, and Giancana became a fixture among Sinatra’s famed Rat Pack, the group of singers and comedians who moved easily through Hollywood, Democratic politics, and organized crime. The actor Peter Lawford, who married Patricia Kennedy in 1954, was a charter member of the clique. In 1960 Giancana began what would become a long-term romance with Phyllis McGuire, one of the three singing McGuire Sisters, then at the top of their career. Bill Woodfield, a Hollywood photographer who was on full-time assignment for Frank Sinatra, recalled in a 1995 interview for this book that during the heyday of Rat Pack glamour, Giancana began showing up almost every day on the set of a movie in which McGuire and Sinatra were starring. Giancana sat next to Woodfield, who was to shoot still photographs of each scene. “I never photographed Sam,” Woodfield told me, “although I took hundreds of Phyllis. A photographer knows what not to shoot.”*
Further direct evidence about a deal between the Kennedy family and Sam Giancana was provided for this book by Jeanne Humphreys, the second wife of Murray Humphreys, a close colleague of Giancana’s. Humphreys, a Welshman who died in 1965, was considered to be the brains and a dominant force behind the Chicago mob, but he was barred from formally becoming its leader because he was not Sicilian. Jeanne Humphreys, who now lives alone and under a different name in the suburbs of a major southern city, had been a teenage bar girl when she began an affair with her husband-to-be in the late 1940s. She was married to the dapper gang leader, who was famed among Chicago journalists for his style and intelligence, from 1957 until 1962. “Murray told me everything,” Mrs. Humphreys said. “I was stuck in the middle of it all. He had to tell me.
“I know all about the Kennedys—the election,” she told me. “It consumed our lives that year [1960].” In her account, Humphreys initially resisted Giancana’s pleas for a political commitment to Kennedy, essentially because Humphreys had himself done bootlegging business with Joe Kennedy during Prohibition and did not trust him. “Murray called him a four-flusher and a double-crosser,” Jeanne Humphreys told me. Kennedy was involved in smuggling liquor from Canada into the Detroit area, Humphreys told his wife, “and hijacked his own load that had already been paid for and took it and sold it somewhere else all over again. He [Humphreys] never stopped talking about what a jerk [Kennedy] was.”
The question was finally put to a vote among Giancana, Humphreys, and three other Mafia leaders in Chicago—Paul Ricca, Anthony Accardo, and Frank Ferraro. Humphreys was the only one to vote against the commitment to Kennedy. “He hated having to go along with the outfit’s vote to back Kennedy,” Jeanne Humphreys recalled. “It was a constant source of aggravation for him. If he was outvoted on something, he was outvoted by the Italians. He’d say the spaghetti eaters and spaghetti benders stuck together. But he went along. The guarantee was that the investigators would lay off the outfit. That was the assurance [they] got from Joe Kennedy.
“I was an airhead,” Mrs. Humphreys added. “I didn’t know then that a president could be elected on the whim of Chicago mobsters. In my ignorance, I thought majority ruled.”
The reminiscences of Jeanne Humphreys were confirmed by a handwritten diary she compiled during her years with Humphreys. The diary, made available in part for this book, provides a seemingly candid and often droll account of her husband’s role in the 1960 election. “It’s ironic,” one entry noted, “that most of the behind-the-scenes participants in the Kennedy campaign could not vote because they had criminal records.” Electoral politics, Jeanne Humphreys wrote at another point, “was a bunch of crooks run by a bunch of crooks.”
A previously unpublished FBI biography of Murray Humphreys covering the years 1957 to 1961 further supports her account. The FBI file, dated May 17, 1961, and also made available for this book, describes the little-known Humphreys as “being one of the prime leaders of the underworld in the Chicago area.” By the mid-1950s, it adds, Humphreys, Giancana, and the voting mobsters were “members of what might be called the governing board of organized criminals in the Chicago area.” Humphreys’ areas of responsibility included “the maintenance of contact with politicians, attorneys, public officials, and labor union leaders in order to influence these people to act in behalf of the interests of the underworld.” The FBI specifically noted Humphreys’ close ties to the Teamsters Union and depicted him as “the go-between” for organized crime and the Teamsters in their joint effort to become entrenched in the lucrative Las Vegas hotel and gambling business.
Sandy Smith, who interviewed Humphreys several times while working for the Chicago Sun-Times in the early 1960s, described him as “the fixer” for the Chicago syndicate. “Humphreys had the ability to go into a judge’s chambers and talk to a judge,” Smith told me. “He could go into the Department of Justice and talk to lawyers there. He could talk to the Internal Revenue Service. Humphreys was a hard guy to dislike.”
Humphreys had been one of attorney Abe Marovitz’s clients in the years before Marovitz became a Chicago judge. “He was like a good businessman,” Marovitz told me. “His talk was different than most hoodlums. He wasn’t a vulgar guy. He controlled unions, lots of unions,” and “they gave substantial money to folks in politics.” But Humphreys’ influence was not based on his appearance, the retired judge noted: “It was strictly muscle. Either you went along with him, or you found yourself shot in the head or someplace. It was just one of those tough things in those days.”
Jeanne Humphreys’ firsthand descriptions of her husband’s attempts to corrupt the electoral process are consistent with Smith’s view and the FBI file. In her account, the mob’s endorsement of Jack Kennedy and its determination to get him elected led to two two-week meetings in Chicago: one in July, before the Democratic convention, and one in late October, before the election. During those meetings, Humphreys and his wife were sequestered in a suite at the Hilton Hotel, as Humphreys coordinated the politicking. “We weren’t staying there,” Mrs. Humphreys said of the Hilton. “We were stuck there—two weeks at a time. I was not allowed to go out, as we were sure we were being surveilled. This was very secret. Murray’s phone rang off the hook. Always politicians and Teamsters.
“This was the whole country,” she added. “The people coming to the hotel were Teamsters from all over. The Chicago outfit was coordinating the whole country—Kansas, St. Louis, Cleveland. They were coming in from everywhere, then fanning out across the country.” The mob-dominated union officials were coming to the hotel suite, Mrs. Humphreys explained, “to get instructions from Murray. When we went back in October, it was just a follow-up, to see that everything went the right way. They got Kennedy elected.”
A diary entry provided more detail of Humphreys’ careful planning. “Lists were everywhere,” Mrs. Humphreys wrote.
Murray was arranging lists in categories of politicians, unions, lawyers and contacts.… I could see the list had at least thirty to forty names.… I didn’t have time to think or care about the election. It was a foregone conclusion anyway and I didn’t doubt that Murray’s endeavors would succeed. He was so confident and low key about electing the president that I adopted the same attitude.… He didn’t expect any accolades and was content to see Mooney [Giancana] bask in the glory and praise.
Government files released under the Freedom of Information Act show that the FBI learned almost immediately that Humphreys had registered, under the name of Fishman, at the Hilton Hotel in Chicago in late October 1960, just as Jeanne Humphreys recounted. Humphreys, aware that he was constantly being monitored, seemed to go out of his way to be misleading. In one telephone call intercepted while he was at the Hilton, the FBI quoted Humphreys as casually telling an associate, “Since I heard all the Irish are voting for Kennedy, I’m voting for Nixon, the Protestant.” Nothing in the FBI documents, as made public, linked Humphreys with the Kennedy campaign.
Jeanne Humphreys, who was in her late sixties when she spoke to me and being treated for cancer, said she first learned of the Kennedy connection when she accused her husband of “partying with the celebrities” while on a trip to the West Coast. He told her, “No, we’re working. Sam is golfing with Joe Kennedy. They’re doing business.” Frank Sinatra had been the “middleman” in arranging the Kennedy-Giancana golf dates. Humphreys told her that Joe Kennedy had promised “to lay off the mob” in exchange for political support from the Giancana outfit.
Mrs. Humphreys recalled that various locals belonging to the Teamsters Union, headed by Jimmy Hoffa, were under pressure to help get out the vote for Kennedy, legally and otherwise. At the time, Hoffa had been instrumental in putting the huge assets of the Teamsters pension fund behind the Chicago outfit’s expansion into the gambling and hotel business in Las Vegas: millions of dollars had been lent to organized crime front men, with millions more in the pipeline. But Hoffa, who became an avid supporter of Richard Nixon, posed a special problem for Humphreys during the election campaign because he became convinced that “by loaning union money to the outfit … he was contributing” to the election efforts of the hated Kennedys. Mrs. Humphreys overheard Hoffa indignantly complaining to her husband after one meeting in Florida that “my members’ money is … going to get that son of a bitch elected.” Humphreys later told her that Hoffa “is a hard man to sell. I have to sell that Robert Kennedy to Hoffa.”
As the mob did its politicking, J. Edgar Hoover was sifting through his agents’ reports and keeping up-to-date files. Joe and Jack Kennedy were careful with Hoover as they were with few other men; Hoover, they knew, did not approve of the candidate’s personal life.
By the late 1950s, according to Cartha DeLoach, one of Hoover’s deputies, Joe Kennedy and the FBI director had become friends. “Two big men who felt it necessary to know each other,” DeLoach told me in an interview. “They both had the same conservative politics. Hoover catered to him, to some extent, and Joe Kennedy catered to Mr. Hoover, knowing of the FBI’s capabilities insofar as getting information. Not using it for blackmail purposes,” DeLoach insisted, “but getting it and having it in files. Strange as it may seem to some people today, who constantly castigate Hoover as an individual who leaked information, who extorted in order to save his job and to protect the FBI, he had a deep sense of loyalty to the presidency.”
Hoover, for reasons not clear, chose to pretend early in 1960 that he knew little about Jack Kennedy when he ordered DeLoach to review the files. “He called in the following day,” DeLoach told me, “and I told him Jack had quite a relationship with Inga Arvad and other sexual escapades. And that, frankly, while he was somewhat of a bright individual, he had a very immoral background. Hoover told me, ‘That is not right. You have misinterpreted the files. You’re talking about the older brother of John F. Kennedy. Go back and recheck those files.’ When he called back, I was able to tell him, ‘I am not wrong. This is the man who is a candidate for the presidency.’ That was the first that Hoover knew about him. Hoover knew nothing about the sexual background until we checked the files.” Hoover was troubled by the files, DeLoach said, because “he did feel that the presidency should be a very dignified office, representing the people of the United States, the strongest nation in the world. Jack Kennedy and his constant acts of immorality certainly offended Hoover.”
By 1960 the FBI director had become a genius at intimidating politicians. He was born in 1895 in segregated Washington, the youngest of four children, and grew up in a solidly middle-class Protestant environment. A stutterer in his youth, Hoover went into adulthood with a series of idiosyncrasies and obsessions that tormented those who worked under him. FBI agents had to meet Hoover’s standards of dress and physical appearance; sweaty palms or a colored shirt could lead to a dismissal. The agents learned not to tell the director what he did not want to know. Hoover sought to control those above him—the presidents and members of Congress to whom he reported—through the secret dossiers he kept in his office. Many of those files were reportedly destroyed after his death, in 1972.
After working his way through law school, Hoover found his first significant job in the Alien Enemy Bureau of the Justice Department, where he dealt with foreigners accused of disloyalty. By 1919 he was the Justice Department’s expert on radicalism and aliens, and in 1920 he took part in the infamous Palmer Raids against suspected communists, which led to more than four thousand arrests. Throughout his career, Hoover remained obsessed with rooting out communists, socialists, and other suspected subversives from American society; his concern was not only for what the radicals did but for what they thought.
In 1924 Hoover was appointed head of the Bureau of Investigation, which later became the FBI, and he moved brilliantly to increase the size, skill, and morale of the agency. He was one of the first to push for the establishment of a national fingerprint center, which revolutionized crime fighting. He also understood the value of public relations. By the mid-1930s, Hoover was constantly striving to personify himself, and his FBI, as being in the forefront of the war against crime, stopping such killers—amid front-page fanfare—as Machine Gun Kelly and John Dillinger. He began in those years what would become three decades of close cooperation with Hollywood, leading to a series of wildly popular “G-man” movies: one, starring James Cagney, fixed Hoover’s public image as the nation’s foremost crime fighter. In 1936, with World War II looming, President Roosevelt authorized Hoover to investigate Nazi and communist subversion in the United States, giving the FBI the right to become entrenched in all areas of domestic surveillance. Hoover expanded the FBI’s use of bugging devices and wiretaps—and also expanded his personal intelligence-gathering on politicians, public figures, and journalists.
Hoover’s hypocrisies and insecurities became more pronounced as his prestige and authority grew. For more than thirty years he took vacations with Clyde Tolson, the FBI’s assistant director, who maintained an apartment close to Hoover’s home. The two men went on at least two extensive vacations a year—never publicly depicted as such—to swanky resorts in Florida and California, where Hoover indulged his fondness for racetrack betting. Hoover’s favorite key lime pie was regularly flown at government expense from Florida to Washington. Rumors about the two bachelors and their personal relationship have persisted until today. Visitors to the Hoover home were astonished to find that the prudish FBI director, who constantly inveighed against what he called the decline of public morality among America’s youth, had installed a gallery of nude photographs in the basement rec room, including one of Marilyn Monroe. Over the years, FBI agents spent thousands of hours maintaining and improving his home. By 1960, as Kennedy campaigned for the presidency, Hoover was insisting that when outside Washington he be driven only in new black Cadillac sedans, which had to be immaculately clean. The drivers were instructed to plan their routes with no left turns—a Hoover edict issued after his car was struck while turning left. When on the road, agents were required to reserve suites only in Hoover-approved hotels, which provided the specified bed, mattress, and down pillows.
Like Jack Kennedy, Hoover knew few limits.
Joe Kennedy learned all about Hoover’s power, and his obsessions, during his disastrous prewar opposition to FDR’s determination to wage war against Nazi Germany. Kennedy had worked hard since then at buttering up the FBI director. His role as a special service contact for the FBI ended when the program was suspended after the war; he was reinstated in 1950 by Hoover as one of two such agents in Boston. At the time, an FBI letter described Kennedy as having “innumerable contacts in the international diplomatic set” and added that he “has expressed a willingness to use his entree into those circles for any advantage the Bureau might desire.…”
No amount of flattery was too much, as Joe Kennedy realized. Kennedy’s FBI files, released under the Freedom of Information Act, are full of praise for Hoover in letters and statements from father, sons, and daughters. One postwar FBI report quoted Eunice Kennedy as telling colleagues at a Conference on Citizenship in Boston that her father had recently met with Hoover and “was very much impressed with the administrative organization and the operation of the bureau.” Jack Kennedy, after his election to the Senate, was quoted in a confidential FBI report to Hoover that said he believed “the FBI to be the only real Government agency worthy of its salt and expressed his admiration for your accomplishments.” In 1953 Joe Kennedy was appointed to serve as a member of a federal commission on government efficiency, which, while accomplishing little, did complete a study on defense spending. The elder Kennedy, according to FBI files, managed to relay word to Hoover expressing “shock” at the extent of Pentagon waste and mismanagement. “The deeper he delves into the matter, the more he appreciates your work,” Hoover was told.
Joe Kennedy’s courting of Hoover paid off in 1956, when he was nominated by Eisenhower to serve on a high-powered new advisory group known as the President’s Board of Consultants on Foreign Intelligence Activities.* An FBI security check ignored the extensive allegations about Kennedy’s involvement in bootlegging during Prohibition and glossed over his dubious record as ambassador to England. A synopsis of the report ended with these words about Kennedy: “He has frequently expressed admiration for the Director and the work of the Bureau.” Kennedy spent six months on the intelligence review panel, and made at least one secret trip overseas to review CIA operations. His mission created mayhem in the CIA station in Rome when Kennedy demanded—and got—access to the names of the agency’s undercover field agents inside the Italian government and the Vatican. Thomas F. McCoy, then a CIA operations officer in Rome, said in an interview for this book, “All he was doing was pushing the view of his right-wing friends in the Vatican—the aging monsignors who were out of things and wishing for the good old days.” McCoy added, “Joe had his own point of view, which many people were supporting” in the aftermath of Senator Joseph McCarthy’s loyalty investigations. “He didn’t want us to support anybody who was mildly left: ‘If they weren’t communists, why were they acting like communists?’”*
Joseph Kennedy was thus no outsider when it came to the good—and the bad—of the American intelligence community. He undoubtedly shared his understanding of the CIA’s clandestine world with his sons Jack and Bobby, and perhaps with J. Edgar Hoover.
In declassified files there is a strong suggestion that Kennedy may have privately briefed Hoover on what he was learning about the CIA, a conversation, if it took place, that would surely have delighted the bureaucratic-minded FBI director, who was often at war with the CIA and other government intelligence agencies. FBI files show that on February 16, 1956, Hoover told his key deputies about a visit the day before with Kennedy, who informed him that he planned to analyze the issue of “duplication of coverage abroad by the military, CIA and the State Department.… I discussed with Mr. Kennedy generally some of the weaknesses which we have observed in the operations of CIA, particularly as to the organizational set-up and the compartmentation that exists within that Agency.” There is no evidence in the publicly released files of any further contact between Kennedy and Hoover about the CIA, but the files do show that Kennedy continued to send flattering personal letters to Hoover as his son began his presidential campaign.
Joe Kennedy’s fawning relationship with Hoover was not the only thing the Kennedys had going for them. The FBI director was then just five years away from reaching the federal government’s compulsory retirement age of seventy, and his overriding interest was to remain in power. Hoover, and Jack Kennedy, understood that only the president of the United States, whatever his private morality, had the authority to keep Hoover on the job. Hoover’s reappointment was assured—but Kennedy first had to win the election.
There was at least one known backup plan in case the Kennedy campaign’s mixture of hard work, charm, money, and gangster connections failed and left Jack Kennedy on election night with only a small plurality of electoral college votes. The campaign feared that the twenty-six unpledged electors in Mississippi, Alabama, and Georgia—fourteen of whom would shortly announce they would vote for Senator Harry Byrd, amid reports that the others might join their revolt—could take away the presidency. The plan was centered, not surprisingly, on money.
Oscar Wyatt, a wealthy oilman, banker, and Democratic Party fund-raiser in Corpus Christi, Texas, spent election night anxiously watching returns at home, as did the rest of the nation. “We didn’t know whether Jack won,” Wyatt recalled in an interview for this book. “If Illinois went against Jack, we’d have to get the Mississippi vote”—the eight unpledged electors in that state. Wyatt was telephoned at home late in the evening by Clifton Carter, one of Lyndon Johnson’s most trusted political lieutenants, and told: “You’ve got to get one hundred thousand dollars to Mississippi tonight.” Wyatt was further told that each of the delegates would cost $10,000. “I owned a substantial interest in a bank in Corpus Christi and got the bank opened up and got the money,” Wyatt told me, adding that getting a bank president to open up in the middle of the night was no easy chore. Wyatt arranged for his private plane to be fueled and readied for an immediate flight to Jackson, Mississippi. It was now eleven P.M., and Wyatt decided to stay at the airport.
At two A.M. Carter telephoned again and told him to hold the plane. “Don’t leave.” A third call came at four A.M. “Don’t leave.” Finally, at six-thirty A.M., Wyatt, asleep on a couch in his hangar, was called a last time by Carter and told, “Daley brought it in. Go to sleep.” The plane returned to its hangar. When interviewed in 1995, Wyatt was chairman of the board and chief executive officer of the Coastal Corporation, in Houston.
The Mississippi electors, without any $10,000 inducements, duly cast their ballots for Senator Byrd on December 19, 1960. Their vote was little more than a gesture; Kennedy defeated Richard Nixon by a total of 300 to 219 in the electoral college (Hawaii’s 3 votes were added later) and was ratified as the thirty-fifth president of the United States.
Hoover, with his access to the secrets of electronic surveillance, knew that the election corruption went far beyond Illinois. But he did not act on what he knew. The day after the election—the day Jack Kennedy announced he would reappoint Hoover as FBI director—Hoover summoned Philip Hochstein, editorial director of the Newhouse newspaper group. “When I got to his office,” Hochstein later told the British journalist Anthony Summers, “I offered my congratulations on the announcement of his appointment by the President-elect. He replied in a surly manner, ‘Kennedy isn’t the President-elect.’ He said the election had been stolen in a number of states, including New Jersey, where my office was, and Missouri, where Newhouse had recently bought a paper.… It was quite a harangue, and I think Hoover wanted me to be part of a crusade to undo the election.… I didn’t tell anyone at the time.”
Sometime shortly after Jack Kennedy took office, the FBI in Chicago forwarded a report on the Illinois election to the Justice Department. “I can tell you,” Robert Blakey, then in Justice, said in an interview for this book, “that the fact that it was stolen was brought to Robert Kennedy’s attention.” Nothing happened.
The lack of action was precisely why Joe Kennedy had insisted after the election that Bobby be nominated as attorney general. Jack, always reluctant to take on his father, at first waffled. “I don’t know what to do with Bobby,” he told George Smathers. “He busted his tail for me.” The two men were talking, Smathers recalled in an interview for this book, while dangling their feet in the water at the shallow end of the pool at Palm Beach. Joe Kennedy was reading the morning papers at the other end. “The Old Man,” Kennedy said, “wants him to be attorney general.” Smathers, a former U.S. attorney who was not an admirer of Bobby’s, was stunned. “He never had a case in his life,” he recalled telling Kennedy. “He never argued in a courtroom. If you make him an assistant secretary of defense, he’ll have a lot of power. It’s an appropriate job for a guy who has never done a damn thing.” Jack Kennedy’s response was intimidating, Smathers recalled: “Why don’t you tell the Old Man?”
Smathers accepted the challenge and walked to the other end of the pool. “‘Excuse me, Mr. Ambassador. Jack and I have just been talking about Bobby. He wants to do something with Bobby. I thought he could be assistant secretary of defense, and then in a year or two he could move up.’ Joe said, ‘Jack! Come here.’ Jack walked over. [Joe] said, ‘I want to tell you, your brother Bobby gave you his life blood. You know it and I know it. By God, he deserves to be attorney general and by God, that’s what he’s going to be. Do you understand that?’ Jack said, ‘Yes sir.’ And so Bobby became attorney general.”
The Republicans quickly learned all they needed to know about Kennedy loyalty. Everett Dirksen, the ranking Republican senator from Illinois, later telephoned Cartha DeLoach and requested a full-scale FBI investigation of the election; he had evidence, he said, that the election had been stolen. “I told him the FBI had received considerable information and we sent that information to the Department [of Justice],” DeLoach recalled. “We’d be glad to receive his information, or any other information, and refer [it] to the attorney general. But Senator Dirksen said, ‘You say turn it over to the attorney general?’ I said, ‘That’s the only recourse we have.’ And he said, ‘Thanks a hell of a lot,’ and slammed the phone down. He knew that Bobby Kennedy was the attorney general.
“And,” DeLoach added, Dirksen “probably knew that the Department of Justice had already advised the FBI not to conduct any further investigation.”
* Woodfield came to understand, he said, that Sinatra considered himself “to be the ambassador between the U.S. government and the mob.” The photographer told of once being on assignment with Sinatra in Miami and accompanying him and some of his gangster friends to a dog track, where several scenes were to be shot. During a break for lunch, Sinatra called out, “Billy, put in a roll and take some pictures for me … just me.” Woodfield then heard one of the gangsters tell another, “Come on. We’re going to get our picture with Frank.” The other responded: “Take a picture? I’m not supposed to be in the country.” The exchange left Woodfield a little unnerved. Pete Hamill told me of once being asked by Sinatra to ghostwrite his autobiography. Hamill, aware that the book would be a bestseller, told the singer that he would consider doing so—but Sinatra would have to tell the truth about the women, the politicians, and the mob guys. Sinatra told Hamill he could live with the first two requirements, but not the third: “I don’t want someone knocking on the fucking door.”
* The committee, which exists today as the President’s Foreign Intelligence Advisory Board (PFIAB), was headed by Dr. James R. Killian, Jr., president of the Massachusetts Institute of Technology, who played a major role in developing America’s satellite intelligence capability. Others on the board included retired general James H. Doolittle; Edward L. Ryerson, retired chairman of Inland Steel; and the Wall Street lawyer Robert A. Lovett. Kennedy resigned from the committee on July 25, 1956, explaining in a letter to President Eisenhower that he was becoming “deeply involved” in political activities on behalf of his son, then seeking the vice presidential nomination.
* Somebody in Washington obviously had qualms about Kennedy’s visit. William L. Colby, who would become director of the CIA, was a senior officer in the Rome station in 1956. Prior to Kennedy’s arrival there, Colby recalled in an interview for this book, he had been given secret instructions from CIA headquarters that he and others in the station were to cooperate with Kennedy about covert operations but were not to provide him with the names of any agents. Kennedy got his way, nonetheless, Colby said, by telling the station: “Either you’re going to give me the names or I’m going to go to the president and quit this job.”