DISGRACELAND – Frank Sinatra Pt. 1: Frankie Is the Reason...That the President’s Dead

Host: Jake Brennan
Date: July 31, 2018

Overview

In this electrifying episode of DISGRACELAND, host Jake Brennan delves into the tumultuous, drama-laden life of Frank Sinatra, illuminating how Old Blue Eyes’ personal ambitions, mob affiliations, and influence over American politics intertwined with—and, as Brennan provocatively contends, contributed to—the assassination of President John F. Kennedy. The narrative draws a direct line from Sinatra’s career low points and his mob-supported comeback, to his pivotal role in JFK’s election, and finally to the ultimate downfall of both Sinatra’s relationship with the Kennedys and Kennedy himself. Through cinematic storytelling, sharp insight, and dark humor, Brennan explores themes of celebrity, power, hubris, and the dangerous overlaps between the entertainment underworld and American history.

Key Discussion Points & Insights

1. Introduction: Sinatra’s Myths, Power, and Hubris

• Sinatra’s reputation as a legend is interwoven with myth, crime, and charisma.
  • “He sent a tombstone to an unfriendly journalist… He’d rather be a Mafia don than the President…” (03:16)
  • He acted as a liaison between Hollywood’s elite and the underworld, especially in the company of gangsters and politicians.
• The central thesis: Sinatra’s boundless confidence blurred into hubris, which, through a web of relationships and favors, contributed to JFK’s assassination.
  • “An act that Frank’s confidence turned hubris was partly responsible for…” (04:11)

2. Sinatra: The Original Pop Star

• Sinatra’s rise:
  • Broke the mold as the first teen idol, a singer whose emotional resonance gave him mass appeal.
  • His ability to seem both vulnerable and authoritative made him irresistible:
    • “The sound of his voice conveyed vulnerability and absolute authority all at once.” (05:12)
• Sinatra’s personal resonance for the host:
  • Brennan identifies with aspects of Sinatra’s persona, torn between street-smart authenticity and performative sophistication.
    • “In Sinatra’s voice, I also hear the contrived eloquence, the street kid who muscled his way into the smart set.” (06:31)
• Fall from grace:
  • By 1951, Sinatra’s career tanked; he was broke, divorced, out of work, and seen as washed up.

3. Comeback: From Here to Eternity & Mob Connections

• Struggles to reclaim career:
  • Frank’s relentless lobbying to play Maggio mirrored his own outsider status.
  • The pivotal role in From Here to Eternity became an obsession.
• Mob intervention:
  • When Hollywood refused, Sinatra went to the Mafia—specifically Frank Costello and mob enforcer Johnny Roselli.
    • “Harry, if we have a problem here, you’re a fucking dead man.” – Johnny Roselli to Columbia Pictures’ Harry Cohn (15:29)
• Triumphant return:
  • Sinatra wins an Oscar (16:59)—a resurrection that made him feel “invincible… hubris, it’s only really hubris if you fail. Otherwise, it’s just confidence.” (17:44)
  • He poured his energy into prolific music releases—pioneering the “concept album” and dominating both film and pop music.

4. The Sands, the Mafia, and Las Vegas

• Sinatra’s investments strengthened his mob connections:
  • Bought into the Sands Hotel—majority-owned by mob boss Frank Costello.
  • Sinatra’s presence turned the Sands into a hotspot, cementing his partnership with gangsters.
  • He happily ran mob errands, seeing himself as “just taking care of business.”
  • “If Frank had to jump on a plane to Havana with a suitcase full of cash from one of the boys… that wasn’t hubris. That was just Frank having the confidence to take care of business.” (21:13)

5. Sinatra, the Kennedys, and Political Power

• The favor that changed history:
  • Joe Kennedy, JFK’s father, summoned Sinatra.
    • “There’s power and then there’s power. The Kennedys had it, Sinatra wanted it…” (25:57)
  • Task: Mobilize mob support in West Virginia to win the presidential primary for John Kennedy.
  • Sinatra delivers, calling in “the boys,” especially Sam Giancana, to rig votes and ensure JFK's victory.
    • “A couple thousand dead Democrats managed to crawl out of the Illinois cemeteries and into voting booths to cast their votes for Jack.” (28:23)
  • Sinatra’s role in Kennedy’s election stoked his sense of omnipotence and deepened his integration with both showbiz and the political elite.

6. The Downfall: Sex, Betrayal, and Estrangement

• Sinatra and JFK’s excesses:
  • JFK and Sinatra bonded over women and parties; Sinatra became JFK’s fixer and “pimp.”
  • Jackie Kennedy despised Sinatra; Bobby Kennedy (JFK’s brother) regarded him as a liability.
  • The real disaster: JFK slept with Judith Campbell, mob boss Giancana's girlfriend—a direct result of Sinatra's introductions.
    • “You’re president, you’re married, you’re sleeping with any woman you want, and you decide to shack up with girlfriend of the most powerful mob boss in the country…” (29:38)
• Cut off:
  • The Kennedy administration severed ties with Sinatra after the scandal, devastating Frank and infuriating the mob, who felt betrayed after having delivered the presidency.

7. Mob & CIA: Conspiring Against Kennedy

• The mob’s broken expectations:
  • The mob believed helping JFK would keep law enforcement off their backs; instead, Attorney General Robert Kennedy ramped up prosecution.
  • The mob’s Cuban casinos, vital sources of revenue, were lost after Castro’s revolution—the U.S., ironically, considered using Mafia muscle to topple Castro, but failed.
    • “Here it was, taking out a contract on the beard, Uncle Sam, no joke, gangster as fuck.” (33:31)
  • Frank, now on the outside, couldn’t help mitigate the tensions.
• The convergence of conspiracies:
  • Various groups—Mafia, CIA, anti-Castro Cubans, and disaffected elites—all saw Kennedy as a threat.
    • “What an epic fuck show.” (34:59)
  • Brennan narrates how self-interest and vengeance can turn uncoordinated discontent into dark, collective action.

8. JFK Assassination: Fallout and Guilt

• Sinatra’s devastation:
  • On learning of JFK’s murder on November 22, 1963, Sinatra spirals into a deep depression and guilt.
    • “…he realized then that despite his clout, his friends, his confidence, he had been powerless to prevent it.” (37:46)
  • Brennan frames Sinatra’s grief as the ultimate reckoning of his lifelong hubris and influence.

Notable Quotes & Memorable Moments

• On mob intervention:
  • “Harry, if we have a problem here, you’re a fucking dead man.” – Johnny Roselli to Harry Cohn, studio head (15:29)
• On Sinatra’s self-image:
  • “He’d rather be a Mafia don than the President of the United States.” (03:31)
• Hubris vs. confidence:
  • “Hubris. It’s a funny thing. It’s only really hubris if you fail. Otherwise, it’s just called confidence.” (17:44)
• On the Kennedy election's dirty underbelly:
  • “A couple thousand dead Democrats managed to crawl out of the Illinois cemeteries and into voting booths to cast their votes for Jack.” (28:23)
• On the assassination’s aftermath:
  • “When Frank Sinatra got word that his friend, the President of the United States, was murdered, he instantly knew why. And he realized then… he had been powerless to prevent it.” (37:46)

Important Timestamps

• 03:16: Show proper begins—Sinatra’s wild stories and criminal exploits
• 05:12: Analysis of Sinatra’s unique appeal & vulnerability
• 09:50–14:13: Sinatra’s fall and relentless campaign for “From Here to Eternity”
• 15:20–17:44: Mafia intervention and Frank’s Oscar-winning return
• 18:00–21:33: The Vegas period, Sands Casino, and deepening mob ties
• 25:47–29:59: The Kennedy saga: Mob muscle, fixing elections, and power brokering
• 34:59: Conspiracy, self-interest, and the storm around JFK’s presidency
• 37:46: Sinatra’s reaction to Kennedy’s assassination and the shattering of his hubris

Tone & Style

DISGRACELAND maintains a cinematic, pulpy, irreverent tone that oscillates between dark comedy and noir tragedy. The narrative voice is direct, occasionally profane, always dramatic, and loaded with a rock ‘n’ roll sensibility.

• “What an epic fuck show.” (34:59)
• Brennan’s storytelling eschews dry journalistic distance for immersive “truth-inspired” drama.

Summary

Frank Sinatra’s story is told as a cautionary tale of ambition, criminal ties, and the dangers of unchecked hubris in the shadowy spaces between entertainment, organized crime, and political power. Through swaggering anecdotes, sharp psychological insight, and explosive historical moments, this episode offers a fresh, entertaining, and conspiratorial take on the tangled fate of a superstar and a president—hinting that Sinatra’s greatest legacy may be as much about chaos and consequence as about music and charm.