The Hustler Files Ep 170

The Hustler Files Ep 169

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.

The Hustler Files Ep 168

BEFORE WE CALLED IT SOCIAL JUSTICE, THERE WAS FREDERICK DOUGLASS

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.

The Hustler Files Ep 167

INVISIBLE CAGES: WHEN FREE ISN’T FREE

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.

The Hustler Files Ep 166

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.

The Hustler Files Ep 165

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.

The Hustler Files Ep 164

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 has 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.

The Hustler Files Ep 163

HE SERVED 22 YEARS 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.

The Hustler Files Ep 162

SOUNDS LIKE TROUBLE: FROM PRISON WALLS TO POWERFUL FICTION

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 sat 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.

The Hustler Files Ep 161

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.