Podcasts: The Hustler Files
The Hustler Files
The Hustler Files – Storytelling That Will Challenge What You Thought You Knew
Join creator and host Lisa Reilly every Saturday morning from 9:32 AM to 10:00 AM, streaming here on WHMP.com, or find us on your favorite podcast platform. Each week, we bring storytelling with grit, purpose, and possibility to break stigmas, reshape narratives, and amplify the voices of justice-involved individuals, advocates, and change-makers. We’ll explore the criminal justice system, addiction recovery, domestic violence, human trafficking, fair-chance employment, and prison reform through powerful storytelling and candid interviews that bring humanity to issues too often overlooked.
Please reach out with questions or comments to thehustlerfiles@outlook.com
The Hustler Files Ep 160
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.
The Hustler Files Ep 159
FROM 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.
The Hustler Files Ep 158
FOUR 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 who’s 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, and 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.
The Hustler Files Ep. 157
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.
The Hustler Files Ep 156
FROM INCARCERATED TO INFLUENCER: THE JESSE CROSSON STORY
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.
The Hustler Files Ep 155
FROM INCARCERATED YOUTH 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 personal conversation, 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.
The Hustler Files Ep 154
WHEN CLASS ACTION WINS OUT OVER RETALIATION
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.
The Hustler Files Ep 153
WHEN YOUR SUPERPOWER STANDS AT THE INTERSECTION OF JUVENILES & 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.
The Hustler Files Ep 152
SHERIFF CALLS ICE ARREST ‘BUSH LEAGUE’
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.
The Hustler Files Ep 151
ONE SYSTEM, TWO PATHS; RESTORATION 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 three thousand 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.
