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

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.”