In this crossover episode, we present a segment from SiriusXM 45's "Sway In The Morning", in which Sway Calloway reflects on his emotional visit to the San Quentin Rehabilitation Center, sharing firsthand stories about the humanity, intelligence, and potential of incarcerated individuals. The conversation explores how rehabilitation programs focused on education, skilled trades, entrepreneurship, and emotional support can dramatically reduce recidivism while improving public safety. Listeners will hear moving calls from former corrections officers, family members of incarcerated individuals, and parents using the discussion as a teaching moment for their children. The episode also examines systemic issues surrounding sentencing, reentry barriers, literacy, poverty, and generational incarceration, while highlighting how hope, mentorship, and practical opportunity can fundamentally change lives.

(00:00:00) Introduction to Sway’s visit to the San Quentin Rehabilitation Center and The Last Mile’s mission
(00:01:38) Sway describes the atmosphere inside San Quentin and the emotional reactions from incarcerated men during his visit
(00:04:24) Discussion about empathy, rehabilitation, and The Last Mile’s impact on recidivism and public safety
(00:07:14) Former corrections officer and social worker discusses prison conditions, resources, and humanity inside the prison system
(00:10:20) Former federal prison recreation director explains how music programs unified incarcerated people and created hope
(00:13:47) Mother calls with her son after a school suspension and uses the conversation as a lesson about choices and consequences
(00:19:22) Sway reflects on prison, bad decisions, and the importance of rehabilitation programs for reentry into society
(00:20:00) Caller shares his cousin’s journey through incarceration, education, and preparing for release after decades in prison
(00:24:25) Sway discusses San Quentin’s rehabilitation initiatives, including service dog programs and the removal of death row facilities
(00:25:53) The Last Mile co-founder Chris Redlitz joins the show to discuss prison reform, education, and the transformation of San Quentin
(00:28:37) Chris Redlitz shares success stories of formerly incarcerated students becoming software engineers at major tech companies
(00:32:52) Discussion about recidivism, workforce training, skilled trades, and preparing incarcerated people for modern employment opportunities
(00:36:32) Sway and Chris discuss hope as a catalyst for transformation and rehabilitation inside prison systems
(00:39:00) Sway and the crew reflect humorously on the prison visit and the realities of prison yard culture and invisible boundaries
(00:42:00) Mike Muse discusses literacy, parenting, education gaps, and the school-to-prison pipeline affecting underserved communities

Information On Sway In The Morning: https://www.siriusxm.com/hosts/sway-calloway
Sway's Youtube: https://www.youtube.com/channel/UCuS96jkLKpTaGB_OWnwZV_A

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

Prison is designed to be a fundamentally abnormal experience—one that removes autonomy, suppresses individuality, and restructures daily life around control and compliance. Yet at the end of that experience, we expect people to return to society as self-directed individuals capable of making decisions, building relationships, holding jobs, and forming identities beyond incarceration.

This episode explores that central tension: if the daily experience of prison is misaligned with the outcomes we want, then the structure of daily life inside facilities becomes one of the most important variables in criminal justice reform. In collaboration with the Brennan Center for Justice, this is part one of a two-episode series exploring their recent national report examining innovative prison reform efforts across the United States focused on normalization, dignity, safety, and rehabilitation.

Featuring insights from LB Eisen of the Brennan Center for Justice, Nick Turner of the Vera Institute of Justice, Restoring Promise director Chloe Aquart, and former participant turned researcher Christopher Belcher, this episode focuses on the foundational ideas highlighted in the report. Through the Restoring Promise initiative, we examine redesigned housing units for young adults built around mentorship, responsibility, restorative practices, and meaningful out-of-cell time.

The conversation explores what it means to humanize correctional environments—creating spaces where people are treated as individuals capable of growth, where staff operate as mentors and stabilizers, and where safety emerges from relationships rather than coercion—suggesting that when incarceration is organized around dignity, prisons can better prepare people for life after release while improving conditions for both residents and staff.

Episode Resources:

• Brennan Center for Justice — Source of the national prison reform report discussed throughout the episode
• Vera Institute of Justice — Developer of the Restoring Promise model
• Restoring Promise — Primary case study for humanizing prison culture
• The Last Mile — Referenced as a workforce and education program example
• Designing for Dignity

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

Episode Outline:

(00:00:00) Tara Trask introduces Gio Hernandez Romero and his wrongful conviction case.
(00:03:17) Growing up in Los Angeles and his family background.
(00:08:39) How police label young people as gang members.
(00:14:19) Being tried as an adult and facing a 50-years-to-life sentence.
(00:16:47) Spending six years in jail before conviction and sentencing.
(00:18:00) Adjusting to life in prison and the loss of hope.
(00:19:00) How his sister and family kept him motivated to keep learning.
(00:23:12) Loyola Law School’s Juvenile Innocence and Fair Sentencing Clinic takes his case.
(00:25:00) The Conviction Integrity Unit’s role in reopening and exonerating his case.
(00:29:14) Broader discussion on wrongful convictions and needed criminal justice reform.
(00:33:00) Joining The Last Mile and learning to code while incarcerated.
(00:35:30) How coding and education restored his purpose and self-worth.

(00:37:49) Returning to freedom and facing culture shock after 17 years.
(00:40:12) Learning to live as an adult for the first time and gaining independence.
(00:49:10) Sharing a message of hope and perseverance with others inside.
(00:55:06) The cell phone evidence that proved his innocence.
(00:57:00) Closing thoughts on gratitude, healing, and the power of reform.

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

April Bosworth is a graduate of The Last Mile program and now a Website Specialist at Televerde, where she previously served as a teaching assistant inside of prison helping other incarcerated women learn coding. Michelle Cirocco is the Chief Social Responsibility Officer at Televerde and the Executive Director of the Televerde Foundation, organizations that for nearly 30 years have pioneered employment and reentry models for incarcerated women. Under their leadership, Televerde has grown into a global B2B sales and marketing firm whose clients include Microsoft, Adobe, Dell, and SAP, offering incarcerated women the opportunity to build careers that lead to long-term success after release. Their work has supported thousands of women, resulting in a 95% post-release employment rate and less than 2% recidivism.

In this conversation, April shares how she discovered coding through The Last Mile, overcame self-doubt, and built confidence by learning problem-solving and resourcefulness—skills that carried her into a corporate role while still incarcerated. Michelle reflects on her own journey through prison and describes how programs like Televerde and The Last Mile provide not just training but also financial independence, dignity, and a bridge to meaningful careers after release. Together they explore critical issues such as imposter syndrome, the stigma of incarceration, and the transformative power of being able to earn a fair wage behind bars. For those interested in criminal justice reform, this episode offers a compelling look at scalable models that reduce recidivism, break generational cycles of poverty, and prove that second chances create value for individuals, families, and businesses alike—making it essential listening for advocates, employers, and policymakers.

Episode Outline:

(00:00:00) Introduction and Guest Backgrounds

(00:01:20) April’s Journey from The Last Mile to Televerde

(00:03:20) Learning Resourcefulness and Problem-Solving in Coding

(00:06:00) Building Confidence Through Asking Questions and Making Mistakes

(00:07:00) Michelle on the Power of Safe Learning Environments in Prison

(00:09:00) The Origins and Growth of the Televerde Model

(00:11:30) Proven Success: Employment, Salaries, and Reduced Recidivism

(00:13:00) Bridging the Gap Between Incarceration and Reentry

(00:14:30) The Role of Loyalty, Gratitude, and Overcoming Imposter Syndrome

(00:16:30) Televerde’s Culture of Belonging and Encouragement

(00:17:30) Messages to People Still Incarcerated – Using Time to Transform

(00:20:00) Michelle’s Personal Story and Life-Changing Advice from Prison

(00:23:00) Explaining Televerde’s Business Model and Client Partnerships

(00:26:00) Televerde Foundation, Employment Rates, and Low Recidivism

(00:28:00) April on Financial Independence While Incarcerated and Beyond

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

In this interview, Shelley shares her extraordinary journey from growing up in a home shaped by addiction to battling her own struggles with substance abuse, incarceration, and federal charges before finding sobriety and purpose. She recounts the turning point of discovering she was pregnant while incarcerated, her persistence in seeking treatment despite systemic barriers, and the faith-driven mindset shift that became the foundation of her recovery. Shelley details the challenges of reentry, including her fight against discrimination during Microsoft’s hiring process and the pivotal role of San Francisco’s Fair Chance Ordinance in securing her first job in tech.

Episode Outline:

(00:00:00) Introduction and Shelley’s Early Life in a Home Shaped by Addiction
(00:04:00) Bartending in North Dakota and Returning to Drug Use
(00:06:00) Entering the Drug Trade and Federal Investigation
(00:09:00) Sting Operation, Surveillance, and Arrest
(00:14:00) Jail Time, Detox, and Facing Withdrawal
(00:16:00) Pregnancy, Sobriety, and Turning Toward Treatment
(00:19:00) Fighting for Admission into a Faith-Based Program
(00:21:00) Surrender, Mindset Shift, and Beginning Recovery
(00:24:00) Transition to Reentry and Dreams of Working in Tech
(00:25:00) Microsoft Job Application and Background Check Challenge
(00:28:00) Invoking the San Francisco Fair Chance Ordinance
(00:31:00) Securing the Job and Excelling at Microsoft
(00:33:00) Rising to Top Sales Rep and Winning Microsoft’s Gold Club Award
(00:35:00) Microsoft Changes Hiring Policies and Launches LEAP Program
(00:37:00) Advocacy for Fair Chance Hiring and Broadening Opportunities
(00:41:00) Founding Winner’s Circle: Mindset, Literacy, and Sales Training
(00:44:00) Message to Incarcerated Listeners: Hope, Programs, and Change
(00:45:00) Expanding Winner’s Circle to 25 Prisons Nationwide
(00:46:00) Closing Reflections on the Power of Stories and Programs

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

Dr. James JC Cavitt is the Executive Director of Project Rebound at CSU Fullerton, a transformative program supporting justice-impacted students as they reenter academic life and broader society. He was previously a founding student of The Last Mile’s inaugural class at San Quentin State Prison, where he began his remarkable journey from incarceration to academia. Today, Dr. Cavitt holds a Doctorate in Marriage and Family Therapy, an accomplished spoken word poet, and a nationally recognized advocate for criminal justice reform. His scholarly work centers on the impacts of incarceration on emotional intimacy post-release—a subject deeply informed by his own life experience.

In this episode, Dr. Cavitt shares an intimate and powerful narrative that begins with a life sentence at age 17 and culminates in crossing the stage as “Dr. Cavitt” decades later. He speaks candidly about the emotional weight of having his dream of becoming a pediatrician denied due to a felony conviction, and how mentorship, community, and programs like The Last Mile helped him reimagine that dream through the lens of healing and mental health. Particularly compelling is his concept of the “trauma equation,” which underscores the importance of understanding the path that leads to incarceration—not just the outcome. For those passionate about systemic solutions, Dr. Cavitt’s reflections on confronting trauma, reclaiming identity, and pursuing education inside prison walls offer a profound blueprint for reform

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

This week, Tara visits Homeboy Industries, an organization that helps gang members and formerly incarcerated people transition into productive, independent lives. Hear her captivating conversation with former CEO of Homeboy, Tom Vozzo.

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche and Ana Sessions at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org