Preview: Teamsters and union politics with Sean O'Brien

On this episode of the Chuck ToddCast, Chuck breaks down the absurdity of the U.S. government repeatedly grinding to a halt over government shutdowns. He explains why disruptions like TSA slowdowns and flight delays could force a faster resolution, why this standoff likely won’t last beyond a couple of weeks, and how Republicans may try to negotiate, only to walk back agreements through budget rescissions—or even consider ending the filibuster to reopen government. Chuck also examines the Democrats’ post-Obama resilience, built on being seen as the “grown ups,” while Trump continues to erode norms, politicize governance, and set the tone for a crasser American culture. From the decisive swing of a 3-5 point “adult constituency” to Trump’s retributive budget plans, fundraising battles in Maine and Michigan, and even Trump’s transactional dealings with Qatar and Pfizer, this episode explores the fragile state of U.S. politics in an era where outrage is constant and functional governance feels increasingly out of reach.

Then, Teamsters president Sean O’Brien joins Chuck to talk about the future of organized labor in an era defined by Amazon, automation, and artificial intelligence. O’Brien warns that AI-driven job displacement could be the central issue of the 2028 campaign, and he argues that technology is being adopted without worker input—repeating mistakes unions made during NAFTA, when labor put too much trust in political leadership. He stresses that unions must be transactional, not partisan, as Democrats increasingly balance business interests while Republicans like Marco Rubio and Josh Hawley show new, if uneven, openness to labor.

The conversation also dives into the political tightrope the Teamsters walk. With a membership that’s 65% behind Trump and Republicans, O’Brien explains why endorsing Kamala Harris was never on the table, why Democrats shouldn’t get credit for fixing problems they helped create, and how bad trade deals pushed states like Ohio from blue to red. From navigating tensions with other unions to weighing in on key 2026 races, O’Brien makes clear the Teamsters are willing to work with anyone who delivers for workers—and even open the door to college athletes unionizing by conference. This is a candid look at the shifting power and politics of America’s labor movement.

Finally, he answers listeners’ questions in the “Ask Chuck” segment and previews the upcoming weekend in college football.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Introduction

01:15 Ridiculous for world’s superpower to have their government shut down

02:00 Flight delays, TSA issues could cause the fastest resolution

04:00 Would be surprising if shutdown lasts longer than a couple weeks

05:00 Vance signaled some willingness to negotiate

06:30 Republicans can agree to demands, then use recissions to renege

07:30 Republicans could end the filibuster and reopen the government

08:30 Nominations should require a 75 vote threshold build consensus

10:00 2013 shutdown got Terry McCauliffe elected as VA governor

11:15 Trump has politicized every aspect of governance

12:00 Russ Vought targeting cuts to only blue states in retribution

14:45 What has kept the Democrats competitive post-Obama?

15:30 Dems have benefitted from being considered the “grown ups”

16:00 Dem activists feel like playing by the rules hasn’t helped them

18:30 Six week clean CR proposal was reasonable

19:45 The “adult” constituency may be 3-5 points, and could be decisive

21:30 Trump’s behavior has been outrageous, but we’ve become numb to it

22:45 We’re in a “political depression”, have a barely functioning government

24:45 There’s no lines Trump won’t cross, there are lines the left won’t

26:15 American culture has become more crass under Trump

28:15 Our sense of decorum is being set by Trump and online MAGA

30:15 Graham Platner raised $3.2 million in Maine senate race

32:00 Is Janet Mills the strongest candidate to beat Susan Collins?

33:00 Being an “outsider” will likely outweigh ideology

35:00 Michigan democratic senate candidates all have strong fundraising

36:00 Trump offers NATO style security guarantees to Qatar

37:00 Airplane gift to Trump paying dividends for the Qataris 

38:00 Pfizer agrees to name website TrumpRX

40:30 Trump nominee pulled after opposition from crypto world

44:00 Sean O'Brien joins the Chuck ToddCast 

44:30 Teamsters have reputation of being a less partisan union 

46:00 Teamsters have a very diverse membership 

47:15 Amazon could be the biggest threat to organized labor 

48:30 The threat of AI to workers 

49:45 AI job displacement could be central issue to 2028 campaign 

51:15 What leverage do the unions have when it comes to AI? 

53:15 3 Democratic governments vetoed bills for automated trucks 

56:30 How are unions dealing with technological change & automation 

58:00 Technology is being adopted without input for labor 

59:30 What mistakes did labor make during NAFTA negotiations? 

1:00:45 Labor made a mistake trusting political leadership with NAFTA 

1:02:00 Democrats used to be the party of labor, now also a party of business 

1:03:00 Labor needs to be transactional and not partisan 

1:05:30 Republicans like Rubio have become more friendly to labor 

1:06:45 Has the Republican shift been rhetorical or substantive? 

1:09:15 Josh Hawley was persuaded to stop supporting Right to Work 

1:10:30 Bad trade deals caused Ohio to flip from blue to red 

1:11:30 No explanation for why Sean wasn't invited to the DNC 

1:13:00 The Teamsters were never going to co-endorse Kamala Harris 

1:15:15 Teamsters have 65% Republican membership 

1:16:45 Labor is the last group taken care of during a bankruptcy 

1:18:30 Democrats don't deserve credit for fixing a problem they created 

1:20:30 What's the relationship like with other labor unions? 

1:22:00 There is some ill-will from other unions for not endorsing Harris 

1:23:00 An endorsement wouldn't move the needle with the members 

1:23:30 How can Democrats win back union members? 

1:25:15 The split between members and leadership over supporting D's 

1:27:30 How can you trust the Republicans? 

1:29:15 Teamsters will definitely weigh in on senate and house races in 2026 

1:30:45 Teamsters would happily accept student athletes as union members 

1:32:45 College football union membership would likely be by conference

1:34:45 Chuck's thoughts on interview with Sean O'Brien 

1:36:00 Ask Chuck 

1:36:15 Has anyone else ever started run for president as early as Trump? 

1:43:45 Thoughts on use of centralized databases for voter rolls? 

1:48:30 Why do government workers get back pay after a shutdown? 

1:53:30 If Josh Shapiro dominates re-election could he leapfrog the Dem field? 

1:56:45 College football preview

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