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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Was New Orleans mob boss Carlos Marcello the man who ordered the hit on President John F. Kennedy?

In this episode, we trace Marcello’s rise from small-time Louisiana gangster to one of the most powerful bosses in America, controlling billion-dollar gambling, racing, and casino operations, and maintaining close ties to figures like Santos Trafficante and Lyndon Johnson. We examine Marcello’s deportation by Robert Kennedy, his alleged revenge plot, and multiple reported confessions tying him to the assassination.

You’ll also hear about Lee Harvey Oswald’s uncle Dutz Murret and his verified work for Marcello’s bookmaking network, as well as how Oswald himself lived amid Marcello-connected underworld hubs in New Orleans. Did Marcello use the Murrets, or others in his Dallas network, to reach Oswald?

From the CIA-Mafia plots against Castro to the classified CAMTEX prison recordings, we pull together the evidence surrounding Marcello’s possible role in the crime of the century.

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In this episode of Solving JFK, we continue our deep dive into organized crime’s potential connection to the assassination of President John F. Kennedy. Picking up where we left off, we examine the lives and activities of Johnny Roselli and Santos Trafficante—two of the most powerful mob figures with ties to both the CIA and anti-Castro operations. From Roselli’s role as a liaison between the CIA and the mafia, to Trafficante’s empire stretching from Tampa to Havana, the web of connections between organized crime, intelligence agencies, and political intrigue only grows more tangled.

You’ll hear about Roselli’s mysterious murder, Trafficante’s alleged involvement, and an explosive claim about Trafficante made by attorney Daniel Sheehan.

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