97: Triple Threat pt.1: Saints & Singers [Frank Sinatra and JFK]

Frank Sinatra would say, "I did it my way," and we would agree. From an early age, he lived an unusual life, raised in a mob bar by a strong-willed mother, gifted with a voice that could melt hearts and a face that could charm anyone. But there’s a side to Sinatra that few people know. A member of the Rat Pack, famous for his many wives and girlfriends, and… a civil rights activist? His friendships stretched from Hollywood’s elite to the most dangerous figures in organized crime and even to the White House. But when his ties to the mob clashed with his loyalty to John F. Kennedy, did Sinatra’s influence take a deadly turn? This week, you’ll get a peek behind the velvet curtain, but trust us, there’s more to Sinatra’s story than any “Somethin’ Stupid” could cover.

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Chapters/Takeaways

[00:00:00] Quick catch-up: Personal schedules, working out, random “cable ponytails,” and the usual comedic chaos
[00:21:59] Saints & Singers: Family dynamics of the Sinatra Family, and Frank’s Italian heritage and the challenges they faced
[00:28:26] Frank Sinatra's Early Life: Frank’s traumatic birth, childhood bullying, and first steps toward singing at his parents’ speakeasy shape his early drive
[00:35:44] Enter Martin Jr.: Frank’s name confusion and how he could have been named “Martin” but ended as “Frank”
[01:02:12] The Big Break: How his gigs with Harry James, Tommy Dorsey, and mob-funded nightclub sessions propelled Sinatra to national stardom
[01:27:25] Rock Bottom and the Rise: A fading career, heartbreak, and mob aid lead Sinatra to an Oscar-winning role, sparking his dramatic comeback
[01:31:04] Las Vegas Years: Frank anchors the Rat Pack, reinvents the Vegas scene, demands racial equality, and tightens ties to underworld clubs
[01:54:41] Enter FBI: J. Edgar Hoover’s agents shadow Sinatra for decades, hoping to expose crimes but failing to pin any illegality on him
[02:04:57] Politics Meets Showbiz: Frank woos JFK with star-studded fundraisers, retools “High Hopes” for the campaign, and basks in presidential glamour briefly
[02:13:51] Becoming the President: Frank’s closeness to JFK unravels under Bobby Kennedy’s mob crackdowns, souring Sinatra’s White House connections
[02:26:44] The Affair: JFK’s relationship with Sinatra’s ex, also involved with Sam Giancana, ropes Frank into presidential scandals and FBI files
[02:35:54] The Theories: Double-crossed mob bosses, enraged they helped elect JFK, fuel conspiracy claims they orchestrated his assassination
[02:41:18] The End & Final Thoughts: Sinatra’s final years, despite controversies, became an influential triple threat marked by music, mob ties, and lasting fame

Photos Referenced:

Frank Sinatra's 1938 Mugshot when he was arrested on a charge of Seduction - courtesy of Michael Ochs Archives / Getty Images	Frank and Nancy Barbato pictured at their wedding on February 4, 1939
The Rat Pack posing in front of the Sands Hotel, circa '62 [L to R: Frank Sinatra, Dean Martin, Sammy Davis Jr., Peter Lawford, Joey Bishop] - courtesy of Michael Ochs Archive / Getty Images	Judith Exner Campbell - courtesy of Metaweb / CC-BY

Frank Sinatra and John F Kennedy pictured together — *Frank Sinatra and JFK - courtesy of AFP / AFP / Getty Images*

Quotes:

"Our bodies don’t have to be constant projects, because I’ve never once met a person that’s like, I’m done. The project of my body is finished. Our bodies are supposed to be lived in and enjoyed." - Grant Thomas
"Nobody has ever failed so badly and come back so huge as Sinatra."
"The other detail that often gets neglected is that Sinatra crossed racial barriers as an artist. His music is a union of Black and White music. People often give Elvis credit for breaking down boundaries in his time, and that’s true, but Sinatra did it first."

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