Former President Donald Trump has always had blue-collar appeal, an attribute largely responsible for his 2016 upset victory over former Secretary of State Hillary Clinton. But this election cycle, Trump and his party have been overtly trying to win working-class voters and union members, who are traditionally a core Democratic constituency.

“Do me a favor. Just get your union guys, your leaders, to endorse me,” Trump said at a campaign stop in Michigan in September 2023, promising that his policies would save auto industry jobs. “I’ll take care of the rest.”

Trump didn’t get that, but he did benefit from something that hadn’t happened in 28 years — the International Brotherhood of Teamsters chose not to endorse the Democratic presidential nominee. The union will sit out this election for the first time since 1996.

Not only that, but the Teamsters released internal polling that found nearly 60% of its members back Trump, with Vice President Kamala Harris’s support in the low 30s.

“Our members are the union, and their voices and opinions must be at the forefront of everything the Teamsters do,” Teamsters President Sean O’Brien said.

It’s a sign that the GOP’s overtures to union voters are beginning to pay dividends, though it remains to be seen whether it will be enough to sway the outcome of this election.

In addition to Trump’s 2023 call for autoworkers to back him, his running mate, Sen. J.D. Vance (R-OH), visited a United Auto Workers picket line last year. Vance was just a senator at the time, and it’s no coincidence he later got the nod as Trump’s vice presidential nominee.

The Vance pick was announced during the first day of the Republican National Convention in Milwaukee, and that night in the Wisconsin city, O’Brien addressed the delegates, becoming the first Teamsters president ever to address the RNC.

“Today, the Teamsters are here to say that we are not beholden to anyone or any party,” O’Brien said. “We will create an agenda and work with a bipartisan coalition ready to accomplish something real for the American worker.”

Democrats have downplayed the Teamsters shifting into neutral as an outlier, pointing out that every other major union has backed Harris and that several Teamsters locals endorsed her as well.

“As the vice president told the Teamsters on Monday, when she is elected president, she will look out for the Teamsters rank and file no matter what,” Harris spokeswoman Lauren Hitt said.

Even now, Republicans are only beginning to make inroads in union support, and there’s no guarantee that the Teamsters or any other union will continue flirtations with the GOP following this year’s election.

Democrats have been much more willing to support labor strikes and dole out dollars directly to unions, with a major example being President Joe Biden securing $36 billion to bail out the Teamsters pension fund in 2022.

Even this year, Trump got on the union’s bad side when he praised Elon Musk for firing workers who threatened to strike.

“You’re the greatest cutter. I mean, I look at what you do,” Trump told Musk. “You walk in. You want to quit? I won’t mention the name of the company, but they go on strike, and you say that’s OK. You’re all gone.”

O’Brien described the remarks as “economic terrorism.”

Any further inroads the GOP makes with labor unions could run into resistance from the party’s pro-business and free-trade wings, which have been dominant forces since the 1980s.

But some on the Right now argue that free trade has rewarded the unfair practices of hostile nations like China and that domestic unions often embrace progressive political priorities that go far beyond supporting workers, such as backing climate change resolutions, advocating social justice, or calling for a ceasefire in Gaza.

“It’s an issue that people in unions are very frustrated with, where the national leadership is entirely unmoored from workplace concerns and entirely focused on these sort of very conventional left-wing talking points,” said Duncan Braid, coalition director at American Compass. “They’re not interested in their unions being engaged in national politics.”

Many Republicans agree that it’s important to distinguish between supporting union members and labor leaders.

“Republicans should stop trying to placate union bosses who care more about Democrat politics than their rank-and-file members,” said David McIntosh, president of Club for Growth Action. “Instead, Republicans should focus on winning these voters’ support at the ballot box by enacting pro-growth policies that create real jobs in America.”

That’s the same sentiment Job Creators Network CEO Alfredo Ortiz expressed.

“Republicans are smart to woo the union vote,” he said. “Union jobs are often most threatened by Democrats’ big government and green agendas. The important distinction is that Republicans must be pro-worker, not pro-union or pro-management per se.”

Still, there are disagreements within the Republican Party about just how much to back unions and how much support the GOP will ever receive from labor entities so closely tied to Democrats. Sometimes, that tension plays out within a single candidate, such as Trump’s inviting O’Brien to speak at the RNC and then praising Musk for strikebreaking.

Arguably, the fiercest pro-labor Republican right now is Sen. Josh Hawley (R-MO), who has joined picket lines with the Teamsters and the United Auto Workers and says everyone in his party should join him.

For his efforts, Hawley got a small campaign donation from the Teamsters, and O’Brien has mentioned Hawley by name as a politician who supports his union.

Hawley sees a big opening for his party with unions, arguing that “standing up for workers is a profoundly conservative cause.” He calls for increased tariffs, an end to electric vehicle mandates, and supporting antitrust enforcement against major corporations, arguing that blue-collar support is the only way the GOP will become a true majority party in future elections.

“If conservatives care about healthy towns and schools and churches, as they always say they do, they should support the kind of work and wages that nourish those institutions and make them possible,” he wrote in 2022.

Hawley got another union endorsement on Sept. 18, this time from the International Association of Sheet Metal, Air, Rail, and Transportation Workers. It is just one crack in the Democratic Party’s union armor, but Republican strategist Alex Conant sees a chance for his party to win at the state and national level if the trend continues.

“Trump’s union supporters are key to his victory,” he said. “It’s why Pennsylvania is so competitive. The more he chips away at this part of the Democratic base, the greater his chances of victory.”