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
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...
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...
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 ...
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...
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...
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...
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...
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...
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, ...
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...
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...
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...
In this week’s episode, Jennifer welcomes Will Onuoha, a lifelong Bostonian, political science and international relations graduate, and a candidate for Boston City Council At-Large. Will’s extensive career in city government spans over 20 years, including a decade as Boston’s Housing Commissioner under Mayor Marty Walsh. Raised in Mission Hill and a beneficiary of community support in the aftermath...
In this week’s episode, Jennifer welcomes Brian Shortsleeve, a distinguished Marine Corps veteran, successful businessman, government reformer, and proud father of three boys. Brian’s career spans service in Bosnia and the Persian Gulf, a leading role in the finance sector, and a notable tenure as the General Manager and CEO of the Massachusetts Bay Transit Authority (MBTA). He also served under Governor C...
In this week’s episode, Jennifer welcomes Danielle Laurenti, a Massachusetts corrections officer with over fifteen years of experience, including service as a sergeant in both female and maximum-security male facilities. Danielle began her career as a young single mother, driven by her passion for law enforcement and desire to support her family. Over the years, she has become an advocate for women’s right...
In this week’s episode, Jennifer welcomes Lew Evangelidis, the long-serving Sheriff of Worcester County, Massachusetts. Lew previously represented Worcester in the Massachusetts House of Representatives before being elected sheriff in 2010. Over his tenure, he has witnessed dramatic shifts in immigration enforcement, border policy, and the intersection of state and federal law enforcement. With extensive firstha...
In this week’s episode of Political Contessa, Jennifer welcomes Scott Brown, esteemed former U.S. Senator from Massachusetts, former U.S. Ambassador to New Zealand and Samoa, and a longtime public servant at both the state and national levels. Scott is recognized for his historic win of the Massachusetts Senate seat in 2010—turning a seat long held by Democrats—and for his dynamic political career, which sp...
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 Develo...
In this week’s episode, Jennifer welcomes Brigadier General John Teichert, a highly decorated national security leader, foreign policy expert, and former U.S. Senate candidate. John Teichert’s distinguished thirty-year career in the United States Air Force included command positions at Joint Base Andrews and Edwards Air Force Base, serving as the nation’s senior defense official in Iraq, and leading ...
In this week’s episode, I dive deep into the state of protests in America and the line between peaceful demonstration and lawlessness. Drawing on my family’s immigrant roots and my experience as an attorney and political strategist, I address the complex questions surrounding our First Amendment rights, the actions of elected leaders, and the consequences of current immigration policies. With a focus on developme...
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