When Jack Ruby stepped out of a crowd in the basement of the Dallas Police Department and fired a single bullet into Lee Harvey Oswald, the nation lost its best chance to learn what Oswald might have revealed about the Kennedy assassination. In Episode 26, we covered the strange events of that weekend in November 1963, from Ruby’s mysterious money transfer to the conflicting stories about how he gained access to Oswald.

In this episode, we go deeper. Who was Jack Ruby? How did a Chicago-born hustler with mob ties end up silencing the most important suspect in modern American history? We trace Ruby’s journey from his early days working for Al Capone, to his years in Dallas running nightclubs and crossing paths with underworld figures, corrupt lawmen, and political operatives.

Was Ruby acting on impulse or under orders? We explore his alleged role as a mob-connected union enforcer, his possible ties to gun-running operations with anti-Castro Cubans, and whether he was “the Chicago Outfit’s man in Dallas.”

This is the first of a two-part deep dive into Jack Ruby’s background, relationships, and activities — and how his underworld connections may finally help explain why Lee Harvey Oswald never made it to trial.

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