Remember Teamsters President Sean O’Brien’s love affair with President Donald Trump? Well, it’s now spectacularly backfiring.
In January 2024, O’Brien met privately with then-candidate Trump. Months later, he spoke at the Republican National Convention, complaining about backlash from “the left” and praising Trump as “one tough SOB.”
“I travel all across this country and meet with my members every week,” he said. “I see American workers being taken for granted, workers being sold out to big banks, big tech corporations, the elite.”
Vice President JD Vance speaks to the media alongside Teamsters President Sean O'Brien on Oct. 30, 2025.
Imagine not only saying that out loud but actually believing that Republicans are the ones who will take on big banks, tech, and the elite.
As The Guardian reported at the time, O’Brien’s speech came just after Trump announced that JD Vance would be his running mate.
“Vance opposed the Pro Act, which organized labor rallied around, and introduced legislation that would legalize company unions, corporate labor formations outlawed by the National Labor Relations Act in 1935,” the publication noted.
Ultimately, the union declined to endorse anyone for president. But in announcing that decision, it revealed that “in independent electronic and phone polling from July-September, a majority of voting members twice selected Trump for a possible Teamsters endorsement over Harris.”
In one of those straw polls, Teamsters chose Trump 60 to 34.
So how’s that working out?
Last year, UPS closed 93 facilities and laid off 20,000 workers because of a “sharp drop in packages sent from China” after Trump imposed tariffs on the country, according to The New York Times.
Last month, UPS announced another 30,000 layoffs and the closure of 24 more sorting facilities. And earlier this week, the company listed the affected facilities, which were primarily in rural and southern communities. It’s also deployed automation across dozens of additional locations.
Teamsters members protest harsh labor conditions on Feb. 20, 2025.
And the Teamsters have been left sputtering about their contract.
“If UPS wants to continue to downsize corporate management, the Teamsters won’t stand in its way,” O’Brien said after last year’s layoffs were announced. “But if the company intends to violate our contract or makes any attempt to go after hard-fought, good-paying Teamsters jobs, UPS will be in for a hell of a fight.”
UPS responded with even more layoffs.
If your union membership depends on global logistics, and you boost a candidate promising sweeping, economy-crushing tariffs while surrounding himself with rabid anti-union people, don’t be surprised when the fallout lands on your own members.
And if your own job depends on it? For the love of God, don’t cheer for the guy swinging the wrecking ball.
Can’t say they weren’t warned.
