The Interview: Teamsters General President Sean O’Brien

How do you defeat Amazon?  We ask that and other burning questions of Boston’s own Sean O’Brien, the most powerful labor leader in all the land.

Photo by Ken Richardson

Boston and beyond, be warned: Sean O’Brien is shaking up the world of organized labor. And he’s got Amazon–along with every other big corporation whose workers the newly elected Teamsters general president thinks he can woo–in his sights. In March, the Medford native and fourth-generation Teamster will officially take over the 1.4 million-member brotherhood, which represents employees as far flung as soft-drink factory workers and cheesemakers. This comes after 16 years spent leading Boston’s Local 25, where he was its youngest president, at age 34. We caught up with the former truck driver to talk organizing (and organized crime), bargaining tactics, and how he plans to go head-to-head against the behemoth that Jeff Bezos built.

You’ve said that you’re going to pursue unionizing Amazon. What’s your plan?

It’s not going to be a traditional organizing drive, because Amazon went from being a book club to a global economy. The traditional tactics of standing outside the gates and handing out cards aren’t going to work, but we’re going to pursue organizing the warehouses because that’s where the majority of their employees are. We’re going to do a few different things. Number one, we are going to have to negotiate strong contracts in similar companies like UPS and DHL, where we have a template to show unorganized workers what benefits they’ll get with unionizing, like healthcare, a pension, a grievance procedure, and, most important, dignity and respect. We also have to get involved in the communities. A lot of these direct employees of Amazon live in communities that are predominantly immigrant workers, so we need to get involved with them through things like church groups.

What about companies that are part of the gig economy—Uber, Lyft, DoorDash, Grubhub?

That all comes under the independent contractor model. They’re not direct employees, and they have to adhere to the policies and procedures set forth by those companies, similar to the FedEx model for home delivery. We’ve got to utilize our political influence to change some of the laws governing them, so it’s easier for us to organize these gig economy companies.

But you’d like to see those companies unionized?

I’d like to see everything unionized, not just those companies. Look, I think we can all agree that over the years, the independent contractor model has skirted a lot of wage and hour laws, and basically circumvents unionization. I’d love to see every single industry represented by a union.

What’s the future of the Teamsters as labor becomes more automated?

As the general president elect, I’m going to fight hard against autonomous vehicles, especially in the trucking industry. They eliminate jobs, number one, and number two, they’re a public safety risk. The other thing that people sometimes lose sight of is that we’ve got this bill that’s going to be providing thousands of jobs to rebuild the infrastructure of the United States. I think automation would be destroying those bridges and highways.

There are a lot of professions that are part of the Teamsters. What’s one that you think would surprise people?

I mean, everything from airline pilots to zookeepers are part of the union. We represent a lot of school administrators, public sector workers, construction, food and parcel delivery, the tugboats in Boston Harbor. We have a very diverse membership. The old joke was that if fire hydrants could be organized, the Teamsters would do that.

During COVID, there’s been so much attention paid to essential workers. Do you think that was just lip service, or is the newfound respect and appreciation genuine?

I would say two things. One, the general public absolutely appreciates us. We’re providing goods and services, whether it’s delivering e-commerce, picking up trash, or making certain that food is supplied to grocery stores. And two, for typical corporate America, we’re only as good as our last at-bat, and they forget who made them a success during the pandemic. A lot of these large companies, like Republic waste, UPS, or the large food service companies, saw their bottom line and balance sheet, in some cases, triple as a result of COVID. But they won’t appreciate us until they have to go into their pockets and reward our members and pay them for their success.

What’s going on with the supply chain?

The supply chain problem is very real, but we wouldn’t have a problem if we weren’t waiting for products to come in from overseas. Had we continued producing and manufacturing goods in the United States over the past several decades, we wouldn’t be in this position.

What are your plans for the new UPS contract?

With the last UPS contract there were some concessions that our members weren’t happy with, like the creation of what’s basically a two-tier wage system. [Fighting against] allowing the company to hire people to deliver packages out of personal vehicles and subcontract work are going to be top priorities in these new negotiations. But also, about 65 percent of UPS is made up of part-timers, and there was always an appetite, 10 years ago, to get a minimum wage of $15 per hour. I think right now, we can all agree that that minimum wage should have a starting point of $20 per hour.

Photo by Ken Richardson

What’s the single most important thing when it comes to negotiating?

Listening to your rank-and-file members. And part of it is making sure that we’re crafting proposals that are in their best interests, and fighting hard and bargaining hard at the table.

There’s an academic who said, “The history of unions is always about failing forward.” Do you think that’s true?

I don’t know what that actually means, to be honest with you.

I think it means that the history of unions is always addressing a problem or grievance, so you’re coming from a position of, “There’s a problem. We need to fix it.” As opposed to “Everything’s hunky-dory.”

Well, everything is not hunky-dory. We have an opportunity, especially in the Teamsters Union, because we are involved in the four major modes of transportation—rail, trucking, maritime, and airlines—and the one thing we have to do better as a labor movement is work together, as coalitions. Oftentimes, we look at things only from the perspective of what’s germane to my union, and if it doesn’t affect me, why would I get involved? But at the end of the day, we’ve got to form better communication, and work together to leverage our political power and make sure we’re passing laws and policies that benefit all workers.

How much time will you be spending in Washington, DC?

My intention is to spend as much time there as needed, but my goal is really to spend more time out in the field, all over the United States, talking to our members in different industries. I truly want to be out with the rank and file, making certain I understand all their wants and needs and carrying that torch forward.

Will Boston still be home?

Oh, yeah, Boston is home. It always will be. I do have to move to DC, but Local 25 is always going to be my local union. It’s always going to be a huge part of my life.

Who’s the most labor-friendly politician today?

In the past year, Joe Biden has done a great job fixing our pensions. There were about 200 pension funds in the United States that were critical and declining. But there are a lot of champions of labor. You’ve got Senator Bernie Sanders. You’ve got Senators Elizabeth Warren and Ed Markey, all of whom have done a great job. There’s Senator Alex Padilla in California, but having a president who isn’t afraid to use the word “union” is huge.

What do you think is the single most important labor law in U.S. history?

The reason we have weekends is because of unions.

Accomplishment you’re most proud of as the head of Local 25?

I’m proud of the fact that when we took over that union in 2006, it was divided, and we were able to bring our members back together, unite, and fight for the greater good. We’ve organized over 4,000 workers. Our health and welfare fund has tripled in size. And we’ve done tremendous work in the communities. Our autism charity is one of the largest fundraisers in the country.

The two most prominent people in labor in this country right now are you and Labor Secretary Marty Walsh. Is it something in the water here? And any chance we’ll ever see a Walsh-O’Brien political ticket?

I will not run for political office. I can promise you that. But the stars aligned, which is great. I was quoted a few months ago saying, “Two Boston guys can solve a lot of problems,” and that’s true right out of the gate. Marty and I were able to resolve a strike in Reno, Nevada, two months ago, just by forming a relationship with the CEO of one of the companies and getting a deal done that was in the best interests of the workers. We’re going to work together on a lot of different initiatives, like Amazon, and whatever else affects workers. It’s comforting to know that someone’s in power who understands the value of workers and the value of a unionized workforce.

Your response to people who bring up the allegations of the Teamsters having historical ties to corruption or organized crime?

Our organization has been around for 118 years, and sometimes people love to focus on what happened 40 or 50 years ago. Then that’s the reputation, no matter what you do, and you can’t get away from it. But the bottom line is that there’s no organized crime presence in the Teamsters Union, where we’re under a consent decree. We’ll be policing our own. We’ve got to make sure that if there is any type of corruption, we deal with it swiftly and take appropriate action.

How much political clout do you think you now have?

I don’t know. I always tried to position my local union to be politically active and work hard for candidates we supported. And I will say this: I have gotten a lot of phone calls from a lot of high-ranking officials in Washington, DC, who probably wouldn’t have called me two years ago. I do think I have potential for new relationships, a seat at the table, and also an opportunity to enlighten folks on how important the Teamsters Union is to this country.

What’s the largest factor that drives corporate greed? Is it executives? Shareholders? Consumers? Is it just sort of built into capitalism?

There’s a lot of greed, but big corporations get away with whatever people allow them to get away with. They think they’re untouchable, but bottom line, it comes down to the majority’s cooperation, especially with the ones that aren’t paying much in taxes, like the Amazons of the world. They could care less about their workers.

Do you think your predecessor, James P. Hoffa, was as effective as his father?

Absolutely not. His father was one of a kind, a true icon of the Teamsters Union. We had tremendous political clout on [Jimmy Hoffa’s] watch. We could have had the same with James P. Hoffa, but he didn’t come up through the ranks. It’s tough to understand an industry that you never worked in, but when you have a famous last name…. Thankfully, once again we’re going to be run by Teamsters who have worked in the industries and the jobs, who understand what they are. That’s what we’re going to need to portray to corporate America and the politicians.

Last, I just have to ask, any idea where Jimmy Hoffa’s body is buried?

I have no idea.

Photo via BrianJackson/Getty Images

By the Numbers

Let’s Get Together

The highs and lows of local organized labor.


Percentage of Massachusetts workers who are unionized.


Number of union members at Market Basket when its workers won their landmark battle to reinstate the company’s CEO in 2014.


Number of former Boston Police Union bosses indicted on criminal charges over the past two years.


Number of months that Boston Globe union members labored without a contract before signing one last fall.


Number of years that the Department of Labor had secretaries who were not union members until Marty Walsh was sworn in.