Disclosure: I am the author of the 1978 book, The Hoffa Wars, about the rise and fall of Jimmy Hoffa. In that book, I also chronicled the proud but often violent history of the pro-union, rank-and-file reform movement within the Teamsters Union.
As a journalist who has investigated the Teamsters and the mob and taken sides by supporting the Teamsters for a Democratic Union (TDU) and its previous incarnations for the past 50 years, I am a long-time, albeit a small-time annual donor to TDU’s Rank & File Education and Legal Defense Foundation—although, for reasons of my own, I did not contribute in 2023.
I did support Sean O’Brien’s candidacy in 2021—although I do not remember ever meeting him at any of a handful of TDU conclaves I have attended over the years.
Sean O’Brien, the 52-year-old president of the 1.3-million-member International Brotherhood of Teamsters (IBT), is at risk of becoming the Rodney Dangerfield of the American labor movement—and he has no sense of humor about it. He is getting “no respect”—or at least not as much as he believes he deserves after recently making two big bets on the national stage.
In the spring of 2018, O’Brien, then-president of Teamsters Local 25 in Boston and an IBT vice president, announced his candidacy to challenge Jimmy Hoffa, Jr., for the union presidency. But, instead of running against the popular O’Brien, the 78-year-old Hoffa, who had served as IBT president since 1998, decided that he was not up for another reelection bid and threw his weight behind IBT Vice President Steve Vairma to succeed him.
With the enthusiastic support of the Teamsters for a Democratic Union—the widely respected rank-and-file reform organization—O’Brien defeated Vairma in November 2021 and was elected as the eleventh general president of the union.
O’Brien was inaugurated on March 22, 2022, at “The Marble Palace,” aka Teamsters headquarters on Capitol Hill.
O’Brien’s first big public moment came during a Senate hearing on March 8, 2023. While in the witness chair, he engaged in a bitter exchange with right-wing Senator Markwayne Mullin (R-Oklahoma), a successful plumbing company executive who was also a Mixed Martial Arts (MMA) fighter with a 5-0 record as a professional.
Mullin, who read aloud several provocative online exchanges with O’Brien, said: “You want to run your mouth? We can be two consenting adults and finish it here.”
Unfazed by Mullin’s MMA status and badass reputation, O’Brien remained cock-strong and fearless, agreeing to oblige Mullin right then and there in the hearing room.
As Mullin rose from his chair and readied for combat, committee chair Bernie Sanders admonished Mullin, reminding him that he was a United States Senator and instructing him to be seated.
Regardless of how inappropriate all of this was, I grudgingly respected the fact that O’Brien had the audacity to stand up to this Republican knuckle-dragger.
O’Brien simply refused to be disrespected.
A few months later—after seeing support for President Joe Biden floundering, especially after his disastrous performance during the June 28 debate with Donald Trump—O’Brien, “a lifelong Democrat,” requested time to speak to the MAGA crowd at the 2024 Republican National Convention in Milwaukee, July 15-18.
According to published reports, many Republican organizers did not want him there. However, Donald Trump—who had met with O’Brien at Mar-a-Lago last January and at a subsequent meeting at The Marble Palace—pulled rank and demanded the booking.
Detailing Trump’s disgraceful record on labor, Alexandra Bradbury, the editor of Labor Notes, wrote in July:
In case there’s any doubt: billionaire Trump, who as an employer has fought unions and stiffed workers, and as a TV personality made “You’re fired” his catchphrase, is not for the little guy. There’s no mystery how labor would fare under his administration. This guy was already president, and we saw the results.
He cut back workplace safety inspectors to their lowest numbers in history. His Labor Board rolled back union rights so far that labor lawyer Robert Schwartz had to delete an entire chapter from The Legal Rights of Union Stewards.
He stacked federal agencies and courts with anti-union zealots who made millions of workers ineligible for overtime pay, made it harder for workers to unionize and easier for bosses to steal wages, and lots more. His Supreme Court made the whole public sector “right to work.” He celebrated a massive tax giveaway to the rich, and never offered a word of support to workers on strike. He tried to slash Medicare, Medicaid, and Social Security. He opposed any increase in the minimum wage.
He waged war on federal employee unions with attacks on their collective bargaining and due process rights, and shut down the government in a stunt that forced them to go without pay for 35 days. He called climate change a hoax and removed references to it from government documents, while workers suffered the effects of fires, hurricanes, and heat waves.
Corporate tycoons and alums of his first administration have put together an even more draconian plan for a second term. They want to abolish overtime pay, public sector unions, the federal minimum wage, prevailing wage agreements, the Department of Education, and child labor laws.
On July 15—with O’Brien’s controversial decision clearly designed to make him the de facto leader of the American labor movement—the Teamsters president spoke in prime time on the GOP convention's opening night.
Delivering a stunning truth-to-power address about the ongoing conflict between labor and management to disbelieving, wide-eyed, slack-jawed conservative delegates, the tough-talking O’Brien defiantly trashed greedy employers and made a pitch for strong trade unions and workers’ rights. . . . In other words, it was not the typical boilerplate address for a Republican convention.
Totally pragmatic and even a bit nihilistic, O’Brien found it to his advantage to kiss Trump’s ring. But at no point did O’Brien take this precious opportunity to utter as much as a harsh or critical word about Trump, no friend of America’s labor movement—just two days after a would-be assassin grazed Trump’s right ear in a sniper attack.
Referring to Trump as “the president,” O’Brien said in his speech:
Hard to believe, anti-union groups demanded the president rescind his invitation. The left called me a traitor. And this is precisely why it's so important for me to be here today.
Think about this, the Teamsters are doing something correct if the extremes in both parties think I shouldn't be on this stage. President Trump had the backbone to open the doors to this Republican convention and that's unprecedented. No other nominee in the race would have invited the Teamsters into this arena.
Now, you can have whatever opinion you want, but one thing is clear. President Trump is a candidate who is not afraid of hearing from new, loud, and often critical voices. And I think we all can agree, whether people like him, or they don't like him, in light of what happened to him on Saturday, he has proven to be one tough S.O.B.
Watching this bizarre scene on national television, many of us thought: “What the hell is this guy doing?”
It looked as if O’Brien viewed Trump, a recently convicted criminal, as a lead-pipe cinch for victory in November and just wanted to jump ahead of the pack and pay his respects to the corrupt and dishonest ex-president.
To his credit, O’Brien had walked into the lion’s den, stood up to this anti-union crowd, gave them an impressive defense of American unions, and then came out of it in one piece.
He must have felt absolutely triumphant as he left the stage.
To those who immediately criticized him, O’Brien remained unbowed and unrepentant. He appeared to have won his risky bet by bearing witness to the coronation of Donald Trump—live and in person. And that was something O’Brien likely assumed that Trump would remember and reward when he regained the presidency after presumably defeating President Biden.
After his speech, O’Brien, in a cover-his-ass moment with reporters, lauded President Biden as “the most pro-labor president we’ve ever had.”
O’Brien was in the driver’s seat, and he was cruising down the highway.
Then, on July 21, O’Brien must have felt a gut punch when Biden announced that he was yielding the Democratic nomination to Kamala Harris—which immediately became nothing less than a world-class, game-changing moment in American history.
During a breathtaking series of events, Vice President Harris unleashed and supercharged unprecedented levels of wild enthusiasm and pure joy among the members of the Democratic Party, countless independents, and even an expanding crowd of “never-Trump” Republicans.
Significantly, O’Brien had earlier parlayed his big bet on the GOP convention with his request to speak at the Democratic National Convention in Chicago, August 19-22. But Democratic Party leaders, who did not share his enthusiasm to speak at both political conventions, ignored him.
In effect, many Democrats felt betrayed by O’Brien for what they viewed as his sheer arrogance and alleged duplicity in Milwaukee. Consequently, O’Brien, embarrassed by the obvious snub, felt disrespected—just as during his confrontation with that MMA hothead at the Senate hearing in 2023.
Meantime, in spectacular form, the Democrats launched their wildly successful convention—sans O’Brien. And, adding insult to injury for the Teamsters leader, party organizers featured UAW President Shawn Fain, who delivered a thrilling pro-union speech that appropriately defied and ridiculed Donald Trump while exposing the ex-president’s disingenuous and insincere pro-worker rhetoric.
Memorably, during his talk, Fain triggered a spontaneous standing ovation when he revealed his “TRUMP IS A SCAB” t-shirt under his sportscoat.
Fain’s speech was so well received that Trump, who was still busy praising O’Brien, angrily called on the UAW membership to remove Fain from office—nothing less than a great badge of honor for the UAW chief.
The reaction among Democrats after Shawn Fain’s speech was, “Sean who?”
In short, Sean O’Brien had made a calculated original wager by appearing at the Republican convention but then lost the subsequent parlay bet when he was ignored by the Democrats and then humiliated when he was upstaged by Shawn Fain.
Strapping himself to The Cross on August 20, O’Brien, clearly upset but feeling so misunderstood, went on Neil Cavuto’s afternoon business program on Fox News, saying: “If the far-left wants to criticize me and attack me, that’s okay. If the far-right wants to do the same, that’s great. I represent 1.3 million hardworking men and women.”
O’Brien’s suggestion was that, by disrespecting him, the Democrats had disrespected the entire membership of the Teamsters Union. . . . But that was utter nonsense. The Democrats simply objected to O’Brien trying to game the system with his bold but failed hedge bet.
On September 16, Vice President Harris and her running mate, Governor Tim Walz of Minnesota, visited The Marble Palace to pay their respects to O’Brien and the IBT’s general executive board, hoping to receive the union’s endorsement. According to published reports, O’Brien, enjoying the home-court advantage, was something less than hospitable with Harris and Walz as the meeting became unnecessarily contentious.
Meantime, O’Brien and the IBT polled the Teamsters membership, showing that sixty percent favored Trump—although some of the union’s leadership legitimately questioned the poll's methodology. The suspicion was that O’Brien, still angry at the Democrats, received the result he wanted.
Consequently, the Teamsters Union’s general executive board made no endorsement.
O’Brien released a statement, saying that neither the Democrats nor the Republicans were “able to make serious commitments to our union to ensure the interests of working people are always put before Big Business.”
To even the most casual observers, that was the motherlode of false equivalencies.
Essentially, O’Brien suggested that neither political party could rise to his personal high standards—even though labor historians widely view the Biden-Harris team as among the most pro-union administrations in American history, confirming what O’Brien had told reporters after his speech to the GOP.
In my opinion, O’Brien’s refusal to make an endorsement—especially under the false pretext of a dubious poll—was really nothing more than retaliation against the Democrats for brushing him off in August.
Inasmuch as the Teamsters have endorsed every Democratic presidential nominee since 1996, O’Brien’s action—or non-action—was nothing less than a backhanded endorsement of Donald Trump, who will cynically continue to use O’Brien as a prop for the remainder of the presidential campaign.
A spokesperson for the Harris-Walz campaign replied in a statement: “The Vice President’s strong union record is why Teamsters locals across the country have already endorsed her—alongside the overwhelming majority of organized labor.”
Indeed, regional Teamsters in California, Florida, Michigan, Nevada, Pennsylvania, and Wisconsin, among others, have defied O’Brien and the IBT’s general executive board by endorsing the Harris-Walz ticket—which further established O’Brien’s role as the villain in this drama.
Ironically, all of this would have worked out beautifully for O’Brien—allowing him to win both bets—if President Biden had remained in the race and not passed the baton to Vice President Harris three days after the Republican convention.
After fifty years of watching and investigating the Teamsters, my advice to Sean O’Brien—who has dramatically and repeatedly overplayed his hand—is:
Cut your losses. Cover your bets. Pay the vig. And then personally and enthusiastically support Kamala Harris for President.
That will be your ultimate redemption and salvation.
If you don’t, you will be among those in the running to win “The James Comey Award” for the 2024 presidential election. And that would be far worse than being remembered as Rodney Dangerfield.
Excellent