It seems almost unfathomable that one of the most admired Presidents in U.S. history may have had ties to mobsters. Nevertheless, in the half-century since President John F. Kennedy's assassination in Dallas, dark allegations have arisen about dealings between JFK and organized crime figures. Some even have charged—though without conclusive proof—that the President's killing actually was a mob hit.
Much of the speculation about an illicit working relationship between JFK and the mafia focuses upon Sam Giancana, the former head of the Chicago crime syndicate, who had a number of apparent Venn-diagram intersections with the President.
Giancana (pictured) had longtime ties to the Kennedy clan, going back to JFK's father, Joseph P. Kennedy, who was involved with Giancana in the bootlegging business during Prohibition. Additionally, Gianciana was an associate of singer Frank Sinatra, a close Kennedy friend, and allegedly was a donor to JFK's 1960 Presidential campaign, at a time when politicians weren't required to disclose their deep-pockets contributors.
There also have been allegations that Giancana secretly helped JFK win the 1960 West Virginia primary, in which he bested fellow U.S. Sen. Hubert Humphrey, D-Minn. In 2009, Tina Sinatra, daughter of Kennedy friend Frank Sinatra, told the TV program "60 Minutes" that the legendary singer—at the behest of JFK's father, Joseph P. Kennedy—approached Giancana. Sinatra allegedly asked Giancana to use mob muscle to pressure local union members to vote for JFK. The request was made through an intermediate, Sinatra, because "it would be in Jack Kennedy's best interest if his father did not make the contact directly," Tina Sinatra explained.
In his 1997 book, The Dark Side of Camelot, investigative reporter Seymour Hersh alleged that the elder Kennedy eventually did meet with Giancana in Chicago, to solicit his support for JFK in the general election.
During the Kennedy Administration, the Chicago mobster, along with other crime figures, is known to have been enlisted by the CIA to plot the killing of Cuban leader Fidel Castro.
Giancana and Kennedy also shared a mistress, Judith Campbell Exner, with whom they were involved with at different times (Kennedy first, then the mob boss). In a 1988 People magazine article, Exner claimed that she arranged a meeting between then-Presidential candidate Kennedy and Giancana at the Fontainbleau Hotel in Miami in April 1960 at JFK's request. "I think I may need his help in the campaign," she claimed that Kennedy told her. Subsequently, Exner claimed, she arranged nine other meetings in 1960 and 1961, and personally witnessed at least one of the sit-downs. In addition, Exner later claimed that she carried mysterious envelopes between Kennedy and Giancana.
Giancana was murdered in 1975 just before he was scheduled to testify to a U.S. Senate committee investigating the CIA, with whom he had participated in a Castro assassination plot.
The suspicions about links between JFK and mobsters also fuel conspiracy theories that the mob may somehow have been involved in the President's murder.
The mob certainly had potential motives. Several mob leaders were upset that Kennedy had failed to overthrow Cuban leader Fidel Castro, who had closed down their lucrative casinos in Havana after he took power in 1959. The President's brother, Attorney General Robert F. Kennedy, further had aroused their animosity by launching a high-profile probe of organized crime and aggressively pursued Teamsters Union leader Jimmy Hoffa (pictured) for alleged corruption and ties to the Mafia.
In 1979, the House Select Committee on Assassinations re-examined acoustic recordings of the gun shots in Dealey Plaza that day, eye-witness accounts, as well as Oswald's possible ties to the Mob, and reported that Kennedy's murder probably was the product of a conspiracy, but found no evidence that organized crime syndicates as a group had played a role. The committee also didn't rule out the possibility that individual mobsters with a beef against JFK could have played a role.
The House assassination committee's chief counsel and staff director, G. Robert Blakey, told the New York Times in 1979 that in his own mind, the link was much clearer. "I think the Mob did it," he said.