Jack Ruby

Mere hours after JFK's murder, lone oddball Lee Harvey Oswald was picked up for the murder. With forty years of hindsight, many people feel it was all too convenient, a neat and tidy solution to the murder. Making things especially tidy was Oswald's murder in the Dallas Police headquarters by a local strip club owner and small-time hoodlum, Jack Ruby.

Ruby burst out of the crowd and shot Oswald, thus ending the possibility of a trial in which potentially explosive information might have come to light. Ruby claimed his reason was the desire to spare first widow Jackie Kennedy the pain and suffering of a protracted trial, where she would have to relive the horrific event over and over. There appears to have been more to the story, however.

Chicago Youth

During his youth, Ruby was a runner for the Chicago Outfit. He sold horseracing sheets and was involved in bookmaking. There are some rumors that Ruby actually worked for Al Capone. While he was making the rounds on the street he became friendly with David Yaras and Lenny Patrick, two hoods that became high-level operatives in the Outfit. Ruby also became involved in the Teamsters Union, where he was suspected in the murder of a union rep.

Jack Ruby

Courtesy of AP Images

Jack Ruby, charged with the slaying of Lee Harvey Oswald, the accused assassin of John F. Kennedy, is surrounded by photographers and reporters before the start of his change of venue hearing in Dallas, Texas, Feb. 10, 1964. Seated with Ruby are two of his attorneys, Joe Tonahill, left, of Jasper, Texas, and Melvin Belli, right, of San Francisco.

More than Just a Nightclub Owner

Ruby moved to Dallas in the 1940s and became a well-liked nightclub owner. His burlesque shows were well attended by gangsters and cops alike. He kept up with his contacts in the mob, as well as with Dallas gangsters. There are some who say that Ruby had no connections to organized crime. This is unlikely.

Ruby — the Nexus

There are a lot of interesting coincidences that tie Jack Ruby to organized crime figures. Chief among them was Santo Trafficante Jr. In 1959, Santo was the guest of Fidel Castro in one of the Cuban dictator's swank jails. According to an eyewitness, Trafficante was visited there by an American gangster, Jack Ruby. As improbable as that may sound, Ruby admitted that he was in Cuba around the same time. The idea that Jack Ruby may have allegedly visited Trafficante in a Cuban prison surprises many because there doesn't seem to be any outward connection between a Dallas nightclub owner and a Florida mob boss.

Ruby's connections to Trafficante start with his companion on that 1959 Cuba trip, Lewis McWillie. Also a Chicago native, McWillie worked in the Deauville casino for Trafficante and a few others owned by the Florida mob boss's associates. McWillie was close with two other Trafficante cronies, Russell D. Matthews and Norman Rothman. In addition to involvement in gambling, all the men, including Ruby, were involved with smuggling weapons to Castro prior to his victory in the civil unrest.

Ruby, McWillie, and Matthews were also in the sphere of influence of Joe Civello, the mob boss of Dallas. Civello's name crops up in numerous conspiracy theories, as do McWillie, Matthews, and of course, Jack Ruby.

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