The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
Hi, I’m Lisa Reilly, and this show is built on one simple belief: true stories can change how we see each other. Each week, I have the privilege to sit down with people from within the various criminal and social justice systems and organizations, including those with lived experience and those working to bring compassion and resources both behind and beyond the walls. All of them approach their lives and work with grit, hope, and purpose, which is what we’re here to share because there’s always a voice ready to challenge what you thought you knew. THIS IS THE HUSTLER FILES
info_outline
CHARLES ROSARIO – HOLDING THE DOOR FOR OTHERS LIKE HIM
10/11/2026
CHARLES ROSARIO – HOLDING THE DOOR FOR OTHERS LIKE HIM
Charlie Rosario spent 19 years in prison. While incarcerated, he was fortunate to be admitted to the Emerson Prison Initiative. This program earned him a bachelor’s degree, and with that education he began to see new possibilities for his life. Now released from prison, he works for the same program, at Emerson, helping other students and returning citizens navigate education and reentry. Charlie also talks about growing up in Worcester, his experience in the youth and adult prison systems, and the persistence it took to reach college, gain parole, and why helping others recognize their own worth has become his purpose.
/episode/index/show/thehustlerfiles/id/43250533
info_outline
MNEESHA GELLMAN – UNLOCKING THE PERSON INSIDE THE PRISONER
10/11/2026
MNEESHA GELLMAN – UNLOCKING THE PERSON INSIDE THE PRISONER
What changes when someone in prison is given the chance to become a college student? Dr. Mneesha Gellman, Founder and Director of the Emerson Prison Initiative, (EPI), in Boston, Massachusetts, believed a rigorous college degree program could help create that change. It didn’t take much with her background in education in prison, human rights, immigration, and the politics of violence to convince her that college behind bars was a necessity. In 2017 she launched EPI, sharing that she was also inspired by the Bard College Prison Initiative which was launched in 2001. Currently MCI - Norfolk is where her students behind the wall pursue an Emerson College Bachelor of Arts in Media, Literature, and Culture and are taught by Emerson professors and guest faculty. Mneesha shares the incarcerated students’ passion for education and the ripple effect beyond the carceral classroom as many students who start their degree path behind the wall not only continue their education, after release, but also are helping others navigate reentry, and inspiring family members to pursue their own goals. Mneesha also created RECOUP which supports formerly incarcerated students with continuing education, employment, housing, healthcare, and other reentry needs.
/episode/index/show/thehustlerfiles/id/43250353
info_outline
KEN W. GOOD – A MILLION-DOLLAR BOND GONE WRONG
10/06/2026
KEN W. GOOD – A MILLION-DOLLAR BOND GONE WRONG
Texas bail attorney Ken W. Good breaks down the often-confusing differences between bail, bond and pretrial release, and examines what happens when the safeguards designed to protect the public fail. This conversation centers on the case of Lee Gilley, a Houston man charged with capital murder in the death of his pregnant wife, Christa Bauer Gilley. After being released on a $1 million bond with GPS monitoring, Gilley removed his ankle monitor and fled through Canada to Italy using a fraudulent passport. How did he get such a significant head start? Ken explains how electronic monitoring alerts are handled, why GPS technology cannot replace human supervision, what happens when a defendant skips bond, and who may ultimately be responsible for the $1 million bond. This episode also explores Texas bail policy, judicial discretion, public safety and Gilley’s continuing fight against extradition.
/episode/index/show/thehustlerfiles/id/43201558
info_outline
RON WADDELL - THE MEN HE REFUSES TO GIVE UP ON
09/12/2026
RON WADDELL - THE MEN HE REFUSES TO GIVE UP ON
A second chance only matters when someone is standing there ready to help you believe your life can actually be different. Ron Waddell, co-founder of Legendary Legacies in Worcester, Massachusetts, knows firsthand how easily a young person can fall through the cracks. After losing his mother at 15, experiencing homelessness and navigating instability without many of the supports young people need, Ron eventually found his own path, and a calling to make sure other young men wouldn't have to find theirs alone. Founded in 2018, Legendary Legacies works with men affected by gangs, violence and incarceration through intensive life coaching, mentorship, workforce development and a deeply relational approach that meets people where they are. With many staff members bringing their own lived experience to the work, the organization is creating something bigger than a program: a community built around brotherhood, accountability, purpose and opportunity. Because sometimes changing a life isn't about erasing someone's past. It's about helping them build a different future, and a legacy for the generations that follow.
/episode/index/show/thehustlerfiles/id/42882240
info_outline
ESTHER & EVE – AN UNWAVERING BELIEF IN HER INNOCENCE
09/12/2026
ESTHER & EVE – AN UNWAVERING BELIEF IN HER INNOCENCE
Twenty years, that’s the sentence she received for refusing to take a plea deal. Now Elizabeth Mercedes Hernandez, a former nurse practitioner, a mother of five and a healthcare professional with no prior criminal record is serving in a Florida federal prison after being convicted of committing healthcare and wire fraud. In this episode, her mother, Esther Pino, and sister, Eve Hernandez, say the government got her story wrong. Elizabeth’s journey from working in the rapidly expanding world of telemedicine to discovering what the prosecutors, at her trial, say was the misuse of her medical credentials and NPI number. Despite cooperating with investigators, refusing a plea agreement and ultimately taking her case to trial, Elizabeth lost her freedom. Esther and Eve share their continuing fight for Elizabeth’s freedom and their larger effort to bring attention to healthcare practitioners they believe have been unjustly prosecuted. This is a story about one family’s unwavering belief in Elizabeth’s innocence, and the questions her case has left them asking about truth, justice and the power of the federal criminal justice system.
/episode/index/show/thehustlerfiles/id/42881460
info_outline
ELIAS HUSAMUDEEN – A RIKERS RESET FOR AMERICA’S MOST INFAMOUS JAIL
09/08/2026
ELIAS HUSAMUDEEN – A RIKERS RESET FOR AMERICA’S MOST INFAMOUS JAIL
Rikers Island has been synonymous with violence, dysfunction and controversy for decades. But as New York City moves toward closing one of America’s most infamous jail complexes, former NYC Correction Officer and union leader Elias Husamudeen believes there’s another option: reinvent it. After 34 years working inside the New York City correction system, Elias brings a perspective shaped by firsthand experience. His ambitious Rikers Reset proposal would dramatically reduce the island’s jail footprint while creating space for education, transitional housing, mental health and medical care, rehabilitation and other resources designed to address what happens both during incarceration and after release. Elias offers his insight about what Rikers is really like behind the headlines, why previous reform efforts have struggled, the enormous cost of closing and rebuilding New York City’s jail system, and why he believes rehabilitation, not simply new buildings is the key to reducing recidivism. Is it time to close Rikers Island, or is it time to completely reimagine what it could become?
/episode/index/show/thehustlerfiles/id/42831820
info_outline
BRIAN KOEHN – FROM WARDEN TO CORRECTIONS REFORMER
08/15/2026
BRIAN KOEHN – FROM WARDEN TO CORRECTIONS REFORMER
For decades, the conversation around corrections has largely centered on two models: government-run facilities which operate 92% of prisons, and private prisons, which own and run the other 8%. But what if there was another option? Creating a third model is Brian Koehn, (pronounced Kane), Founder and CEO of Social Purpose Corrections, the nation's first nonprofit corrections organization and the third leg in the proverbial correction stool. After more than three decades leading prisons across the country, Koehn walked away from a successful career with one question he couldn't ignore: ‘After All It is Called Corrections’, which then asks the question, ‘If we call it corrections, are we actually correcting anything?’ Brian’s understanding and experience brings to light information that is not readily discussed such as the culture inside American corrections, the challenges facing correctional officers, why leadership matters, and whether a nonprofit, outcomes-based model, like SPC could reshape how correctional systems operate. From staff retention and rehabilitation to innovation and accountability, this conversation challenges long-held assumptions about what corrections are and what it could become. Whether you agree with Brian's vision or not, this episode asks an important question: How do we create safer facilities, stronger leadership, and better outcomes for everyone involved?
/episode/index/show/thehustlerfiles/id/42444505
info_outline
DUSTY TURNER - 31 YEARS BEHIND BARS BUT FREEDOM ISN'T FREE YET
08/04/2026
DUSTY TURNER - 31 YEARS BEHIND BARS BUT FREEDOM ISN'T FREE YET
The truth surfaced years before justice finally prevailed, but for Dusty Turner, freedom wasn't the end of the story. After spending 31 years in prison for a crime he maintains he did not commit, Dusty has chosen a path unlike many wrongly convicted people. Rather than quietly rebuilding his life, he's stepped into the public eye through documentaries, podcasts, interviews, and a massive, daily, social media campaign, run by his team of advocates and posted under the @freedustyturner handle. In Dusty’s own words, sunlight is the greatest disinfectant, and that mantra helps him fight for his own exoneration, every single day. In this candid conversation, Dusty reflects on surviving decades behind bars, the emotional toll of knowing he was innocent, now living each day under electronic monitoring, and why he believes sharing his story publicly is part of his life's purpose. He also discusses his new mission to advocate for justice-involved veterans and help others who may have been wrongfully convicted. Dusty's story isn't just about freedom. It's about perseverance, purpose, and the belief that the truth deserves to be heard, even when justice takes decades to catch up.
/episode/index/show/thehustlerfiles/id/42246060
info_outline
CHERRI GREGG & YVONNE LATTY - DYING ON THE INSIDE: AGING WOMEN IN PRISON
07/19/2026
CHERRI GREGG & YVONNE LATTY - DYING ON THE INSIDE: AGING WOMEN IN PRISON
America's prisons were built for punishment, not to become nursing homes. Across the United States, thousands of incarcerated men and women are growing old behind bars, facing chronic illness, declining health, and the possibility that prison will also become the place where they die. This week we speak with Emmy Award-winning journalist and attorney Cherri Gregg and investigative journalist Yvonne Latty, co-creators of the powerful NEW podcast series Dying on the Inside: Women Lifers at Muncy Prison. Together they discuss what they discovered inside Pennsylvania's oldest women's prison, the women serving life sentences, the emotional toll of reporting these stories, and the larger questions surrounding redemption, aging, justice, and compassion. They also explore Pennsylvania Senate Bill 1400 and why the conversation about elderly incarcerated people is becoming one of the most urgent issues facing corrections today. Sometimes the hardest stories to tell are the ones that ask us to reconsider what justice looks like decades after a sentence begins.
/episode/index/show/thehustlerfiles/id/42145815
info_outline
TARYN VANDERPYL & TRESSA JUMPS - HEALING THE TRAUMA COMES FIRST
07/19/2026
TARYN VANDERPYL & TRESSA JUMPS - HEALING THE TRAUMA COMES FIRST
You don't have to be incarcerated for this conversation to matter. We all have had a yesterday experience that shaped us, wounds that followed us, and patterns we sometimes don't even realize we're repeating. This week we conclude our first-ever trilogy with a most meaningful yet simple lesson. Over the past few episodes, we introduced you to Oregon's Transformative Justice Community, their innovative programs at Coffee Creek Correctional Facility, and the volunteer-run CREW Safe Rides program that helps women return home safely after release from prison. Now we turn to what may be the foundation for lasting change. Educator and Transformative Justice Community co-founder Taryn VanderPyl, along with healing curriculum developer Tressa Jumps share a new trauma-informed healing curriculum created specifically for incarcerated women. Together, they explore why lasting transformation begins long before release, how unresolved childhood trauma often shapes adult choices, the difference between healing and simply serving a sentence and why understanding what happened to someone can be just as important as understanding what they did. Because it just may be that healing is one of the most powerful forms of rehabilitation.
/episode/index/show/thehustlerfiles/id/42145565
info_outline
KYLE BLACK - YOU ARE WORTHY OF LOVE, DIGNITY AND HOPE
07/03/2026
KYLE BLACK - YOU ARE WORTHY OF LOVE, DIGNITY AND HOPE
In this episode we return to Oregon to continue the story of CREW (Connecting Resources to Empower Women) and meet Client Services Specialist Kyle Black. Once incarcerated herself for almost three decades at Coffee Creek Correctional, Kyle now spends her days driving newly released women, from the same prison, to probation appointments, safe housing, treatment programs, and the first chapter of a new life. But these aren't simply rides, they are conversations filled with fear, hope, shame, courage, grief, and possibility. Kyle speaks candidly about the tragic events that led to her incarceration, the decades she spent in prison, rebuilding a relationship with her daughter, and why every woman deserves to leave prison knowing someone believes in her future. Because sometimes the shortest journey becomes the one that changes everything.
/episode/index/show/thehustlerfiles/id/41957525
info_outline
DR. LATOYA BOSWORTH- FREDERICK DOUGLASS AND THE FIGHT FOR SOCIAL JUSTICE
07/03/2026
DR. LATOYA BOSWORTH- FREDERICK DOUGLASS AND THE FIGHT FOR SOCIAL JUSTICE
In the annals of American history there is one speech delivered in 1852, by a former slave, that stood at the precipice of what today, we call social justice. This week on The Hustler Files Dr. LaToya Bosworth of Mass Humanities explores the enduring legacy of Frederick Douglass and the Massachusetts statewide initiative, Reading Frederick Douglass Together. His speech “What to the Slave is the Fourth of July” still resonates around the world, and each year in Massachusetts, from public parks to correctional facilities, communities gather to read Douglass's powerful words aloud, discovering that his message about freedom, justice, humanity, and hope, the building blocks of social justice, remains as relevant today as ever. In honor of America’s 250th Anniversary, Dr. Bosworth discusses storytelling, historical memory, invisible barriers, community healing, and why understanding our shared past may be one of the most important ways to shape our future. Because some stories aren't just history, they're still changing lives.
/episode/index/show/thehustlerfiles/id/41957060
info_outline
DR. SHEENA MEADE - INVISIBLE CAGES AND THE CLEAN SLAYE INITIATIVE
06/22/2026
DR. SHEENA MEADE - INVISIBLE CAGES AND THE CLEAN SLAYE INITIATIVE
What happens when one mistake follows you for the rest of your life? Dr. Sheena Meade, CEO of the Clean Slate Initiative, calls it ‘invisible cages’ and for her it was 2004 and an $87 bounced check that led to her arrest. Despite making restitution, that arrest still appears on her record, today, and has created a lifelong lesson about second chances, collateral consequences, and turning her pain into purpose. These barriers are not lost on Sheena as there are millions of Americans still in invisible cages, even long after they've paid their debt to society. It was Sheena’s personal journey that led her to becoming one of the nation's leading voices for automatic record clearance, criminal justice reform, the importance of owning your narrative, and how it is possible to emerge from life's most difficult moments. This is a conversation about resilience, redemption, freedom, and what it truly means to live your legacy out loud.
/episode/index/show/thehustlerfiles/id/41716580
info_outline
DR. TARYN VANDERPYL- AT COFFEE CREEK, NO WOMAN WALKS ALONE
06/21/2026
DR. TARYN VANDERPYL- AT COFFEE CREEK, NO WOMAN WALKS ALONE
At Coffee Creek Correctional Facility in Oregon, there's a simple belief: no woman should walk alone. This week we’re speaking with prison scholar, educator, researcher, advocate and Safe Ride creator, Dr. Taryn VanderPyl. For more than a decade, Taryn has worked alongside incarcerated and formerly incarcerated individuals, listening to their experiences and helping amplify voices too often left out of conversations about justice and rehabilitation. The discussion explores the surprising role of prison Lifers Clubs, the power of peer accountability, and the creation of the Transformative Justice Community (TJC). Taryn shares how a group of incarcerated women helped design CREW, an innovative reentry initiative focused on trauma recovery, safe transportation, housing support, and protecting vulnerable women from exploitation and trafficking upon release. The conversation also examines post-incarceration syndrome, the emotional realities of reentry, the importance of community, and why those with lived experience are often best equipped to guide others through the journey home. This episode is a powerful look at healing, accountability, second chances, and the women working to ensure that no one leaves prison alone.
/episode/index/show/thehustlerfiles/id/41716315
info_outline
CHANDLER DUGAL-BREAKING STEREOTYPES BEHIND AND BEYOND THE WALL
06/14/2026
CHANDLER DUGAL-BREAKING STEREOTYPES BEHIND AND BEYOND THE WALL
"Every success that I have isn't just for me. It's disproving stereotypes." When Chandler Dugal entered the correctional system right after graduating college, few could have predicted what the next three years would look like. During his incarceration, Chandler earned a graduate certificate in Homeland Security Studies, completed a Master's in Public Administration through Penn State and became the first person at Maine Correctional Center to begin remote employment with a Manhattan law firm. And if that wasn’t setting the bar, both literal and figurative higher, he competed in debates, via the National Prison Debate League, against some of the nation's top universities, and began building the foundation for what will soon be a legal career. In this episode Chandler shares his journey through incarceration, education, technology, family support, and personal accountability, and what can happen when correctional systems truly invest in preparing people for life beyond prison. Today, Chandler is a senior paralegal, Director of Operations for the National Prison Debate League, author of a growing Substack chronicling his incarceration experience, and an incoming law student at Northeastern University School of Law.
/episode/index/show/thehustlerfiles/id/41641270
info_outline
A LIFE ASSIGNMENT MONTAGE - ONE QUESTION, MANY ANSWERS
06/11/2026
A LIFE ASSIGNMENT MONTAGE - ONE QUESTION, MANY ANSWERS
For more than three plus seasons, every episode of The Hustler Files has ended with the same question: "At this moment in your life, what do you believe is your life assignment?" The answers have been inspiring, surprising, deeply personal, and often transformative. In this special compilation episode, we revisit some memorable responses from guests across The Hustler Files universe, so many individuals whose journeys have been shaped by incarceration, redemption, second chances, public service, advocacy, leadership, faith, resilience, and personal growth. It is in these reflections that we are reminded that purpose is rarely a destination. Purpose evolves as we learn, heal, serve, and discover new ways to impact the lives of others. Whether you're searching for direction, navigating change, or simply curious about the paths that shape us, every Hustler Files episode offers a glimpse into the wisdom, humanity, and hope that have become our shows hallmark. Because sometimes the most important question isn't what you've done, it’s what you're here to do next.
/episode/index/show/thehustlerfiles/id/41613455
info_outline
SEAN ELLIS -22 YEARS IN PRISON FOR A CRIME HE DIDN’T COMMIT
06/07/2026
SEAN ELLIS -22 YEARS IN PRISON FOR A CRIME HE DIDN’T COMMIT
What happens when the justice system gets it wrong? For Sean Ellis of Boston, he served 22 years for the murder of a Boston police detective, a crime he didn’t commit. After two hung juries and a third conviction, Sean faced the reality of dying behind bars while fighting to uncover evidence that had been withheld for decades. Sean shares the devastating impact of wrongful conviction, the challenges of rebuilding a life after exoneration, and the emotional toll of losing years to a system that failed him. He also discusses his work, now, as Director of the Exoneree Network at the New England Innocence Project, supporting individuals and families navigating the trauma of wrongful incarceration and reentry. This conversation explores justice, resilience, accountability, healing, and what it takes to ensure that the truth is never buried forever.
/episode/index/show/thehustlerfiles/id/41565990
info_outline
JEAN TROUNSTINE - POWERFUL FICTION IN HER NEW BOOK, SOUNDS LIKE TROUBLE TO ME
05/20/2026
JEAN TROUNSTINE - POWERFUL FICTION IN HER NEW BOOK, SOUNDS LIKE TROUBLE TO ME
What happens when decades spent behind prison walls helping others tell their stories inspires a powerful debut novel. In this episode of The Hustler Files, we sit down with longtime prison activist, educator, and author Jean Trounstine to discuss Sounds Like Trouble to Me, a gripping story shaped by the emotional realities of incarceration, abuse, survival, justice, and hope. Jean shares how years of teaching incarcerated women, directing theater programs behind bars and witnessing lives transformed inside the justice system ultimately led her to write her first novel! This conversation explores the real-life experiences that inspired her characters, the emotional complexities of trauma and redemption, and the powerful stories too often hidden from public view. The discussion also takes a deeper look at women’s incarceration, abuse behind prison walls, and the courage of those fighting for justice and change. It's a conversation about storytelling, humanity, and the belief that truth whether through fiction or lived experience can challenge what we think we know.
/episode/index/show/thehustlerfiles/id/41365195
info_outline
DAISY DIAZ - A MOTHERS JOURNEY PLANTING ONE SEED AT A TIME
05/10/2026
DAISY DIAZ - A MOTHERS JOURNEY PLANTING ONE SEED AT A TIME
Behind every prison sentence is a family story. In this deeply personal Mother’s Day episode of The Hustler Files, you’ll meet Daisy Diaz, a justice-impacted woman and mother who shares how it felt to be the ugly duckling of her family and live on the streets beginning at the age of 12. From navigating her addictions, to her rollercoaster of incarceration, and then separation from her own children, Daisy shares a raw and honest account of a life shaped by trauma yet transformed by resilience. She opens up about the emotional toll of “mother-child” visits in prison, and the reality that while one person serves the sentence, families serve time too. Now 11 years clean, Daisy reflects on rebuilding her life, repairing relationships, and stepping into her purpose: helping other women find their way forward by planting seeds for them to follow. This episode is a powerful reminder that second chances don’t just change one life, they can change generations.
/episode/index/show/thehustlerfiles/id/41240705
info_outline
RAHSAAN HALL -THE EMOTIONAL EPICENTER OF A CRIMINAL RECORD
05/10/2026
RAHSAAN HALL -THE EMOTIONAL EPICENTER OF A CRIMINAL RECORD
Opportunity, advocacy, and second chances is always a priority conversation when 1 in 3 Americans are justice-impacted. In this episode we highlight, for an inaugural conversation, Rahsaan Hall, President & CEO of the Urban League of Eastern Massachusetts. This enlightening conversation explores the Urban League’s mission, its national impact with 93 cities under the Urban League umbrella, and its frontline leadership in championing the Clean Slate Coalition. While there is still no Clean Slate law, in place, in Massachusetts, Rahsaan breaks down the realities of criminal records in Massachusetts where access to employment, housing, and opportunity is often shaped by a past that may no longer reflect who someone is today. Rahsaan speaks to the push for Clean Slate legislation, the effort to automate record sealing, and why removing these barriers is critical not just for individuals, but for families, communities, and the broader economy. As we learn from each episode, behind every record is a story and every story has the power to change how we see each other.
/episode/index/show/thehustlerfiles/id/41240460
info_outline
BRANDON DOWNEY & LINDSEY WATZEK - FELONIES TO FUTURES, TWO STORIES OF SECOND CHANCE HIRING
04/30/2026
BRANDON DOWNEY & LINDSEY WATZEK - FELONIES TO FUTURES, TWO STORIES OF SECOND CHANCE HIRING
April is Second Chance Month, and this episode brings two powerful stories that show what can happen when opportunity meets determination. First, we welcome back Brandon Downey, who first joined us in Episode 19 while rebuilding his life after incarceration. Now, several years later, Brandon returns to share how recovery, persistence, and the support of second chance employers helped him transform his future. Today, he is working at the Hampshire County Jail in reentry services, mentoring others, and rebuilding his life as a father. Then, we head to Ohio to meet Lindsey Watzek of JBM Packaging, a company known for its commitment to Fair Chance hiring. Lindsey shares how a felony connected to addiction once left her feeling hopeless, but through the support of a recovery-friendly workplace, she has built a stable, independent life and is now working toward becoming the first female supervisor at her company. Two journeys. Two employers who said yes. And two powerful reminders that when people are given a real opportunity, everything can change.
/episode/index/show/thehustlerfiles/id/41077525
info_outline
TAMMY FRANKLIN - FOUR INCARCERATIONS WASN’T FAILURE, IT WAS FINDING FAITH
04/30/2026
TAMMY FRANKLIN - FOUR INCARCERATIONS WASN’T FAILURE, IT WAS FINDING FAITH
What does it take to rebuild a life after four incarcerations, across four different decades, and stay the course when the path isn’t easy? Today we welcome Tammy Franklin of Prison Fellowship, a woman, mother and wife whose lived experience, at every decade in her life, challenged her with incarceration, until a powerful transformation from God led her to serve others walking the same difficult road. Tammy shares how finding that faith with the only prayer she knew; ‘God, please help me’ was the final turning point to help her rebuild her life and find her purpose, with mentorship and love from the ‘church women with the sparkly eyes’. Now working with Prison Fellowship, Tammy uses her voice to support justice-impacted individuals and families, offering guidance rooted in real-life experience. Her story is one of resilience, redemption, religion; all daily commitments required to stay on her path, one step at a time. This conversation reminds us that second chances are not just given; they are built, step by step, through courage, accountability, hope, and help from above.
/episode/index/show/thehustlerfiles/id/41077290
info_outline
PAUL COWLEY - THIEF, PRISONER, SOLDIER, PRIEST (a book by guest Paul Cowley)
04/30/2026
PAUL COWLEY - THIEF, PRISONER, SOLDIER, PRIEST (a book by guest Paul Cowley)
In this powerful episode we hear the remarkable story of Paul Cowley, a man whose life journey reflects the true power of hope, faith, and second chances. After experiencing the consequences of poor choices that led him into prison, Paul’s life took an unexpected turn when a compassionate military officer offered him a second chance, a unique moment that would ultimately change the direction of his life forever. That act of belief sparked a transformation rooted in faith, discipline, and purpose. Drawing inspiration from Proverbs 13 “Hope deferred makes the heart sick”, Paul shares how hope and God became the foundation of his healing and growth. While for many years he dedicated his life to helping others find hope in the midst of hardship, encouraging those who feel lost to believe that change is possible. Today Paul is the Managing Director of Second Chance Partnership, an organization, in partnership with Iceland Foods, helping ‘prison leavers’ find work and a living wage through the same second chances that once changed his own life. This episode is a powerful reminder that hope can restore what despair once tried to take, and that sometimes one person’s belief in you can change everything.
/episode/index/show/thehustlerfiles/id/41076275
info_outline
JESSE CROSSON - FROM INCARCERATED TO SOCIAL MEDIA INFLUENCER
04/15/2026
JESSE CROSSON - FROM INCARCERATED TO SOCIAL MEDIA INFLUENCER
Meet Jesse Crosson, author of The Best Part of Prison, founder of the Second Chancer Foundation, an inspirational voice for second chances, and now a social media influencer. But that wasn’t how it all started. At just 18 years old, Jesse’s life changed forever after a robbery and shooting led to a 32-year prison sentence. What followed was nearly two decades behind bars, time that could have defined his life in one direction but instead became the foundation for profound personal growth. During his incarceration, Jesse found mentors, discovered the power of reading and writing, earned a college degree, and began reshaping his identity. After serving nearly 19 years, he was granted clemency and released, stepping into a world transformed by technology, opportunity, and responsibility. Today, Jesse uses his lived experience to help others find freedom, not just from incarceration, but from the emotional and mental barriers that hold people back. Through his foundation, public speaking, and widely followed social media platforms, he’s found a voice for good, a voice that says, even the hardest obstacles can become opportunities for growth.
/episode/index/show/thehustlerfiles/id/40888235
info_outline
PRAY’Eon JACKSON - FROM JUVENILE DETENTION TO COMMUNITY LEADER
04/14/2026
PRAY’Eon JACKSON - FROM JUVENILE DETENTION TO COMMUNITY LEADER
Today we meet Pray’Eon, a young emerging leader whose already young life journey reflects the power of second chances and personal transformation. Once involved in the justice system and placed in a juvenile detention center at a young age, Pray’Eon now uses his lived experience to guide others and advocate for positive change. Through resilience, reflection, and mentorship, he has transformed his past into purpose and is now stepping into leadership through his work with the Coalition for Juvenile Justice (CJJ). In this very personalconversation: Pray’Eon shares how his early experiences shaped his worldview, the lessons he learned while navigating the justice system, and his commitment to helping young people avoid the same pitfalls. He speaks openly about unity, responsibility, and the importance of lifting others rather than turning against one another. This episode is a strong and inspirational reminder that leadership CAN grow from adversity, and that the voices of young people with lived experience, like Pray’Eon are essential to shaping stronger, safer communities, everywhere.
/episode/index/show/thehustlerfiles/id/40879710
info_outline
DAVID MILTON & KAYLA GHANTOUS - THE $7 MILLION PRISONERS’ RIGHTS CASE
03/22/2026
DAVID MILTON & KAYLA GHANTOUS - THE $7 MILLION PRISONERS’ RIGHTS CASE
Access to justice stops at the prison gates unless you happen to be incarcerated in one of the few states in the U.S. that has prisoner legal services available. For 9 plaintiffs and another 150 incarcerated men at the Souza-Baranowski Correctional Center in Massachusetts, legal help from Prisoner Legal Services and Hogan Lovells Law Firm was able to offer legal support, and won a $7 million landmark case, against the correctional center. In this episode of The Hustler Files, Lawyers of the Year, in Massachusetts, David Milton and Kayla Ghantous discuss the critical role of organizations dedicated to advocating for prisoners facing legal challenges, while incarcerated. While civil legal services exist for housing, benefits, and family matters, far fewer resources are available to those behind bars, leaving many without the legal support they desperately need. This conversation shines a light on the growing demand for prisoner legal advocacy, the gaps in access to justice, and why these services are more essential than ever, because justice should never depend on where you are.
/episode/index/show/thehustlerfiles/id/40578655
info_outline
MELISSA MILCHMAN - WHEN YOUR SUPERPOWER IS CHANGING JUVENILE JUSTICE
03/18/2026
MELISSA MILCHMAN - WHEN YOUR SUPERPOWER IS CHANGING JUVENILE JUSTICE
As attorney, youth advocate and Executive Director of the Coalition for Juvenile Justice, Melissa Milchman’s “superpower” is bringing people and organizations together to improve the lives of children and youth, and strengthen communities across the U.S. Even today her mother says she’s been wearing her superhero cape since she was a child. In this episode, Melissa shares how collaboration across various juvenile justice systems, through her organization, regardless of politics or changing landscapes, remains essential to protecting young people and creating safer communities. As someone deeply committed to youth advocacy and justice reform, Melissa believes progress happens when leaders stay focused on a shared mission: ensuring children and youth have the support, opportunity, and the community they deserve.
/episode/index/show/thehustlerfiles/id/40527800
info_outline
SHERIFF KEVIN JOYCE - THE ICE ARREST THAT SPARKED A SHOWDOWN
03/08/2026
SHERIFF KEVIN JOYCE - THE ICE ARREST THAT SPARKED A SHOWDOWN
When a routine evening in Portland, Maine turned into a highly publicized arrest involving Federal Immigration Authorities: it sparked questions far beyond one incident and triggered a Sheriff showdown. In this episode, Cumberland County Sheriff Kevin Joyce unpacks the events surrounding the arrest of a correctional officer trainee by ICE during a federal operation known as Operation Catch of the Day. What followed triggered national headlines, protests, and a ripple effect inside the Cumberland County justice system including the removal of all ICE detainees from the county jail, and new scrutiny of hiring practices and cooperation between local and federal law enforcement. Sheriff Joyce shares his firsthand account of the arrest, the complicated legal and jurisdictional issues involved, and why he chose to publicly challenge what he called ‘bush league’ tactics used in the operation. This conversation explores what happens when the Office of Sheriff, federal law enforcement, and immigration policy collide and test both principle and partnership.
/episode/index/show/thehustlerfiles/id/40357690
info_outline
DISTRICT ATTORNEY DAVID SULLIVAN- RESTORATIVE JUSTICE VS. PUNISHMENT
03/02/2026
DISTRICT ATTORNEY DAVID SULLIVAN- RESTORATIVE JUSTICE VS. PUNISHMENT
Northwestern Massachusetts District Attorney David Sullivan is always up for a powerful conversation that challenges conventional ideas of justice, and what it truly means to serve a community. From traditional prosecution to innovative restorative justice practices, Sullivan shares how his office is working to balance accountability with opportunity, giving both victims and offenders, a voice in the process. Rooted in a model that dates back threethousand years, restorative justice shifts the focus from punishment to repairing harm, creating space for dialogue, responsibility, and transformation. Through real-life examples and candid insights, this conversation offers a rare look inside the evolving role of a modern District Attorney and the systems working to create lasting change. This episode is a reminder that justice isn’t always about punishment. Sometimes, it’s about understanding, accountability, and the possibility of a different outcome.
/episode/index/show/thehustlerfiles/id/40281630
info_outline
BROOKE KAUFMAN & GRADY MITCHELL- WHEN HOPE AND ACTION JOIN HANDS
02/22/2026
BROOKE KAUFMAN & GRADY MITCHELL- WHEN HOPE AND ACTION JOIN HANDS
In Part 2 of the conversation with the Seattle Clemency Project, we are joined by Brooke Kaufman, Director of Communications and Author, at the SCP, and client Grady Mitchell. In a deeply personal look at what clemency truly means, not just in policy, but in people’s lives, Grady shares his journey of transformation, purpose, and paying forward the hope he was given. It was his hope that helped him face unimaginable personal challenges with unwavering strength, during his 37-year incarceration. This episode goes beyond the legal process, revealing the human impact of second chances in a system where parole does not exist. Through stories of resilience, advocacy, and belief in human potential, this conversation is just another reminder that redemption isn’t just possible, it’s lived, every day.
/episode/index/show/thehustlerfiles/id/40192065