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‘He’s a force’: Teamsters head Sean O’Brien, who just reached UPS deal, has deep Mass. labor roots

International Brotherhood of Teamsters general president Sean O'Brien spoke to UPS Teamster members in Brooklyn on July 14.Casey Kelbaugh for The Boston Globe

Sean O’Brien’s handle on X, formerly known as Twitter, kind of says it all — @TeamstersSOB.

The man who brought UPS workers to the brink of what would have been one of the largest strikes in US history, and then to a tentative agreement Tuesday on a generous new deal, isn’t afraid to play rough. The International Brotherhood of Teamsters general president is a tough-talking former heavy-equipment driver from Medford with family roots in the union dating back to the days of horse-drawn wagons.

O’Brien, who led Local 25 in Charlestown for more than 15 years, vowed to make the Teamsters a more militant organization when he was elected in late 2021, and so far, he’s living up to that promise.


He’s tangled with a senator and been called “a bigger bully than Donald Trump” on CNBC. The bio on his X account says: “Fighting for workers is a full-contact sport.”

At the same time, O’Brien can be a peacemaker. He has helped mend a major rift between Teamsters leadership and long-disgruntled union activists, leading to 97 percent of members authorizing a strike next week if the contract wasn’t settled. Members will vote on the tentative agreement next month.

International Brotherhood of Teamsters general president Sean O'Brien joined UPS Teamster members for a practice picket line outside the UPS Customer Center in Brooklyn on July 14.Casey Kelbaugh for The Boston Globe

Leading up to the deal between the world’s biggest package delivery company and one of the largest unions in the country, O’Brien, 51, made the rounds of TV news shows and crisscrossed the country to rally with workers holding practice picket lines. In a recent webcast, he invoked his local upbringing when he told members he had asked the White House not to get involved.

This was the union’s fight, and no one else’s.

“My neighborhood where I grew up in Boston, if two people had a disagreement and you had nothing to do with it — you just kept walking,” O’Brien said.


UPS called the deal a “win-win-win agreement” but declined to comment on O’Brien’s role. The last time workers went on strike, in 1997, the work stoppage lasted more than two weeks.

“We demanded the best contract in the history of UPS, and we got it,” O’Brien said in a statement. “This contract sets a new standard in the labor movement and raises the bar for all workers.”

Wages for part-time warehouse workers were a major sticking point during negotiations, and the tentative agreement for the roughly 340,000 Teamsters at UPS would boost existing part-timers’ pay by an average of 48 percent over the next five years.

UPS employees worked throughout the pandemic, delivering COVID vaccines before they were eligible to get vaccinated themselves. Meanwhile, the pandemic was a boon for the company as online shopping skyrocketed. UPS, which handles about a quarter of the country’s parcel deliveries, made a record $100 billion in revenue last year.

Jane Fallon, a Local 25 shop steward who scans packages at the South Boston UPS facility, was happy to see O’Brien stand up for part-timers. Fallon, 60, of Milton, has worked for UPS for 12 years and makes $21.50 an hour, just 50 cents more than new hires, and usually starts her work day at 4 a.m.

In 2018, a majority of UPS workers, including Fallon, voted against a tentative contract agreement, but it was pushed through anyway because of a voting technicality, leaving “a sour taste in your mouth,” she said. O’Brien, on the other hand, listens to workers, Fallon said: “The rank and file matters to him.”


O’Brien, who oversees 1.2 million Teamsters, is a part of a new generation of bold labor leaders who aren’t afraid to take on corporate interests. In March, O’Briens aggressive nature was on display when he clashed with Senator Markwayne Mullin at a Senate committee hearing after Mullin came after him, telling O’Brien, “you need to shut your mouth.” O’Brien bristled, calling Mullin, a business owner, a “greedy CEO” and accusing him of hiding money.

O’Brien then took to Twitter to call Mullin a clown and a fraud. “Anyplace, anytime cowboy. #LittleManSyndrome,” he wrote, alongside a picture of Mullin behind a podium, standing on a platform circled in pink — apparently to show he was trying to look taller.

Donald Broughton, managing partner at the transportation analysis firm Broughton Capital, called O’Brien “a bigger bully than Donald Trump” on CNBC recently, saying that his true objective in the UPS fight was gaining credibility to organize Amazon workers — which the Teamsters have been actively working to do.

International Brotherhood of Teamsters general president Sean O'Brien cheered on UPS workers at a rally in Los Angeles.Damian Dovarganes/Associated Press

Renee Sacco, a lifelong family friend who shared a locker with O’Brien in high school — and swears he still remembers the locker combination — isn’t surprised when she sees O’Brien lash out when challenged. Her parents and O’Brien’s taught them to stand up for themselves and for others, she said, acknowledging that a line sometimes get crossed. But with O’Brien, it’s all in the name of protecting people, said Sacco, whose father was also a Teamster.


“He makes everybody feel like he has their back,” she said.

Off the clock, though, O’Brien can be a softie, Sacco said, especially when it comes to his two sons, Sean Jr., 22, a fifth-year apprentice in the plumbers’ union, and Joseph, 19, who is starting at Suffolk University in the fall.

“His personal life is very different,” said Sacco. “He doesn’t want to fight. He’s very quick to apologize.”

O’Brien loves being a dad — “the best title I’ve had in my life,” he said in a Globe interview. He and his wife split up when his sons were young, and O’Brien cherished the weekends spent in the car, talking, as he took them to play sports. Even though they’re both adults now, he worries now more than ever, he said: “It’s tough to let go at times, I’ll be honest with you. I do lie in bed at night worrying about their future. . . . They’re the most important things in my life.” Then he corrects himself. “Most important people — they’re not things. Sometimes they act like things,” he said, laughing.

O’Brien’s family has been involved with the Teamsters for four generations. His great-grandfather made deliveries around Boston in a horse-drawn wagon; his grandfather was a truck driver and later a business agent for Local 25; and his late father was a transportation coordinator for the union’s motion picture division. Three of his uncles have been involved in Local 25, and his older and younger brothers are also members.


International Brotherhood of Teamsters general president Sean O'Brien spoke to UPS Teamster members.Casey Kelbaugh for The Boston Globe

“It was all around Sean,” said his mother, Eileen O’Brien, who lives in Wakefield. “He couldn’t dodge it.”

O’Brien questioned everything as a child, said Eileen O’Brien, 75, who grew up in public housing in Charlestown, the granddaughter of an Irish immigrant: “You couldn’t brush him off. He would stay at it until he got an answer he understood.”

O’Brien was a linebacker and captain of the football team at Medford High School and made the statewide Shriners all-star team. But success on the field didn’t come easy. “I wasn’t the most gifted athlete,” he said, “so I was always working harder after practice in the weight room.”

O’Brien worked for Local 25 in high school unloading trucks for concerts and Broadway shows. He went to the University of Massachusetts Boston but quit after one semester to go to work hauling heavy equipment. “I loved being a Teamster,” O’Brien said.

Within a few years, he was a shop steward, serving as a union representative for fellow workers. And in 2006, at the age of 34, O’Brien became the youngest president in the history of Local 25, currently representing more than 12,000 members in Boston and Southern New England.

His talent for the work, and hard-nosed tactics, showed early. Tim Madden, a retired UPS driver and former shop steward in Watertown, attended grievance hearings with O’Brien and said he had a knack for finding a supervisor’s weakness and using it against him: “Sean always says, the way to take on the schoolyard bully is get right in his face and stare him down.”

He is also always prepared, well dressed, and hours early, Madden said. “Sean dots every ‘i’ and crosses every ‘t’ himself,” he said. “The man does not make mistakes.”

Madden said he was fired at least 19 times for “insubordinate behavior” in his 32 years at UPS: “Usually I was back to work the next day with back pay because of Sean.”

O'Brien spoke at a rally with UPS workers on April 2.Matthew J. Lee/Globe Staff

In the past, the Teamsters union was better known for corruption and ties to organized crime than for protecting workers. Between 1957 and 1988, three general presidents were sentenced to prison terms, including Jimmy Hoffa, who disappeared in 1975 and is widely believed to have been killed by the mob. William McCarthy, who led Local 25 for 35 years and became national president in 1988, agreed to operate the union under federal oversight to keep it from being prosecuted for racketeering charges. The next Local 25 president, George Cashman, was sent to prison for extortion and falsifying work orders.

O’Brien’s father, William O’Brien, known as Billy, was briefly linked to a 1994 incident involving Local 25 members who were later sentenced to life in prison for racketeering and a string of armored car and bank robberies, including one in Hudson, N.H., in which two guards were killed. Billy O’Brien allegedly reserved a moving truck used during the Hudson robbery, according to initial news reports of a federal indictment, but was never charged. He died in his sleep in 2012 after a day on the job, and 51 years as a Teamster.

The movie division of Local 25 has had a particularly troubled past, with several officials convicted of federal racketeering and conspiracy charges. In 2014, the union’s general secretary-treasurer pleaded guilty for his involvement in attempting to extort jobs from a nonunion TV production crew for “Top Chef” when it was filming in Milton; four other members indicted for threatening violence and yelling racist and misogynistic slurs were found not guilty.

O’Brien’s leadership has been transformational for the union’s activist arm. Under Hoffa’s son, James P. Hoffa, who ran the Teamsters for more than two decades until O’Brien took over, the union granted concessions to the company in every contract, said David Levin, staff director of Teamsters for a Democratic Union, a grass-roots organization pushing for reform that previously had few friends in the union hierarchy. At conventions, union officials wore buttons that said “TDU Sucks,” he said. But since O’Brien took over and started repairing decades of division, there has been a “monumental shift.”

“Before, the union was weak because the top leadership was cozy with employers and distant or hostile to the members,” Levin said. “With Sean, it’s exactly the opposite. He stands with the members in order to stand up to employers.”

O'Brien spoke as the Teamsters Union members joined members of the Writers Guild of America and the Screen Actors Guild on strike outside Amazon Studios in Culver City, Calif., on July 19. CHRIS DELMAS/AFP via Getty Images

TDU hasn’t always seen eye to eye with O’Brien, however. He enraged TDU in 2013 when he was caught on tape threatening TDU members in Rhode Island who were backing an opposition candidate to lead Local 251. “They need to be punished,” he said at a rally, leading to a two-week suspension without pay.

O’Brien later apologized to the members. and the TDU member at the center of the incident, Matt Taibi, who won the election and still leads Local 251, now serves on O’Brien’s executive board. “People make mistakes,” Taibi said.

At Local 25, O’Brien created a culture of supporting all workers, said Darlene Lombos, head of the Greater Boston Labor Council, noting that it was the union’s reminder that Teamsters don’t cross picket lines that led Boston Starbucks employees to strike around the clock. Lombos worked with O’Brien and his staff on the campaign to organize immigrant parking lot attendants in 2014 when she led Community Labor United and was impressed both by his ability to inspire workers, and by him personally.

“I think people saw him as ooh, the big Sean O’Brien,” she said, “and he was always genuine and friendly and kind.”

Red Sox executive Larry Cancro got to know O’Brien in the early 2000s after the labor leader organized a group of Teamsters to walk in a fund-raising event for the local chapter of Autism Speaks, chaired by Cancro at the time. But he didn’t stop there, Cancro said. O’Brien joined the board of the group, lobbied for a bill requiring insurance coverage for autism treatment, and organized an annual fund-raising gala: “He really jumped in with both feet.”

Cancro describes O’Brien as contemplative, willing to consider different points of view, and — with his burly build and shaved head — the ultimate Teamsters ambassador: “There’s no caricature of a union leader in a movie that seems more like a union leader than Sean.”

O’Brien serves on the board of the Massachusetts Port Authority, which runs Logan Airport, and he was crucial to the airport workers’ fight for a higher minimum wage, said former Massport executive director Tom Glynn. Now, as one of the most powerful labor leaders in the country, Glynn said, O’Brien’s fight for UPS employees could have a ripple effect on workers everywhere.

“He’s not someone who has sought the limelight, but his impact is very significant,” Glynn said. “He’s a force in a way that people are going to see.”

Material from Globe wire services was used in this report.

Local 25 members watched as Sean O'Brien, the newly elected general president of the International Brotherhood of Teamsters, spoke in Charlestown in 2021. Jessica Rinaldi/Globe Staff

Katie Johnston can be reached at katie.johnston@globe.com. Follow her @ktkjohnston.