Political Contessa

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...

In this week’s episode, Jennifer welcomes Kendall Qualls, a US Army veteran, business executive, and the newly announced candidate for governor of Minnesota. Kendall’s remarkable life journey began in poverty, growing up in Harlem and later in an Oklahoma trailer park. After working his way through college delivering pizzas, he served as an artillery officer in the Army and later earned his MBA from the Un...

In this week's episode, I offer my unfiltered perspective on one of the nation’s most controversial stories. As an attorney, political strategist, and commentator, I’ve devoted my career to grassroots activism, public policy, and challenging conventional wisdom across the political spectrum. My work places me at the center of debates on law, order, and immigration, and today, I’m sharing my direct ta...

In this week's episode, Jennifer welcomes Payton McNabb, a determined advocate for the elimination of biological males participating in women's sports and the protection and fairness of girls’ and women’s sports. Payton is a former three-sport high school athlete from rural North Carolina whose life changed abruptly, due to existing state policy at the time, after she suffered a traumatic brain injury during a vo...

In this week’s episode, Jennifer welcomes Deirdre Sullivan, an emerging author and mother of four daughters based in the Boston area. Deirdre began her writing journey with a passion for storytelling that was sparked in high school and continued through the publication of three children’s books. As her children grew, so did her writing style, leading her to explore adult fiction and ultimately craft a debu...