How a Teamster Leader’s Flirtations With Trump Have Divided the Union

Under Sean O’Brien, the union president, the Teamsters have given $45,000 to both the Democratic and Republican conventions, and he met with Donald J. Trump at his Mar-a-Lago resort in January.

Sean O’Brien, the president of the International Brotherhood of Teamsters, has framed his decision to speak at the Republican National Convention next week as a savvy maneuver to keep the union’s doors open to whoever prevails in November’s presidential election.

But his open flirtation with former President Donald Trump has divided the union’s leadership, rankled some of its 1.3 million members and set up a showdown over the Teamsters’ eventual endorsement that has undermined President Joe Biden’s standing with organized labor just when he needs it the most.

“We will not allow the working-class labor movement to be destroyed by a scab masquerading as a pro-union advocate after doing everything in his power to destroy the very fabric of unions,” James Curbeam, the national chair of the Teamsters National Black Caucus, wrote in a blistering letter to Teamsters members after O’Brien announced a meeting with Trump earlier this year.

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On Monday, a Teamsters spokesperson, Kara Deniz, defended what she framed as bipartisan overtures and shot back at O’Brien’s critics.

“The Teamsters have never been afraid of democracy, but self-interested ideologues — on the left and the right, within and outside the union — are terrified of democracy,” she said.

It was only last November that O’Brien burst into the national consciousness. The Teamsters president, who was elected to his post in 2022, nearly got into a fistfight with a pro-Trump Republican senator, Markwayne Mullin of Oklahoma, during a Senate labor committee hearing. In 2022, after his election, O’Brien was appearing with that committee’s left-wing chair, Sen. Bernie Sanders, I-Vt., at rallies against “corporate greed.”

But more recently, O’Brien has cut a more bipartisan image. His union wrote checks for $45,000 to both the Democratic and Republican conventions. He met with Trump at his Mar-a-Lago resort in January, then brought the former president to a Teamsters executive board meeting Jan. 31 to talk over labor issues and dangle an endorsement.

In May, O’Brien snapped photos with Dana White, president of the UFC and a longtime friend of Trump’s. He then sought out speaking slots with both conventions — and landed one in Milwaukee with the Republicans.

For weeks, the union’s leadership has downplayed the idea that all this was leading toward a more formal embrace of the presumptive Republican nominee, saying the Teamsters represent workers of all political persuasions.

“General President O’Brien looks forward to addressing a crowd that hasn’t traditionally been open to union voices,” Deniz said. “But that is what democracy is all about.”

The Teamsters have yet to make a presidential endorsement, and, Deniz said, this year’s protracted process has been “the most democratic, inclusive and transparent it’s ever been in our 121-year history.” It has included roundtable discussions with every major candidate, 300 town hall meetings at locals and straw polls in May, the results of which have still not been announced.

But for Trump, who has pushed hard for union votes, with or without union leadership endorsements, the O’Brien invitation was a victory. Organized labor, at least for now, remains strongly behind Biden’s reelection, and the president has worked hard to keep unions by his side.

The Biden administration’s National Labor Relations Board has been staffed with pro-union officials, a marked departure from Trump’s. Biden’s three signature domestic achievements — the $1 trillion infrastructure bill, a $280 billion measure to rekindle a domestic semiconductor industry and the Inflation Reduction Act, which included $370 billion for clean energy to combat climate change — all contained pro-union provisions that have particularly helped Teamsters, who drive trucks and work construction sites.

And his COVID relief bill, the American Rescue Plan, included the one measure that Teamsters leaders wanted the most: a huge bailout of pension plans that will restore retirement accounts at the union for three decades. Virtually every major union, including the umbrella AFL-CIO, has already endorsed Biden for reelection.

Yet Trump remains a draw to the working-class voters Biden desperately needs. As O’Brien toys with both sides, any Teamsters effort to educate and organize its members before November has been put on hold, according to John Palmer, a Teamsters executive board member and vice president at-large, and other Teamster officials.

“We aren’t in a rush to judgment, and we don’t make decisions until after the conventions,” Deniz said.

For Trump, even having O’Brien at his convention is a triumph.

“When I am back in the White House, the hardworking Teamsters, and all working Americans, will once again have a country they can afford to live in and be respected around the world,” Trump wrote on his social media website Truth Social.

O’Brien’s efforts have prompted remarkable dissent within the famously tight-knit union and a leery response from conservative business groups.

Outside the arena where the convention will unfold, the Center for Union Facts, an anti-union group, has posted billboards calling the Teamsters “two-faced” and warning that the union has spent 99% of its advocacy on “left” causes.

The forceful response from O’Brien’s leadership team to internal disagreements has been equally surprising.

Palmer refused to attend the leadership meeting with Trump, instead releasing a letter to O’Brien in which he called Trump a “known union buster, scab and insurrectionist.”

Weeks later, the union’s general counsel, David O’Brien Suetholz, sent Palmer a four-page letter listing 24 media reports in which Palmer’s name had appeared, demanding confirmation in writing that he was authorized to speak on behalf of the union in each of the articles and requesting a list of “every document you shared with a member of the media” concerning Trump’s interview with the union.

“There’s not a more Trump-like figure in the labor movement,” Palmer said of O’Brien. “It’s in his nature.”

Early this year, the union filed a copyright infringement case against an internet forum that members have long used to discuss issues and where recent posts have featured differences of opinion about O’Brien’s approach to Trump. The union brass demanded it stop using the Teamsters name and logo on its website.

When Rick Smith, a Teamsters member and podcaster, spoke out against O’Brien “platforming Donald Trump” on an episode of his show, the Teamsters president had what Smith called “an encounter” with him at a crowded party in Pennsylvania. According to Smith, he demanded an on-air apology if Smith wanted a relationship with the union he had been a member of for 35 years.

Smith didn’t give it, though he did say, “I do agree with Sean O’Brien of 2018 where he wrote on his Facebook page after Trump’s State of the Union address, ‘We refuse to remain silent as Trump dismantles all we’ve fought for.’”

Palmer said the straw polls taken in May showed Trump with the support of a healthy 37% of Teamsters members, but Biden with a clear lead, 46%.

After the executive board met with Biden, Palmer added, virtually every member present said the union had to back the president. But O’Brien wanted to string out the process as he courts Republican support.

“But you know,” Palmer added, “you can pick up a snake and play with it, but if you play with it enough, it’s going to bite you eventually.”

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