The Hustler Files with Lisa Reilly - Stories That Challenge What You Thought You Knew

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 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.

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.

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.

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.

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 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.