PBD Podcast #665 Summary: Teamsters Union President Targets Amazon - Sean O’Brien
Date: October 11, 2025
Host: Patrick Bet-David (PBD)
Guest: Sean O’Brien, President of the Teamsters Union

Overview

This episode features an in-depth conversation between Patrick Bet-David and Sean O’Brien, the youngest president of the Teamsters Union. The discussion explores the evolving role of unions in modern America, the union’s confrontational stance against Amazon, the complicated relationship between unions and capitalism, and O’Brien’s personal background and leadership philosophy. The audience is treated to transparent dialogue concerning labor, business ownership, political engagement, worker protections, and memorable moments from O’Brien’s confrontational public life.

Key Discussion Points & Insights

1. The Role of Unions vs. Capitalism (01:01–06:54)

• Corporate America as the “Enemy”: O’Brien criticizes the greed of large corporations, claiming they forget the workers who create their profits, especially after labeling them "heroes" during COVID. “They are despicable on what they do to working people.” (01:01, O’Brien)
• Unions as Conscience: O’Brien frames unions not as anti-capitalist roadblocks but as the "conscience" of capitalists, advocating for fair recognition and rewards for workers.
• Union Achievements: The Teamsters union organized 90,000 new members in three years and played a vital role during the pandemic.

2. Teamsters at the RNC & Bipartisan Outreach (03:01–09:32)

• Historic RNC Speech: For the first time in 121 years, a Teamsters president speaks at the Republican National Convention. O’Brien emphasizes bipartisanship, noting he would have given the same speech at the Democratic National Convention if invited. “It wasn’t a partisan speech at all. It was about American workers and how valuable we are.” (03:33, O’Brien)
• Speech Authenticity: O’Brien resisted attempts by RNC officials to edit his speech; Trump told him, “I don’t give a fuck what you say. Say what you want.” (07:44, O’Brien), underlining a preference for authenticity over party scripting.
• Audience Reaction: O’Brien skillfully began his RNC speech by saluting Trump’s resilience, then criticized capitalism, observing the crowd’s confusion about whether to clap.

3. Unions vs. Amazon (12:34–15:32)

• Amazon as “Enemy #1”: O’Brien singles out Amazon for its anti-union tactics, exploitative employment practices, and reliance on high-attrition, non-career jobs. “They are despicable... probably the biggest enemy we have right now.” (13:58, O’Brien)
• Employment Practices: Amazon utilizes a 1099 contractor model to avoid direct employment responsibilities, requiring contractors to purchase vehicles and uniforms from Amazon and follow Amazon policies, but denying them W2 status and benefits.
• California Decision: Recent legal wins are exposing Amazon’s direct relationship with drivers, setting organizing precedents.

4. The Uber & Lyft 1099 Debate (17:30–22:13)

• Skepticism About “Unionized” Rideshare Drivers: O’Brien argues that Uber and Lyft’s concession to allow drivers to “unionize” is a masquerade, as there’s no real collective bargaining power for contractors, and jobs could be displaced by autonomous vehicles.
• Proposal: O’Brien advocates for rideshare drivers to be made direct employees. “Uber and Lyft should make them direct employees.” (20:15, O’Brien)
• Host’s Counterpoints: Patrick highlights the flexibility and entrepreneurship of 1099 work, such as in real estate, questioning the feasibility and desirability of eliminating all independent contractor status.

5. Small Business Owner Protections vs. Unionization (22:13–30:33)

• Business Risks: The host underscores the risks entrepreneurs take, including mortgaging property. O’Brien recognizes these risks but maintains that the 1099 system creates wage, hour, and tax abuses, and bankruptcy laws often leave workers last in line for compensation.
• Real-Life Examples: Discussion of cases like Yellow Freight, where bankruptcy left thousands without pensions or wages.

6. Pensions, 401(k)s, and Economic Security (30:33–39:38)

• Pension Decline: The show explores the steep loss in defined-benefit pensions across the U.S. over recent decades, with companies increasingly reneging on promises (e.g., United Airlines).
• Union Model: Teamsters focus on collectively bargained employer-paid pensions and voluntary 401(k)s, aiming not to burden workers with retirement investment risk.
• O’Brien’s View: “No one has ever successfully retired off a 401k. No one.” (32:07, O’Brien)

7. Union Culture, Productivity, and Criticisms (39:38–51:39)

• Handling Criticism: The host acknowledges events are sometimes harder at union hotels. O’Brien responds that union workers are better trained and more productive, though he concedes every industry has a problematic minority.
• Negotiation Tactics: O’Brien recommends listing five job security/prosperity items and asking any employer to sign; if they won’t, “you need us.” (38:33, O’Brien)

8. Life as a Teamster & O’Brien’s Background (10:53–12:23; 62:00–66:43)

• Motivation: O’Brien grew up immersed in Teamsters culture and loyalty, inspired by his family’s multi-generational membership. "That's all I ever wanted to do in my life." (11:10, O’Brien)
• Leadership Path: Rose through every position, starting as a shop steward. “I wanted that job since I was 8 years old.” (63:54, O’Brien)
• Mob Connections (Historical): O’Brien distances today’s union from organized crime, acknowledging earlier connections due to big projects, pension funds, and urban construction: “Thankfully, it's not like that anymore.” (66:43, O’Brien).

9. Political Engagement and Profiles (54:16–61:26)

• Candidate Interactions: O’Brien recalls pointed exchanges with Kamala Harris and difficult sessions with Biden’s campaign but praises their process transparency and willingness to answer questions.
• Membership Political Diversity: Majority still slightly Democratic, but many members have shifted due to focus on economic (not social justice) issues.
• Major States: Largest Teamster concentrations: California (~150,000 members), New York, Chicago.

10. Memorable Moments: Senate Showdown & Media Virality (77:36–81:35)

• Markwayne Mullin Senate Faceoff: O’Brien’s viral Senate hearing nearly turned physical after Twitter sparring. O’Brien says they later met, hashed things out, and are now friendly, working together on bipartisan labor legislation.
• Comic Relief: O’Brien’s mother chastises him after the hearing appearance: “You just got us all fucking audited. Like, seriously, can't you behave?” (79:02, O’Brien)
• Legacy: “We're working on the FASTER Labor Contracts Act... for American workers.” (80:51, O’Brien)

Notable Quotes & Moments (with Timestamps)

• On delivering an unedited speech at RNC:
  “I don’t give a fuck what you say. Say what you want.” — Donald Trump relayed by Sean O’Brien (07:44)
• On Amazon as the ‘enemy’:
  “They are despicable... probably the biggest enemy we have right now.” — O’Brien (13:58)
• On converting RNC crowd:
  “Win them over, bring them in, give him a hug, and then slap them, right?” — O’Brien on his RNC speech tactics (09:08)
• On Uber and Lyft’s 1099s:
  “Uber and Lyft should make them direct employees. Right.” — O’Brien (20:15)
• On pensions:
  “No one has ever successfully retired off a 401k. No one.” — O’Brien (32:07)
• On lifelong ambition:
  “I wanted that job since I was 8 years old. Get out of here. Absolutely did.” — O’Brien (63:54)
• On Senate hearing viral moment:
  “You stand your butt up.” — O’Brien to Senator Markwayne Mullin (78:48)
• On mother’s reaction:
  “Oh, that's real, real nice. Real nice, Sean. I go, why?... You just got us all fucking audited.” (79:02)

Timestamps for Key Segments

• [01:01–06:54] The need for unions, corporate America as “enemy,” COVID-19, essential workers
• [03:33–09:32] First Teamster speech at RNC, speech editing stories, audience strategy
• [12:34–15:32] The case against Amazon: employment, organizing, legal actions
• [17:30–22:13] 1099 issues: Uber, Lyft, employee vs. contractor model
• [22:13–30:33] Risks and rewards for business owners and system abuses
• [30:33–39:38] Pensions, retirement security, union vs. 401(k) approaches
• [39:38–51:39] Union productivity, criticisms, contract negotiation advice
• [62:00–66:43] O’Brien’s personal Teamsters story, leadership style, family influence, mob history
• [77:36–81:35] Viral Congressional showdown and its real-world aftermath

Final Thoughts & Tone

The episode is a robust mix of fiery union advocacy, humor, and mutual respect. O’Brien is unapologetically pro-worker, occasionally confrontational, and deeply loyal to union ideals, but he's also pragmatic, open to business realities, and values bipartisan solutions. His storytelling, especially about his RNC speech and the viral Senate moment, adds entertainment and candor—making the episode as informative as it is engaging.