In an unexpected political convergence, Sean O’Brien, the president of the Teamsters union, announced he had met privately with Donald Trump – raising questions about who the Teamsters will endorse in 2024 and drawing anger from the union’s progressive members. The meeting came amid efforts by Joe Biden and the thinning field of Republican challengers, led by Trump, to appeal to workers and labor organizations. And it followed three years of declarations from Biden and his administration that it would deliver to workers the most pro-union presidency in US history. The Teamsters, a union of 1.3 million members in sectors including packaging, trucking, manufacturing and logistics, promoted the meeting on its official channels, thanking Trump for “taking time during this private meeting to listen to the Teamsters’ top priorities” and announcing an upcoming roundtable with the former president and rank-and-file union members. In a separate announcement, Trump shared a photo of himself and O’Brien flashing a thumbs-up from the former president’s Mar-a-Lago quarters. But Teamsters leaders on the left say they were caught off guard by the meeting. When O’Brien was elected in 2021 to lead the union, it was in part due to the support of a progressive labor coalition that viewed O’Brien as a hopeful alternative to the union’s old guard, affiliates of the famed Hoffa family, whose control of the union, once known for its militancy, had ushered in an era of corruption and scandal. The O’Brien slate promised to restore the Teamsters as a fighting union. “I still can’t believe it,” said Richard Hooker Jr, the secretary treasurer of Teamsters local 623 and vice-president of the Philadelphia AFL-CIO board. “As leaders, we have to do a better job of explaining to our members that a vote for Trump is a vote against your pension, a vote for Trump is a vote against organizing workers, a vote for Trump is another vote against the working class.” On a special Martin Luther King Jr Day podcast this week, Hooker and Chris Silvera, the secretary-treasurer of local 808 in New York, chatted about the photo. “They’re not Republicans any more – they should just throw that name out,” Silvera said of the former Trump administration. “They’re Confederates.” Jess Lister, a shop steward in Georgia and member of the Teamsters LGBTQ caucus, who has helped lead a campaign to organize part-time UPS workers, called the meeting “a slap in the face”. Lister added that she did not support any of the frontrunner candidates or Biden, but said she viewed the Trump meeting as especially galling given his record of stacking the courts with anti-union judges and overseeing a National Labor Relations Board (NLRB) that issued rulings making it harder for workers to organize. “He has a longstanding history of racism, of hate towards women, towards minorities, towards the LGTBQ community – he is not accepting of other people,” Lister said. “Our union president shouldn’t even entertain the idea of a meeting. That shouldn’t have even been on the table.” The Teamsters have put forward an open invitation to presidential candidates to meet with their members and leadership. But Trump is apparently the first real contender to take them up on their offer – prior engagements included the long-shot candidates Asa Hutchinson, Robert F Kennedy Jr, Marianne Williamson, Cornel West and Dean Phillips. The union vote is coveted and can help decide elections, especially in relatively union-dense swing states like Michigan, Wisconsin and Pennsylvania. Trump in 2016 found unexpected support from some Teamsters members whose ranks have historically voted Democratic. Kara Deniz, a spokesperson for the Teamsters, said she had not heard from members concerned about the Trump meeting and said candidate meetings represented a good-faith effort to inform members about candidates for office. “It does a disservice to our members to ignore the frontrunner on the Republican side,” said Deniz. According to Deniz, Biden has also agreed to meet with the union. Teamsters for a Democratic Union (TDU), the historically left-leaning rank-and-file caucus that supported O’Brien’s campaign, did not reply to requests for comment. In meeting with Trump, the Teamster leader split from most major labor organizations, many of which have roundly rejected Trump’s third bid for office. The United Auto Workers (UAW), which last year elected a union leader who – like O’Brien – promised to bring democracy and militancy to the labor group, rejected offers to meet with Trump during their strike this fall and said a possible second Trump turn would be a “disaster”. “I see no point in meeting with him because I don’t think the man has any bit of care about what our workers stand for, what the working class stands for,” the UAW president, Shawn Fain, said. Trump instead met with non-union auto workers during the strike, where he told his audience that the UAW had “to endorse Trump, because if they don’t, all they’re doing is committing suicide”. The UAW has also so far refrained from endorsing Biden. “Our endorsements are going to be earned,” Fain told CBS’s Face the Nation in September. “We’ve been very clear about that, no matter what politician.” On 26 September, Biden, in a historic bid for the union’s support, joined a UAW picket line in Michigan. Unions can play an important role in elections, throwing resources and support behind labor-friendly candidates and often serving as a key component of the Democratic coalition. Biden vowed to establish himself as the “most pro-labor president” in US history, and his administration has ushered in modest wins through NLRB rulings speeding up union representation elections and adding sanctions for employers who break the law during union elections. At least 13 member unions of the AFL-CIO, the largest US labor federation, have re-endorsed President Biden ahead of 2024. In a September statement, the federation condemned Trump, calling his record “catastrophic for workers”. “We can’t afford another four years of Trump’s corporate agenda to take away our hard-fought gains and destroy our unions,” they wrote.