South Boston Resident Rachel Pearson to Challenge Ed Flynn for City Council Seat in 2027

Looks like the local 2027 election season is already heating up in Southie.
According to The Boston Globe, South Boston resident Rachel Pearson plans to challenge longtime District 2 City Councilor Ed Flynn in next year’s election.
Pearson, 44, is a substitute teacher and community organizer who previously served as president of the South Boston Moms Club. She also sits on the board of Julie’s Family Learning Program and has lived in South Boston for 12 years.
A first-time candidate, Pearson told the Globe she’s ready to bring new leadership to District 2, which includes South Boston, Chinatown, and parts of the South End.
Pearson has also supported Mayor Michelle Wu, donating approximately $1,000 to her campaigns since 2024. She told the Globe she has spoken with Wu about running but did not say whether she would seek the mayor’s endorsement.
Flynn, a lifelong South Boston resident, was first elected to the City Council in 2017 and previously served as council president. He has frequently challenged the Wu administration on issues including public safety, city spending, and staffing.
According to the Globe, Flynn had nearly $1 million in campaign funds as of early November.
Pearson is expected to officially launch her campaign on Thursday at The Playwright in South Boston.
You can read the full story in The Boston Globe.

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.

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