With almost 1.5 million members, the Teamsters is the fourth-largest trade union in the country. Their past close affiliation with Democrats meant that money and volunteers poured into Teamsters headquarters on Capitol Hill, destined for Democratic Party campaigns and causes.
All that began to change in 2024 when Teamsters General President Sean O’Brien delivered a historic address at the Republican National Convention in Milwaukee. In his speech, O'Brien recognized that while the Teamsters leadership might vote Democratic, the rank and file majority supported Donald Trump. He noted that his Big Labor faction is “not beholden to anyone or any party” and thanked Trump for “opening the RNC’s doors to the Teamsters union.”
“Our members are working people whose interests cut across party lines,” Kara Deniz, a Teamsters spokesperson, told Politico. “And there’s no value in living in a bubble … where you only talk to certain people to the exclusion of others.”
O'Brien created the D.R.I.V.E. political action committee — Democrat, Republican, Independent Voter Education — and began to donate considerable sums of cash to Republicans.
Trump got nearly 60% of the Teamsters' vote in 2024, but it's more than the presidential race that the Teamsters are backing. The union gave the National Republican Congressional Committee $5,000 in the second quarter. They contributed a combined $62,000 to nearly two-dozen Republican candidates in battleground districts. They also gave to GOP Sens. Deb Fischer of Nebraska, Lisa Murkowski of Alaska, Jon Husted of Ohio, and Dave McCormick of Pennsylvania. And they donated $50,000 to the Republican Attorneys General Association in June.
Starting from nothing to donating tens of thousands of dollars to Republicans is a startling political development. Does it signal a general evening-out of contributions from labor unions to both parties?
If Democrats don't wake up, it will happen.
A Teamsters vice president, Joan Corey, said [Kamala] Harris told her that the union “better get on board” and seemed to think she was “going to win with you or without you.”
Mr. O’Brien described Ms. Harris’s attitude and body language as “smug,” saying it “turned the majority” of Teamsters board members “off her.” The union didn’t make an endorsement, the first time it stayed neutral since 1996 and just the second time since 1960.
At the RNC, Mr. O’Brien said he meets with his members “every week” and sees “an American worker being taken for granted … sold out to Big Banks, Big Tech, Corporations, and the elite.” The speech drew applause and hosannas that, for Teamsters, countered the long-standing caricature of the GOP as the party of big bosses.
O'Brien says that democratic socialist Sen. Bernie Sanders hasn't spoken to him since that 2024 appearance at the GOP National Convention. That kind of behavior rankles O'Brien, making him less likely to listen to Democrats in the future.
“Labor unions are finally recognizing that their memberships are made up of workers from across the political spectrum,” said first-term GOP Rep. Rob Bresnahan. The congressman received $5,000 from D.R.I.V.E. for his 2026 campaign.
Tariffs may be in bad odor with some elites, but they resonate with working-class Americans.
"As Mr. Trump’s tariffs prod companies to bring manufacturing and even film production back home, Teamsters are taking note of who is addressing their concerns," notes the Sun's Dean Karayanis.
Sometimes, that's all it takes to turn a Democrat into a loyal Republican.
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