Let the 2027 election season begin

Résumé détaillé

Rachel Pearson, a South Boston substitute teacher and community organizer, plans to challenge Boston City Councilor Ed Flynn, taking on the the body’s longest-serving and most well-funded member.

There are 350-something days until Boston voters head to the polls for the municipal election next November, but Boston’s City Council races are unofficially kicking into gear this week.

The first target: One of Boston Mayor Michelle Wu’s loudest council critics.

Rachel Pearson, a South Boston substitute teacher and community organizer, plans to challenge Boston City Councilor Ed Flynn, taking on the body’s longest-serving and most well-funded member in one of the most moderate corners of the city.

Pearson, a Democrat and first-time candidate, is casting her candidacy as a chance for “new leadership” in the district that covers South Boston, Chinatown, and parts of the South End.

She said she has talked with Wu about running against Flynn, and has made frequent, small-dollars donations to the mayor totaling roughly $1,000 since 2024. She’s also given to Wu’s allies on the council, including Sharon Durkan and Ruthzee Louijeune, though Pearson declined to say whether she would seek Wu’s endorsement in her run.

“I want everyone in District 2 to feel included and welcomed,” she said. “We have a lot of work to do with how we’re supporting our families.”

It wasn’t long ago that Flynn served as council president, presiding over a tenure that included a bitter redistricting fight and saw other council members rocked by scandal. Flynn more recently has become the main opponent to Wu’s agenda in City Hall, offering a reliable “no” vote on nearly all of the proposals that the second-term mayor or her allies on the council pitch.

His critiques of the Wu’s administration are many. Flynn has urged the city in the past to hire hundreds more police officers, and this year he called for a hiring freeze. Flynn was rumored to have considered, but ultimately decided against, challenging Wu in 2025 before she easily captured a second four-year term.

While Pearson didn’t criticize Flynn by name in an interview, she nodded to the role he’s assumed as Wu’s antagonist-in-chief on the 13-member…

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