President Joe Biden met Tuesday with one of the few unions yet to endorse him, making the case for its backing amid flirtations with former President Donald Trump.

Biden has already wrapped up the endorsements of most nonpolice unions, calls himself the most pro-union president in history, and made the case that the International Brotherhood of Teamsters should back him as well.

“The Biden-Harris campaign is proud to have the support of the AFL-CIO, AFSCME, AFT, UAW and many other unions,” Biden’s campaign said following the meeting with Teamsters President Sean O’Brien. “We hope to earn the support of the Teamsters as well.”

The Teamsters represent 1.3 million transportation workers at UPS and other companies and raised eyebrows earlier this year with a $45,000 donation to the Republican National Committee, the union’s first donation to the RNC in 20 years.

That donation came the same day that Teamsters leaders met, for the second time this year, with Trump, who has heavily courted union members despite lacking support from union leadership. Though the Teamsters made an equal donation to the Democratic National Committee, even the split donations represented a departure from precedent.

“Within the union itself, I have tremendous support,” Trump said following his meeting with O’Brien. “They like what I do. They never had a better four years than they had during the Trump administration. I can say that for a lot of businesses and a lot of people, African American, Asian American, Hispanic American, they had the best four years they’ve ever had.”

Efforts to reach the Teamsters for comment were unsuccessful.

There has long been a gap between the political activity of union leaders and the voting habits of rank-and-file union members. Biden won 56% of union votes in 2020 to Trump’s 40%. But unions gave nearly 90% of their political contributions to Democrats.

Biden launched his 2020 presidential campaign at a Teamsters hall in Pittsburgh, with labor organizations contributing $27.5 million to back his White House bid.

The Teamsters endorsed Biden during that election cycle and backed Hillary Clinton and Barack Obama before him. It last endorsed a Republican presidential candidate in 1988.

Still, its status as a holdout in the endorsement sweepstakes is part of a long-standing independent streak, argues labor union expert Dan Bowling.

“Teamsters have always been a little independent,” said Bowling, who teaches labor courses at Georgia State University’s law school. “They endorsed Richard Nixon, for example, which was a big deal when that happened.”

Bowling predicted the union will probably endorse Biden in the end, though he could also see it taking a “members decide” stance, and says there’s maybe a 25% chance it endorses Trump.

Trump has actively courted other union endorsements, or at least the votes of union members, during the current cycle. When Biden visited a United Auto Workers picket line in Michigan last September, Trump spoke at a nonunion shop and promised he’d be better for workers.

Trump attacked electric vehicles as bad for workers, an issue that could be at play with Teamsters as well.

“[Electric vehicles] are built specifically for people who want to take a very short trip,” Trump said. “They say the happiest day when you buy an electric car is the first 10 minutes you’re driving it. And then after that, panic sets in because you’re worried, ‘Where the hell am I going to get a charge to keep this thing going?’”

People in the audience hoisted “Union Members for Trump” signs, although the UAW later endorsed Biden.

Union votes will be closely watched this fall, as traditional union states like Wisconsin, Michigan, and Pennsylvania could stem the tide of the election. Trump won all three en route to his upset win in 2016, then Biden flipped them to take the 2020 election.

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The president is hoping to win enough union votes to keep those states in his corner this time around and looks to the Teamsters to again throw their official support behind him to accomplish that goal.

“The president appreciated the opportunity to discuss his historic, pro-union record with the Teamsters today,” his campaign said.