Why Union Members Flipped On Democrats & Supported Trump | Chuck Todd Politics Podcast

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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