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October 2, 2025 42 mins

In this week’s episode of Political Contessa, Jennifer welcomes Boston City Councilor Ed Flynn. Ed has represented District 2 since 2018 and previously served as City Council President from January 2022 to January 2024, acting as the "backup mayor" when the mayor is unavailable. As part of a historic Boston political family, Ed is the son of former mayor Raymond Flynn and has dedicated much of his career to public service, including more than 20 years in the US Navy. Known for his advocacy on safety, fiscal responsibility, and quality-of-life issues, Ed is widely respected for his tenacity, focus on local concerns, and steadfast commitment to Boston neighborhoods.

Jennifer and Ed dive into the seismic shift on the Boston City Council, examining the transition from moderate to more radical approaches and their impact on key city issues. This episode highlights Ed Flynn's outspoken critiques of council priorities, including the neglect of local public safety, rising property taxes, and lawless city streets, in favor of national and international causes. Ed calls out open drug use, lawlessness in bike and scooter transit, challenges with affordable housing, and contentious regulations that drive away developers. The discussion also covers the dangers facing city residents, including alarming incidents in neighborhoods such as Beacon Hill and the Boston Common, as well as ongoing battles over support for the Boston Police Department. Throughout, controversial topics surface, including resistance from council colleagues to enforce basic laws and the struggle to refocus attention on the core responsibilities of city government.

 

"Boston is like the wild, wild west; we just can't allow anyone to do what they want to do in the city just because they feel like it." ~Ed Flynn

 

This week on Political Contessa:

  • The transformation of the Boston City Council from moderate to radical ideology
  • Neglect of neighborhood services, safety, and infrastructure in favor of national issues
  • Escalating open drug use and distribution of over 80,000 needles monthly
  • Public safety crises, including lawlessness, human trafficking, and frequent break-ins
  • Declining support for and staffing of the Boston Police Department
  • Impact of increased property taxes and regulatory challenges on housing and affordability
  • Unregulated bike lanes and scooter use are worsening city safety and public frustration
  • Persistent calls from Ed Flynn and allies for a return to local, constituent-focused governance

Connect with Ed Flynn:

X
City Councilor Ed Flynn Official Page
Ed for Boston Official Campaign Website

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