The Teamsters are one of the most powerful unions in America, and for decades they’ve endorsed the Democratic Party’s nominees for president. They have yet to endorse a candidate for 2024, but recently they’ve raised some eyebrows by getting cozy with former President Donald Trump.
Teamsters General President Sean O’Brien met with Trump twice in January, including a private visit to Mar-a-Lago, after which the union posted a photo of the pair. Then news came out that the Teamsters donated $45,000 to the Republican National Committee’s convention fund — the maximum amount allowed from the union’s political action committee. It appears to be the most significant contribution that the Teamsters have made to the RNC in two decades.
What’s going on?
Organized labor experts say that O’Brien appears to be strategically positioning himself, both for internal political reasons and because he could be trying to put a good word in with Trump in case he wins the election. That maneuvering raises two concerning questions. One, is a major union playing footsie with Trump because it views President Joe Biden as particularly weak in this election cycle? Second, could this process result in the union effectively nudging some on-the-fence union members and their communities to think of Trump as anything but the foe of labor he really is?
O’Brien rubbing elbows with Trump as a tactical maneuver could be costly.
The Teamsters are a massive, politically diverse union, with 1.3 million members, including UPS drivers and many other kinds of transportation workers. Nelson Lichtenstein, a labor historian at UC Santa Barbara, estimates that around 40%-45% of its membership leans Republican. Though the Teamsters have, like other labor unions, largely backed Democrats during their history, they were one of the few unions to back Ronald Reagan, and the only major labor outfit to support George H.W. Bush in his 1988 campaign. This political spread is partially why it makes sense that the union interviews political candidates across the political spectrum. The Teamsters have held roundtable discussions with independent candidates Robert Kennedy Jr. and Cornel West, as well as Democratic challengers to Biden like Rep. Dean Phillips of Minnesota.
A meeting with Biden is expected in March — and labor experts say an eventual endorsement of Biden is all but certain. (NBC News reports that in December, “the Teamsters PAC donated $45,000 each to a slew of Democratic organizations, including the DNC’s legal fund, the Democratic Senatorial Campaign Committee’s legal fund, the DNC’s building fund, the DNC’s convention fund and the Democratic Congressional Campaign Committee’s legal fund.”) But holding meetings with Trump twice, including one on his home turf, and sending an eye-catching donation seem like an above-and-beyond effort to court the right.
There are three possible explanations.
First, O’Brien, who has been Teamsters president for less than two years, may be calculating that he can enhance his own re-election prospects by showing off his ability to connect with Trump and appearing extra attentive to the political leanings of a huge part of his constituency. On an ideological level, O’Brien is not a far-left labor leader, and that might make him more at ease with politicking across the political aisle.
Second, given that a Biden endorsement remains probable, O’Brien’s courtship of Trump can be read as a tactical move to buy credibility with the rank-and-file members who are undecided or at least not firmly committed to either major-party candidate. O’Brien’s calculation may be that he can buy himself and the union more credibility in their eventual endorsement of Biden by engaging with Trump prior to it. Third, O’Brien’s outsize attention to Trump could represent a wager that Biden is a weak candidate, and that the Teamsters can hedge their bets by trying to forge a bond with Trump in case he gets elected. In theory, this might all sound benign, but there’s reason for concern. O’Brien rubbing elbows with Trump as a tactical maneuver could be costly. Even with an eventual Biden endorsement, the openness toward Trump — and particularly his photo with O’Brien — may leave many some workers under the impression that Trump could advance worker interests. If Biden were overtly hostile to unions or Trump were an uncommonly labor-friendly Republican then perhaps this display of agnosticism would make sense, but the opposite is true: Biden has been an uncommonly vociferous ally of labor, while Trump’s presidency was marked by championing plutocracy and a sustained assault on worker rights. So implying that Trump is worthy of sustained attention is remarkably reckless from a union political education perspective. And there is no realistic prospect of Trump being nice to the Teamsters — or any union — if he gets re-elected just because of some schmoozing. The Teamsters were not able to convince Trump to help them with their financially troubled union pension plan, but Biden delivered. The Teamsters’ leadership’s attempts to get in Trump’s good graces effectively misleads not only the rank-and-file members, but themselves. The Teamsters’ awkward politicking is a proxy for a broader issue — the Democrats usually win the vote of organized labor, but by far narrower margins than they should in battleground states, considering the two parties’ respective records and platforms. So while Biden has done a lot of good work supporting union workers rhetorically and with policies like his appointment of bold reformers to the National Labor Relations Board, he could still do more. Biden could sound a little more like Bernie Sanders, and adopt sweeping new policies like directing federal money to workers to help them organize, Hamilton Nolan, the author of “The Hammer: Power, Inequality, and the Struggle for the Soul of Labor,” told me. “What Biden needs is the rank-and-file people in the Teamsters to feel energetic about him. If they did then you wouldn’t see Sean O’Brien doing this in the first place,” he said.
Zeeshan Aleem is a writer and editor for MS NOW. 
