Boston city councilor says harassment, intimidation has escalated as he considers 2025 mayoral bid

Boston City Councilor Ed Flynn said the harassment and bullying he’s long experienced intensified against him when his name started getting tossed around as a candidate who might challenge Mayor Michelle Wu in 2025.

Flynn, a moderate Democrat, said he’s been the target of escalating “cyberbullying” on social media and protests that have occurred outside his South Boston home and more recently, at a fundraiser that was held for him last month.

He also sees the frequent moves his City Council colleagues — a number of whom, he said, have political alliances with the progressive Wu administration — have taken to “block” or oppose his policies as their attempts to “intimidate,” “isolate,” and “undermine” him for “political reasons” and to “protect Mayor Wu.”

“I feel like my colleagues have intentionally isolated and tried to diminish the work that I’m working on,” Flynn told the Herald after his request to add a late-file Council resolution in support of striking dock workers was blocked. “When I speak about challenges facing the city … this pushback is enhanced and extreme.”

“I think my colleagues are working closely with the city administration to discredit me and undermine the issues I’m working on,” he added.

Flynn, the City Council president last term and son of former Mayor Ray Flynn, is increasingly being seen as an antagonist to the mayor, particularly in recent months that have seen him opposing some of Wu’s major policies, like her plan to increase commercial tax rates, and highlighting public safety issues at a time when the Wu administration has been hailing Boston as the “safest major city” in the country.

The rise of his public profile, boasted as of late with his confirmation of persistent rumors that he was considering a bid to challenge Mayor Wu in 2025, have led, he said, to intensified harassment online, and from protesters.

Flynn said he’s drawn the ire of protesters for years, pointing to anti-vaccination demonstrations that took place outside his home while city mandates were in place during the pandemic, and is now getting “harassed from the bike community” over his opposition to bike lanes. He also sees himself as being targeted for his “support for the Jewish community of Boston,” or rather Israel amid the Israel-Hamas War.

Flynn, a Navy veteran of Operation Enduring Freedom, said he requested a police response at a fundraiser reception last month in Dorchester, due to harassment protesters were directing at him — including by calling him a “traitor” — and attendees as they were walking in and out of Florian Hall.

He went to cut down the protesters’ Donald Trump flag that was affixed to a pole, but later changed his mind to avoid a confrontation, Flynn said.

A social media post from Catherine Vitale, who ran for an at-large seat on the City Council last year and described herself as an attendee of that “Trump 2024 standout,” notes that “many Republican/conservative voters vote for Ed because they think he’s ‘conservative,” while taking issue with what they see as his lack of support for former President Trump.

“I just thought it was appropriate to have the police officer present to ensure there was no confrontation,” Flynn said.

He had his staff report an Aug. 16 post to X, formerly known as Twitter, to be investigated for bullying and harassment. The post had directed an insult at him, while stating that the local user’s intention was to take the “account public in the hopes that cyberbullying does work.”

Citing that and other online harassment, Flynn said he sees the end goal of certain people as being to try to intimidate him so that he chooses to not to run for mayor, and to step down from the City Council — due to both their personal dislike for him and opposing political views.

“I would say that it doesn’t impact me, but that would be inaccurate,” Flynn said. “I think any time you’re bullied, it does have an impact, but it’s not the first time I’ve been bullied or intimidated, so I’m just trying not to let these incidents impact me and my family.”

Flynn declined to comment on whether similar incidents have extended to his wife and their two college-aged children.

“I’m not going to let people intimidate me,” he said, “and it’s not going to impact my decision on whether or not I remain in elective office and my future plans.”

While Flynn’s mention of public harassment is new, he and his closest ally on the Council, Erin Murphy, cited similar concerns about the dynamics on the City Council last month.

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The “challenging” work environment on the City Council, when coupled with a “lack of support” from the Wu administration, Murphy said at the time, led her to pursue a failed bid as clerk of the Suffolk Supreme Judicial Court.

Two former Wu staffers who received the mayor’s endorsement in last fall’s election, Enrique Pepén and Henry Santana, said last month that they see things differently, while addressing criticism raised by Flynn and Murphy.

“As a city councilor representing all of Boston, I am committed to working with my colleagues, regardless of political differences, to deliver for our residents,” Santana, an at-large councilor, said in a prior statement to the Herald. “Boston deserves a City Council that works together even when we don’t always agree.”

Pepén made similar remarks last month.

“Collaborating with my colleagues on issues that impact our residents has been a priority of mine since day one,” Pepén said in a prior statement, adding, “We work best when we focus on collaborating and working for our residents.”

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