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How the Outfit Killed JFK
  • November 21, 2011 : 20:11
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[Editor's Note: It has been nearly 50 years since the assassination of John F. Kennedy and America is no closer to distinguishing fact from fiction. Many have tried, throwing theories at the wall to see what sticks and still we are left to wonder what happened on that fateful day in Dallas, November 22nd, 1963. 

Appearing in the November 2010 issue of Playboy, investigative author Hillel Levin attempts to unravel the details of the FBI's investigation and the Warren Commission's findings surrounding the daylight murder of an American icon. The following is the article in full.]

Having just retired from the FBI, Zack Shelton traveled in 2002 from his Texas home to reminisce with old Chicago comrades. They met over meals, at places that had once been their hangouts. Most of them were also retired, gray and beefy. They wore open-necked shirts and khakis or jeans. Back in their bureau days they had been a lean and edgy crew—dark suits and ties were standard attire. Together they had put the first cracks in the previously impervious shell of Chicago’s Mafia, known as the Outfit.

Now Shelton was on a similarly quixotic task. He believed a small-time criminal locked up in an Illinois prison may have committed the greatest crime of their time. His name was James Files, and he had once been a driver for the Outfit’s most feared hit man. Files told Shelton both he and the hit man were in Dallas when John F. Kennedy was assassinated. Files even claimed that he had fired the fatal shot from behind a fence on the infamous grassy knoll.

Shelton knew it sounded preposterous, but he had reason to take Files seriously. When he repeated the Files confession to his old buddies, Shelton was prepared to be laughed out of the restaurant. Instead, they all listened intently. In fact, like Shelton, some of them also had their own revelations about the assassination or knew other agents who had. They regretted never having had a forum in which to air them.

“There’s one thing about FBI agents,” says Shelton. “They’re damn good investigators. They don’t operate on the basis of theories. They deal in facts, and the facts have never supported the Warren Commission’s conclusion that Lee Harvey Oswald was the lone assassin.”

The evidence, Shelton believes, shows that organized crime orchestrated Kennedy’s murder. An increasing number of historians agree, but they still don’t know who the shooter—or shooters—may have been. There is also virtually no understanding of the Outfit’s role in the conspiracy.

If Special Agent Shelton learned any lesson during his eight years in Chicago, it was never to underestimate the Outfit or Tony Accardo, the man at its helm for five decades. Unlike the Mafia dons on the East Coast, Accardo had little interest in the public spotlight or absolute power. After he took control of the Outfit, in the mid-1940s, he built what is now acknowledged to be the biggest empire in the history of American organized crime, with rackets extending from Chicago to California.

Accardo was willing to divide the spoils by geography rather than by family. Inside Chicago that meant five groups, each with its own boss. Although most of these mob bosses were Italian, they were not necessarily related to those who worked for them. Their associates and underlings could be Greek, Jewish or German. Depending on where an illegal act took place, unaffiliated criminals—even weekend poker players—had to pay a street tax to the local Outfit boss. Failure to pay could result in a beating or death.

Shelton’s fellow agent Jim Wagner transferred to Chicago from New York and immediately recognized how crime in Chicago was organized. “The Outfit had a superior business model because it used geography instead of family,” he explains. “You didn’t have the blood feuds like in New York, where different families fought over the same territory.”

Nothing fueled the Outfit’s expansion as much as its influence on unions—the International Brotherhood of Teamsters in particular. The union’s pension fund, which was run out of Chicago, financed construction of the Outfit’s first casinos on the Las Vegas Strip. As he did in his hometown, Accardo was willing to let other mobsters play—but on his terms.

A key component of the Outfit’s success was its infiltration of the Democratic Party in Chicago’s First Ward. Mob operatives influenced the election of judges, who then found reasons to throw out charges against the Outfit. The mob’s political connections also helped it buy voting cards from residents of Chicago’s public housing projects that it could then punch for its favored candidates. When a slender margin in Illinois ensured Kennedy’s electoral victory over Richard Nixon in 1960, Shelton says, “the mob really did believe it gave Kennedy the election.”

If that was true, the Kennedy administration showed little gratitude. Attorney General Robert F. Kennedy made organized crime his signature issue, lighting a fire under J. Edgar Hoover and the FBI, which had previously gone easy on the Mafia. In the last year of the Eisenhower administration the Justice Department convicted only 35 low-level mobsters. By the end of 1963 RFK had pushed that number to 288, including high-ranking bosses. More alarming for the Outfit, while it was using the Teamsters pension fund to build casinos, RFK targeted Teamsters president Jimmy Hoffa with a team of investigators known as the Get Hoffa squad. The squad’s first indictments against the union leader were for accepting payoffs from trucking companies and for subsequent jury tampering in those trials. In the summer of 1963 it brought new charges involving pension funds.

Five months later, JFK was assassinated. G. Robert Blakey, then a member of RFK’s Justice Department, was well aware of what organized crime had at stake in snuffing out the Kennedy administration’s onslaught. “It seemed obvious that if there was a conspiracy, it would be from the mob,” says Blakey. In Brothers, a recent book on RFK, author David Talbot quotes Bobby telling a confidant after JFK’s assassination: “If anyone was involved, it was organized crime.” According to Blakey, neither Hoover nor JFK’s successor, Lyndon Baines Johnson, wanted to open that can of worms. “The risks of where that investigation would lead were too high,” says Blakey. “It was much more convenient for Oswald to be the lone assassin.”

In the late 1970s Blakey served as chief counsel for the U.S. House Select Committee on Assassinations, which took a second look at the Warren Commission’s findings. On the basis of acoustical evidence, Blakey’s investigators determined there was a “high probability” that more than one gunman fired at the president and that “individual members” of “organized crime” may have been involved. The committee also found that Hoover had kept the FBI’s organized crime task force out of the investigation and didn’t pursue leads tying Oswald and his killer, Jack Ruby, to the Mafia.

But back in 1963, if the Warren Commission had called in the FBI agents monitoring the Outfit, it probably wouldn’t have learned much. Although it was the dawn of electronic surveillance and mob leaders were supposedly unaware of the bugs planted in their meeting places, the FBI never had enough information to bring a major case against the Outfit in the 1960s. “Unfortunately,” Blakey says, “we learned later that the surveillance was incomplete.”

In Chicago, for example, agents never fully understood the executive nature of the Outfit’s hierarchy. They thought Sam “Momo” Giancana ruled the Outfit. Giancana was the Chicago mob’s most flamboyant boss after Al Capone, but he remained in power only until 1965. It’s now clear Giancana always answered to Accardo. According to Blakey, no bug or wiretap ever caught Accardo talking to Giancana. Because of Accardo’s understated ways, the media, law enforcement and even some local criminals never completely knew the extent of his control.

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  • Anonymous
    Where is Tosh Plumlee today? It seems old man history now supports Plumlee's story and background. He appears to be a very deep operative over a very long period of time.
  • Anonymous
    During Clay Shaw's trial an appellate panel ruled the Warren Commission Report "inadmissible" as evidence due to it being fiction.The only time it was subjected to legal or judicial scrutiny. Ray Guiducci-Most Overlooked Fact, July 20,2012.
  • Anonymous
    Most Overlooked Fact: During Jim Garrison's trial of Clay Shaw an Appellate Court panel threw out ,as inadmissible evidence, the Warren Commission Report due to it being FICTION.The only time Commission Report faced legal scrutiny.
  • Anonymous
    The Plumlee CIA connection. Yes. It does appears Plumlee is a CIA central character; Cuba, Kennedy, Contra and beyond. WOW!