Honestly with Bari Weiss

Why Unions Went for Trump


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The question of who represents the working class is probably the hottest debate in American politics. Is it Republicans? Democrats? Or socialists like Zohran Mamdani?

Pundits can debate that question all they want, but the undeniable test is: Who do the unions believe stands for working people?

For a century, unions were undeniably Democratic. And in 2021, Joe Biden tried to carry on that tradition. He went as far as to say: “I intend to be the most pro-union president leading the most pro-union administration in American history.” Then in 2023, he became the first sitting president to walk a picket line, joining United Auto Workers in their strike against General Motors, Ford, and Stellantis.

But as the Democratic Party went left, and then further left, many union members—who were reliable Democratic voters—broke the mold and voted for Donald Trump—nearly half of union households, to be exact.

Was it Trump’s hatred of the North American Free Trade Agreement (NAFTA)? His promise to bring manufacturing back? His unbridled bravado? Or was it the left’s preoccupation with boutique issues?

The shift was palpable when Teamsters president Sean O’Brien spoke at the 2024 Republican National Convention despite being a lifelong Democrat. It felt like a new era.

We’ve reported extensively on how the Democratic Party lost the working class. But now, six months into Trump’s second term, are working-class Trump voters happy with their choice? And how has Trump been for labor in America?

O’Brien—the voice you heard at the RNC—is the president of the International Brotherhood of Teamsters, representing 1.3 million union workers. It’s one of the biggest unions in the country. As Sean puts it, “They represent airline pilots to zookeepers and everyone in between.” That “in between” includes truck drivers, warehouse workers, mechanics, baggage handlers, construction workers, and UPS drivers—UPS is their largest employer. Basically, Teamsters have organized workers in every occupation imaginable.

And more than his role as Teamsters president, Sean himself is a fourth-generation union member, having joined the Local 25 at 18 as a heavy-equipment driver in Boston. He’s spent 34 years in the union and has a unique vantage point from which he sees American labor.

Today on Honestly, Bari asks Sean: Why did he speak at the RNC? How has Trump been for labor—given his coziness with Elon Musk, DOGE, and his new big, beautiful bill? Can Democrats win union workers back? And can unions find their footing again? How does he plan to organize Amazon—he has some choice words for Jeff Bezos. And how do we ensure more American workers have access to middle-class wages, quality healthcare, and strong pensions?



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