The Boss: Sean O’Brien and the Teamsters Attempt an Extreme Makeover

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sean brien union president teamsters local 25

Portrait by Jason Grow

Every spring, Teamsters Local 25, Boston’s most notorious union, hosts a gala downtown. It’s likely the only mainstay on the city’s social calendar where working stiffs with mustaches, bellies, and leather Teamsters vests share a dance floor with suits from the State House.

The event benefits Autism Speaks, a charity to which Local 25 has contributed hundreds of thousands of dollars. Nearly a thousand guests show up, including, in recent years, Senator Elizabeth Warren, Congressman Joe Kennedy III, and Mayor Marty Walsh, as well as film director David O. Russell and actor Chris Cooper. Ben Affleck lends his name to the event as a committee member. And standing at the center of it all like a beloved prom king is Local 25 president Sean O’Brien.

Stout, barrel chested, and with a shaved head, O’Brien has a look that says, You don’t want a piece of me. A former linebacker, he never sets foot on the dance floor but sustains a steady jig posing for photos with old friends and personally shaking hands with each newcomer. “If he ever stops for too long,” a partygoer says, “a line of people forms who want to talk to him. He’s the life of the party.”

In total, O’Brien has raised more than $5 million for charitable causes. “He’s not just cutting checks,” says Larry Cancro, who sits on the board of Autism Speaks New England alongside O’Brien. “He’s one of our most active members.” Over the years, he has managed to turn philanthropy into an altruistic and pragmatic calling. O’Brien, of course, is no dummy. After all, high-visibility largesse is good for his true concern: rehabilitating the Teamsters’ image.

For most of its history, Local 25 was not the type of organization to host parties at posh hotels. Members were more likely to turn up in federal court: The union had ties to Whitey Bulger’s Winter Hill Gang; one of its former presidents spent time behind bars; its rank-and-file members have been convicted of crimes ranging from armed truck robbery to embezzlement; its officers once had a reputation for shaking down movie crews. In 2011, a retired union member was found dying on a train platform carrying $180,000 in mysterious cash.

O’Brien swears he’s trying to clean up this longtime mess. Local 25’s side business used to be crime; now it’s philanthropy. Once a nearly exclusive club for men of Italian and Irish descent, it now counts hundreds of East African immigrants among its ranks. In the past, threatening strikes and pounding fists on tables won concessions from employers; now the union reaches deals through what O’Brien calls his negotiating “finesse.” O’Brien’s friends in high places—including Massachusetts House Speaker Robert DeLeo, state Attorney General Maura Healey, and Warren—have looked on with admiration. Former Governor Deval Patrick even appointed him to the board of directors of Massport, which employs hundreds of Local 25 members.

Meanwhile, O’Brien, 44, has climbed the ranks of the International Brotherhood of Teamsters (IBT), one of the most powerful labor unions in the world. In addition to leading Local 25, he is the head of the IBT’s governing council in New England and a vice president of the international body (a position he is defending in this month’s international Teamsters election). He is also a close ally of Jimmy Hoffa Jr., the IBT’s president—a job O’Brien could one day fill.

But cracks in the union’s—and O’Brien’s—new image are starting to show. Last year, five Teamsters from Local 25, including O’Brien’s second in command, were indicted on federal extortion charges. O’Brien himself has been suspended from union duties for threatening voters in a Teamsters election. His admirers describe these incidents as aberrations and defend their friend as a champion of the working class—and of Charlestown, Local 25’s historical home. O’Brien’s critics, meanwhile, call him a strongman who perpetuates the union’s long-standing culture of thuggery.

From a distance, trouble with the feds and accusations of heavy-handedness might sound pro forma in the world of Local 25. This time, though, O’Brien’s troubles extend far deeper, rooted in ex–labor leader Walsh’s mayoral administration and a controversial extortion investigation that has ensnared City Hall officials. Carmen Ortiz, Massachusetts’ tenacious United States attorney, has indicted two members of Walsh’s staff, Ken Brissette and Tim Sullivan, for allegedly withholding permits from organizers of the Boston Calling music festival until they hired unionized workers. Then there’s the whole Top Chef incident.

Two years ago, Local 25 discovered that a TV crew for the cooking-competition show was filming in the Boston area with nonunion workers. A dozen or so Teamsters confronted the show’s crew at a restaurant in Milton, forming a picket line and allegedly shouting slurs such as nigger, fag, and slut. According to an indictment, some of the members tried to force their way into the restaurant, and car tires were slashed.

Then the real trouble hit. A federal indictment came down alleging that a City Hall official, later identified as Brissette, had warned two Boston restaurants where Top Chef was planning to film that they’d have trouble with Local 25 if they allowed a nonunion crew on their premises. Federal prosecutors framed the warning as collusion with Local 25 and indicted the five Local 25 Teamsters.

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Massachusetts U.S. Attorney Carmen Ortiz has been criticized by former Attorney General Martha Coakley for prosecuting City Hall officials and members of Local 25. / Photograph by Steven Senne/AP Images

From the start, Ortiz’s critics—a loud and growing club—have cried foul. This isn’t extortion, they say; it’s just a pro-union administration lending a helping hand to working men and women. With the supporters of O’Brien and City Hall pitted against Ortiz and the U.S. Justice Department, however, the probe sheds a light on two very different and colliding Bostons. In one world, the city and O’Brien are tireless champions of the working class and Ortiz is a villain. (Ortiz makes the characterization easy thanks to a history of pursuing low-level offenders.) In the other version, O’Brien leads a gang masquerading as a legitimate outfit, and the city is so in bed with labor that it’s willing to look the other way.

Driving both views is a deeper anxiety about the city’s identity. Is Boston a place where blue-collar power brokers look out for friends and neighbors? Or is it the free-market center of tech and finance that the mayor and governor pitch to outsiders? Our pro-union and pro-business leaders would have us believe there’s room for Boston to be both. If the animosity brought on by O’Brien and Ortiz is anything to go by, though, this town may only be big enough for one Boston or the other.


Between the rusted trusses of I-93 and the old Schrafft’s candy plant in Charlestown, there’s a red-brick block of a building standing alone in a concrete landscape. For decades, this has been the headquarters of Teamsters Local 25. It is also the place where O’Brien more or less grew up.

“We’re a Teamsters family,” says O’Brien, whose mother and father came from multigenerational lines of Teamsters. “The topic of conversation at the dinner table was always the union.” O’Brien joined Local 25 as a teenager. He unloaded trucks in the Theater District, drove tractor-trailers, delivered milk, and—between layoffs—worked on movie sets. Today, all three O’Brien boys—William III, Michael, and Sean—are longtime Local 25 members.

Nearly five years ago, their father, William, went to bed after an all-day shift driving a truck and died in his sleep. O’Brien was devastated. “I can’t say enough how much he loved his father,” says Joe “Okie” O’Connor, a longtime Teamster. O’Brien told me, simply, “I idolized my father.”

Billy O’Brien, as he was known in Charlestown, instilled in his son a deep loyalty to the Teamsters. “Everything we had, we knew why,” O’Brien says. “We had a house, we had food on the table, we had a vacation once a year because of the Teamsters.” When Billy was growing up in Charlestown, the younger O’Brien says, “There were only four professions—policeman, fireman, longshoreman, or Teamster—and the Teamsters were paid the most.”

Of course, there was at least one other trade available to young Townies: robbery. FBI statistics show that in the 1980s and 1990s, no other ZIP code produced as many armored-car robbers as 02129. In some corners of Charlestown, robbery was such a part of the culture then that locals printed T-shirts with a leprechaun clutching a bag of cash over the words “Boston Bandits.”

In tight-knit Charlestown, where a code of silence protected criminals, the line between the bad guys and the workaday laborers was sometimes blurry. Nowhere was this truer than within the ranks of the O’Brien family’s beloved Local 25. During the 1960s, Local 25 members frequented Marshall Motors, a garage on Somerville’s Winter Hill where Bulger regularly hung out. Jimmy Flynn, an alleged associate of the Winter Hill Gang, was also a representative of Local 25, and other gang members maintained ties to Local 25 for decades.

When the armored-car-robbery craze started, the Teamsters were in the thick of it. “There was a lot of intersection between the armored-car-robbery community and Local 25,” says a former federal prosecutor. Most notorious was a crew of Local 25 members that robbed dozens of banks and armored cars in the early 1990s (and likely inspired Ben Affleck’s movie The Town). The gang was finally caught after a botched heist led to the slaying of two guards.

Meanwhile, Local 25’s movie crew, where Sean O’Brien worked and his father was a transportation coordinator, was earning a reputation for extorting Hollywood filmmakers. In 1994, a top representative of Local 25’s movie crew was convicted on federal conspiracy charges connected to a mob-related scheme to extract bribes from movie executives. As recently as 2000, union and police sources told the Herald that a union member beat up a snack-truck operator who was working on a film set considered to be Local 25’s turf. It didn’t take long for Tinseltown to get the message: Steer clear of Boston.

When Sean O’Brien, then 34, became the president of Local 25 in 2006, he inherited all of this history and the responsibility to clean up his union’s crime and image problems. The stakes were even higher because of Massachusetts’ newly enacted film tax credit, designed to lure filmmakers back to the state. As he often does, O’Brien took charge, flying to L.A. to convince film executives that it was a “new day” for the Teamsters. State officials made a similar pitch. The tax credit came with the promise that Boston had changed—that contrary to the city’s depiction in so many Hollywood films, it was no longer run by thugs.


It’s hard to imagine anything Sean O’Brien would have liked to see published less than these words: “We’re gonna bash that pretty face in, you fucking whore.” According to a Top Chef crew member quoted by Deadline Hollywood, a film-industry website, this is how a member of Local 25 welcomed the show’s host, Padma Lakshmi, when she arrived at Milton’s Steel & Rye restaurant in April 2014. After Deadline broke the story, the details published were inflammatory. The news landed in the papers, and even though the union dismissed the story as “fiction at best,” it threatened to reverse nearly a decade of O’Brien’s efforts toward making the union respectable.

Within the union, O’Brien is not exactly a reformer. Like IBT president Jimmy Hoffa Jr., he’s a member of the old guard. Both men are from a Teamsters family. Hoffa Jr.’s father, the IBT president through the 1960s, was a convicted felon who famously disappeared in 1975 after a scheduled lunch with mobsters. Hoffa’s sins and those of other corrupt leaders from the past cast a shadow on today’s old guard. “We shouldn’t be held responsible for things that happened in the ’50s,” O’Brien says. “The Teamsters were a very controversial group in the ’60s, ’70s, and ’80s.” His opponents, reformers within the Teamsters who want to unseat the old guard, claim that O’Brien and Hoffa represent a continuation of leadership from the union’s dirty days.

In 1992, it seemed as though the progressive wing might seize control of the union. George Cashman, no friend of O’Brien’s father, became president of Local 25 by campaigning as a reformer. In 2003, however, he was sent to prison after pleading guilty to extortion and conspiracy to embezzle from an employee benefit program. Three years later, O’Brien decided to run for president. After watching a self-proclaimed reformer be exposed as a crook, O’Brien delivered a new message. “We needed to go back to our old-school values,” he railed. “Go back to what made us successful.” Ultimately, his conservative pitch won over Local 25 members. “The good guys won,” O’Brien says, laughing. “By a margin of 3 to 1.”

Much of O’Brien’s rhetoric is restorative. He invokes a past when Teamsters could count on a high-five-figure income, a “Cadillac” health insurance plan, and a big pension. He decries the forces that he says threaten this middle-class ideal: “corporate greed” and “fat cats who care more about the bottom line than about families being able to provide.”

The message resonates. Monthly meetings in the union hall’s auditorium attract hundreds and resemble political rallies with speeches and cheering. John Murphy, a Local 25 officer, recently asked O’Brien where he was hiding the Kool-Aid. Even O’Brien’s opponents concede that Local 25’s membership is overwhelmingly behind him. Drawing on the term “Townies,” they disparagingly call O’Brien’s fans “Seanies.”

Seanies, however, are growing in number. When O’Brien came to power, Local 25 had 8,300 members. Now there are more than 11,000. To grow his ranks, O’Brien organized 1,000 parking-garage attendants in the Boston area, many of them East African immigrants who had no advocate before becoming Teamsters. As the Big Dig wound down, Local 25 took in laid-off construction workers and put them to work on film sets or trained them as truck drivers.

In his greatest consolidation of union power, O’Brien absorbed Teamsters Local 82, after that South Boston chapter had some “problems”—O’Brien’s word. These issues consisted of an illegal hiring system, fraudulent unemployment insurance claims, and, most cinematically, a union enforcer allegedly bloodying a dissident’s face. Many of the perpetrators—collectively named the Perry Crew after Local 82’s ringleader, John Perry, an old-guard Hoffa ally—were convicted of various crimes and jailed. Teamsters brass transferred the union’s remaining members into Local 25 in 2012.

At the time, the Local 25 reboot under O’Brien’s leadership was going swimmingly. O’Brien had joined the board of Autism Speaks New England and was raising millions of dollars for charity. He strengthened his ties to Democratic politicians with endorsements and campaign contributions. Mayor Walsh appeared with him on the cover of the union’s magazine, and Attorney General Healey praised him in interviews. Hanging in the union hall, there’s even a photo of Senator Warren in the driver’s seat of a Local 25 tractor-trailer giving a thumbs-up. She signed the photo, “Sean, Thanks for all the driving lessons. —Elizabeth.”

O’Brien is adept at playing small ball, too. In Charlestown, Local 25 runs blood drives and O’Brien hands out winter coats at shelters. He even deployed hundreds of Teamsters to protect Boston Marathon bombing funerals from Westboro Baptist Church protests. Daniel Mahoney, the priest of the Catholic church up the hill from the union hall, says, “Sean has told me so many times, ‘Anytime somebody is hurting, please let us know.’”

Mahoney, from a union family himself, laments that unions like Local 25 are “looked upon in disfavor.” Unions get a bad rap, he says, “because there’s a few bad apples in the barrel, as in every profession.” He views O’Brien as a quiet hero, grappling alone with the union’s historical failings and present-day missteps. “It’s lonely at the top,” Mahoney says, “because we’re only as good as the people around us. I told that to Cardinal Law once and he didn’t care for it. When I said it to Sean one day, he said, ‘I agree with you. It’s lonely at the top sometimes.’”


teamsters top chef boston mayor marty walsh

After the so-called Top Chef incident in April 2014, Mayor Marty Walsh enjoyed food from local contestant Stacy Cogswell with two of the show’s hosts, Padma Lakshmi and Richard Blais. / Photograph by David Moir/Bravo/NBCU Photo Bank/Getty Images

The Top Chef incident raised the uncomfortable question of what kind of organization Local 25 really is: a thuggish club from the past or a reformed, modern union under O’Brien’s careful watch? Citing his lawyer’s advice, O’Brien declined to comment on the Top Chef case, leaving pals such as Healey in the unenviable position of trying to condemn the alleged misdeeds while reiterating her support for the union. O’Brien’s defenders would have you believe that the alleged crimes were the work of a few rogue members out of step with O’Brien’s rehab effort.

O’Brien’s detractors, on the other hand, have seized on the incident and sought to tie it directly to him. They point out that Mark Harrington, one of the five indicted Teamsters, was O’Brien’s second in command. (In September, Harrington agreed to plead guilty to a charge of attempted extortion, but did not agree to cooperate with the government.) Reformers who’d like to see O’Brien ousted contend that the Top Chef case provided a rare public glimpse at the true identity of Local 25 and its leader.

To bolster their case, they point to an incident three years ago, during another Teamsters election, when O’Brien campaigned in Rhode Island for incumbent union boss Joe Bairos in a battle against reformer Matt Taibi. Speaking to several hundred Teamsters, O’Brien jabbed a finger in the air and said, “Anybody who takes on my friend Joe Bairos and his team…they got a major problem. They’ll never be our friends. They need to be punished.” The comment sparked a scandal and the Teamsters’ Independent Review Board—established in 1989 to root out corruption—suspended O’Brien for two weeks. O’Brien called his comment “a poor choice of words.”

His political opponents, however, found the remark to be much more troubling—and menacing. As vice president of the Teamsters’ New England council at the time (he’s now the head), O’Brien oversaw disciplinary hearings. “That council has a long history of being used to punish dissidents,” says David Levin, an organizer with the reform movement Teamsters for a Democratic Union (TDU). “People knew very well that’s what he was talking about.” O’Brien defends himself, telling me, “I’ve never retaliated against a member. Whether they’re a dissident or not a dissident, I’ve worked tirelessly to make sure members are taken care of.”

In September, the New England council punished two dissidents, reformers from the Rhode Island local where O’Brien made his controversial remark. Ken Paff, a founder of TDU, views the punishment—30-day suspensions, currently stayed until further review by the IBT—as the most recent “attack” in O’Brien’s feud with reformers. The suspensions stem from an accusation that the two reformers tried to have another Teamster fired from her job. The election supervisor, another independent Teamsters watchdog, had already investigated the case and decided that only a minor infraction had occurred.

Since Matt Taibi—who is now running against O’Brien for his international VP position—was also accused (and cleared) in the case, O’Brien recused himself. But the council is packed with members of the old-guard Hoffa slate. Also, O’Brien’s supporters are chummy with the accuser in the case, who attended O’Brien’s campaign-fundraising booze cruise on Boston Harbor earlier this year. The TDU has publicly called the council a “kangaroo court.” O’Brien declined to comment.

Hearings can take on a different tenor when O’Brien’s allies are the accused. One Local 25 member, who spoke on the condition of anonymity, says O’Brien hasn’t always been an impartial judge on the council, adding, “He helped defend John Perry,” the crooked boss of Local 82, when Perry faced charges before the council. In a transcript of Perry’s hearing, Perry’s accusers complain that important documents were not being entered into the record. When they protested, O’Brien overruled them, saying, “Despite what you may think, we do have some integrity at this board…. And we think Brother Perry does, [too].”

Recently, Teamsters reformers have criticized members of the old guard for being loyal to one another to a fault. Earlier this year, one of Hoffa Jr.’s highest-ranking officials, Rome Aloise, was the subject of a 122-page report by the Independent Review Board, which charged him with years of corrupt practices. Despite the allegations, which Aloise denies, he remains on the Hoffa slate in this fall’s election. When I asked O’Brien about Aloise, his only comment, perhaps unsurprisingly, was “Innocent until proven guilty.”


In July, the Huffington Post published a piece criticizing Ortiz for prosecuting City Hall officials and members of Local 25. “This Federal Prosecutor Is Building a Career Indicting the Good Guys,” the headline read. In the piece, former Attorney General Martha Coakley criticized Ortiz’s priorities, saying, “You’d like to think the focus would be on those organizations like human trafficking rings, drug smuggling rings, the kind of organizations that in and of themselves represent a threat to safety.”

The article also quoted Harvey Silverglate, a contrarian Cambridge lawyer who’s never seen a federal investigation he liked. Ortiz “has a long history of what I consider to be highly questionable prosecutions,” he said, “particularly against political figures,” possibly referring to her cases against former Massachusetts House Speaker Salvatore DiMasi and her naming of DeLeo, the current House speaker, as an “unindicted co-conspirator”—a controversial legal tactic—in another case.

There was also that disastrous leak involving Marty Walsh. In 2012, a wiretap recorded Walsh, then a labor leader, saying he had told a real estate development company it would have trouble with permitting if it didn’t hire union workers. (Walsh declined to comment. A spokesperson directed me to his previous public comments in the Globe, where he said that it had been his job as a labor leader to advocate for more jobs, but that as mayor now, he grants no one special treatment.) How did the recording get out? And what does it have to do with Ortiz? In the Huffington Post article, Coakley implied that the U.S. Attorney’s Office was the source. Ortiz denies this.

The central allegation against Brissette—the head of the city’s entertainment office, indicted on extortion charges—is that he threatened to withhold permits from businesses, specifically the organizers of Boston Calling, if they didn’t hire union workers. He allegedly made the demand to Boston Calling days before the festival was scheduled to begin and after the organizers had hired all of the workers they needed. For Local 25’s part, prosecutors allege that the confrontation at Steel & Rye was their way of making good on threats that they’d disrupt the shoot unless the production company hired union labor. Silverglate questions whether the union’s and the city’s behavior is actually illegal.

Another question is whether it’s right. When the state, the city, and O’Brien pitched a new Boston to Hollywood, is this really what they were promising it would look like?

Throughout my reporting, I routinely heard O’Brien described as a bully who’s willing to do anything to stay in power and keep collecting his fat Teamsters salaries. From his three elected positions, in 2015 alone he earned $274,272. David Levin, the union reformer, reiterated the allegation that O’Brien uses intimidation to keep members in line. Whether or not Levin’s right, O’Brien’s opponents have one essential thing about him wrong. His motivation isn’t cynical—far from it. He’s a zealot: a true believer in the church of the International Brotherhood of Teamsters. He dismisses his opposition—the heretics—as “splinter groups” and “dissidents trying to attack us.”

In my final interview with O’Brien, I mentioned I’d spoken with Matt Taibi, the challenger for his international VP position. What did Taibi have to say? O’Brien asked. That you have contempt for the democratic process and don’t tolerate dissent, I told him. O’Brien looked at his press handler (always present during our interviews), and back at me. We were sitting at a heavy conference table in his wood-paneled corner office. He said he stops listening when there are too many “four-clap words.”

Do you want to respond? I asked.

“No, I don’t want to respond to that,” he said. Then he added, “I’m probably the most transparent person in America.”

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