Flaherty decides to leave a Boston City Council plagued by political infighting

Michael Flaherty, a 20-year veteran of the Boston City Council, plans to step down at the end of his term, adding another twist to what’s already been a tumultuous year for the council.

The announcement late Wednesday was a surprise. Flaherty had filed papers to run for his at-large seat for an eleventh term, but now he’s withdrawing from the race against the backdrop of a council plagued by political infighting and personal attacks.

“It is now time to turn the page and move on to the next chapter in my life,” Flaherty wrote in a statement.

The son of a South Boston state legislator, Flaherty is a well-known face in Boston politics and was the lead vote-getter in multiple citywide election cycles. He ran unsuccessfully for mayor against Tom Menino in 2009.

Former colleagues marveled at Flaherty’s recall for people’s names and where they’re from, down to their ward and precinct.

“He could tell you what color house you lived in if you gave him the address,” said former City Councilor John Tobin, who now works for Northeastern University.

Flaherty was just 30 when he was first elected to the Boston City Council in 1999. He was one of the very first elected officials in Boston to publicly support legalizing same-sex marriage.

He made headlines in 2019 while fighting then-councilor Michelle Wu’s proposal to charge for residential parking permits — earning the nickname "Five-car Flaherty" when he revealed how many cars his family owned.

But he now represents the older, more conservative wing of the council. He is often at odds with the more recently elected progressive councilors, especially over issues like proposed cuts to the police budget.

Those fights have become much more intense and personal over the past year. The council’s efforts to draw new district lines devolved into shouting matches and drew a federal lawsuit, funded in part by Flaherty and his allies.

In their budget meeting last month, Councilor Frank Baker compared the body to “pigs,” fighting over scraps. Councilor Tania Fernandes Anderson said she was the target of online racist and Islamaphobic abuse, and without naming names, accused other councilors of fueling it.

“I think it’s good for Boston and I think it’s good for politics that the ideological differences amongst the Democratic party are on display,” said Erin O’Brien, an associate professor of political science at UMass Boston.

But “it has gotten very personal,” she said. “You don’t want to show up to work and have character assassination going back and forth.”

The council’s reputation is also being impacted by members’ actions outside city hall. Councilor Ricardo Arroyo was named a player in a federal ethics probe that ultimately led to U.S. Attorney Rachael Rollins’ resignation. And last month, he agreed to pay a $3,000 fine for violating state conflict of interest laws for representing his brother in a legal matter.

Last weekend, Councilor Kendra Lara was charged after crashing her car into a home in Jamaica Plain. A police report indicates she was driving with a revoked license, in a car that was unregistered, uninsured, and had an expired inspection sticker.

City Council President Ed Flynn seemed to inject those personal issues into the political realm with a rare public rebuke this week, calling out the two by name.

He wrote that the people of Boston “want elected officials who show maturity, take responsibility as adults, and demonstrate the ability to follow the same basic rules and norms as the people they serve.”

At their last council meeting Flynn shouted down Lara and banged his gavel as she tried to move a public hearing from the committee he had chosen into the one she chairs.

O’Brien, the UMass Boston professor, said that in this context, Flaherty’s about-face on running for reelection makes a lot of sense.

“If you don’t like your job, and you have another option, a lot of people leave,” she said.