Teamsters at a crossroads: Rank-and-file challenge takes on O’Brien’s alliance with Trump

The upcoming election for the leadership of the International Brotherhood of Teamsters — one of the largest and most powerful unions in the United States — could reshape the direction of the labor movement itself.

In November 2026, 1.3 million Teamsters will choose between incumbent General President Sean O’Brien and Richard Hooker Jr., a Philadelphia Teamsters leader who has become a leading critic of the current administration.

This election is about more than who sits at the top. It’s a fight over the union’s soul — whether it will stand with the working class or side with the bosses and politicians who exploit it.

A dangerous political turn

Under O’Brien, the Teamsters have drifted sharply to the right.

Once calling Donald Trump “our enemy,” O’Brien now praises him as “one tough SOB.” He met privately with the billionaire politician and even spoke at the 2024 Republican National Convention.

Hooker warns that this alignment “puts every working-class person in jeopardy.”

Trump, he points out, is a union buster who has cut jobs, eliminated labor protections, and attacked workers’ rights. He weakened the National Labor Relations Board and OSHA, and cheers on union-busting bosses.

O’Brien, who rose to power in 2021 as a self-styled reformer after the Hoffa era, has since courted the same corporate and right-wing forces he once criticized. His administration has shifted Teamsters’ political spending toward corporate-aligned and Republican-backed PACs.

To Hooker and many activists, this weakens labor solidarity and distances the union from the broader working-class movement.

Breaking the system of fear

The debate is also about democracy inside the union itself.

Hooker says the Teamsters have long been ruled by “a system of fear, bullying, retaliation, and intimidation” — a system that mirrors the boss’s own tactics. He accuses O’Brien of acting “like a king who expects blind loyalty.”

Hooker argues that members, not top officials, should set the union’s direction — from contract enforcement to grievance procedures to leadership accountability. His message is simple: the rank and file should have the power to decide how their union is run.

Fighting for jobs, pensions, and the future

At UPS — the largest Teamster employer — workers say the grievance process is slow and unclear. Hooker calls for transparency, direct communication, and stronger representation against management pressure.

Automation is another looming challenge. As logistics corporations rush to bring in robotics and artificial intelligence, thousands of Teamster jobs — and pension contributions — are at risk.

Hooker says the union must anticipate these changes and fight to protect wages, hours, and job security as technology transforms the industry.

A new chapter in Teamsters’ history

If elected, Richard Hooker Jr. would become the first Black president of the Teamsters — a historic breakthrough in a union whose membership includes large numbers of Black and Brown workers, even though its leadership remains overwhelmingly white.

Hooker’s campaign is more than a personal bid for office. It’s part of a growing rank-and-file movement to make the Teamsters once again a fighting union rooted in its diverse membership.

Which path forward?

The 2026 election offers a clear choice.

O’Brien’s camp defends a top-down union that cuts deals with bosses and courts the far right in the name of “access.”

Hooker’s campaign calls for a member-driven union — one that rejects collaboration with anti-worker politicians and puts power back in the hands of the rank and file.

It’s a choice between accommodation and transformation, between a union that adapts to the billionaire class and one that fights to defeat it.

The outcome will echo far beyond the Teamsters — across every shop floor where workers are asking the same question: Whose side is our union on?