The 1960 presidential election between John F. Kennedy and Richard Nixon was one of the closest in modern American history. It was not decided until the early morning hours of November 9, more than six hours after the polls closed, when NBC finally called Illinois for Kennedy. That state, and with it the presidency, was won by a margin of just 8,858 votes out of 4.7 million cast.
In Chicago, Mayor Richard Daley's machine delivered the city for Kennedy by roughly 450,000 votes. At the Kennedy compound in Hyannisport, Massachusetts, champagne bottles popped and celebration erupted. But another celebration was reportedly taking place that same night in the back rooms of Chicago clubs controlled by the Outfit.
There, according to the account, Sam Giancana, the most powerful mob boss in America, smiled and told his associates, "We did it. We put a president in the White House." According to Giancana's brother Chuck, Sam expected payment. The deal was said to be simple: help get Jack elected, and in return, he calls off the heat.
The Kennedys did not call off the heat. They turned it up. And in the mafia's world, one rule never changes: betray us and you pay, president or not.
The story begins in the summer of 1960, when Joseph P. Kennedy had a problem. His son Jack was running for president, and the race was tight in swing states like Illinois and West Virginia. Joe Kennedy, a former bootlegger and millionaire patriarch, knew how to solve problems. He had worked with organized crime during Prohibition, and now he needed them again.
According to John Kanah's daughter Antoinette and Frank Sinatra's daughter Tina, Joe Kennedy reached out to Sam Giancana through Frank Sinatra. Tina Sinatra told 60 Minutes that Joe Kennedy knew her father had access to Giancana and that her father was on an errand. The meeting allegedly took place in Chicago, involving Joe Kennedy, Sam Giancana, and Tony Accardo.
The terms were that the Outfit would deliver union votes in Illinois through Teamsters connections. In return, when JFK won, the Justice Department would back off. As Chuck Giancana wrote, "I help get Jack elected, and in return, he calls off the heat."
The Outfit delivered. In Chicago's mob-controlled wards, Kennedy won by landslide margins, and he carried Illinois by 8,858 votes. Without Illinois, Nixon wins. The mafia had delivered, and now it was the Kennedys' turn.
On January 20, 1961, John F. Kennedy became president. One of his first acts was appointing his brother Robert as attorney general. Bobby Kennedy did not want the job. He had spent three years as chief counsel for the Senate Rackets Committee, investigating labor corruption and organized crime. "I didn't want to spend the rest of my life chasing bad men," he told his father. But Joe Kennedy insisted, and Bobby accepted.
He then did exactly what he said he did not want to do. He spent the rest of his life chasing bad men, except this time the bad men were the ones who had helped elect his brother. By the time Bobby left office in 1964, his Justice Department had indicted 687 organized crime figures, with a conviction rate of nearly 90 percent.
His targets included Sam Giancana, the Chicago Outfit boss; Carlos Marcello, the New Orleans godfather; Santos Trafficante, the Tampa mob leader; and Jimmy Hoffa, the Teamsters president with deep mob ties. These were the same men who had helped JFK win, and now they were being hunted relentlessly.
In May 1961, Bobby announced his first major drive in Chicago targeting Giancana's operations. He assigned 50 Justice Department lawyers, launched simultaneous raids in 22 states, and arrested 128 people in illegal gambling operations. It got worse. In April 1961, Bobby had Carlos Marcello arrested and deported to Guatemala without a hearing and without due process, simply thrown on a plane and dumped in Central America. Marcello eventually made it back, but he never forgot.
According to FBI informant Edward Becker, Marcello told associates in September 1962, "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." He was talking about the Kennedys. Kill Bobby, and JFK would keep investigating. Kill JFK, and Bobby loses his power. The investigations stop, and the heat ends.
Sam Giancana felt the same betrayal. According to Chuck Giancana, Sam was furious. Bobby Kennedy was orchestrating what would become the largest attack on organized crime in the nation's history. The Outfit had delivered Illinois, and the Kennedys had responded with war.
By 1963, mafia bosses had three reasons to want Kennedy dead. The first was the crackdown. Bobby's war was destroying their operations. Giancana faced constant FBI surveillance, Marcello faced deportation, Trafficante faced RICO investigations, and Hoffa faced multiple prosecutions. If Kennedy stayed president, the mob's empire would collapse.
The second was Cuba. Castro had shut down mafia casinos in Havana, wiping out millions in revenue. The CIA recruited Giancana, Trafficante, and Johnny Roselli to kill Castro. The mob agreed, asking no fee, because they wanted Cuba back. But after the Bay of Pigs, Kennedy pulled back. There would be no invasion and no assassination plots. Trafficante allegedly said after JFK's death, "Now we can get back into Cuba."
The third was honor. In Sicilian culture, betrayal demands vendetta. A deal was made, and the Kennedys broke it. That could not stand, even if it meant killing a president. The House Select Committee on Assassinations concluded that Marcello, Trafficante, and Giancana had motive, means, and opportunity. Hoffa allegedly said, "When you cut down the tree, the branches fall with it. Kill the president, the attorney general loses power."
In July 1963, according to mob lawyer Frank Ragano, Jimmy Hoffa summoned him. Hoffa gave Ragano a message to deliver to Carlos Marcello and Santos Trafficante in New Orleans. The message was, "Jimmy wants you to kill the president." Ragano delivered the message at the Royal Orleans Hotel. According to his autobiography, Mob Lawyer, Marcello and Trafficante did not seem surprised. They listened. They did not say yes. They did not say no. But Ragano believed they acted.
The plan, if it existed, was sophisticated. Use Lee Harvey Oswald as the fall guy, a loner and communist sympathizer with ties to both the Soviet Union and Cuba, the perfect patsy. And if Oswald was captured alive, eliminate him quickly before he could talk.
Enter Jack Ruby. Ruby was a Dallas nightclub owner with deep mob connections. He ran errands for the Chicago Outfit and knew Sam Giancana. He had visited Santos Trafficante in a Cuban jail in 1959. His phone records before the assassination showed calls to associates of Marcello, Trafficante, and Hoffa. According to the HSCA, Ruby's phone records were like an inventory of mafia leaders. Two days after Kennedy's assassination, Ruby shot Lee Harvey Oswald on live television. Oswald died. The patsy was silenced, and the investigation dead-ended.
On November 22, 1963, at 1:30 p.m. Central time in Dallas, President Kennedy was dead. In New Orleans, Carlos Marcello was in federal court on trial for fraud. The verdict came in shortly after news of Kennedy's death: not guilty. Marcello was acquitted. That evening, he hosted a celebration dinner. Was he celebrating his acquittal, or something else?
In Miami, according to mob lawyer Ragano, Santos Trafficante raised a glass and made a remark about the slain president. In Washington, Jimmy Hoffa heard the news and told Ragano, "I told you they could do it. I'll never forget what Carlos and Santos did for me." Then he added the key line: "This means Bobby is out as attorney general."
He was right. Bobby Kennedy resigned in September 1964. The war on organized crime lost its general. Prosecution slowed. The heat died down. The mob had solved its Kennedy problem.
The proof is circumstantial, but consider the pattern. Jack Ruby's connections and phone records show calls to associates of Marcello, Trafficante, and Hoffa before the assassination. FBI informant Jack Van Lanningham claimed Marcello confessed to orchestrating the hit using two professional killers and Oswald as the fall guy. Hoffa told Frank Ragano, "I'll never forget what Carlos and Santos did for me. This means Bobby is out as attorney general."
Trafficante's deathbed confession came in 1987, as he was dying of kidney failure. Trafficante allegedly told Ragano, "Carlos messed up. We shouldn't have killed Giovanni. We should have killed Bobby." The 1979 House Committee concluded that Kennedy was probably assassinated as a result of a conspiracy, and that Marcello, Trafficante, and Hoffa had motive, means, and opportunity.
But key witnesses died before testifying. John Kanah was murdered in 1975, shot seven times. Roselli was murdered in 1976, dismembered in an oil drum. Both had been scheduled to testify before Congress.
Did the mafia kill JFK for betraying them? The evidence is compelling but not conclusive. Multiple mob figures confessed or hinted at involvement. Ruby's mafia connections are documented. The motive is clear. But proving conspiracy requires hard evidence: documents, recordings, living witnesses. The mob made sure those did not exist.
The code of silence held. Witnesses died. Evidence disappeared. What we know is this: a deal was made in 1960. The mob delivered Illinois. Joe Kennedy promised leniency. But JFK declared war instead. The mob felt betrayed, and in their world, betrayal demands a response.
Did that response happen in Dealey Plaza? Maybe. Probably. But we will never know for sure, because the only people who know are dead, and dead men tell no tales.