United States of Kennedy

Episode: RFK vs. Jimmy Hoffa

Hosts: Lyra Smith & George Civeris

Guest: Dan O’Sullivan (co-host, The Outfit podcast)
Release Date: October 6, 2025

Brief Overview

This episode explores the legendary feud between Robert F. Kennedy (RFK) and Jimmy Hoffa, the storied Teamsters union leader with deep ties to organized crime. Hosts Lyra Smith and George Civeris, joined by Mafia historian Dan O’Sullivan, examine RFK’s crusade against corruption in America’s unions, the intertwined relationships between the Kennedys and the mob, how public perception and political ambition fueled the drama, and the lasting impact of these events on labor and American politics.

Key Discussion Points and Insights

The Kennedys, the Mob, and American Power

• The Kennedy Family’s Underworld Ties

  • Joseph Kennedy, patriarch, was famously rumored to have been a bootlegger but was actually a well-connected tycoon with Hollywood and considerable dealings involving the Chicago political machine and organized crime. ([05:37])

    “He was very well sourced and had many contacts in the underworld at that time.”
    — Dan O’Sullivan ([05:37])

• 1960 Election and Mafia Influence

  • The “Chicago connection” — allegations that the Mafia helped swing the 1960 presidential election in Illinois to JFK, with Frank Sinatra serving as an intermediary between the legitimate and criminal worlds.

    “Frank Sinatra was often used by organized crime as a kind of cutout to the legitimate world, and Frank Sinatra, being a mob groupie, was happy to play that role.”
    — Dan O’Sullivan ([07:13])

Jimmy Hoffa: Rise, Power, and Corruption

• Who Was Hoffa?

  • Rose to rule the Teamsters, America's largest and most powerful union, transforming labor organizing but attracting notoriety through corruption and mob involvement. ([14:52])
  • The Teamsters’ pension fund used as a slush fund for the Mob.

• Corruption and the Mob

  • Hoffa’s alliance with organized crime began in the 1940s and quickly became inseparable from his leadership style.

    “He had very, very close ties to Italian Americans and to the Mafia from an early point in his career. And they never went away... if you let them in once, they’re there forever.”
    — Dan O’Sullivan ([16:37])

• Union Democracy Suppressed

  • Hoffa’s leadership was autocratic and maintained through violence or intimidation, with dissidents inside the Teamsters quickly silenced.

    “If you were a dissident Teamster... you could expect violence to be visited upon you.”
    — Dan O’Sullivan ([19:06])

RFK’s Anti-Mafia Crusade: Ambition, Shortcomings, and Showmanship

• RFK’s Motivation and Methods

  • Took on the Rackets (McClellan) Committee to make a name for himself, driven as much by ambition as principle.

    “This entire crusade was so clearly a way to make his name rather than some sort of deep moral belief that he had.”
    — George Civeris ([23:42])

  • His efforts inadvertently helped Hoffa gain power by dislodging rival Dave Beck.

    “Like with the kingpin strategy, what do you do? Well, Jimmy Hoffa was trying to replace Dave Beck, so you aided him immensely in rising to the national presidency. And Kennedy regretted that after the fact.”
    — Dan O’Sullivan ([21:16])

• The Senate Hearings: Drama and Dysfunction

  • RFK’s televised interrogations of Hoffa made for reality-TV spectacle but were legally ineffective.

    “Kennedy is kind of out of his element in this stuff. He’s right on like 90% of the stuff. But he’s inept... the questioning is kind of pointless.”
    — Dan O’Sullivan ([24:22])

  • Hoffa exploited the spectacle, using tactics like the “stare” and feigning memory lapses—refusing to plead the Fifth, frustrating Kennedy. ([33:27])

    “He seems to be outsmarting him in the stare... audiences and Teamsters and blue-collar people really like this — that it seems like he’s outsmarting this preppy, supercilious guy.”
    — Dan O’Sullivan ([33:27])

• Public and Political Fallout

  • The Kennedys’ anti-mob efforts were admired by many, especially among Irish Catholics, but also played into Southern and business anti-union agendas.
  • Legislation targeting unions followed the hearings, hardening labor law and arguably weakening union power. ([36:40])

The Complexity of Union Corruption

• Selective Outrage and Employer Complicity

  • The focus on union corruption ignored the complicity—and even instigation—by employers, who often benefited from “deals” with mobbed-up unions.

    “Employers are also equally victim and co-conspirator in labor racketeering. In fact, you could argue more responsible in the sense that union members are the ones who lose out on any kind of corrupt deal.”
    — Dan O’Sullivan ([37:10])

• Was it Pro-Labor or Anti-Union?

  • The hearings had a dual flavor: cleaning up labor’s image while quietly advancing anti-labor Southern and business interests.

Notable Moments & Quotes

• Comparing Mob and Elite Corruption

  “If the politicians are in bed with the mob, and if everybody who's in charge is in bed with them, then why shouldn't I be...?”
  — Lyra Smith ([40:22])

• Hoffa’s Chilling Remark After JFK’s Death

  “As Jimmy Hoffa says to a reporter in Nashville that day, Bobby Kennedy’s just another lawyer now. Which is kind of a chilling thing to say, to be honest.”
  — Dan O’Sullivan ([41:52])

Major Segments & Timestamps

• Intro and Set-up: [02:20–03:54]
• Kennedy Family & Mafia Origins: [05:21–08:53]
• Fact-checking Mafia Myths: [08:53–10:47]
• Who Was Hoffa? Power and Corruption: [14:38–18:48]
• Inside the Teamsters & Mob Relationship: [18:48–19:06]
• RFK Gets Involved — The Rackets Committee and Strategy: [20:47–24:22]
• Showmanship, Ambition, and Public Perception: [29:49–36:40]
• Labor, Power, and Politics: [36:40–40:22]
• RFK’s Mob Crusade: Success or Failure?: [40:22–41:52]
• Kennedy Assassination Theories (Hoffa’s Role): [45:34–48:37]
• Hoffa’s Fall and Aftermath for the Teamsters: [50:51–54:42]

Kennedy Assassination Conspiracies

• Did Hoffa Have a Role in JFK’s Death?
  • Dan O’Sullivan recaps journalist Dan Moldea’s extensive reporting, connecting Hoffa, the Teamsters, Jack Ruby, and key Mafia figures to the events around the Kennedy assassination.
  • Motive: Mafia and Hoffa wanted revenge on the Kennedys for relentless prosecution and broken deals.

    “This theory goes that he aided the Mafia, who was also under assault, to get them off their backs, get Bobby Kennedy out of the attorney General job... Carlo Marcello in New Orleans... says in Sicilian, I need to get the stone out of my shoe. That was the saying he used. And the stone in the shoe is Jack Kennedy, not Bobby.”
    — Dan O’Sullivan ([45:41])

Legacy and Lasting Impact

• Hoffa’s Downfall, Fitzsimmons, and Even More Corruption

  • After Hoffa’s imprisonment, Frank Fitzsimmons became Teamsters president, but his decentralization of power only worsened mob influence within the union.

    “Every one of those guys has mob ties and can do whatever he wants.”
    — Dan O’Sullivan ([51:30])

• Where Are the Teamsters Today?

  • Continuous struggles with corruption and reform; echoes of old mob ties persist, even as the union’s politics shift in contemporary times.

    “Now it’s run by Sean O’Brien. It’s a much cleaner union. But... Sean o’ Brien is Donald Trump’s biggest ally among unions, even though the current Trump administration is without a doubt the most anti union administration in American history... Maybe everything old is new again.”
    — Dan O’Sullivan ([53:01])

Conclusion

The RFK-Hoffa rivalry is a window into the blurry lines between legitimacy and criminality in mid-20th-century American politics and labor. It highlights how anti-corruption crusades can be as politically expedient as they are righteous; how ambition, class, and media spectacle shaped the era; and how legacies—both criminal and political—can persist and resurface in new guises. The Teamsters, once the jewel of labor power and mob infiltration, continue to wrestle with their past as new figures and alliances emerge.

Further Listening

• For more on organized crime, listen to Dan O’Sullivan’s podcast, The Outfit.

Summary by AI Podcast Summarizer — All quotations and attributions follow the original episode. Advertisements and non-content audio omitted.