In this week’s episode, Jennifer welcomes Anne Brensley, a select board member from Wayland, Massachusetts, an accomplished attorney, finance professional, and small business owner. Anne is a first-generation American, adopted from Honduras, whose life journey includes profound experiences as a caregiver, community leader, and mother. With more than 15 years of entrepreneurial experience, senior leadership in banking, and a law degree, Anne brings determination and resilience to her campaign as she seeks the office of Lieutenant Governor of Massachusetts.

 

Jennifer and Anne discuss the unique landscape of Massachusetts state politics, where candidates for Governor and Lieutenant Governor run independently, the underestimated power of the Lieutenant Governor’s office, and what it takes to run – and win – as a Republican woman in a predominantly blue state. Anne shares her gritty approach to leadership, emphasizing the urgent need for more practical, solution-oriented governance and fearless advocacy for local communities. The conversation tackles controversial criticisms of the MBTA Communities Act, the state’s high cost of living, outmigration of young professionals, and the lack of focus on “ownership” opportunities for the next generation. Anne positions herself as a voice for those impacted by stagnant, one-party rule and outlines a vision for connecting Statehouse policy to the everyday needs of families and municipalities. Listeners will hear candid commentary on party politics, local government, and Anne’s determination to use her diverse background as an asset for Massachusetts.

 

“I think we have a major issue with ownership for young people. I mean that across the board, young people nowadays… they’re being deprived of ownership.” ~Anne Brensley

 

This week on Political Contessa:

• Anne’s inspiration for running for Lieutenant Governor and leading from the ground up in Massachusetts
• The critical impact of local politics and the need for a direct line from municipalities to the state’s executive office
• The challenges of being a Republican woman entering statewide office in a predominantly Democratic state
• The overlooked potential for the Lieutenant Governor to serve as a change agent, not just a ceremonial figure
• The urgent need to address Massachusetts’s housing affordability and retention of young professionals
• Why Anne believes the MBTA Communities Act is missing the mark on homeownership and local empowerment
• The importance of fearless, resilient leadership and grassroots campaigning over data-driven, detached strategies
• Anne’s commitment to pragmatic, bipartisan problem-solving in government and her call for more women to run for office

Connect with Anne Brensley:

Website: www.anne2026.com

Resources Mentioned:

• Anne Brinsley’s campaign for Lieutenant Governor of Massachusetts
• The MBTA Communities Act
• Tip O’Neill’s “All politics are local”
• Kelly Ayotte’s messaging on New Hampshire and Massachusetts

Support Anne or get involved:

Volunteer or contribute at www.anne2026.com

 

 

 

 

 

 

 

 

 

 

Awaken Your Inner Political Contessa

 

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