Sean O'Brien came up through Boston's Teamsters Local 25. He now runs the whole International Brotherhood of Teamsters, 1.3 million members, one of the most diverse rank-and-file armies in American labor. Remember that number and that diversity, because it is exactly what he put on the auction block.

In July 2024, O'Brien became the first Teamsters president in history to address a Republican National Convention, in prime time, in front of a room built around Donald Trump. He praised Trump from that stage, calling him "one tough SOB." A union that had backed Democrats for decades watched its leader walk into the other party's convention and hand it a labor celebrity's blessing.

Then he went further. O'Brien publicly tweeted that Senator Josh Hawley was "100% on point" for an article attacking corporate diversity, equity, and inclusion efforts and, in Hawley's own words, "the religion of the trans flag." Read that slowly. The head of a union full of Black, brown, immigrant, and LGBTQ workers went out of his way to co-sign an attack on the very idea of inclusion.

His own house revolted. The official Teamsters account posted a statement condemning the Hawley endorsement, then hastily deleted it. Union Vice President John Palmer called the RNC decision "unconscionable." A member of the executive board said flatly that he was "embarrassed." This was not outside noise. This was the union's own leadership recoiling in real time.

And here is the betrayal in black and white. The Teamsters' own governing documents pledge that the union is "pro-union and pro-equality" and commit to full respect for LGBTQ workers and their families. O'Brien did not just drift from that promise. He publicly applauded the politicians writing the playbook against it. A leader is supposed to carry his members' values into the room. He carried the opposition's.

Now think about who pays for that image. Boston's unions, especially the building trades, carry a long and documented history of shutting Black workers out, and that reputation still keeps Black families at arm's length from one of the surest ladders into the middle class this country ever built. When the most visible union boss in America, a Boston product no less, cozies up to a movement openly hostile to diversity, he hardens the very stereotype that unions are hostile to Black people. Every worker he pushes away with that message is a family locked out of union wages, union benefits, and union pensions. That is not just a bad look. It is fuel on the racial wealth gap, and it makes the lie that unions are anti-Black a little more believable to the people who most need to know it is a lie.

Then came the silence that said everything. For the first time in decades, the Teamsters declined to endorse in the presidential race, even as its own president cozied up to the ticket that labor leaders across the movement warned was on the bosses' side. The AFL-CIO's Liz Shuler put it plainly: Trump and Vance stand with the bosses, and workers would not be fooled. O'Brien apparently would be.

So the question for every Teamster, and for the Boston labor community that made him, is simple. When your president trades the union's multiracial, pro-equality foundation for a prime-time slot and a pat on the head from the anti-union right, who is he actually working for? And who gets left standing outside the hall he just handed away?

Boston built Sean O'Brien. Boston's workers can also tell him what they think of the trade. The Teamsters have offices and a membership with a voice. Use it, and make him answer for the stage he chose.