The Hustler Files

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...

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 Fo...

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...

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 o...

"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 t...

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 indiv...

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 challen...

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 year...

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...

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...

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...

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 r...

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 hi...

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 defi...

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...

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 landm...

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...

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...

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...

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 hi...

In Part 1 of a two-part conversation, we sit down with leaders from an organization working at the intersection of justice, advocacy, and second chances. The Seattle Clemency Project is a lifeline for so many incarcerated individuals who may have been eligible for parole, if the State of Washington had a parole system.  Musa Abul-Mateen, Executive Director of SCP, and a formerly incarcerated indiv...

From surviving abuse, instability, and homelessness to building a national nonprofit to helpfoster children, this is the powerful journey of Rob Scheer, founder of the organization Comfort Cases. After experiencing firsthand the harsh realities of the foster care system where children often carry their belongings in trash bags, Rob turned his story into a movement focused on restoring dignity, com...

From a felony to the CEO of a Global foundation, Michelle Cirocco knows firsthand that second chances work, because she lived it. After serving time in prison, Michelle rebuilt her life by taking a job at a call center, inside a local correctional facility. Today, she leads the Televerde Foundation, helping incarcerated and formerly incarcerated women gain workforce credentials, employment, and lo...

Tore Price was serving time behind the wall, in Michigan, when he learned about the Inside-Out Prison Exchange Program being taught by the University of Michigan. According to Tore, there were 1,000 incarcerated individuals who rushed to sign up for the weekly class with students from the University. With only 15 slots available lady luck was definitely on Tores side. When asking him to describe t...

While prisons in the United States offer a variety of educational pursuits, it only took a brief conversation between a college educator and an incarcerated individual for the Inside-Out Prison Exchange Program to be born. Four decades later, the Inside-Out Prison Exchange Program is still going strong, thanks to Founder, Lori Pompa. Lori's vision to bring her students, from Temple University to i...