FROM PRISON TO PURPOSE WITH THE POWER OF GRACE
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
Release Date: 10/08/2025
FROM INCARCERATED TO INFLUENCER: THE JESSE CROSSON STORY
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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,...
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FROM INCARCERATED YOUTH TO COMMUNITY LEADER
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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...
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WHEN CLASS ACTION WINS OUT OVER RETALIATION
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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...
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WHEN YOUR SUPERPOWER STANDS AT THE INTERSECTION OF JUVENILES & JUSTICE
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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...
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SHERIFF CALLS ICE ARREST ‘BUSH LEAGUE’
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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...
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ONE SYSTEM, TWO PATHS; RESTORATION VS. PUNISHMENT
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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,...
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WHEN HOPE MEETS ACTION: LIVES RECLAIMED
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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...
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FINDING HOPE IN A NO-PAROLE STATE
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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 individual, and Jennifer Smith, Co-Founder and Development Director of SCP explore the shared humanity behind the system, challenging assumptions and the critical work being done to support...
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FOSTERING CHANGE, ONE CHILD AT A TIME
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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, comfort, and a sense of worth to kids in crisis. In this conversation, Rob shares the deeper challenges within foster care, including trauma, invisibility, and the long-term impact on children who...
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IT’S OKAY TO SAY THE F WORD
The Hustler Files with Lisa Reilly - Stories That Will Challenge What You Thought You Knew
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 long-term success. With over 5,000 women served and a recidivism rate that is under 2%, Televerde’s model is transforming reentry outcomes and economic impact across states like Arizona and...
info_outlineWhen Cary Sanders speaks, his calming tone and gentle cadence would never give you a clue that he had been arrested 17 times by the time he was 17. Cary’s journey from his tumultuous past and time behind the wall to his current position as CEO of JUMPSTART South Carolina can only make one believe that Cary’s life has been guided by a higher power, and he would agree. At JUMPSTART, Cary leads a transformative re-entry program that begins in prison, highlighting the power of faith and second chances while helping break cycles of crime and addiction. Tune in to hear his inspiring journey of hustle, redemption, and impactful work he and his volunteers are doing to not only help others find their purpose but to support those returning to the community with housing, jobs, and other re-entry services.