On this episode of the Chuck ToddCast, 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.

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Sean O’Brien joins the Chuck ToddCast

00:30 Teamsters have reputation of being a less partisan union

02:00 Teamsters have a very diverse membership

03:15 Amazon could be the biggest threat to organized labor

04:30 The threat of AI to workers

05:45 AI job displacement could be central issue to 2028 campaign

07:15 What leverage do the unions have when it comes to AI?

09:15 3 Democratic governments vetoed bills for automated trucks

12:30 How are unions dealing with technological change & automation

14:00 Technology is being adopted without input for labor

15:30 What mistakes did labor make during NAFTA negotiations?

16:45 Labor made a mistake trusting political leadership with NAFTA

18:00 Democrats used to be the party of labor, now also a party of business

19:00 Labor needs to be transactional and not partisan

21:30 Republicans like Rubio have become more friendly to labor

22:45 Has the Republican shift been rhetorical or substantive?

25:15 Josh Hawley was persuaded to stop supporting Right to Work

26:30 Bad trade deals caused Ohio to flip from blue to red

27:30 No explanation for why Sean wasn’t invited to the DNC

29:00 The Teamsters were never going to co-endorse Kamala Harris

31:15 Teamsters have 65% Republican membership

32:45 Labor is the last group taken care of during a bankruptcy

34:30 Democrats don’t deserve credit for fixing a problem they created

36:30 What’s the relationship like with other labor unions?

38:00 There is some ill-will from other unions for not endorsing Harris

39:00 An endorsement wouldn’t move the needle with the members

39:30 How can Democrats win back union members?

41:15 The split between members and leadership over supporting D’s

43:30 How can you trust the Republicans?

45:15 Teamsters will definitely weigh in on senate and house races in 2026

46:45 Teamsters would happily accept student athletes as union members

48:45 College football union membership would likely be by conference

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