In the last episode, we rewound Jack Ruby’s life long before the basement of the Dallas Police Department and found a man deeply entangled with organized crime, Cuban gun-running, and people far more powerful than he let on.

This episode goes deeper into Ruby’s world and asks how far inside that orbit he really was. We explore Ruby’s stint as an FBI informant, his close relationship with casino manager Lewis McWillie, and the allegation that Ruby visited Mafia boss Santos Trafficante in prison. We also look at Ruby’s ties to Carlos Marcello and analyze the unusual series of long-distance calls he made in the weeks leading up to November 22, 1963.

Finally, we turn to one of the strangest chapters in the Ruby story: the involvement of psychiatrist Dr. Louis Jolyon West — a figure whose role feels stranger than fiction.

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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Did the mafia have a hand in the assassination of President John F. Kennedy? In this episode, we examine the explosive relationship between the Kennedy Administration and organized crime — and the mob bosses who had the motive, means, and opportunity to strike back.

Robert Kennedy’s war on the mob ramped up federal prosecutions and surveillance like never before, enraging mafia leaders across the country. We’ll look at how FBI wiretaps captured mobsters talking openly about killing both Kennedys — and what the House Select Committee on Assassinations ultimately concluded about mafia involvement.

Then, we dive into the lives and connections of three key figures potentially linked to the JFK Assassination, including

• Jimmy Hoffa – the Teamsters boss with a grudge against RFK and rumored ties to mob assassins
• Meyer Lansky – the “mob accountant” who built an empire from New York to Cuba and Las Vegas
• Sam Giancana – the Chicago boss tied to both the Kennedys and the CIA’s secret anti-Castro plots

From wiretaps to mob meetings, this episode unpacks how deep the hatred ran — and whether it was enough to lead to murder.

👉 Next episode: Mafia (Part 4) – Johnny Roselli & Santo Trafficante

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In this episode, we look at what the Church Committee had to say about the CIA’s efforts to assassinate Cuban Revolutionary leader Fidel Castro in partnership with the Mafia through cut-out Robert Maheu.

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In this episode, we look at a brief history of the mafia leading up to 1963, including the Apalachin, New York meeting, the McClellan Committee, and whether the Chicago mob played a part in the Kennedy-Johnson ticket winning the election in 1960.

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In this episode, we’ll get an update on the state of the JFK Records, talk about the McCone Rowley memo that keeps coming up, and go over some thoughts on LBJ and more. We are joined by distinguished author and screenwriter of Oliver Stone’s Destiny Betrayed, Jim DiEugenio, as well as Canadian attorney, national archives explorer, and JFK records act expert Andrew Iler, and attorney and JFK Records expert, Mark Adamczyk.

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