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Teamster President Sean O’Brien has not only praised Donald Trump from the podium of this summer’s Republican National Convention, and expressed doubts about the worker-cred of Kamala Harris. He also effectively compelled his union’s executive board not to grant a Teamster endorsement to Harris in this year’s election, to take a "no-endorsement" stance instead, even though many members of that board then proceeded to have their own regions and locals endorse Harris once they emerged from the boardroom.

But O’Brien wasn’t always so bullish on Trump. In fact, when he was running for the Teamster presidency in 2021, he was demonstrably down on Trump and full of praise for Joe Biden’s and the Democratic Congress’s enactment of the economic recovery bill earlier that year that included a multibillion-dollar rescue for a Teamster pension fund that covered roughly 400,000 of its retired members. The Senate had voted 50-to-50 on the bill; it only passed because Vice President Harris broke the tie by voting aye.

How do I know that O’Brien expressed these sentiments during his campaign? I know because he said so during the September 1, 2021, debate he had with his opponent for the office of Teamster president, Steve Vairma. I know because I was one of the panel of journalists asking questions at that debate, and I was actually the panelist who asked him about Trump. I recently came across the transcript of that debate. Here are the relevant passages.

Initially, I asked both candidates, "You had some folks voting for Trump, some of your members, instead of Joe Biden. How do you analyze that?" O’Brien responded, "You know, it’s unfortunate that a lot of our members voted for Trump," before turning to other comments. I then followed up:

How would you go forward in trying to help your members who did vote for Donald Trump maybe to come to the same position that both of you, and the Teamsters Union as such, advocated? What would you say to them now? What would you say to them when you become President?

O’Brien responded:

I would say we made the right choice. We made the right choice in Biden. Under his first order of business, with the American Recovery Act, he was able to fund pensions until 2051. That wouldn’t have happened unless we had retirees, boots on the ground, rank-and-file members starting this process.

I later relayed a question from the audience about what solutions the two candidates had to ensure the viability of Teamster pensions going forward, to which O’Brien responded, "One of the biggest solutions that happened was, obviously, the American Recovery Act being passed. I want to commend everybody who worked hard on that."

Which, of course, included the above-mentioned Biden and Harris.

It’s not easy to say what exactly changed O’Brien’s mind about Trump once Trump left office—since O’Brien was down on him as late as September 2021. In justifying his pro-Trump "neutrality," he cited a poll of Teamster members. That poll said nothing, of course, about the hundreds of thousands of Amazon workers who are the primary focus of the Teamsters’ organizing campaigns—indeed, who are the future of the Teamsters if the union is to retain its status as a powerful force for American workers.

In just the past few weeks, the Teamsters have had a breakthrough of sorts in organizing Amazon delivery drivers, hundreds of whom have voted to join the Teamsters in New York and a Los Angeles suburb. This has been a complicated process, since these drivers, like virtually all Amazon drivers, are nominally employed by contractors, even though they work full-time driving Amazon trucks and wearing Amazon uniforms. It’s only since the Los Angeles region of the National Labor Relations Board filed suit against Amazon one month ago at one L.A.-area contractor. Once those drivers voted to unionize, Amazon terminated its contract with the contractor—a form of illegal firing if Amazon was legally their real employer.

And here’s where the difference between Trump and Biden-Harris becomes all-important. In 2020, Trump’s appointees to the NLRB ruled that such joint-employer relationships as those between Amazon and its contractors were not subject to U.S. labor law, and that the Amazons of the world had no responsibility for what happened to drivers who nominally worked for contractors. Early this year, however, Biden’s appointees to the NLRB restored joint-employer responsibility for companies like Amazon. It was based on that ruling that the L.A. region sued Amazon last month.

Both that ruling and that suit have been hailed in Teamster press releases. Their releases about their subsequent organizing successes among Amazon drivers have hailed those rulings as well.

Does O’Brien read those releases? Does he understand the difference between a Trump NLRB and a Harris NLRB, and what that difference means for the future of the union he heads? Does he care, or does he have other concerns that are not readily apparent?