Reflections on a Conversation with a Man Who Spent 25 Years in Prison and Chose Love Over Fear
I recently sat down for lunch with Sam Harris at Saltine in Norfolk. Sam is someone I met at the 2024 Returning Citizens Luncheon, and his story has stayed with me ever since.
Sam spent 24 years, 8 months, and 10 hours in prison. But that’s not what makes him remarkable. What makes Sam remarkable is what he did with those years, and what he’s doing now.
While most of the world operates from fear when it comes to formerly incarcerated people, Sam chose a different path. He chose love. Not the soft, sentimental kind, but the fierce, practical kind that shows up as service.
Sam went in during his early 30s and came out in his 50s to a world that had completely changed around him. But here’s what makes Sam different: he understood something most people miss.
Reentry doesn’t start when you walk out of prison. It starts on day one inside.
A World Transformed
“When I went in, smart phones weren’t really a thing,” Sam told me. “I came out and suddenly everyone had smartphones. There was email, text messaging, social media. Everything had changed.”
But it wasn’t just technology. It was everything. Cash had been king when he went in. Now it was almost useless. Kiosks had replaced human cashiers in many places, and Sam found himself afraid to use them. What if he did something wrong? What if it looked like he was trying to steal?
“If I made a mistake at a kiosk, it would just be an honest mistake,” Sam explained. “But for someone like me, if something went wrong and it looked like I was trying to steal, that could potentially be a third strike. That’s a life sentence over a simple mistake.”
The fear is real. The stakes were impossibly high. And the system offered almost no preparation.
Fear vs. Love in the System
The system Sam navigated was built on fear. Fear of crime, fear of the other, fear that people can’t change. That fear creates policies that warehouse rather than heal, that punish rather than restore.
But Sam chose to operate from love. While other men might have become bitter or withdrawn, Sam became a counselor, a peer support specialist, a mentor. He started men’s groups because he understood that healing happens in relationship, not isolation.
Sam told me about trying to open a bank account 24 hours after his release. He had two forms of ID, but the bank wanted three. His social security card wasn’t considered valid identification.
“I told them, ‘Look, I’m 24 hours out of prison,’” Sam said. “You could see the reaction. Suddenly I had the Scarlet Letter on me.”
This is what reentry looks like for most people. You’re handed $40 and told you’re on your own. You’re expected to navigate a world that’s completely different from the one you left, with systems that seem designed to trip you up.
But Sam had prepared differently.
The Courage to Go Back
While we were talking, Sam mentioned he’d recently gone back to the prison where he’d served some of his time. He went through the front door this time, something he’d never done before.
“When that gate closed behind me, I felt this fear inside me,” he said. “But I was there to help.”
Think about the courage that takes. Going back through those gates, hearing that sound, feeling that fear, all to help other men who are where you used to be. Sam does this work because he knows that the system is broken.
The question isn’t whether people deserve a second chance. The question is whether we’re going to give them the tools to succeed or set them up to fail.
Building Something Different
Now Sam is co-founder of the Re-Entry & Recovery Alliance, a nonprofit he started with Keira Moore Majeed. Their mission is simple: “Breaking barriers, building futures. Empowering second chances for those impacted by incarceration.”
They provide housing, advocacy, substance use support, education, mental health services, and comprehensive reentry support. But more than that, they understand what Sam learned in prison: healing has to start before you walk out the door.
“The one piece of advice I give everyone,” Sam told me, “is get yourself a therapist.”
Here’s a Black man who spent almost 25 years in the system and he is telling other men that therapy is the answer. This flies in the face of everything our culture tells men about strength and self-reliance. But Sam knows that fear-based masculinities keep men isolated and broken. Love-based healing happens in community.
The Real Question
“People talk about needing to pay our debt to society,” Sam said. “But how do you pay your debt to society from inside a cell? How is being locked away from society serving anyone?”
Sam’s point hit me. Real debt to society gets paid when people are healed, transformed, and contributing. When they become mentors instead of statistics. When they break cycles instead of continuing them.
The crimes that land people in prison are almost always rooted in trauma, addiction, and desperation. Until we address those root causes, we’re not solving anything. We’re just warehousing human potential.
What Healing Actually Looks Like
I feel like Sam’s approach through the Re-Entry & Recovery Alliance is different. They believe reentry should start the moment someone enters the system, not when they leave it. They focus on empowerment, not punishment. They understand that successful reintegration requires support, not abandonment.
Most importantly, they know that healing is possible. Sam is living proof. So is every person their organization helps transition back into community.
This isn’t just about individual transformation, though that matters enormously. It’s about recognizing that public safety comes from healing, not warehousing. That communities are stronger when everyone has a chance to contribute. That second chances aren’t just good for the people receiving them, they’re good for all of us.
The Bigger Picture
Sitting across from Sam at that Norfolk restaurant, I was struck by something. Here was a man who had every reason to be bitter, angry, hardened by his experience. Instead, he’d chosen to dedicate his life to helping others avoid the pitfalls he’d faced.
That’s what love in action looks like. Not the romanticized version, but the roll-up-your-sleeves, walk-back-through-those-scary-gates, build-something-better kind of love.
Sam’s story reminds me why this work matters. Not just for the people directly impacted, but for all of us. Because when we create systems that heal instead of harm, everyone wins.
If you want to learn more about Sam’s work, check out the Re-Entry & Recovery Alliance at rraalliance.com. It think they’re doing the kind of work that actually makes communities safer by making people whole.
Because real safety doesn’t come from locking people away. It comes from helping them find their way home. At least that is what I think.