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.

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143: Apple AI at WWDC, with Sebastian de With & Ben Sandofsky

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