“A true friend,” Oscar Wilde remarked, “stabs you in the front.” What would dear Oscar have made of Teamsters President Sean O’Brien? Elected as a union militant, with the support of longstanding reform organization Teamsters for a Democratic Union (TDU), O’Brien has spent the last two years shepherding the lambs of the American working class straight to the slaughter via his endorsements and promotions of some of the most reactionary, anti-labor politicians in the land.

I was complicit in this. Back in 2021, I was a Teamster working in logistics. I both voted and campaigned for O’Brien, giving money and time to his campaign. I got up early to talk to Teamsters at plant gates and hand out leaflets. Why did I do it? Perhaps I was smarting over Bernie Sanders’s crushing 2020 defeat. I wanted to win this time, and any victory would do. Perhaps I was overawed by O’Brien’s endorsement by TDU and unwilling to listen to O’Brien critics like Joe Allen and Andy Sernatinger or ask difficult questions.

There were indeed difficult questions to be asked about how such a steadfast defender of the Teamsters hierarchy was transformed, by some strange alchemy, into a reformer. In 2014 O’Brien was suspended from the union due to his threats against opposition candidates in a local election. The following year, members of O’Brien’s Teamsters Local 25 yelled threats and racial slurs at Top Chef’s Padma Lakshmi during a strike. At the 2016 Teamsters convention, O’Brien told a delegate opposing the incumbent slate “You are a punk. I know who you are. You are nothing,” leading to formal charges. O’Brien’s road to Damascus moment came only when he was fired from his position as UPS negotiator by the incumbent Hoffa administration in 2017. It was certainly a handy conversion for someone looking to run for higher union office.

O’Brien’s campaign in 2021 was a rout. His Teamsters United slate won every region of the union except Canada. Shortly thereafter I decided to leave my Teamster job and move on to the next phase of my life. For the next few years, there was nothing to make me think I’d come to regret my role in O’Brien’s election. He spoke out against corporate greed alongside Bernie Sanders and Sara Nelson of the Association of Flight Attendants. He stood up to Oklahoma’s Senator Markwayne Mullin, an anti-labor millionaire who speaks like he took too many shots to the head during his brief MMA career. I only occasionally checked in to see how the new administration was doing during the 2023 UPS contract negotiations, but it seemed like a huge victory. What was there to be worried about?

Yet O’Brien underwent a change comparable to another bald guy once touted as a progressive hero: Pennsylvania’s Senator John Fetterman. Fetterman, readers will recall, campaigned on a promise not to “be a Joe Manchin or Kyrsten Sinema-type Senator" and entered office in 2023 with comparisons to Bernie Sanders. But then a startling metamorphosis took place, where the onetime populist became a staunch genocidaire eager to “get back to killing” Palestinians and an opponent of abolishing ICE.

2024 erased whatever residual affection I’d had for O’Brien. That year he not only spoke of Donald Trump as a man “proven to be one tough SOB” at the Republican National Convention, he promoted as “100% on point” a transphobic article by Senator Josh Hawley. This Compact article on “the promise of pro-labor conservatism” assailed corporate America for “using [their] profits to push diversity, equity, and inclusion and the religion of the trans flag.” Seemingly under duress, O’Brien sent a circuitous, lawyerly letter to the Teamsters LGBTQ+ caucus in which he claimed his promotion was meant “in no way intended to support negative criticism of social issues” and apologized “having caused consternation and confusion among members of the LGBTQ+ caucus.” He promised to “keep advocating for our LGBTQ+ members as I have from day one.”

That promise wasn’t worth the paper it was printed on. O’Brien’s love letters to Hawley preceded a full-scale embrace of the American right generally, and the Trump administration specifically, even as they have inaugurated a wave of anti-LGBTQ legislation. Under O’Brien the Teamsters donated $5,000 to Hawley and fifty grand to the Republican Attorneys General’s Association. O’Brien hosted Ohio Gubernatorial hopeful Vivek Ramaswamy—who called the LGBTQ movement “a cult”—on his self-aggrandizing podcast Better Bad Ideas. Ramaswamy’s 2026 campaign for governor of Ohio has likewise been endorsed by the Ohio Teamsters.

O’Brien even kissed and made up with Markwayne Mullen, the Senator he got into a shouting match with over the union-friendly PRO Act. (Or is it more than kissed? C-Span captured this witless attempt at humor from Mullen: “I do joke with my new friend here [O’Brien]...that if we had a relationship, I would be the man in the relationship.” When the cameras cut over to O’Brien he looked as if he’d rather be having teeth pulled.)

After O’Brien’s fawning at the RNC, the Teamsters International announced they would not be supporting either Kamala Harris or Donald Trump for president. Shortly thereafter, Teamster locals and joint councils representing a vast majority of the union’s membership (Including those led by International officers who voted not to endorse anybody) voted to endorse Harris. At the Nation and n+1, John Nichols and Luis Feliz Leon took this as a rebuke of O’Brien. But in hindsight, it looks like a much more cynical balancing act to appease both candidates. If Trump won, they could point to the international’s non-endorsement; if Harris won, they could point to the endorsements by joint councils and locals.

There has been a phenomenon within the union’s leadership of working towards Trump. Whatever Trump says, the union leadership leaps to support, often without looking. When Trump called for a 100 percent tariff on foreign films—a vague term given how many U.S. productions are filmed in Canada and elsewhere—Hollywood’s Teamsters went right along with it. Never mind how many Canadian Teamsters there are in film and television whose jobs would be threatened by these tariffs or Trump’s broader trade war with Canada. They didn’t vote for O’Brien in the first place. Likewise, Trump’s purge of the unionized federal workforce elicited a comment on Fox News from O’Brien that the President “thinks he’s within his right” to fire union workers.

Under O’Brien the Teamsters went on record supporting the president's pick for Secretary of Labor, Lori Chavez DeRemer, and O’Brien himself wrote an op-ed calling her “The Pro-Worker Choice for Labor” in Compact. Under questioning, DeRemer admitted she no longer supported the section of the PRO Act weakening state anti-union right-to-work laws. This bothered O’Brien not a bit. On Fox, he said that he and his bosom buddy Josh Hawley were working on a version of the PRO Act that “may not include [a ban on right-to-work]” O’Brien seemed to say that right-to-work laws could be “what works” for certain states. At least, that’s how the vehemently anti-union National Right to Work Committee interpreted his remarks in a post on X.

(Incidentally, Chavez DeRemer has failed to use her cabinet position to lobby on behalf of any significant labor reforms. She has, however, praised Trump’s firing of the head of the Bureau of Labor Statistics over his daring to report an unfavorable jobs report. She is currently under investigation by the inspector general for carrying on an inappropriate sexual relationship with a subordinate, “abusing her office by taking staff to strip clubs, drinking alcohol on the job and taking personal trips at taxpayer expense.”)

Queerphobia and watering down labor law reform are not the only reactionary directions O’Brien is heading. On his podcast, O’Brien discussed immigration with Hawley. “I think the biggest problem,” O’ Brien said, “is people are trying to protect illegal aliens that come over here and commit crimes.” He continued: “Social issues are all well and good, but protecting illegal immigrants that come into our country to commit crimes and steal jobs, that’s a tough pill to swallow.” Teamsters Mobilize, a new reform movement within the union, put out a statement calling O’Brien’s remarks “an insult to everyone, especially all Teamsters and children of immigrants. There is no room for nationalism and xenophobia in the Teamsters.”

During New York City’s mayoral election last year, O’Brien’s podcast provided a forum. Not for the ultimate winner, Zohran Mamdani. No, O’Brien hosted disgraced former governor and sex pest Andrew Cuomo to explain his plans to “resurrect the Democratic Party.” After Mamdani’s win, O’Brien was joined by Thomas Gesauldi (President Teamsters Joint Council 16) and Kevin McCafferey (President Teamsters 707, and elected Republican) to discuss the incoming democratic socialist. It’s not a coincidence that Joint Council 16, which includes Teamsters 707, endorsed Cuomo in both the Democratic primary and general election, and there was no representative of Teamsters 804 or 808, which had endorsed Mamdani. One can almost feel the consent being manufactured as McCaffrey fretted over Mamdani “chas[ing] business out of” New York City and everyone sniped at Mamdani’s previous calls to reallocate police funding and campaign promises of free buses. A more balanced debate would result if Ted Cruz and Marco Rubio sat down to discuss the legacy of Fidel Castro.

O’Brien’s open hostility toward Mamdani is just part of a broader attack on left-wing politics. Showing his capacity for throwing people under the bus once they’ve served their purpose, O’Brien turned on the democratic socialist he’d been happy to share a stage with a few years prior. On X, O’Brien mocked Bernie Sanders and Alexandria Ocasio-Cortez over their use of a private plane for their “Fighting Oligarchy” tour. We can assume that Teamsters officials only fly coach.

In his podcast guests, statements, and endorsements, O’Brien has established a deliberate pattern of behavior. Therefore, when the Teamsters trumpeted their endorsement of incumbent Republican Greg Abbott in this year’s Texas gubernatorial election, it should not have been a surprise, although the reaction was swift and negative. The Teamster leadership’s embrace of far-right politicians like Hawley, Abbott, and Ramaswamy is not a glitch, a fluke, or an accident, but part of a broad political strategy to curry favor with some of the most anti-labor politicians in the country.

Even if there is some argument to be made for labor working across the aisle with certain Republicans in order to pass legislation favorable to unions, O’Brien has also made nice with various right-wing media creatures who have no appreciable clout in Congress. He was an honored guest on white nationalist Tucker Carlson’s podcast. He brought in one the strongest supporters of the Israeli genocide in Gaza, Batya Ungar-Sargon, to address the Teamsters Women’s Conference. It was a ghoulish sight. Israel’s weapons do not discriminate when it comes to Palestinian women and trade unionists; they are killed all the same. Attendees received a copy of Ungar-Sargon’s latest book in their gift bags. Ungar-Sargon’s offering could be considered a valuable gift under certain circumstances, if, for example, the hotel had run out of toilet paper.

What has been gained by O’Brien’s podcast pugilism and right-wing flattery? Not the PRO Act, which remains mired in Congress and is still opposed by Trump and Vice President J.D. Vance. Not a repeal of right-to-work laws, which Abbott continues to support after his long career railing against “Big Labor.” Not federal help organizing Amazon, which refuses to sign a union contract with Amazon Teamsters in New York.

Instead, Trump has appointed a former UPS and Amazon safety compliance officer to head OSHA, despite both companies’ poor safety records. Union-busting lawyer Crystal Carey was nominated to serve as chief counsel for the National Labor Relations Board. Federal employees have seen their unions decertified under flimsy justifications of “national security.” ICE has even showed up to Teamster picket lines to intimidate strikers. Even the seemingly historic UPS contract is coming apart amidst dozens of hub closings and tens of thousands of layoffs. Labor’s birthright has been sold for a mess of very bad pottage.