O’Brien’s speech was significant not only because it was the first time the president of Teamsters, which boasts 1.3 million members nationwide, spoke at the Republican convention but also because he was invited to make the speech even though the union had not endorsed a candidate in the presidential election. 

In September, the union finalized its decision to stay out of the presidential race for the first time since 1996, ending a streak of six presidential elections in which the union endorsed the Democratic nominee. At the same time, the union released polling of its membership that showed strong support among the rank and file for Trump. 

It was a massive blow to the Democratic Party, which has long identified itself as the party of the working class and leaned on labor unions such as the Teamsters for its get-out-the-vote efforts in union-dominated states such as Michigan and Nevada.

But for O’Brien, the decision to peel his organization away from its historic partisan alignment proved to be a bet that paid off in spades. In the months since the election, Trump has shouted out the union boss by name on multiple occasions and, at the urging of the Teamsters, nominated former Rep. Lori Chavez-DeRemer, a union-friendly Republican from a Teamsters family, to be his labor secretary.

While it may be hard to believe, the detente and rapprochement between the Republican Party and the Teamsters took years to come to fruition. It is a project that started in earnest when O’Brien was elected as the union’s general president in 2021 in a landslide victory that was as much a repudiation of the previous leadership of the union as it was a mandate for O’Brien to lead the union in a different direction.

If anyone has ever looked the part of a blue-collar union boss, it’s O’Brien, whose family ties to the union run as thick as his Boston accent. His great-grandfather was an Irish immigrant who settled in Boston and was a member of the Teamsters chapter there, Local 25. That started a four-generation run. O’Brien’s grandfather and father were truck drivers and members of Local 25, and finally, so is O’Brien.

In his office at the Teamsters headquarters in Washington, D.C., O’Brien spoke of the union as an extension of his family. “There was some good times growing up, some tough times, and this one organization that never wavered from that commitment to us, and that was a Teamsters union, and I am forever beholden and grateful to it.”

The Teamsters, O’Brien said, were “everywhere” when he was growing up. “The Teamsters were sponsoring Little League. They were sponsoring youth hockey programs. They were doing food drives. God forbid there was any catastrophic incident that happened in and around Local 25 or the jurisdiction. The one organization that was all there first and longest was the Teamsters union.”

But the organization O’Brien leads today is starkly different from the one his father, grandfather, and great-grandfather were a part of. Union membership has declined significantly from its high point in the mid-20th century, when over 30% of workers in the United States were members of a union. Today, that number is closer to 10%, and in private sector workplaces, it’s even lower, at barely 5%.

The decline in union membership mirrors the nation’s broader manufacturing decline. Industrial centers, such as Youngstown, Detroit, and Middletown, Ohio, which is Vice President JD Vance’s hometown, were dominated by union members. As those towns lost their industrial bases and declined, so did union membership. 

The Teamsters today, as they always have been, are largely a conglomerate of transportation workers. The union’s largest employer is UPS, which employs 300,000 members. But the Teamsters’ 1.3 million members also count airline pilots, truck drivers, and, most recently, Amazon warehouse workers, a group O’Brien has worked particularly diligently to organize and bring into the Teamsters fold.

But it is O’Brien’s work with Republicans that has turned the most heads in Washington and beyond. For years, the notion that a major union would give the time of day to a Republican politician was unheard of. But Sen. Josh Hawley (R-MO) told the Washington Examiner that began to change after a small group of Republicans voted against forcing railway workers on strike to accept a contract they didn’t like.

“What I really appreciate about Sean is that No. 1, he’s a straight shooter,” Hawley said. “This is a guy who doesn’t care about the politics of it. He’s fearless, he’s incredibly independent, and he just wants what’s best for working people.”

For his part, O’Brien doesn’t see his job as partisan, and the way he talks about his political engagement hearkens back to a moment that feels entirely foreign to the current. “I don’t care if you’re a Republican, you’re a Democrat, independent, or whatever you are,” he said. “If I get the opportunity to talk to you and tell you how valuable we are, how important we are, I’m going to take that opportunity.”

“I want results, not excuses,” O’Brien said. “I can make excuses all day long. I could sit in my chair here and think about every move that’s being made across the street [at the Capitol], or every move that’s being made anywhere, and have my own opinion and just continuously attack it. Well, what’s the solution? What would you be doing differently? So, those are the questions that I tend to ask myself a lot.”

By meeting with Hawley and other Republicans such as Sens. Roger Marshall (R-KS) and Bernie Moreno (R-OH), O’Brien is already doing things differently. But beyond O’Brien meeting with prominent GOP members and even cultivating a relationship with the president, his different approach is yielding results.

Shortly after Trump won the election, O’Brien and the Teamsters successfully lobbied the then-incoming president to appoint Chavez-DeRemer to lead the Department of Labor over the objections of many Republicans who had concerns about the nominee’s history of co-sponsoring legislation backed by labor unions. While Chavez-DeRemer has yet to be confirmed, few would argue that her nomination would have happened if O’Brien had not shown a willingness to engage with Trump. 

“We’ve had a lot of conversations,” O’Brien said of his relationship with Trump. “There’s a lot of things we agree on. There’s a lot of things we don’t agree on. And the things we don’t agree on, we’re going to continue to work through and talk about them.”

By simply speaking with Republicans, O’Brien has put some policy meat on the bones of a political realignment that has seen the working class abandon the Democratic Party in droves. Hawley has begun circulating a legislative proposal that would mark the largest reform to federal labor law in decades, and he has lined up bipartisan support.

“The Republicans all along said they wanted to be the party [of working] people,” said O’Brien, who still calls himself a Democrat. “So, they’ve got a great opportunity from now until 2028 to actually prove that. The Democrats … forgot who they actually worked for. … You look at Big Tech and some of the big donors to the Democratic Party, and who were heavily involved in the Harris-Walz campaign. Those are the same big corporations that the Democrats once accused the Republicans of being in bed with.”

While his less partisan approach to political engagement has arguably yielded more substantive results than the years the organization spent tying itself to the Democratic Party, O’Brien doesn’t feel any sense of vindication. “It’s about doing what our members want us to do. … I think … especially after seeing how working people voted in this election, I think everybody, including the Teamsters union, will be more focused on rank-and-file members and what their wants and needs are.”

THE GREAT REALIGNMENT: WHAT TRUMP’S VICTORY MEANS FOR THE GOP COALITION

The Teamsters president may not claim any vindication, but his approach is encouraging some copycats among his counterparts in other major unions. United Auto Workers President Shawn Fain, who spoke at the Democratic National Convention and aggressively campaigned for Democrats up and down the ticket while labeling Trump an anti-union “scab,” has suddenly found a soft spot for the GOP and taken steps to engage with Republican senators.

Hawley, who recently met with Fain, said it would not have happened if it were not for O’Brien’s willingness to chart a new path for his union. “I think he’s shown that it doesn’t pay to just be the pet of the Democratic Party. What have they done for working people? What have they done for union members? In the last four years, not a heck of a lot. They’ve sent their jobs overseas. Their wages have gone down. They’ve cut their benefits. I think O’Brien has got the right formula.”

Jeremiah Poff is a Restoring America editor for the Washington Examiner.