Teamsters Boss Claims Harris Lost the Union After Demanding They ‘Better Get on Board”

Teamsters Boss Claims Harris Lost the Union After Demanding They ‘Better Get on Board”

Teamsters Boss Sean O’Brien went off on the Democrats, especially then-Vice President Kamala Harris, on Bari Weiss’s “Honestly” podcast.

O’Brien explained what happened behind the scenes, leading to the Teamsters not endorsing either presidential candidate, and why the Democrats have lost the working people.

Harris

O’Brien claimed Harris lost the Teamsters because of her attitude. It’s very reminiscent of Hillary Clinton, who also thought she would easily beat Donald Trump.

So high and mighty:

O’BRIEN: We had a general executive board meeting, probably around June of 2024 and there was an event that one of our vice presidents, Joan Corey, she’s out of my local, she went to, I know if it’s an Emily’s List event the day before our general executive board and Vice President Harris was there. And so they do a photo op line.

So Joan goes in the line, and Joan says, “I’m Joan Corey. I’m a vice president with the Teamsters Union.”

And she [Harris] pointed her finger at Joan and said, “Teamsters better get on board.” And so Joan says, “Excuse me?” “Yeah, Teamsters better get on board. I don’t know why you haven’t endorsed me yet.”

So she comes back and she tells me this, and I’m like the nerve, like the nerve, right? So that happens, and then we eventually get her in before our general executive board. And again, like you said, there was 16 questions. They all had the same 16 questions. You know, Trump might answer nine of them, or whatever. Biden only answered about five or six.

And then Harris’s campaign, or people were trying to negotiate how many she was going to answer, and said, we’re only going to answer three. And it was like a one hour deal, one hour venue. And so she really didn’t answer the questions. And then I was we, you know, on the fourth question, my chief of staff slides me an index card and says, This is the last question she’s not answering anymore, because she wanted to, like, pontificate and give her speech of why the country’s the way it is, why we should endorse her. And she did that a little bit.

And then at the end, her closing was, “Listen, I’m gonna win with you or without you.” And it was like such a smug answer, like, okay, and that turned the majority of people in that room off her because we do what we call a hot wash, and the hot wash is important, because instead of pointing out what everybody did bad as a leader after every critical situation or critical mission, I would start out saying, “This is what I could have done better. This is what we should have did.”

So I did the same thing. Maybe we should ask this question, post mortem. Post Mortem, right? So after that comment, after that body language, you know, you can tell someone’s body language totally. You could smell it a mile away.

And then once we announced that there was going to be no endorsement, that’s when, you know, that’s when all the keyboard warriors came out and the attacks from the DSA, you know, my friends that were allegedly my friends that were, you know, high rank incentives on the Democratic Party. You know, they didn’t have a problem taking a check for $550,000 for, you know the national PAC, but you know, once I spoke at the RNC, then I was, you know, no good.

Democrats

Why did Democrats lose the working class? Well, working people aren’t stupid. Sure, we care about social issues, but we care more about having a job so we can put food on the table, have a roof over our head, and save money for retirement.

Food, shelter, and money become even more critical when you have children! Your list of financial responsibilities grows, including college, cars, and, for some, private school. Plus, you want to save even more in case something happens to you and make sure your family is taken care of.

Our family’s well-being takes priority.

Democrats forgot what’s important:

WEISS: When I was growing up, Democrats were the party of working people. Democrats were the party of labor unions. Like that was just baked in.

O’BRIEN: It was like, it was like 10th grade geometry. It was a given.

WEISS: Exactly. So I want you to, like, pretend you are one of those 65%. Why are those people, steel man, their argument for me, okay, tell me why they’re voting for Trump, because the average Democratic senator or congressman will say, “What is wrong with these people? They are voting against their economic interests, and they don’t see it that way. So why are they voting?”

O’BRIEN: They’re first and foremost, you know, our members are pretty sophisticated. They’re a lot more educated. And you know, formulating opinions, you know, to make such a vast change doesn’t happen overnight.

I mean, you look back and you think about this, and I say this a lot, over the last 20 years, 16 out of those 20 years was a basically Democratic controlled country, right? And when you look back, what did working people get out of those 16 out of 20 years? You look at the Obama administration, right? We had a we had a Democratic House, Democratic Senate, Democratic president. And our biggest platform, when I say our biggest platform for labor, was the Employee Free Choice Act. That should have been a layup. We should have got that. We didn’t get that right.

Joe Biden fixed pensions, and I’m glad he did, because one of mine was fixed. But he fixed, he fixed a problem that was created by the Democrats in 1980 when they passed deregulation, right? And we lost 400,000 members in the Teamsters Union and the trucking industry, which we lost 400,000 jobs, you lost good companies that were forced into bankruptcy, which you weren’t getting pension contributions on, and it kept deteriorating. Then it deregulation flew through many other industries, and Ted Kennedy introduced a bill. Joe Biden signed off on it. Ronald Reagan signed off on it. So people forget why we’re in that spot.

So whenever someone say, “Oh, Joe Biden, fix your pension. He was the greatest president for union.” He was a great president for union people. He fixed the pension. Yes, he did, but he broke it as well. Because, you know, and I say this all the time, it’s like me playing street rock in my neighborhood in 1980. I break my mother’s window. 40 years later, I decide to fix it. Right? Should I get accolades for a problem that I helped create? So, you know, when I talk about things like that, but you know, the Democrats seem lately that, you know they’re not, my thing is, I always look at it from a simple perspective.

You’re paying me to do something, or if you’re electing me to do something, I work for you. Okay, where the Democrats lost, and I think you made a good point earlier, they fell in love with their captors. They fell in love with big money. They fell in love with big tech, and they forgot who they truly representing working people. You know why? Because they’re not in their communities, not in their neighborhoods. You know, they’re not talking to the people that they’re paid to represent. And when you talk to people one on one, look, I can sit in my office all day every every day, and try and solve problems over the phone, and I’m not going to get a true testimonial what is actually going on. And I told you earlier, like I’m in workplaces, my partner and I, we’re in workplaces, you know, three days, three different states per week, and we’re not talking to leaders or anybody else. What going on the shop floor is talking to rank and file members. That’s where you get the best gage, and that that discipline should hold true. And I think the Democrats forgot that they need to be in their communities where they represent, talking to people, finding out and identifying the issues that are truly matter.

Look, this whole election for the Democrats was based on social justice issues. Our members, you know, the team says, and I can speak for the Teamsters, we saw a lot of those social justice issues by negotiating the strongest contracts, by fighting for rights, fighting for diversity, fighting for, you know, equality in the workplace. And it seemed like this narrative of the social justice issues, it didn’t identify with our members.

Our members identify with more money in their pockets, more job protection, better pensions, core issues, core issues and a path, a path from the start of your job into a career, into retirement. I mean, it’s simple block and tackling, and that’s not what that’s not what our members wanted to hear.

Democrats were always the party of the working class. Why did so many of them vote for Donald Trump?@TeamsterSOB: Democrats “fell in love with big money. They fell in love with big tech—and they forgot who they truly represent: working people.

This whole election for the… pic.twitter.com/52ELgyTzVh

— Honestly with Bari Weiss (@thehonestlypod) August 5, 2025

AOC

Weiss and O’Brien continued the discussion by naming names, especially people like Rep. Alexandria Ocasio-Cortez (D-NY).

Last September, O’Brien reminded AOC that union members in her district supported Trump. Harris ended up taking AOC’s district, but man, Trump gained way more voters than he had in 2020.

Cosplaying is an excellent description for AOC and others:

O’BRIEN: AOC? Absolutely not. Oh, because she’s, you know, she’s, again, another social justice warrior. You know, she’s personally called me out. I’ve never met the woman in my life, but you know, she just doesn’t, you know, and even you look at how they voted in her district, I mean, I would, I would spend majority of my time in my district identifying what my people need, instead of, you know, trying to put myself on the ballot for 2028.

WEISS: But these are people, AOC, [Zohran] Mamdani, we can name a few others who are maybe you would say they’re just cosplaying as like pro labor politicians, like they’re saying all the things, like, “We stand up for working people!” That’s their whole platform. Why do you say that that’s bullsh*t?

O’BRIEN: But do they know that? It is bullsh*t. Because I’ll tell you why. This last election, Joe Biden walked a picket line with the UAW. Awesome. He should. I’ve had 250 strikes in three years.

The only politician has walked one of my picket lines has been Josh Hawley, and recently we have a couple in Boston. You’ve had the whole congressional district in Massachusetts walking. But other than that, they’ve never been picking lines.

We were, we were fighting Amazon, where we were looking for letters of support. There’s people that you just mentioned that didn’t sign our letters or didn’t show up yet. They want to call you out on everything that they don’t, you don’t agree with them on. They’ll call you out saying he’s not right, like AOC is in some like crazy DSA chat or something, whatever it is saying, “Sean O’Brien shouldn’t be allowed to represent the teamsters union.” Why? Because I don’t agree with you. Like, what? Should you not be allowed to be in Congress because you don’t agree with me? I don’t agree with you.

It’s like, lady, I’ll put up my record against yours when it comes to defending working people. I’m not out here for a press conference or a photo shoot. We’re actually out there, doing the work, negotiating the contracts, organizing and, you know, right in her district, you know, I mean, we have, we struck Amazon. I think she showed up like the last day. Chuck Schumer wouldn’t even sign a letter of support.

Teamsters president @TeamsterSOB: The idea that politicians like AOC stand for working people is “bullshit.”

“Lady, I’ll put my record against yours when it comes to defending working people—I’m not out here for a press conference or a photo shoot. We’re actually out there doing… pic.twitter.com/javCFpUd36

— Honestly with Bari Weiss (@thehonestlypod) August 5, 2025

Bernie Sanders

Sen. Bernie Sanders (I-VT) cut off O’Brien after he spoke at the RNC.

Just wow:

WEISS: Let’s talk about Bernie Sanders for a second…

O’BRIEN: He doesn’t talk to me anymore.

WEISS: Why?

O’BRIEN: I don’t know.

WEISS: When did he stop talking you?

O’BRIEN: Right after I spoke at the RNC.

WEISS: Did you used to talk to him a lot?

O’BRIEN: All the time. I did rallies with him around the country.

WEISS: And then what happened?

O’BRIEN: Just went totally silent, just whenever. I think he looks at as a betrayal of not endorsing the Democratic Party. He’s never said that, but his his whole attitude and access has completely, completely changed towards us. You know?

I mean, we called him last week, or my staff called him last week because we’re working bipartisan on this bill for the faster labor standards contract, which is basically a thinner version of the pro act. And, you know, he’s got a problem with it, and staff was not too nice to my staff. So it’s like, you know, we’re only as good to people when we’re carrying that water.

But I guess, you know that doesn’t matter. I mean, look, I like the guy. I have respect for him. I saw him on Joe Rogan, I don’t know.

I mean, this is the problem with politics. People take things too personal, and when you don’t go along to get along because you’re actually, you know, listening to people you represent, and they don’t talk to you anymore, that’s the problem. It’s fine.

Teamsters president @TeamsterSOB says Bernie Sanders stopped talking to him after he spoke at the RNC in 2024.

“His whole attitude and access has completely changed towards us.” pic.twitter.com/H9Sug9jT6D

— Honestly with Bari Weiss (@thehonestlypod) August 5, 2025

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