The Chuck ToddCast

Interview Only w/ Sean O’Brien - Why Union Members Flipped On Democrats & Supported Trump

Oct 2, 2025
Sean O’Brien, the President of the International Brotherhood of Teamsters, dives into the evolving landscape of labor in today's world. He discusses the looming threats of automation and AI, warning that they could shape the political agenda by 2028. O’Brien emphasizes the need for unions to be transactional, not partisan, highlighting a significant shift as 65% of Teamsters lean towards Republicans. He reflects on past trade deal mistakes and the importance of worker input in technological advancements, advocating for a proactive approach to protect jobs.
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INSIGHT

Why Teamsters Are Politically Flexible

  • The Teamsters are large and unusually politically flexible because of their diverse membership and history since 1903.
  • Sean O'Brien says they support whoever advances members' interests, not automatically one party.
ANECDOTE

Teamsters’ Organizing With Amazon Labor Union

  • The Teamsters joined forces with the Amazon Labor Union after the New York win to organize Amazon and challenge third-party leasing schemes.
  • O'Brien calls third-party leasing a "scam and a shell game" harming worker rights.
INSIGHT

AI As A Central Political Risk

  • O'Brien warns AI and automation threaten both blue- and white-collar jobs and could reshape the 2028 campaign agenda.
  • He argues AI will eliminate middle-management and analyst roles while boosting CEO pay unless labor captures the gains.
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