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Political Contessa
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Political Contessa

Author: Jennifer Nassour

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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.

190 Episodes
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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. Jennifer addresses concerns over transparency and financial impropriety among prominent Democrats, debates the expansion of health care to undocumented immigrants, and accuses state leadership in Massachusetts of ignoring the will of the voters. She also takes aim at what she perceives as a double standard regarding accusations of authoritarianism, arguing that real examples of unchecked political power can be found within the Democratic Party. This episode dives into controversial topics such as the government shutdown’s effect on military families, the use of taxpayer funds for undocumented immigrants, and the refusal of Massachusetts officials to allow for legislative audits despite overwhelming voter support. Jennifer lays out her case for fiscal conservatism, limited government, and prioritizing veterans and vulnerable citizens over what she calls “illegals.” Her remarks reflect her views on the failures of Democratic leadership at both the federal and state levels, warning that continued disregard for public sentiment will have electoral consequences as key states prepare for the next election cycle. "They said, 'Of course there will be families that are going to suffer, but it's one of the few leveraged times we have.' It's disgusting. It's absolutely sickening." ~Jennifer This week on Political Contessa: Impact of the government shutdown on families, the military, and government workers Criticism of the Democratic leadership’s handling of the shutdown and use of leverage Examples of Republican lawmakers supporting constituents during the crisis Allegations of financial impropriety among elected officials Debate over health care expansion to undocumented immigrants Ongoing partisan conflict over immigration, crime, and public safety Accusations of authoritarian behavior and disregard for voter mandates in Massachusetts Concerns over government spending and fiscal priorities Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.  See omnystudio.com/listener for privacy information.
  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 impact of a one-party system, and the urgent need for citizens to demand real accountability. Jennifer details the escalating costs of state-run shelters, exposing that Massachusetts taxpayers shelled out nearly $1 billion in fiscal year 2025 alone. Originally intended for mothers, children, the elderly, and veterans, these shelters now mainly house migrants, a shift that sparks debate as to who deserves taxpayer-funded support. She sharply criticizes the governor for halting public financial reports and the legislature for refusing to honor the voters’ demand for government audits. Citing incidents within shelter facilities and the looming threat of more tax increases, Jennifer calls on listeners to pay close attention, vote, and pressure leaders for transparency. The episode is a bold call to action as Jennifer challenges Massachusetts residents to reclaim financial oversight and elect leaders who uphold the public trust. "We all have to be accountable to our families, to our bosses, to our employees, to our friends, to our significant others. Why are elected officials not held to that standard?" ~Jennifer Nassour   This week on Political Contessa: Massachusetts taxpayers spent nearly $1 billion on state-run shelters in fiscal year 2025. Shelter programs have shifted primarily toward housing migrants. The Healey administration stopped publishing shelter spending reports. Bipartisan legislation required temporary fiscal reporting but has now expired. Calls for increased transparency and accountability in government spending. Voters overwhelmingly supported greater audit authority, which the legislature has ignored. Criminal incidents within shelter facilities have sparked public outrage. Pandemic funds are running dry, increasing pressure for new tax hikes.   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.  See omnystudio.com/listener for privacy information.
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, including more than 20 years in the US Navy. Known for his advocacy on safety, fiscal responsibility, and quality-of-life issues, Ed is widely respected for his tenacity, focus on local concerns, and steadfast commitment to Boston neighborhoods. Jennifer and Ed dive into the seismic shift on the Boston City Council, examining the transition from moderate to more radical approaches and their impact on key city issues. This episode highlights Ed Flynn's outspoken critiques of council priorities, including the neglect of local public safety, rising property taxes, and lawless city streets, in favor of national and international causes. Ed calls out open drug use, lawlessness in bike and scooter transit, challenges with affordable housing, and contentious regulations that drive away developers. The discussion also covers the dangers facing city residents, including alarming incidents in neighborhoods such as Beacon Hill and the Boston Common, as well as ongoing battles over support for the Boston Police Department. Throughout, controversial topics surface, including resistance from council colleagues to enforce basic laws and the struggle to refocus attention on the core responsibilities of city government.   "Boston is like the wild, wild west; we just can't allow anyone to do what they want to do in the city just because they feel like it." ~Ed Flynn   This week on Political Contessa: The transformation of the Boston City Council from moderate to radical ideology Neglect of neighborhood services, safety, and infrastructure in favor of national issues Escalating open drug use and distribution of over 80,000 needles monthly Public safety crises, including lawlessness, human trafficking, and frequent break-ins Declining support for and staffing of the Boston Police Department Impact of increased property taxes and regulatory challenges on housing and affordability Unregulated bike lanes and scooter use are worsening city safety and public frustration Persistent calls from Ed Flynn and allies for a return to local, constituent-focused governance Connect with Ed Flynn: XCity Councilor Ed Flynn Official PageEd for Boston Official Campaign Website Awaken Your Inner Political Contessa Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts. Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn  Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.  See omnystudio.com/listener for privacy information.
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 emphasizes the difference between free speech and incitement. With passionate calls to restore civility and unite around shared values, Jennifer urges listeners to reject hatred and work collaboratively toward healing and progress in American democracy. “You don't just walk in and decide that the person who's there is wrong,  and you are right, and you're going to take matters into your own hands.” ~Jennifer   This week on Political Contessa: The assassination of Charlie Kirk and public reactions The urgent need to restore respect in political and personal life Generational influence on values and expectations Role models: the responsibility of leaders, educators, and parents Controversial commentary from both left and right Constitutional limits of free speech versus hate speech Impact of social media on fueling polarization How respect and civility can bring unity and progress   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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 comebacks, and now politicians like Gavin Newsom are trying to play copycat instead of offering something new. Both parties, in my view, are failing to deliver the grown-up leadership and serious candidates we all deserve. Instead, we’re bombarded by social media wars, distractions about cultural issues, and nonstop grandstanding. It’s time for our political discourse to move past the childish antics and get back to candidates who focus on policy, substance, and real solutions. “Don’t act like an arrogant asshole. Don’t act like a child. Don’t act like we should put you in, you two in a sandbox.” ~Jennifer This Week on Political Contessa: The rise of snark and sarcasm in political messaging How Trump’s style turned American political talk on its head Why Newsom’s imitation game just isn’t working My frustration with the lack of serious leaders from both parties How Democrats are losing voters by focusing on cultural wedge issues Why we need a new wave of policy-driven candidates Stories from being the only woman shaking things up in political meetings Why it’s time to demand maturity and real leadership, for once   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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 measures like the 2014 Trust Act challenge national laws and the expectations placed on local leaders. I dissect Attorney General Pam Bondi’s letter demanding Boston’s compliance with ICE, the broader implications of refusing to cooperate with federal immigration enforcement, and how these policies can put public safety at risk. I lay out my concerns about how city and state officials handle alleged criminal non-citizens, the results of releasing individuals with criminal records, and the strain this brings to Massachusetts’ justice system. Throughout, I call out blue state leaders for what I see as prioritizing political ideology over real community safety, arguing that the Supremacy Clause firmly puts federal authority above local policy. This episode takes a hard look at the humanitarian and public safety issues at play, with an eye on the political consequences for leaders and communities alike. “No one wants a criminal living amongst them. It's a public safety issue. No one wants that.”~Jennifer Nassour This week on Political Contessa: Boston’s sanctuary city status facing federal pushback● The impact of the 2014 Trust Act on police cooperation with ICE● Attorney General Pam Bondi’s call for compliance with federal law● Concerns about releasing alleged criminal non-citizens into the community● Strain on criminal justice resources in Massachusetts● The implications of the Supremacy Clause in immigration enforcement● Critique of blue state leadership and public safety priorities● Political consequences for Democrats and Republicans in upcoming elections Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.  See omnystudio.com/listener for privacy information.
  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 of the Charles Stewart era, Will is a self-described centrist and humanitarian, mentored by the late Mayor Tom Menino and dedicated to practical solutions for Boston’s toughest challenges. Jennifer and Will dive into Boston’s escalating housing crisis, shortcomings in public education, and the ongoing humanitarian disaster at Mass and Cass. Will shares his frustration with the current City Council’s focus on national controversies instead of local needs, calls out the grandstanding on issues like international conflict resolutions and ICE enforcement, and outlines actionable ideas for affordable workforce housing reform. The discussion includes strong criticism of leadership that ignores the city’s most vulnerable residents, especially seniors, and exposes hidden consequences of illegal immigration, human rights violations, and the exploitation of undocumented workers. Will’s campaign is bolstered by endorsements from notable former city leaders and first responders. He urges Bostonian's and supporters nationwide to help restore professionalism and common sense to City Hall. “The United States government is having a difficult time…so I don’t know what makes the city council think a resolution from them is going to make an international conflict go away.” ~ Will Onuoha   This week on Political Contessa: Housing as the city’s top crisis and policy failures that deter new development Underperformance in Boston Public Schools and the connection between literacy and incarceration rates Harsh realities and humanitarian failures at Mass and Cass, Boston’s opioid crisis epicenter Exorbitant property taxes and lack of senior protections in Boston Grandstanding over national and international issues instead of solving local problems Workforce housing solutions and the power of public-private partnerships Dangers and exploitation facing undocumented immigrants in Boston The need for constituent-centered service, honesty, and a return to professionalism on City Council Connect with Will Onuoha: Website: willforboston.com Email: info@willforboston.com Instagram: @willforboston Facebook: Will for Boston Resources Mentioned: Preliminary Election Date: September 9th General Election Date: November 4th Boston’s “Analysis of Impediments” Housing Ordinance (April 2022)     Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
    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 Charlie Baker, where he earned a reputation for instituting fiscal discipline within Massachusetts state government. Brian is currently running for Governor of Massachusetts, committed to revitalizing economic growth and restoring common-sense leadership. Jennifer and Brian dive into the critical challenges facing Massachusetts under current one-party Democratic rule, highlighting the rapid escalation in state taxes, fees, and regulation. Brian shares controversial insights on Governor Maura Healey’s policies, including her handling of the state's $62 billion budget, the ever-increasing utility bills, burdensome business climate, and spending on migrant shelters. The conversation exposes the exodus of young people and businesses from Massachusetts, the shrinking private sector job market, and the lack of government accountability. Brian details his bold plans to cut taxes, streamline government spending, audit wasteful state programs, and restore fiscal health—all while emphasizing the importance of keeping families and economic opportunity in the state. This episode is a must-listen for those interested in the future trajectory of Massachusetts policy and politics. “Healey’s spending is completely out of control. In the last three weeks, she announced that she’s still spending over $3 million a day on the migrant shelter program.” ~ Brian Shortsleeve This week on Political Contessa: Massachusetts’ record $62 billion budget under Governor Healey The impact of rising taxes, fees, and utility costs on working families and seniors The migration of young people and businesses from Massachusetts to states with better economic climates How government waste and lack of auditing has led to outrageous contract spending The decline in private sector job growth and lost opportunity for middle class families Prioritization of spending on migrant shelters over local needs such as police, education, and public defenders Brian Shortsleeve’s systematic approach to government reform and fiscal discipline The urgent need for checks and balances and balanced leadership in Massachusetts Connect with Brian Shortsleeve: Brian Shortsleeve for Governor     Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.  See omnystudio.com/listener for privacy information.
    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 rights within the corrections system, particularly in response to recent Massachusetts laws requiring female officers to conduct strip searches on transgender inmates. Danielle shares her personal story as both a public servant and a sexual assault survivor, bringing a critical perspective to evolving workplace safety issues.   Jennifer and Danielle delve into the controversial changes brought about by the 2018 Massachusetts crime bill, which mandates that strip searches in correctional facilities be conducted based on inmates’ gender identity rather than biological sex. Danielle details the psychological and ethical challenges faced by female corrections officers asked to perform invasive searches on biologically male inmates, citing both personal trauma and the broader issue of consent. The discussion uncovers the lack of training, union consultation, or opportunity for officers to opt out, raising concerns about workplace harassment, women’s rights, and public safety. They explore federal and state discrepancies, compare procedures in other settings like TSA, and emphasize the ongoing fight for equal rights and consent within the corrections profession. This episode confronts the intersection of gender identity, legal mandates, and women’s workplace autonomy, while advocating for systemic change and greater awareness.   “The law is exposing women to sexual situations with men they don’t know, men they are not consenting to. They’re being forced; they’re being threatened. And you’re creating new victims and you’re revictimizing previous victims.”~Danielle Laurenti   This week on Political Contessa: How Danielle Laurenti began her career as a corrections officer in Massachusetts The impact of the 2018 Massachusetts crime bill on corrections officers’ roles Federal vs. state law in handling strip searches of transgender inmates Danielle’s experience as a sexual assault survivor in the workplace The lack of training and union involvement prior to policy changes The ethical and psychological impact on female officers carrying out invasive searches Comparisons to consent protocols in other public settings, such as the TSA The call for equal rights and consent for corrections officers Resources: Independent Women’s Forum (IWF) Article on Danielle’s story Massachusetts Department of Correction   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.    See omnystudio.com/listener for privacy information.
    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 firsthand experience and a commitment to public safety, Lew brings a nuanced understanding of the challenges facing Massachusetts communities, particularly in light of recent controversies around immigration and law enforcement collaboration.   Jennifer and Lew discuss the evolving landscape of immigration policy, focusing on the impact of federal executive orders, state “sanctuary” policies, and the contentious relationship between local law enforcement and ICE. The episode addresses the fiscal, public safety, and social consequences of current migration patterns, with Lew offering candid criticism of both state and federal decisions. They debate the effectiveness of prior administrations in border security, critique Massachusetts’ handling of migrant housing and public funds, and tackle the effects of political polarization on public safety. Throughout, Lew emphasizes his philosophy of being tough on crime while remaining compassionate and accessible to the community. The episode raises controversial points about the unintended outcomes of immigration policy, the misallocation of taxpayer funds, and the strain on local services, challenging listeners to consider who truly benefits from prevailing policies.   “If a man, 30 years old with a beard looked 30, he said he was 16, there was nothing you could do. He was a minor. He was allowed into the country.” ~Sheriff Lew Evangelidis   This week on Political Contessa: Shifting immigration policies from Obama to Trump to Biden The role of state and local officials in enforcing—or resisting—federal immigration laws Misallocation of $3 billion in state funds for migrant housing instead of addressing homelessness among citizens Impact on schools, hospitals, and local communities as public services are strained Detrimental effects of “sanctuary” policies on public safety and law enforcement collaboration The impact of political polarization and the disappearance of the political middle in Massachusetts The real-world consequences for crime victims and vulnerable residents as a result of the current immigration enforcement posture The importance of putting the needs of resident citizens first and restoring common sense to public policy Connect with Sheriff Lew Evangelidis: Worcester County Sheriff’s Office: https://www.worcestercountysheriff.com/ Worcester County Sheriff’s Office on Facebook: https://www.facebook.com/worcestersheriff Instagram: https://www.instagram.com/sherifflew     Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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 spans local, state, and international service. He is also a decorated military veteran, dedicated musician, and proud husband, father, and grandfather. Scott has recently announced his candidacy for the United States Senate in New Hampshire, where he was born, bringing his extensive experience and bipartisan approach to the forefront in a pivotal election. This episode dives into today’s most pressing political debates, from border security and sanctuary cities to the fairness of women’s sports and government spending. Jennifer and Scott pull no punches as they examine the impact of progressive policies on law enforcement, illegal immigration, and the economic freedoms that define the so-called “New Hampshire advantage.” Scott provides candid criticism of his opponent’s stances on open borders and men competing in women’s sports and outlines concrete conservative solutions—from ending the tax on tips to expanding child tax credits. The conversation also confronts the polarization of Congress, the rise of political extremism on the left, and the dire need for fiscal reform to secure America’s financial future. This episode is packed with controversial viewpoints, clear calls to action, and Scott’s insight on the challenges and responsibilities of seeking public office in turbulent times “It takes people like me and your listeners to really get involved at this local school committee, selectmen, and do it.” ~Scott Brown Today on Political Contessa: Scott Brown is running for U.S. Senate in New Hampshire, emphasizing his extensive experience, from serving as a local selectman to Senator and Ambassador. Criticism of Democratic stances on open borders, sanctuary cities, and support for illegal immigrants over law enforcement. Strong disapproval of biological men competing in women’s sports and its impact on Title IX and female athletes. Advocacy for no tax on tips, child tax credits, and government incentives for American families and workers. Emphasis on the need for work requirements and accountability within welfare and SNAP programs. Call for fiscal conservatism, reducing government waste, and tackling the national debt through energy independence and responsible spending. An assertion that Republicans are now the party of working people and compassion, contrasted with what Brown sees as Democratic elitism and extremism. Encouragement for listeners to get personally involved, volunteer, or donate to the campaign as an act of civic engagement. Connect with Scott Brown: Scott Brown Official Campaign Website: https://www.scottbrown.com Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
    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 international affairs for both the Air Force and Space Force. He is recognized for his principled leadership, commitment to mentoring future generations, and extensive experience navigating complex military, diplomatic, and political challenges both domestically and internationally.   This episode features an in-depth discussion on the recent conflict in the Middle East, focusing on the pivotal events since October 7, 2023, the continuing threat posed by Iran as the world’s largest state sponsor of terrorism, and the shifting dynamics of American foreign policy. Jennifer and John challenge listeners to consider uncomfortable realities: rising social division, loss of civic respect, the threat of national complacency, and the dangers of echo chambers in news and politics. John offers provocative insights into the Biden administration’s perceived weaknesses, critiques the global consequences of past and current U.S. leadership, and shares firsthand accounts from the front lines in Iraq and Israel. The conversation draws powerful links between domestic civility, international security, and the enduring importance of values, respect, and leadership in uncertain times.   “A good leader or a good politician should not walk into a room mouth first, but ears first, to understand what’s going on.” ~ John Teichert   This week on Political Contessa: Iran’s destabilizing influence and state-sponsored terrorism The consequences of American complacency on national security The role of mutual respect and peaceful protest in American democracy How propaganda shapes public understanding of international conflict Lessons from working with adversaries and seeking common ground The critical strategic alliance between the U.S. and Israel Leadership principles from military and political service The importance of stepping outside one’s echo chamber to listen and learn   Connect with John Teichert: WebsiteLinkedInX Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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 developments in California and Massachusetts, I share personal perspectives on civic engagement, public safety, and the pressing need for reform. I confront the controversies around looting, violence in the streets, and the responsibilities of those in public service. I address the strain on local and state resources caused by the ongoing immigration crisis, highlight the struggles faced by both immigrants and native citizens, and call out leaders, regardless of party, for fanning the flames rather than solving problems. Throughout the episode, I challenge the status quo, demand a return to decency in governance, and argue for a fair but firm approach to both protest and immigration that can lead to a better future for everyone. “A peaceful fucking protest has nothing to do with burning up cars, looting stores, or throwing stones at police officers.” ~Jennifer Nassour This week on Political Contessa: Differences between peaceful protest and violence in public demonstrations The impact of sanctuary policies on law enforcement and public safety My criticism of politicians who stoke confrontational activism Exploring the legal immigration process versus entering illegally My family’s personal stories of immigration and resilience The strain on public resources from the immigrant crisis in Massachusetts Concerns about the quality of leadership at the local and federal levels My argument for effective immigration reform and economic opportunity   Awaken Your Inner Political Contessa Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
    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 University of Michigan. Kendall’s professional career spans innovation startups, private sector businesses, and nonprofits, making him a compelling advocate for strong conservative principles and a living embodiment of the American dream.   Jennifer and Kendall dive into a candid discussion about the current political climate in Minnesota and across the nation. The conversation tackles controversial topics, including the narrative of systemic racism, the collapse of family structures in minority communities, the shifting Democratic Party influenced by socialist and Marxist elements, and the impact of failing education systems and crime rates in urban areas. Kendall criticizes the rhetoric of leaders like Ilhan Omar and Tim Walz, raising concerns about divisive speeches and ineffective leadership. He shares his vision for restoring economic prosperity, public safety, and education in Minnesota by returning to foundational American values of faith, family, and hard work. The episode explores the challenges faced by communities, the manipulation of political narratives, and the slow exodus of voters from the Democratic Party.   “It's a dirty, ugly business. When you lift up the carpet and you look underneath this thing. We're fighting a battle of good versus evil in a lot of cases.” ~Kendall Qualls   This week on Political Contessa: Kendall’s journey from poverty in Harlem and Oklahoma to business leadership and public service How Ilhan Omar’s rhetoric inspired Kendall to enter politics The impact of crime, family structure collapse, and failed leadership in urban minority communities The shift in the Democratic Party and its implications for moderate voices The failure of social programs to address core issues in minority communities The effect of divisive political rhetoric on public safety and community integrity Kendall’s three-fold plan for Minnesota: economic prosperity, public safety, and education reform The potential for a political shift in Minnesota with strong conservative leadership   Connect with Kendall Qualls: Campaign Website: kq4mn.com   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
    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 take on the events rocking California and the country at large.   This episode digs into the recent clashes in California, where ICE agents and detention centers became the focal point for riots, forcing President Trump to deploy 700 Marines to Los Angeles alongside the National Guard. I tackle what this means in a sanctuary city, address the legal and moral intricacies of illegal immigration, and critique how local officials are dealing with the fallout. From the devastating impact on small businesses to the divided loyalties of politicians, I unpack why Trump’s hardline policies are no surprise to those who supported him and highlight the consequences of ignoring campaign promises. My commentary challenges the mainstream narrative and critiques elitist leadership, while examining the difficult choices our leaders face when addressing public safety, immigration, and community trust.   “If you are here illegally and doing something illegal, like being in the country illegally, it's time to tell people who came in in the last four years, three years, two years, year, you're going to get kicked out.”   Today on the Political Contessa: I discuss the deployment of 700 Marines to Los Angeles to address riots. I highlight how President Trump’s immigration enforcement policies remain at the center of national debate. Sanctuary city policies restrict what law enforcement can do during civil unrest. Illegal activities by recent immigrants are presented as justification for stricter immigration actions. Small businesses suffer most from property damage during riots. Local officials’ defiance of federal immigration law is escalating tensions with the President. Leaders earn voter support by keeping campaign promises on immigration. Elected officials need to prioritize their constituents’ interests over their own.   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  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 volleyball game against a male player who spiked the volleyball onto Payton's head. Unable to continue athletic competition, Payton has since dedicated herself to speaking out for the protection of girls in sports, serving on the Stand for Women Advisory Board with the Independent Women’s Forum, and testifying across several states to inspire legislative changes. Jennifer and Payton delve deeply into the controversial and headline-making topic of transgender participation in girls’ sports, raising urgent questions about safety, fairness, and the impact of policy on real lives. Payton reveals the physical and emotional aftermath of her injury—concussion, brain bleed, permanent whiplash, and PTSD—and recalls the lack of empathy shown by the opposing team, school administrators, and even the player involved. The conversation exposes how the egregious legislation once prioritized inclusion transgendered women (biological males) at the direct expense of the safety of all female athletes, and how Payton’s testimony contributed to the law changing in North Carolina. Payton emphasizes that stories like hers, often dismissed as rare, affect not just individual players but entire communities and families. She courageously shares her vision for a future where girls can compete without fear, calling for truth, common sense, and genuine compassion in the ongoing debate over the future of women’s sports. “The protections of this one man overrode the protections of every girl and every parent.” ~Payton McNabb This week on Political Contessa: Payton McNabb’s journey from promising athlete to national advocate The sports injury that ended her volleyball career and changed her life Navigating the aftermath: medical diagnoses, PTSD, and the emotional toll North Carolina’s previous policies allowing biological males to compete in girls’ sports and how that changed How teams, communities, and families are impacted by “just one” such injury The lack of accountability and empathy from the schools and the athlete who caused her injury Why Payton feels called to share her truth and stand up for other girls Payton’s hope for a safer, fairer future for girls’ and women’s sports   Connect with Payton McNabb and Resources Mentioned: Independent Women's Forum: https://www.iwf.org/   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
    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 debut murder mystery novel inspired by real-life events closely connected to her community. Deirdre is also a participant in Jack Grapes’ Los Angeles-based writing classes, which have helped her transform thousands of words of personal journaling into a fully developed manuscript form.   Jennifer and Deirdre discuss the challenges and rewards of reinventing oneself after years spent raising a family, particularly for women returning to the workforce or creative pursuits. This episode delves into controversial topics, such as the Karen Read trial in Massachusetts—a case that significantly influenced Deirdre’s novel and has captivated local media and social media spheres. The conversation openly navigates the intimidation of sharing deeply personal creative work, the nuances of portraying real-life inspiration in fictional form, and the subtle power dynamics within upper-tier social circles. Listeners will appreciate insights into why embracing vulnerability, authentic storytelling, and active listening are essential in both the arts and everyday life.   “It’s so easy for people to critique and sort of knock us down. So you do have to have some thick skin to be—to shut out that noise.” –~Deirdre Sullivan   Today on Political Contessa: Reinvention is possible at any stage, especially for mothers considering new beginnings after raising children. Personal experiences and local headlines can serve as powerful inspiration for fiction writing. Authenticity in storytelling comes from writing for oneself rather than catering to outside expectations. Portraying community figures in fiction requires careful blending of character elements to avoid overly obvious real-life parallels. Crafting a novel is an intensely personal endeavor; sharing it publicly requires confidence and resilience in the face of criticism. Early morning solitude is a productive time for creative work, allowing for uninterrupted focus and concentration. “Cozy murder” is a unique subgenre that blends relatable settings and humor with the mystery of crime. Listening and observation in everyday life provide rich material for creative writing.   Connect with Deirdre Sullivan: Instagram: @deirdresullivanauthorFacebook: Deirdre Sullivan Author Resources and references mentioned: Jack Grapes’ writing classes (Los Angeles-based, available online) Deirdre Sullivan’s Children’s Books     Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
  In this week’s episode of Political Contessa, Jennifer welcomes Scotia Hille, Executive Director of Act on Mass. Scotia’s career began in climate policy, where she worked on national campaigns and later shifted her focus to improving government transparency in Massachusetts. With a background in science and policy, and a dedication to holding elected officials accountable, Scotia now leads advocacy efforts for legislative reform and open government, aiming to strengthen democracy in one of the nation’s least transparent state legislatures.   Jennifer and Scotia dive into the urgent issue of transparency and accountability in the Massachusetts legislature, a topic that crosses party lines and draws advocates from across the political spectrum. The conversation uncovers how Massachusetts lacks fundamental nonpartisan research support for lawmakers, making it the only state in the country without this basic legislative office. Jennifer and Scotia expose the “mob-like” leadership structure, the culture of committee stipends for little or no work, and hidden budget earmarks that slipped past the public and lawmakers. They critique the lack of local news scrutiny, the persistence of backroom deals, and the enormous barriers facing reformers. The episode also sparks debate over term limits, full-time versus part-time legislatures, stagnation from entrenched leadership, and the role of citizen coalitions like the Coalition to Reform Our Legislature. The discussion reveals controversial comments about power hoarding, lack of individual lawmaker autonomy, and misuse of taxpayer dollars, urging listeners to demand more from their elected representatives.   “It's very much run almost like a mafia, where leadership calls a lot of the shots.” ~Scotia Hille   This week on Political Contessa: The origins and mission of Act on Mass and Coalition to Reform Our Legislature Massachusetts is the “least transparent” state legislature in the country The complete absence of a nonpartisan legislative research bureau in Massachusetts The power dynamics and control tactics used by legislative leadership Stipend reform and the existence of “ghost committees” that rarely meet The connection between committee assignments, added salary, and political loyalty Lack of individual roll call votes and the use of consolidated amendments to conceal spending Decline in local journalism and its impact on holding the legislature accountable Connect with Scotia Hille and Resources Mentioned: Act on Mass Website: https://actonmass.org Democracy in Decline Report (referenced research): https://report.actonmass.org Coalition to Reform Our Legislature (KROLL): https://reform-ma.org Twitter: @Act_on_Mass For more insights on statehouse transparency and reform in Massachusetts, follow Act on Mass and join the Coalition to Reform Our Legislature’s weekly meetings.   Awaken Your Inner Political Contessa   Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.   Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts   Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.See omnystudio.com/listener for privacy information.
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