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July 17, 2025 31 mins

 

In this week’s episode of Political Contessa, Jennifer welcomes Mike Kennealy, Republican candidate for Governor of Massachusetts. Mike is a lifelong Massachusetts resident, business leader, and father. With nearly two decades of experience in private equity and twelve years devoted to public service, Mike's impressive career includes serving in Governor Baker’s cabinet as Secretary of Housing and Economic Development, as well as turning around the Lawrence Public Schools. Mike has also served as finance chair of the Massachusetts Republican Party and worked with the Boys & Girls Clubs of Boston to improve outcomes for youth in some of the state’s most underserved communities.

Jennifer and Mike dive into the realities of political leadership in Massachusetts, highlighting what makes New England Republicans unique and contending with the state’s overwhelming Democratic dominance. Mike shares his vision for achieving equal opportunity across Massachusetts, shining a light on entrenched achievement and life expectancy gaps between communities just miles apart. They discuss controversial topics, including the state’s multi-billion dollar migrant crisis, leadership shortcomings in the current administration, and the failure to address root causes of inequity despite progressive rhetoric. Mike contrasts his “coalition-builder” approach with what he sees as Beacon Hill's passivity, emphasizing the urgent need to listen, innovate, and act on behalf of all residents. The conversation challenges sound bite politics and calls for real solutions to ensure Massachusetts isn’t just number one in averages, but in opportunities for every community.

“I made a conscious decision when I was 45 that I was going to leave the business world behind and dedicate the rest of my days professionally to public service here in Massachusetts.” ~ Mike Kennealy

This week on Political Contessa:

  • The unique identity and priorities of New England Republicans
  • The critical achievement and life expectancy gaps between different Massachusetts communities
  • Mike’s leadership experiences: from private equity to turning around Lawrence Public Schools
  • Failures of the current state leadership to address the crisis and seize the opportunity
  • How Massachusetts loses young people due to unaffordable costs and limited opportunities
  • The state’s costly response to the migrant crisis and its impact on local communities
  • Initiatives to ensure equal educational and workforce opportunities for all residents
  • The importance of coalition-building and listening across party lines

Connect with Mike Kennealy:

Campaign Website

 

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