A glacier of hostility has divided the GOP from organized labor for two generations. Last week, Sean O’Brien, the president of the Teamsters, took a pickaxe to that glacier with a widely discussed speech at the Republican National Convention. And he’s just getting started—his critics on the left be damned. As he told me Monday in his first major interview since the RNC appearance, “people can stay on the far left and be spectators, and on the far right as well, but I really don’t take it personally. Because they’re not in the game, they’re not playing.”
“He’s just getting started—his critics on the left be damned.”
Judging by some of the hysterical reactions among progressives, you’d think O’Brien had spent his 17 minutes onstage renouncing the basic precepts of trade unionism. What he actually did was spotlight corporate America’s sinister campaign to undermine the rights and bargaining power of America’s wage-earners—in front of a right-wing audience unaccustomed to seeing America’s political economy from the point of view of the labor movement.
O’Brien’s RNC appearance also represented a simple concession to the reality of his rank and file’s political views—a concession too many in the mainstream leadership of the labor movement refuse to make. When he assumed the presidency in 2022, he told me, he had to reckon with “a large, diverse membership” of Democrats, Republicans, and independents. “So we wanted to make a conscious effort to reach across the aisle and work with legislators who, regardless of their political affiliation, have working people’s best interests in mind.”
The Republican O’Brien singled out for extensive praise—Sen. Josh Hawley of Missouri, a Compact contributor—has emerged as a prototype of what such cross-partisan pro-labor collaboration might look like. It was Hawley who, in early 2023, set in motion what had come to be considered unthinkable: a Republican Party willing to hear, and address, the labor movement’s concerns.
“I saw how Hawley was not corruptible at all in his fight against corporate America,” O’Brien said, “how he really defended his positions unwaveringly, regardless of the consequences.” The Teamsters had identified Hawley as a potential ally “based upon a lot of positions he was taking” and his grilling of corporate executives at Senate hearings. With a Teamster strike brewing at Garybar Electric in Missouri, O’Brien approached Hawley. He told the senator about “how a national right-to-work proposal from the Republican Party wouldn’t work for working Americans or help people in his district—in fact, it would be worse.”
The result: Hawley visited striking workers on the picket line, and he publicly declared his opposition to a national right-to-work measure.
O’Brien recalled, “Right then and there, I said, ‘This is a person who has courage and conviction.’ I grew up in a city neighborhood. You always judge people by what it’s like to hang out with a guy outside of work. And when I hang out with [Hawley], he’s a guy who has a high moral compass, he’s a guy who calls balls and strikes. … What he says and what he does, there is no wavering on it.”
That doesn’t mean O’Brien and Hawley always see eye-to-eye: “We’re not always going to agree on everything, because he has a certain constituency that he has to serve; and I definitely have a different constituency, that’s for certain. But on the stuff that we can work together on, there’s no reason why a line in the sand should ever be drawn.”
The son and grandson of Teamsters, the 52-year-old O’Brien grew up in Medford, Mass., and joined the union as a Boston trucker after a single semester at the University of Massachusetts, eventually being elected president of the national union in 2022. His industrial life has coincided with the decline of both American manufacturing and labor unionism. With private-economy union density—the share of workers belonging to a union—not budging north of 6 percent, O’Brien has resolved to try something new: resurrecting labor as an independent force, rather than an adjunct of the Democratic Party.
“Over the past 20 years,” he told me, “Democrats—and I’m a lifelong Democrat—have always told us what we wanted to hear, but oftentimes not delivered on what they said they were gonna do. But it was the best alternative we had. Because there was such a divide between both parties … that we would forgive [Democrats] quite easily when they didn’t do something for us and continue to invest in them.”
“The relationship yielded political office for elected Democrats, but crumbs for labor.”
Too often, the relationship yielded donations and political office for elected Democrats, but crumbs for labor. The experience bore a clear lesson for O’Brien: “Partisanship is not working. To get something really done for the American worker, both union and nonunion, we gotta get out of that thought process of one party line.”
But is he worried about self-proclaimed Republican populists disappointing the cause, their “pro-worker” talk amounting to just that? “There is rhetoric on both sides, Democrat and Republican, when it comes to supporting workers,” replied O’Brien. “And I always have to remind people that in 2008, we had a Democratic president, we had a Democratic House, a Democratic Senate. Labor’s biggest ask at that time was the Employee Free Choice Act”—a bill that would have eased union elections—“and you couldn’t get consensus on that.”
The better approach, then, is an openness to both parties—and a corresponding toughness with both: “Accountability is huge in my life. And if you say you’re gonna do something, you need to try and get it done to the best of your ability. Credibility defines your character, your organization’s character. So we were committing to supporting people who were gonna support our issues.”
Labor’s rapprochement with Republicans, O’Brien added, is still in an “infant stage. And you know, J.D. Vance has been super-supportive of a lot of our issues. We got many legislatures that are Republican that we have worked with. So this is a work in progress. Once we start actually accomplishing goals and objectives collectively, you’re going to see people step out of the rhetoric portion of this and actually get involved and get good things done.”
What’s needed now is smaller trust-building steps—“easy layups” that would allow pro-worker Republicans to prove their mettle. These include more even-handed appointments to the National Labor Relations Board; strengthening the Occupational Safety and Health Administration; collaborating with the labor movement in workforce development (one of the movement’s great untapped gifts) as part of a broader industrial strategy; protecting aggrieved workers when firms go bankrupt; above all, “reforming our antiquated law,” which is “used as a weapon by the company, where it should be used to deter bad behavior and support working people.”
These steps could lead, eventually, to bipartisan enactment of the PRO-ACT, a law aimed at reversing the pro-employer drift of the American labor regime—or at least, of something like the current PRO-ACT. That takes persuasion and a willingness, perhaps, to work piecemeal. “I think far too often,” O’Brien said, “we get so invested in a platform that we’re not open to having a discussion to find common ground in a PRO-ACT that works for everybody. If you’re not having those conversations and explaining and articulating the pros and cons, that’s a problem.”
He went on: “I like J.D. Vance a lot. I have not had the conversation on the PRO-ACT with him. But I’m confident that we can piece together something that works for American workers, and allows them to join a union free of retribution or retaliation, with a real provision that mandates that a collective bargaining agreement needs to be secure with a year with arbitration.” What won’t work is: “I want my version [of the PRO-ACT] and my version only.”
As for the labor left’s venomous rage on the X app (formerly known as Twitter), O’Brien is unflappable. “There’s a lot of people on the left are attacking” the RNC speech, he said, “saying I should never have been there. But they don’t have a problem when we donate $500,000 to the left.” Besides, “our members, 1.3 million members, I can’t just represent one party or affiliation. I gotta represent every single party and respect that process.”
He added: “It gets so personal” with hard-liners on both sides. “It plays into the hands of corporations and of foreign countries that want to see us fail. And this divide is detrimental to our country. The far left and the far right should take a step back and … see if they’re actually helping or hurting. That’s all I’ll say. I’m going to stick by my convictions, I’m going to stick by the guidance of my members, and do the job. And if we fail, hey, it’s gonna be a great story. And if we win, it’s gonna be an even better story, right?”