Frank Sinatra Pt 2: New Evidence, Secret Favors, and Three Dead Men. This is Frank Sinatra — Connected, Compromised, and Cornered

DISGRACELAND

Jake Brennan

True Crime, Music, Society & Culture

4.6 • 13.1K Ratings

🗓️ 1 July 2025

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Frank Sinatra was never just a pop star. In this second chapter of his story, Frank isn’t merely brushing shoulders with gangsters—he’s one of them. Backed by new research and newly released secret intelligence files, this episode unpacks how the Voice became a mafia asset. When Sinatra’s son is kidnapped, before he calls the police—he calls notorious gangster Sam Giancana. And what follows is one of the darkest, bloodiest chapters in music and organized crime history. Is Frank Sinatra the most gangster musician of all time? Tell Jake at 617-906-6638, [email protected], or on socials @disgracelandpod. To see the full list of contributors, see the show notes at ⁠⁠⁠⁠⁠⁠⁠www.disgracelandpod.com⁠⁠⁠⁠⁠⁠⁠. To listen to Disgraceland ad free and get access to a monthly exclusive episode, weekly bonus content and more, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠⁠⁠⁠⁠⁠⁠. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠⁠⁠ Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠ (formerly Twitter) ⁠⁠⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠TikTok To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Transcript

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0:00.0	Double Elvis.
0:06.0	Oh, that's my prime delivery.
0:09.0	What, already?
0:10.0	Only one thing can match the buzz of Primes fast delivery.
0:13.0	And that's the buzz of Primes entertainment.
0:16.0	What are we watching?
0:17.0	Heads of State, that new action comedy with Idris Elba as the Prime Minister,
0:20.0	John Sina as the president and Priyanka Chopra Jonas, as their only hope.
0:24.1	Looks like a blast.
0:25.4	From fast delivery to explosive entertainment, it's on Prime.
0:29.6	For only $899 a month, join now.
0:32.3	Content includes limited ads, subscription or to run news.
0:34.6	For more information, go to amazon.com.uk.U.K. slash Prime.
0:37.6	Disgrace Land is a production of Double Elvis. This is a story about the voice, the weasel, about the boot, and guys named Lucky,
1:04.6	Momo, and handsome Johnny. This is a story about the mafia and about one musician's position in the mafia. This is a story about the mafia and about one musician's position in the mafia.
1:14.4	This is not a story you've likely heard before.
1:17.6	This is not just a story about a singer who needed the mob's help.
1:21.6	It's about a pop star who was expected to deliver for the mob over and over again
1:27.3	and in a way that only made mafia members were expected to deliver for the mob over and over again and in a way that only made mafia members
1:30.6	were expected to deliver. This story is based on recent research from a newish book that
1:36.8	pulls from a trove of previously unreleased secret files from Los Angeles Police Intelligence
1:43.4	and FBI documents.
	...

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