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In a crowded field of Cambridge City Council candidates, Timothy R. Flaherty is arguably the most controversial. But after living in Cambridge for nearly 60 years, the former prosecutor sees himself as a unifying force in an otherwise polarized Council.
Flaherty is running without seeking endorsements from special interest groups, which he said contributes to the Council’s polarization.
“The polarization is driven in many ways by the process of councilors seeking those endorsements, and then I think they vote along those endorsements lines, and that doesn’t do any benefit to the city as a whole,” Flaherty said.
While the Council generally agrees on largely progressive policies, members have become increasingly divided over housing issues — namely, attempts to increase housing density in the city.
“The biggest thing for the City Council is to elect people who’ll move past the polarization and begin to compromise on important issues in the city,” Flaherty said. “We’ve got to start understanding that there are big questions that are being decided upon, and they have consequences.”
Flaherty said his 25-year career as a defense attorney has made him prioritize understanding both sides of an issue, something he said does not happen on the Council.
“I think that sometimes people just don’t listen and they don’t consider the other argument from a different perspective, and I’m going to encourage that,” he said.
But some Cambridge residents have been quick to criticize his career. Flyers appeared around the city attacking Flaherty for a 2016 incident where he pled guilty to a misdemeanor in state court. According to a press release from the U.S. Attorney’s Office for Massachusetts announcing the plea agreement, Flaherty, who had represented a client accused of a hate crime, paid the alleged victim $2,500 and encouraged him to ignore messages from law enforcement.
In a September statement to The Crimson, Flaherty wrote that he pled guilty “because in a confusing encounter I allowed the person who claimed to be a victim leave without signing the paperwork I had given him.”
He has also publicly rebuffed the accusations, distributing letters across the city in response to the flyers. He labeled the flyers “illegal and false,” and called those that distributed the letters “cowards” for not signing the materials.
Flaherty has also been criticized for his involvement in City Councilor Paul F. Toner’s ongoing legal case, representing the councilor as he faces charges for patronizing a high-end brothel network. Toner’s charges have generated monthslong backlash, resulting in residents, a majority of his fellow councilors, and state representatives, to call on him to resign.
Flaherty said he sees his campaign as separate from the embattled councilor, despite Toner being an open supporter of his election.
“Paul and I are friends. We’re very different people. He may view things very differently than me. I would hope that some of the people who supported Paul would also support me, but there’s no correlation,” he said.
Like Toner, Flaherty is proud to have grown up in Cambridge, and uses his upbringing to inform many of his policy priorities. This is particularly evident in his approach to housing, where he advocates for a “regional approach” that would zone Cambridge by squares and neighborhoods rather than establish a wholesale zoning.
“It operates as if housing in Cambridge is an issue in a silo,” Flaherty said. “It’s clearly a regional issue, and it’s got to be dealt with with regional solutions.”
Flaherty also believes that his deep knowledge of the city as a lifelong resident will bring a useful perspective to the Council, one that will be lost with Toner not seeking reelection.
“Having a historical perspective, and maybe an encyclopedic knowledge about Cambridge, is very beneficial to someone being on the City Council. I know every neighborhood like the back of my hand,” Flaherty said. “But I also think I bridge the divide between someone who’s grown up in Cambridge and someone who’s come here for school.
Flaherty’s ties to the city are clearly evident in his campaign’s well-stocked war chest. He is the frontrunner in the fundraising race by a wide margin, and he believes it is for good reason.
“Does it demonstrate that I’ve got a strong network both in Cambridge and beyond Cambridge? Yes, I hope it does, because I certainly think that I’ve earned that over my lifetime,” Flaherty said.
On a Council often focused on more highbrow policy, Flaherty sees himself as a candidate focused on the day-to-day issues affecting Cambridge residents.
“What I really think the city should be focusing on are the real issues and real people’s lives that are happening every single day in this city,” Flaherty said. “That’s what I’d like to do.”
—Staff writer Shawn A. Boehmer can be reached at shawn.boehmer@thecrimson.com. Follow him on X @ShawnBoehmer.
—Staff writer Jack B. Reardon can be reached at jack.reardon@thecrimson.com. Follow him on X @JackBReardon.
