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

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.’”