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The Power Of A Second Chance

Greg Eskridge speaking at an Uncuffed graduation in San Quentin in 2024

What does it mean to receive a second chance?

Imagine a life where your past forever casts a shadow over every new step, where your mistakes define your future, where every door is shut to you, and where all potential next stages are always several permanent hurdles away. This level of hopelessness would stop most of us from even trying to move forward.

This is why second chances matter. A second chance is more than a do-over; it’s a doorway, an opportunity to express parts of yourself you may never have known before. For me, KALW and Uncuffed opened this doorway twelve years ago, giving me the chance to tell my story in ways I hadn’t imagined. In that media center at San Quentin, I was not just a voice; I was a human being with insights, pain, and dreams, and KALW gave me the chance to be seen and heard as such.

From the beginning, these audio platforms became more than a creative outlet for me; they became transformative spaces. Through Uncuffed, I found myself reaching out to communities I had left behind, connecting with people who knew the weight of my story and still saw me as worthy. When I sat in front of that microphone, it became a canvas, allowing me to paint a picture of a future unchained from my past mistakes. I learned to strip away layers of self-doubt and to find the humanity that was always within me, waiting to emerge.

Greg with his sister Keri Washington

Before I came home, KALW didn’t just offer me a platform—they gave me something far more profound through Uncuffed: a sense of purpose, security, stability and the dignity of being seen. The staff saw my humanity and the value in my story, not my past mistakes. While prison is a place designed to dehumanize, to isolate, to make people feel as if they are nothing more than the worst thing they’ve ever done, KALW and Uncuffed didn’t accept that. They saw potential in me and invested in it. They offered me my first real job, a role that isn’t about erasing my past but about building on it. And when I was released, the Uncuffed and KALW staff—past and present—were there at the gate, arms open wide. They weren’t just colleagues; they were family.

But this brings up a question: what does society truly believe about second chances? Are they genuine, or do they come with invisible strings attached, forever tying us to our pasts? Too often, society freezes us in time, locking us in a single moment, a single choice. Can we imagine the toll that takes on someone’s spirit, the pain of being reduced to one decision? I’m not asking for my past to be forgotten. All I ask is to be seen fully—not defined by that one choice, but as someone who has grown beyond it. Can we grant each other that kind of grace? Can we look at each other and see the whole story?

Greg speaking at St. Ignatius High School

Through the radio, I found a path to heal. Speaking my truth wasn’t just cathartic; it became a bridge to others. I realized that my redemption wasn’t just mine; it was part of a larger, shared journey. I began to see myself not only as a person who had faltered but as someone who could guide others to light, to understanding. These platforms taught me to listen deeply, to understand the weight of someone else’s silence, to recognize the courage it takes to share a painful truth.

These second chances are rare, but they are the seeds of transformation. With every broadcast, with every conversation, I am reminded that a second chance is a sacred gift—a call to rebuild, to lift others up, to share honestly. These opportunities redefine what’s possible, and through them, I’ve learned that we can reshape not just ourselves but the communities we touch.

This piece was brought to you by KALW Speaks, a monthly series of essays from KALW staff and contributors, exploring the ideas that drive our work. Each of these essays reflect our commitment to innovation and invites you into a deeper conversation about the future of public media.

Learn more: From A Whisper To A Roar.

Greg Eskridge is a founding member of the Uncuffed radio program and podcast. For over a decade in San Quentin, Greg fostered an atmosphere of professionalism and dedication which led to the program producing great content and winning numerous awards. On July 23, 2024, Greg was released from San Quentin prison after serving 30 years and 25 days. He was welcomed by family, friends, and both current and former members of the KALW team. A few months later, Greg began working full-time as Uncuffed’s first Leadership Fellow, preparing him for leadership roles in the program. Greg looks forward to continuing to elevate the voices of system-impacted individuals.