TOM O’BRIEN, the developer who once worked inside Boston City Hall under Mayor Thomas Menino, is now weighing a campaign for the top job.
Sources familiar with O’Brien’s thinking confirmed that he is considering a campaign against Mayor Michelle Wu, who is running for a second four-year term. The Boston Globe first reported on O’Brien’s potential bid this morning.
If O’Brien enters the race, he would join a field that currently includes Josh Kraft, son of New England Patriots owner Robert Kraft. Josh Kraft, who has lived in Newton and Brookline, moved to Boston at the end of 2023 and last month launched a mayoral campaign, his first bid for public office.
Kraft has pulled in nearly $400,000 for his effort, with money coming from family members and top business executives such as Herb Chambers, the car dealership magnate, and Jim Davis, the chairman of shoemaker New Balance.
But his campaign has hit turbulence in recent days, first with a fundraising invitation sent out by two supporters and featuring a New York City skyline, as well as the city seal, which isn’t allowed on political material. A TV interview on Channel 5 that aired on Sunday showed Kraft stumbling in some of his answers, and further fueled behind-the-scenes calls from Wu opponents for O’Brien to consider wading in, according to political insiders watching the race.
The stumbles came as Wu was in the national spotlight, defending the city’s immigration policies in front of a hostile House Oversight Committee in Washington, D.C.
“It is clear some developers are willing to do whatever it takes to buy this office,” a Wu campaign spokesperson said in a statement Monday afternoon. “It seems like Josh Kraft is not turning out to be what they expected and now they are shopping for a new option.”
During her time in office, Wu has clashed with some executives in Boston’s real estate sector, who have balked at her push for more environmental regulations, bike lanes, and a proposal that shifts more of the property tax burden to commercial real estate owners to avoid a spike in residential tax bills this year. The proposal died in the state Senate after real estate interests lobbied against it.
O’Brien has worked for the last 16 years at HYM Investment Group, where he is the CEO and a founding partner. The company has helped develop several massive real estate projects, including New Balance’s Boston Landing in Brighton and Suffolk Downs on the East Boston-Revere border.
From 1993 to 1999, he worked at the Boston Redevelopment Authority under Mayor Menino as director and chief of staff. “Around that time, rumors began to swirl that Menino felt threatened by O’Brien, who was talented, driven, and perhaps worst of all, universally well liked, and in 1999 O’Brien was ousted from the BRA,” according to a 2020 profile in the alumni magazine of Suffolk University, where O’Brien received a law degree.
O’Brien, who lives in a luxury residential building steps from City Hall and across from the One Congress tower his company was involved in building, did not respond to requests for comment.
As Wu allies cheered her testimony in Washington, they and her campaign ramped up her reelection effort over the weekend. Five unions – representing health care workers, higher education employees and property service workers – became the latest labor groups to endorse Wu on Saturday. Union endorsements are coveted for the money and people on the ground they provide.
At a separate event on Sunday, state Rep. Michael Moran, the second-highest ranking Democrat in the Massachusetts House after Speaker Ron Mariano, ripped into Kraft, caustically mocking him for recently leaving Moran a voicemail introducing himself.
Moran, a House lawmaker for the last 20 years, told the crowd of Wu supporters that he found Kraft wanting to be mayor, after moving to the city in 2023, “offensive,” “arrogant,” and “insane.”
“I mean, I would never in my wildest dreams think about doing something like that,” Moran said in an audio recording obtained by CommonWealth Beacon. “That I think so highly of myself that I’m going to have my dad buy me a condo in the North End and I’m going to run for mayor. Who does that? Nobody does that. Unless of course you have a father who’s Robert Kraft.”
When asked about his recent move to Boston, Kraft has noted that he has worked in communities like Dorchester and Mattapan for 35 years.
“Mike Moran is a tireless leader in both the neighborhoods he serves and citywide, and a devoted public servant,” Kraft said in a statement. “I would be honored to work with him if I’m elected Mayor in November.”
The statement did not address O’Brien’s possible candidacy and the campaign declined comment.
The mayoral race could draw in other candidates as well. North End restaurateur Jorge Mendoza Iturralde has previously said he is interested in a run for mayor, and perennial candidate for public office Althea Garrison is weighing a run.
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