CROSSING THE LINE — For the most part, the Republican National Convention in Milwaukee last month went exactly as expected — a coronation for Donald Trump. Except, that is, for one speech that rankled partisans on both sides. That would be Teamsters President Sean O’Brien’s fiery, pro-worker, anti-corporate speech to Republican delegates on the convention’s first night. In addition to alienating some Republicans who chafed at its tone, O’Brien’s speech — which a fellow Teamster leader dubbed “unconscionable” — sparked a backlash within organized labor, where unionists accused O’Brien of lending credibility to a party that has done little to support the policy priorities of unions. O’Brien has now attracted a challenger for the union’s internal presidential election in 2026. O’Brien’s RNC speech revealed the tensions within the labor movement in recent years as union leaders wrestle with the challenge of Trump-supporting rank and file members and the new populist-orientation of the Republican Party. The address also served to remind Democrats that organized labor’s support can’t be taken for granted in November. “The problem that union leaders have right now is that they historically have emphasized economic issues,” said Paul Clark, a professor of labor and employment relations at Penn State University. “The frustration for unions is that they can’t address the social and cultural issues that are pulling more working people toward Trump and Republicans.” “O’Brien knows that a whole lot of his members are registered Republicans and are supporting Donald Trump,” added Clark. “It’s a percentage that he would ignore at his peril.” Historically, the Teamsters have been a more conservative union. The union has endorsed Republicans for president in the past, such as Richard Nixon, Ronald Reagan and George H.W. Bush. But the challenge facing Teamsters leadership today is a familiar one across unions. The number of union members supporting Republicans has grown markedly in recent years, with several polls from earlier this year suggesting that the trend could be accelerating in 2024. That’s leading to a tricky situation for union leaders, who must reconcile that development with the traditionally pro-union record of the Democratic Party. Under the Biden administration, for example, Democrats included tens of billions to bail out union pensions in the American Rescue Plan, named pro-union lawyers to the National Labor Relations Board and have voiced continued support for the PRO Act, which would make it easier for workers to unionize. Much of organized labor, including the United Auto Workers and the teachers unions, has already fallen in line behind Kamala Harris following President Joe Biden’s withdrawal from the presidential race. Still, failing to win over the Teamsters union, which has over 1.3 million members, would constitute a blow to Democrats. In the wake of O’Brien’s RNC speech, the relationship is strained. The union said that Harris had not yet responded to a request to have a roundtable discussion with Teamsters’ leaders, and that O’Brien had not received an invite from Democrats to speak before the Democratic National Convention in Chicago. Teamsters’ rank and file are currently voting on the candidates to show their presidential preference, but union leaders will ultimately make the final endorsement decision. The backlash against O’Brien began even before his speech. John Palmer, a vice president of the Teamsters, wrote a column attacking O’Brien’s choice to speak before the RNC in the Las Vegas Sun, writing that doing so “only normalizes and makes palatable the most anti-union party and president [Trump] I’ve seen in my lifetime.” Palmer later published a letter declaring his candidacy against O’Brien in 2026, writing that the Teamsters president was “kissing the ring of a man that had scabbed a picket line” and that “we have successfully estranged ourselves from the rest of the labor movement.” As politically perilous as his RNC speech was, it elevated O’Brien’s national profile and represented a rare opportunity for a union leader to speak directly to a large audience of Republicans. “The part that is unprecedented is O’Brien attacking corporate America for being anti-worker,” said Robert Bruno, the director of the labor education program at the University of Illinois, Urbana-Champaign. “I can’t think of any Republican convention where a speaker, let alone a union president, spoke so critically of the base of the Republican Party. He went in there and stunned the crowd.” Kara Deniz, a spokesperson for the Teamsters, said that the convention’s large television audience made it an ideal platform to spread a pro-worker message. Over 18 million Americans tuned in for the first night of the convention, according to Nielsen. During his address, O’Brien attacked the Republican Party for standing in opposition to unions, declared that the Teamsters are “not beholden to anyone or any party” but also nodded toward Republicans who have made limited public displays of support for unions, such as Missouri Sen. Josh Hawley and vice presidential candidate J.D. Vance. (Both Hawley and Vance have received poor marks on their pro-union voting records from the AFL-CIO.) “We are going to support the elected leaders who support workers,” said Deniz for the Teamsters. “We are not just going to blindly support candidates based on their past record if they’re not doing something for us at the moment.” Welcome to POLITICO Nightly. Reach out with news, tips and ideas at nightly@politico.com. Or contact tonight’s author at pederschaeferwriting@gmail.com.
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