Michael Flaherty, the 54-year-old son of a state representative, has had a front row seat to Boston politics from the time he was born.

He blew up campaign balloons and helped with mailings as his father, Michael Flaherty Sr., kept running for reelection, serving for more than two decades before he became a judge. Governors, including Ed King and Michael Dukakis, visited their home in South Boston.

The son was a State House kid, but in 1991, his focus turned to City Hall. He has been in and out of the building since then, first working for the Boston Redevelopment Authority while making his way through Boston University Law School.

He won an at-large seat on the City Council in 1999, knocking out Albert “Dapper” O’Neil, a conservative member who opposed school desegregation and a statue honoring Martin Luther King Jr. With time as a prosecutor on his resume, he was back in the building, and he eventually wielded the gavel given to City Council presidents. In 2009, he gave up his seat to challenge Mayor Thomas Menino, losing by 16,355 votes as Menino headed toward his fifth and final term.

Menino retired in 2013, and Flaherty pulled nomination papers. But this time, it was another try for his old seat, which he won back. He was sworn in alongside future mayor Michelle Wu, who had just won her first two-year term on the Council.

Ten years later, Flaherty will be out again. He stunned the city’s political establishment last week by withdrawing his name from contention for one of the four at-large slots this year.

“I went back and forth on it. I was torn,” Flaherty said in a phone interview on Tuesday, at times growing emotional talking about the time in elected office that has gone by, as he put it, in the “blink of an eye.”

“I have no regrets,” he said, having met people across the city and forging lasting friendships. “I just felt it was time,” he added. “It was time to put spending time with my wife and kids first and refocus on the next chapter,” which involves Adler Pollock and Sheehan, where he has worked as a business and real estate attorney since 2006.

The ongoing chaos within the City Council influenced his decision. Members have gone to war over the budget, the redrawing of City Council districts, and other items large and small. Just in the month of June, one councillor has been slapped with an ethics fine, another has crashed her car, and another has compared his colleagues to pigs.

“Unfortunately, these days the public is tuning into the Boston City Council not for the good work and the substance of some councillors, but for the antics of other councillors,” Flaherty said.

Recalling when he first took office in 2000, Flaherty said he was considered a fiscal conservative and social liberal. “‘Progressive’ has morphed into socialism, particularly on the council today,” he said. “When I started on the City Council, I was viewed as progressive in light of the positions I took when nobody else took them, like marriage equality.”

He pushed the Community Preservation Act, which has funneled tens of millions of dollars toward affordable housing, open space, and historic preservation projects. He also focused on responding to constituents and their requests, remembering the advice from his late mother, Margaret “Peggy” Flaherty: “Always call people back.”

At last week’s ribbon-cutting for the reopening of the renovated Curley Community Center, also known as “L Street” and a few steps from Flaherty’s home, Wu said she was shocked and “devastated” by Flaherty’s announcement, calling him a friend, adviser, and confidant. With Flaherty’s departure in January, Wu will become the longest-tenured elected official in city government. “It’s hard to imagine life without running into Councillor Flaherty just about anywhere you need help,” she said.

Flaherty would often give her a ride to events when she was a councillor, Wu recalled. “What I remember most, wherever we would be going to that next meeting or event, someone inevitably would start waving down the car once they saw him and make him stop in the middle of the street to thank him for something that he had done, when no cameras were present, when someone just needed help,” she said. “That’s who Michael is, inside and out.”

Marty Walsh, the former mayor who recently served President Biden as labor secretary, said Flaherty was always willing to have a conversation, even when they disagreed. “It was never a public fight,” he said. “We would have a back and forth. That’s how politics should be.”

Asked about the upcoming election, Flaherty said he hopes “voters will hit the reset button and elect councillors who are willing to work together, willing to put aside egos and political differences for the betterment of our city. The fighting and the vitriol have to stop.”

The outgoing councillor, who keeps a close eye on the numbers that pour out of the wards and precincts across the city, pointed to several district races that could heat up as the Sept. 12 preliminary approaches. But there’s no mayor’s race on the ballot, and Flaherty’s withdrawal means there won’t be a preliminary for the at-large candidates. The eight, with three incumbents and five challengers, will go straight to the November election.

“Anything can happen in an off-year, low turnout election, which this one will be,” Flaherty said.

As for whether he plans another run for elected office, Flaherty demurred. After his announcement, the city’s chattering class had already started wondering if he would set his sights on another seat, perhaps register or clerk of courts.

“Those are just political rumors,” he said. “My focus right now is finishing out my term, working hard over the next six months to honor my commitment to the voters, residents and taxpayers, as well as my supporters.”

Flaherty’s withdrawal upends at-large campaign
South Boston’s Michael Flaherty’s last-minute decision to pull his name from the list of at-large City Council contenders is reshaping this year’s race, as it opens one of the four citywide slots on the 13-member panel.

The withdrawal, which came last Wednesday (July 5), the last day that candidates could do so, also means there won’t be a Sept. 12 preliminary for at-large candidates. (In districts where there are more than two candidates, a preliminary is needed to narrow the field to two ahead of the November election.)

The other at-large incumbents – Julia Mejia and Erin Murphy, both of Dorchester, and Ruthzee Louijeune of Hyde Park – are running for reelection. Mejia was first elected in 2019, and Murphy and Louijeune won office in 2021, when Michelle Wu and Annissa Essaibi George left their at-large seats to run for mayor.

Five challengers are on the ballot, including Henry Santana, a Wu aide who lives in Dorchester and has also worked for former District 8 Councillor Kenzie Bok, and Bridget Nee-Walsh, a South Boston ironworker who fell short in a 2021 run for at-large. The others are Mattapan’s Clifton Braithwaite, who has worked on various campaigns in the past, and two Dorchester residents known for protesting pandemic-era public health policies on vaccines and masking.

Nee-Walsh is holding a campaign kick-off July 18 at South Boston’s Clock Tavern.

In a statement after Flaherty’s exit, Nee-Walsh’s campaign called her a “team player” and said that “she enters the race once more, to continue advocating on behalf all of Boston’s residents, knowing that it will take a collaborative effort to move the dial forward.”

In June, Mejia led the field in fundraising, pulling in $26,539 and ending the month with $44,605 in cash on hand. Murphy raised $26,098, and has $88,687, while Louijeune raised $17,883 and has $138,000. Santana raised $6,598 and has $13,136. Fundraising totals that are publicly available for the rest of the field ranged from $0 to $1,177.

Santana had his kick-off at the end of June in Mission Hill, where he grew up in public housing. After Flaherty’s announcement, he picked up endorsements from East Boston state Sen. Lydia Edwards and Gabriela Coletta, who succeeded Edwards on the City Council after winning the District 1 seat in 2022. Former District 6 Councillor Matt O’Malley has also endorsed Santana.

“Henry is the public servant we need right now. He is a professional, trustworthy, independent thinker. He is a coalition builder who is effective and kind,” Edwards said in a statement. “He can work with anybody and will fight for everybody.”

Bok, Santana’s former boss who left the Council earlier this year to take the top job at the Boston Housing Authority, had previously endorsed him.