The mob felt betrayed in 1963. Chicago godfather Sam Giancana had helped Kennedy win the 1960 election through skulduggery, and Miami mobster Santos Trafficante had aided the CIA in its assassination attempts on Castro. But rather than pledging their loyalty, the Kennedys launched an all-out campaign against organized crime. Attorney General Robert Kennedy first went after Teamster boss Jimmy Hoffa and then deported New Orleans syndicate boss Carlos Marcello to Guatemala. Pushed around long enough, and angry at the president for going soft on Castro—who had shut down its lucrative Cuban casinos—the mob made someone an offer he couldn’t refuse. Oswald was either its hit man or its patsy. Upon his arrest, the mob dispatched Jack Ruby to silence him.


Authors John H. Davis (The Kennedy Contract) and David Scheim (Contract on America) and veteran journalist Jack Anderson.

Strange Details

In 1975 and 1976, during the course of congressional investigations of the mob and the CIA, Sam Giancana was gunned down in his kitchen, Jimmy Hoffa “disappeared,” and Las Vegas mobster Johnny Roselli—who had told Jack Anderson that Ruby was ordered to silence Oswald—was dismembered, stuffed into an oil drum, and tossed off the coast of Florida.

• Kennedy and Judith Exner, one of Giancana’s molls, were introduced in 1960 by Frank Sinatra and carried on an affair for more than two years; Exner says she often carried envelopes from the president to the mobster.

Reasons to Believe

• In 1979 the HSCA concluded that Hoffa, Marcello, and Trafficante all had the “motive, means, and opportunity” to assassinate Kennedy.

• Hoffa had told a federal informant that he would like to kill RFK but that his brother was the more desirable victim because “when you cut down the tree, the branches fall with it.”

• Marcello—according to Las Vegas promoter Edward Becker—once coolly explained why it was better to target JFK than RFK: “If you cut off a dog’s tail, the dog will only keep biting. But if you cut off its head, the dog will die.”

• An FBI informant testified before the HSCA that Trafficante told him in 1962 that the president “was going to be hit.”

• In 1992 Frank Ragano, a longtime lawyer for Hoffa and Trafficante, told the New York Post that the two mobsters and Marcello had agreed to kill the president. Ragano claimed that Trafficante said on his deathbed: “Carlos f—ed up. We shouldn’t have gotten rid of Giovanni [John]. We should have killed Bobby.”

• Oswald’s uncle and surrogate father, Dutz Murret, was a bookie in the Marcello organization, and his mother, Marguerite, dated members of Marcello’s gang.

• When Ruby was a teenager in Chicago, he ran errands for Al Capone. As an adult, he had ties to members of the Giancana, Hoffa, Marcello, and Trafficante families. In 1959 he visited Trafficante in his Cuban jail cell, where Castro had thrown the mobster after the revolution.

• Two days before the assassination, a prostitute and heroin addict named Rose Cheramie told a Louisiana state policeman that she had been en route to Dallas with two men “who were Italians or resembled Italians” and were planning to kill Kennedy. After the assassination, she told Dr. Victor Weiss at East Louisiana State Hospital that “the word in the underworld” had been that Kennedy was going to take a mob bullet. She also said that Oswald and Ruby “had been shacking up for years…They were bedmates.”

Reasons Not to Believe

• The HSCA was ultimately “unable to establish any direct evidence” of mob complicity.

• Chicago FBI agent William Roemer, who spent hours listening to wiretaps of mobsters after the assassination, said they were “gleeful” but did not talk of a conspiracy.

• There is no proof that Ruby was anything more than a small-timer on the periphery of the Dallas underworld.

• Hoffa, Trafficante, and Marcello were cautious men, yet killing JFK was a rash solution—one that would only have brought on more heat from RFK. And why would a bunch of seasoned killers rely on a loser like Oswald?

• Cheramie—who had spent time in mental hospitals and who had a history of providing the FBI with false leads—was in the throes of heroin withdrawal when she told her story. After the assassination, she said that she had once worked as a dancer for Ruby, whom she knew as Pinky, but there is no evidence that she did. Nor is there reliable evidence that Oswald and Ruby ever knew each other.

Recent Developments

In 1993 Illinois cop killer James Files confessed to Kennedy’s murder. Claiming to have been an Army paratrooper in Laos, a trainer of Cuban exiles for the Bay of Pigs invasion, and the personal driver for Chicago mobster Charles Nicoletti, Files said that he fired from the grassy knoll while Nicoletti shot from the Dal-Tex Building. In 1994 the New York Post ran a story on Files titled “Call This JFK Tale Knoll and Void.”