Danny Fingeroth is an author, historian, and former Marvel Comics editor, known for his work on Superman on the Couch and Disguised as Clark Kent. His latest book, Jack Ruby: The Many Faces of Oswald’s Assassin, explores the man who killed Lee Harvey Oswald.

Jack Ruby remains an enigma—was he a mob-connected hitman, a patriotic vigilante, or just a desperate nightclub owner seeking attention? In this episode, Fingeroth takes us through Ruby’s life, from his rough Chicago upbringing to his ties with law enforcement and organized crime, leading up to the moment that made him infamous.

We explore Ruby’s complex psychology, his fears of antisemitic backlash after JFK’s assassination, and his shocking decision to kill Oswald on live television. Our conversation also examines his rapid mental decline in prison, his conspiracy claims, and the lingering question: Did Jack Ruby know more than he admitted?

Danny's book on Jack Ruby: https://amzn.to/4bmzgTO 📚

Chapters:

00:00 Why write a book about Jack Ruby?

08:46 Ruby's gangster side

20:07 The bond with his family

25:24 Frank Sinatra plays a role in this story?

28:33 The assassination explained

41:10 Jack's trial

48:23 The psychology of Jack Ruby

53:23 Conspiracy theories