Political Contessa

Political Contessa

Women on the right need a safe space to discuss politics, policy, news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech. Before we can even out the number of women in our local, state, & federal governments, we need to empower women to feel comfortable and confident discussing these and other topics. My name is Jennifer. I’m a single mom of three girls living in Boston. I’m a lawyer with two political science degrees, and I have no problem talking politics with people who disagree with me. I spent three years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I’m a frequent analyst on Newsmax, Fox News Radio, and Boston Media. As a Republican in a blue state, I know a few things about how to disagree agreeably. Join me for fascinating conversations that engage and clarify every week. For more information and resources, visit Political Contessa.

Episodes

February 19, 2026 21 mins

 

 

In this week’s episode, Jennifer takes center stage. Jennifer is an experienced attorney and political strategist, known for her leadership as former Chairwoman of the Massachusetts Republican Party and as the founder of Pocketbook Project. Jennifer has built her career championing conservative values, government transparency, and women's participation in politics across Massachusetts. Her work continues to focu...

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In this week's episode, Jennifer discusses the recent assassination of Charlie Kirk and the troubling responses that followed on social and mainstream media. She dives into the alarming increase of hate speech, the breakdown of respectful discourse, and the pressing need for adults and leaders to set better examples for the next generation. The episode challenges both sides of the political spectrum for fueling divisiveness ...

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In this week’s episode, Jennifer welcomes Ann Brensley, candidate for Lieutenant Governor in the Commonwealth of Massachusetts, and Adrienne Simeone, founder of the Mama Bear Effect nonprofit and a mother of four. Ann Brensley is recognized for her focus on parental involvement and educational policy reform, emphasizing the importance of family values in governance. Adrienne Simeone, an advocate for children&rsq...

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In this week’s episode, Jennifer welcomes Professor Marc Defant from the University of South Florida. Marc is a renowned geology and geochemistry professor specializing in the study of volcanoes, the geochemistry of volcanic rocks, and mantle processes. With decades of experience researching volcanoes worldwide—including Russia—Marc has recently explored the intersection of evolutionary psychology an...

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In this week’s episode, Jennifer welcomes Susan Molinari and Beth Brooke to dive into the shocking disparities and outdated standards in the way car safety is measured for women in the United States.

They reveal that despite decades of progress, female crash test dummies are still largely absent from critical safety testing, putting women at greater risk of injury and death. They address controversial facts such li...

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In this week’s episode, Jennifer celebrates a major milestone as she marks her 200th episode. Jennifer is a political strategist, attorney, and founder of the Pocketbook Project, an organization dedicated to supporting women who run for office and empowering conservative women to have their voices heard. With over three decades of experience in politics, Jennifer has frequently appeared on television and radio and is known fo...

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In this week’s episode, Jennifer tackles the ongoing government shutdown and its wide-ranging impact, sharply criticizing Democratic leadership for leveraging struggling families as political pawns. She highlights actions taken by Republican lawmakers to help their communities during the crisis, while alleging that many Democratic officials are out of touch and prioritize their own benefits over those of ordinary Americans. J...

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Georgia Polemenakos a Public Administration Professional with over 7 years of experience in various roles within the Massachusetts state government. She has a strong track record in political action, legislative relations, and effective public policy advocacy. Georgia is particularly interested in Women's Leadership and Empowerment, which she explored during her fellowship with the Women's Public Leadership Network. S...

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In this week’s episode, Jennifer welcomes Jesse Littlewood, the campaign manager for the Coalition for a Healthy Democracy. Jesse has extensive experience working on democratic reforms, particularly focusing on increasing civic engagement and advancing policies that make elections fairer and more competitive. Raised in Oregon, Jesse brings insight from strong ballot initiative states and is now leading efforts t...

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What could young female voices do to improve the world for their own generation? Women drive 70 to 80 percent of all consumer purchasing though their buying power and influence, yet their views, opinions, and voices are seldom heard on the political platform when it comes to fiscal responsibility. Women are the child-bearers and, often, the primary child caregivers, yet our voices are often muted when it comes to topi...

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In this week’s episode, Jennifer welcomes her daughter, Georgia Brucato, a senior at Elon University majoring in Strategic Communications. Georgia joins the show for a thought-provoking discussion as part of her final class project, bringing her perspective as a young woman aiming to enter politics. As the daughter of a single mother, of Syrian descent and Christian background, Georgia offers a compelling intersection ...

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In this week’s episode, Jennifer is joined by Alyson Sullivan Almeida, the Republican State Representative for the 7th Plymouth District in Massachusetts. Alyson is a dedicated legislator, a young mother of two, and has served in office since 2019. Raised in a politically active family, Alyson brings her deep understanding of statehouse affairs and her passion for advocating for women’s issues and victim protecti...

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In this week’s episode, Jennifer welcomes Jaclyn Corriveau, a dedicated foster parent, court advocate with CASA Boston, and passionate supporter of vulnerable children in Massachusetts. Jaclyn has opened her heart and home to teens in the foster care system and has firsthand experience with the challenges facing both children and the system meant to protect them. A single woman with a strong record of public service an...

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October 30, 2025 10 mins

 

In this week’s episode, Jennifer tackles the ongoing government shutdown and its wide-ranging impact, sharply criticizing Democratic leadership for leveraging struggling families as political pawns. She highlights actions taken by Republican lawmakers to help their communities during the crisis, while alleging that many Democratic officials are out of touch and prioritize their own benefits over those of ordinary Ameri...

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In this week's episode, Jennifer Nassour takes the spotlight solo to dissect the controversy over shelter spending and transparency in Massachusetts. A veteran advocate for government accountability and a leading voice in state politics, Jennifer brings sharp analysis to the recent decisions of Governor Maura Healey’s administration. Her commentary dives deep into the fiscal responsibility of elected officials, the imp...

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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, in...

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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, ...

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In this week's episode, Jennifer discusses the recent assassination of Charlie Kirk and the troubling responses that followed on social and mainstream media. She dives into the alarming increase of hate speech, the breakdown of respectful discourse, and the pressing need for adults and leaders to set better examples for the next generation. The episode challenges both sides of the political spectrum for fueling divisiveness and emp...

Mark as Played

 

After spending years as the only woman in rooms full of political power players, I’ve picked up more than a few things about messaging, bravado, and what actually lands with voters. If you’re craving someone who cuts through the noise with sarcasm, honesty, and zero patience for posturing, you’re in the right place.

Let’s call it like it is Trump changed the game with his snark and sharp comeb...

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In this week’s episode, I’m diving into one of the most important and contentious topics facing Boston today: the city’s sanctuary policies, the upcoming mayoral race, and what it all means for public safety and local governance. With my experience in politics and advocacy, I break down the direct conflict between Boston’s Mayor Michelle Wu and federal authorities, examining how sanctuary city measure...

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