Elections and council politics

Flaherty was first elected to the council in November 1999 as an at-large member. His election resulted in the unseating of longtime incumbent Dapper O'Neil.^[2] He was then re-elected to four additional two-year terms, holding office until January 2010.

After serving as vice president of the council in 2001,^{[citation needed]}, Flaherty was reelected to the council in November 2001. In January 2002, Flaherty was elected by his fellow city councilors to serve as the council's president. Mayor Thomas Menino, who Flaherty had established a strong relationship with, had maneuvered to secure Flaherty the votes needed to become council president.^[3] During Flaherty's two-consecutive terms as council president, the council numerous times violated the state's open meetings law, for which it was successfully sued by Kevin McCrea, leading the council to plead guilty in 2008 to having violated the state's open meetings law between 2003 and 2005 by meeting illegally to discuss projects of the Boston Planning Agency (Boston Planning & Development Agency) and an outbreak at a Boston University bio-laboratory.^[3][4] Flaherty also was regarded as somewhat autocratic in his leadership of the council, often using parliamentary rules to prevent debate on matter that he regarded as immaterial for the council to discuss.^[3]

Flaherty was reelected in November 2003. He was the city council election's top vote-getter. Flaherty's margin of victory over first runner-up Felix D. Arroyo was 5,671 votes, which was the widest margin since the council had been restructured in 1983.^{[citation needed]} After the newly elected council took office in January 2004, Flaherty was elected by the council members to serve a second-consecutive term as the council's president.^{[citation needed]}

Flaherty won reelection in November 2005, again placing as the city council election's top vote-getter. He received only 14,000 fewer votes than Mayor Menino had in the coinciding 2005 Boston mayoral election. Viewing Flaherty's rising stature as a political threat, Menino successfully maneuvered to get Maureen Feeney elected council president in January 2006 instead of Flaherty. In turn, Flaherty became a vocal critic of the mayor. Flaherty gave particularly strong opposition to a proposal by the mayor to relocate the city government headquarters from the existing Boston City Hall to a new city hall along the city's waterfront.^[3] Flaherty won reelection in November 2007 and was once again the city council election's top vote-getter. Flaherty did not run for re-election in November 2009, instead opting to run for mayor of Boston.

LGBTQ rights

Flaherty established political ties to the city's gay community.^[5] Flaherty was the first city officeholder in Boston to voice support for same-sex marriage. He also gave his support to an ordinance prohibiting discrimination against transgender individuals.^[6] In 2023, Flaherty stated that his early support for same-sex marriage was what he was proudest of from his time on the council.^[7]

Elections and council politics

In the November 2013 election, Flaherty was returned to the council as an at-large member.

Flaherty was reelected in November 2015, November 2017, November 2019,^[16] and November 2021. In 2021, he was the lead vote-getter in both the September primary and the general election.^[17][18] Flaherty had considered the possibility of running in the 2021 Boston mayoral election,^[19] but did not run.

In his eighth term (2018 and 2019), Flaherty served as chair of the Committee on Government Operations.^[20] In his ninth term (2020 and 2021), Flaherty served as chair of the COVID-19 Recovery Committee and vice chair of the Committee on Government Operations.^[1]

In July 2023, Flaherty announced that he would not be pursuing an additional term in office.^[21] Flaherty cited discord on the council and a desire to spend more time with his family as his motivations for retiring from the council.^[18] Flaherty has stated that he has no immediate plans of running for other office.

Housing

Flaherty worked on the Jim Brooks Act, a home-rule petition which (if approved by the state government) would have enacted a number of measures to protect tenants against eviction, including a city prohibition on no-cause evictions.^[22][23] The bill passed the council in October and was soon after approved by Boston Mayor Marty Walsh to be referred to the Massachusetts General Court (the state legislature) for passage.^[24] However, the legislation did not receive traction in the state legislature.^[22]

In February 2023, Flaherty expressed reservations about the rent stabilization home rule petition that Mayor Michelle Wu had sent to council.^[23] He cited the years-earlier stall in the state legislature of the Jim Brooks Act he had helped to create, Flaherty urged city council members to not to passing a rent control home rule petition (which would need state approval to become law) unless there was a desire by state legislators to enact as law.^[22] He also expressed worry about the possibility that rent stabilization would put landlords with smaller property portfolios at a disadvantage in competing against those holding larger portfolios.^[25] In March 2023, when the petition came to a vote, Flaherty proposed an amendment to exempt properties or Boston-resident landlords who own fewer than six units and live within one of the units themselves. However, the amendment failed after only receiving support from three other councilors. He voted for the petition, which passed the council 11–2. He also voted the same day to advance Wu's home-rule petition to reform the Boston Planning & Development Agency, which also passed the council 11–2.^[26]

Other matters

In 2015, anticipating a possible legalization of recreational marijuana in Massachusetts, Flaherty proposed that the city adopt a text amendment prohibiting either medical marijuana dispensary or recreational sales outlets from being located within 2,500 of each other in hopes of preventing a large proliferation of marijuana sales points in any singular community.^[27]

Flaherty received media attention in April 2019 for comments he made regarding a proposal to charge for resident parking permits. In a City Council hearing on the issue, he stated that bus stop spacing and stop length were a major cause of the city's parking woes and instead suggested coordinating with the MBTA to start a conversation about removing some of them. His comments were met with backlash from the public and transportation advocates, with many pointing to his ownership of five cars in a city as the real problem.^[28][29][30] The Twitter hashtag "#FiveCarFlaherty" was used by many to voice their opposition to his comments.^[28][29]

In April 2021, Flaherty was among a group that voted against legislation, which was nevertheless passed by a 7–5 vote of the City Council, that restricted the use of rubber bullets, tear gas, and pepper spray by the Boston Police Department.^[31]

City Council

† write-in votes

† write-in votes

Mayoral