The Teamsters Boss Who Calls Himself S.O.B.

At a rally in Atlanta last month, Teamsters President Sean O’Brien addressed hundreds of union members with the combative attitude that has come to define his leadership style.

“We’ve organized, we’ve strategized, and now it’s time to pulverize this white-collar crime syndicate known as UPS, ” he said to cheers and applause from hundreds of UPS truckers and warehouse workers. A month earlier O’Brien had tweeted a photo of a tombstone with the logo of Yellow, the trucking company that he was also wrestling with at the time.

At a time when the share of U.S. workers represented by unions has dropped to historic lows, O’Brien is taking on employers using 21st-century tools like aggressive social-media posts and inflammatory rhetoric.  

O’Brien is celebrating a big victory and reeling from a stunning defeat. He secured a new five-year contract with UPS that promises sizable raises for 330,000 Teamsters and wins back some concessions workers made in prior deals. He was also confronting the abrupt collapse of Yellow, which left 22,000 Teamsters out of work.

With a shaved head and the muscular frame of a man who played linebacker in high school, O’Brien looks like he stepped out of central casting. The 51-year-old grew up in a blue-collar family in Medford, Mass., and joined the union at 18, after one semester of college. He started off as a trucker, hauling heavy equipment for a crane-rental company.

His father was a lifelong Teamster and his two brothers are members. In fact, O’Brien is a fourth-generation Teamster, tracing his roots back to a great grandfather, who made deliveries in a horse-drawn wagon in Boston soon after immigrating from Ireland.

O’Brien brandishes his initials S.O.B. in his social media handle and his bio says, “Fighting for workers is a full-contact sport.” His deft use of social media, his airing of labor grievances in TV appearances and his combative stance against companies have made him popular among the rank-and-file workers.

He showed up at the Hollywood writers’ picket lines outside studios in Los Angeles. In the early days of the writers’ strike, Teamsters-represented truck drivers have turned around rather than cross picket lines to enter studio lots, disrupting film shoots.

His rapid rise to the top of a union with 1.2 million members has included some detours. During the last round of UPS contract talks, in 2017, O’Brien was ousted as lead negotiator by then-president James P. Hoffa,

The Teamsters union is best known for representing brown-clad UPS workers and truck drivers, as well as the union’s corruption scandals and alleged past ties to organized crime. The Teamsters also represent workers who package fruit and vegetables in California, brewers in St. Louis and zookeepers in Pennsylvania. 

Now it has its sights on America’s biggest e-commerce company, which employs vast numbers of drivers and warehouse workers.

“We have a strategy. We want to organize Amazon—500,000 members doing the same job that you do every day,” O’Brien told the UPS workers at the Atlanta rally. Amazon declined to comment.

Robert Travis, president of the Independent Pilots Association, representing around 3,400 UPS pilots, recently met O’Brien at the Teamsters’ headquarters, opposite the Capitol in Washington, D.C. Travis said O’Brien came to the lobby to greet him and bring him up to his office.

“My interaction with Mr. Hoffa was limited. I tended to communicate more with that administration’s No. 2,” said Travis, referring to O’Brien’s predecessor, who retired in 2022. “With Sean O’Brien, he makes himself accessible to the other pilot associations and unions. And I found that to be very refreshing.”

In 2018, the UPS agreement was voted down by rank-and-file members, but the union pushed ahead with the contract on a technicality. After Hoffa announced his retirement, the union held an election for his replacement in 2021. In a race between a candidate who was endorsed by Hoffa and O’Brien, O’Brien won. He officially took office in 2022. 

“The last two contracts, 2013, 2018, there was a lot of flexibility given to UPS,” said O’Brien in an interview in February. “Whatever concessions have been given, UPS has taken advantage of. And it hasn’t been in the best interests of our members.” 

As the latest UPS-Teamster negotiations kicked off in the spring, O’Brien promoted the union’s agenda in media appearances. This was a change from the way union leaders handled the negotiation in 2018, where they were more tight-lipped. The Teamsters also brought in rank-and-file members to serve on the negotiating committee, offering a more personal perspective in the talks. 

“The rhetoric is more bellicose, more inflammatory, and certainly much more populist” than past union administrations, said Bruce Chan, an analyst at Stifel who covers UPS, FedEx and other freight companies.

Chan said one of the early signs that collective bargaining was becoming a bigger challenge for companies in the transportation industry was when the Teamsters pushed back against proposed operating changes by Yellow early this year. 

The latest UPS-Teamster agreement included a 48% average total wage increase over the next five years for existing part-time workers. The agreement also means UPS drivers will remain the highest-paid delivery drivers in the country, with the average top rate at $49 an hour. The drivers currently make around $42 an hour after they’ve been employed for four years.  

The agreement, which has yet to be ratified by membership, comes amid the fallout at Yellow, where thousands of Teamster-represented drivers, clerks, forklift operators are now out of a job. 

Yellow’s financial troubles started years ago, with prior bankruptcy scares and bailouts. It was debt-laden when a recent freight downturn added further pressure. Yellow management sought to streamline its operations and defer pension contributions. 

The Teamsters said members had given concessions over the years to Yellow and would no longer do so. In July O’Brien threatened a strike, spooking customers, who pulled their freight from Yellow and hastened its end. 

In a lawsuit filed against the Teamsters a few days before the company ceased operations, Yellow alleged that O’Brien rebuffed its efforts to negotiate for months, “choosing instead to direct profanities at Yellow and its executives and even to gloat at Yellow’s impending demise.” 

O’Brien denied the claim, saying that the company had been mismanaged. 

Some Teamsters-represented workers at Yellow said on social media they felt like the union could have done more for them, and that their plight had been overlooked in favor of the UPS deal. 

Yellow workers are represented by more than 150 locals, which are now working to find them jobs in freight and other industries, a Teamsters spokeswoman said, adding that the union has reached labor agreements with other freight companies in recent months.

“I know there’s going to be criticism because of the position we are taking with Yellow, but it’s necessary,” O’Brien said at the Atlanta event. “We’re going to have fights, we’re going to have sacrifices, we’re going to have losses. But at the end of the day, the biggest thing we have to do is stay united.”

Write to Esther Fung at [email protected]