• A deeper understanding of the lasting impact of solitary confinement
• Insight into the internal work required for successful reentry
• A vision for how lived experience can inform meaningful justice reform

In this episode of the Prison to Promise Podcast, Dr. Craig Waleed speaks with Gregory Winbush about rebuilding life after incarceration. Gregory shares how family support, mentorship, and personal determination helped him move forward after prison and eventually receive a pardon that restored opportunities and rights. The conversation explores the challenges of reentry, the importance of pro-social support systems, and Gregory’s current work helping others clear their records and find hope beyond their past mistakes.

What does it really take to rebuild a life after prison?

In this powerful episode of the Prison to Promise Podcast, host Craig Waleed sits down with Charlotte-based community leader and reentry advocate Shaheedah Ross.

After spending years incarcerated, Shaheedah Ross emerged determined to transform her experience into purpose. Today, she works to create pathways for justice-impacted individuals seeking opportunity, dignity, and a second chance.

In this conversation, Dr. Waleed and Shaheedah discuss:

• The reality of rebuilding life after incarceration • The hidden barriers people face during reentry • How lived experience shapes authentic leadership • Why communities must rethink second chances • Turning personal adversity into collective impact

This episode is a powerful reminder that people are more than the worst moment of their lives—and that leadership can rise from places society often overlooks.

If you believe in second chances, redemption, and community transformation, this conversation is for you.

• Book Launch: April 4, 2026 at Allegra Wesbrook Library, Charlotte, NC

In this episode of the Prison to Promise Podcast, host Dr. Craig Waleed sits down with prison reform advocate and Justice Ambassador Jesse Crosson for a powerful conversation about transformation, accountability, and the long road from incarceration to purpose.

Jesse shares his deeply personal story of entering the criminal legal system as a young man and spending years behind bars before experiencing a profound shift in how he understood responsibility, harm, and redemption. Through education, faith, and mentorship, Jesse began rebuilding his life from the inside out.

Today, Jesse works to advance criminal justice reform and restorative justice practices across the country. In this conversation, he reflects on the importance of human dignity, the challenges of reentry, and why people closest to the problem are often closest to the solution.

This episode explores what it means to confront the past honestly while working to build a future rooted in accountability, healing, and community transformation.

Understanding Freedom, Community, and the Power of Walking With One Another

In this deeply reflective episode of Prison to Promise, Dr. Craig Waleed sits down with Lorenzo Trout for an honest conversation about what freedom really means—long after the prison gates open.

Lorenzo shares his journey of navigating life after incarceration and the quiet, often unseen challenges that come with rebuilding identity, trust, and purpose. Together, they explore the essential role of community support, mentorship, and human connection in sustaining real change. From formative lessons learned in a juvenile detention center to the transformative impact of equine therapy, Lorenzo reflects on the experiences that helped reshape how he sees himself and the world around him.

This episode also lingers on the power of “small seeds”—the moments, relationships, and acts of care that may seem insignificant at first but grow into life-altering forces over time. Above all, Lorenzo offers encouragement to those still in the process of becoming—reminding us that transformation is rarely loud or linear, but it is always possible.

This is a conversation about freedom beyond release, healing through connection, and the courage it takes to walk alongside others while learning how to walk whole again.

From Felon to Forbes: The Powerful Transformation of Trent Griffin-Braff

In this inspiring episode of Prison to Promise, Dr. Craig Waleed sits down with entrepreneur and change-maker Trent Griffin-Braff to explore a journey defined by loss, growth, and extraordinary transformation.

Trent opens up about his early life and the challenges that led him into the system, as well as the life-altering moment of missing his daughter’s birth—a catalyst that sparked his commitment to change. Listeners will hear how Trent went from working as a janitor to becoming a successful entrepreneur, ultimately earning recognition from Forbes.

This episode dives deep into:

• Breaking cycles and redefining success

• Turning pain into purpose

• Building businesses that create community impact

• Finding your own path—no matter your past

• Encouragement and hope for those currently incarcerated

Trent’s story is a testament to what’s possible when determination meets opportunity. Whether you’re navigating reentry, supporting someone who is, or simply looking for a story of resilience and redemption, this episode will challenge, inspire, and uplift.

🎧 Tune in to hear how one man turned a prison sentence into a platform for purpose—and how you can begin rewriting your own story.

In this powerful episode of Prison to Promise, Dr. Craig Waleed sits down with Kevin Palmer, founder of Eighteen WHEELIN CDL Training, to explore how trucking can become a true pathway to second chances for formerly incarcerated individuals. Kevin shares his personal turning point—how trucking became more than a paycheck and instead offered stability, structure, and purpose after incarceration. Together, they unpack what reentry really requires: not just a job, but the wraparound supports, mentoring, and advocacy needed to help people succeed in a highly regulated and often exclusionary industry.

This episode dives into: Work as reentry, not just employment. Navigating background checks, insurance barriers, and employer bias. Challenging systemic obstacles in CDL and transportation careers. Redefining long-term success after incarceration. Building futures that reduce recidivism and strengthen communities.

Kevin’s work shows what’s possible when lived experience meets purpose-driven leadership. Whether you’re impacted by incarceration, working in reentry, or interested in workforce development that actually changes lives, this episode offers insight, inspiration, and real-world solutions. Tune in to hear how the open road can become a road to restoration—and how reentry can be reimagined as opportunity, not limitation.