From Prisoner to Prison Owner: Kerwin Pittman’s Blueprint for Second Chances

Beer Runner to Advocate

Kerwin Pittman grew up military. Both parents served in the Air Force, and he was born in Germany before the family moved to rural North Carolina when he was three. But by age 11, after a major flood forced them to relocate to Raleigh, Kerwin found himself in his grandmother’s “liquor house”, what they call social houses now. “I actually was a beer runner growing up in my grandmother’s liquor house and entertainment for those who kind of indulge a little too much,” Kerwin told me. “We would do Steve Urkel dances, different things. And they would give us money.”

The entertainment was fun, but the neighborhood wasn’t safe. Every night brought the same ritual. “My uncle would scream out, hit the floor when we heard gunshots. And so we have to jump on the floor,” Kerwin explained. “So my memories was fun of my uncle’s voice. Screaming, hit the floor.” They’d drop wherever they were, getting in the bathtub, playing, whatever, because bullets could come through the house at any moment.

At 13, Kerwin met gospel singer Shirley Caesar while selling drugs down the street from her church. She pulled up in her Jaguar, called him over, and invited him to visit her church. Years later, after Kerwin became an advocate, Caesar reached out asking him to help one of her nephews who was locked up in Virginia. She never knew he was that same young boy.

The Path to 11 and a Half Years

Kerwin went all the way into street life. “Kerwin Pittman is kind of the guy if he’s gonna do something, he’s gonna go all the way in,” he said. His father had “succumbed to the drug epidemic,” and his mother was a disabled veteran. The role models he found were “those who was able to kind of perpetrate violence was the ones that was respected the most.”

The nightmare landed when a fight with a rival gang turned into a shooting. Though Kerwin never fired a shot himself, he was charged along with others who did. “Yeah, I might didn’t shoot a shot, but it was just a lot of the things that I had got away with. My past really atonement catching up for me,” he reflected. He took a plea deal: 11 and a half to 14 and a half years.

At 19, walking into prison at 125 pounds and five-foot-eight, Kerwin expected the worst. But the older men surprised him. Instead of preying on the young guys, many wanted to mentor them. One man called 99, because “the system gave me 99 years”, would tell Kerwin on the yard: “Mighty, make the main thing the main thing. When you go home, make sure you always making the main thing the main thing.”

365 Days in the Hole

Kerwin got moved around constantly during his sentence, over 10 different facilities, shipped 10 times. He went to every custody level twice and got busted back from each one. The worst stretch was 365 days in solitary confinement.

“We’re talking about a room the size of a parking space,” Kerwin said. He was alone 23 hours a day, coming out only for showers in full restraints, “shackled from my feet to my waist, to my hands. And you can’t essentially wash with your handcuffs to your waist.”

After six or seven months, a unit manager allowed him a phone call. They put him in full restraints, ankle shackles, chains to his waist, hands cuffed in a locked box, and shuffled him to the office. His mother answered. She started crying immediately. His grandmother was there too. “I said, great, she started crying. I said, I got a two for one. I called both of them.”

Walking back to his cell after that 15-minute call changed everything. “As they began to put me back in my cell, it was like shackles began to come off of my mind. And I really realized that I was doing, yes, I was doing time, but the people that loved me the most was doing time with me. And I was hurting them.”

The Light Switch Moment

That phone call was “like a light switch.” Hearing his mother and grandmother cry replayed in Kerwin’s head every time he thought about acting up. “I really realized that I had to change not only for me, but for my family. Like it was other people who was depending on my success or failure when I came home.”

Kerwin spent his last months in the hole reading and studying. Two hours on psychology. Two hours on history and John Henrik Clarke. Two hours on military strategy. Hour of working out. Western novels for entertainment. And planning a nonprofit in his mind.

When he finally got out of solitary, he wasn’t the same person. His friends wanted to talk about BET Awards and Nicki Minaj. “I wanted to talk about Socrates and philosophy and different things. So the people who are hung around with begin to shift.”

First Week Out, First Press Conference

Before release, the chaplain asked what Kerwin planned to do. “I’m going to be an advocate. I’m going to be an activist,” he said. The chaplain looked at him like a parent hearing a kid say they want to be an astronaut. “What’s your plan B?” the chaplain asked. “It ain’t no plan B. That’s what I’m going to do.”

Within a week of coming home in 2018, Kerwin met advocates through a friend who was dating someone with an organization in Raleigh. The next week, he was in front of cameras doing a press conference about law enforcement issues. He’d found his core team.

Buying the Prison That Once Held People Like Him

Today, Kerwin runs Recidivism Reduction Educational Program Services and owns something unprecedented: a decommissioned prison. He’s recognized as the first formerly incarcerated person in U.S. history to purchase a decommissioned prison and transform it into a recidivism reduction campus focused on workplace development, behavioral health, education, and second chances.

The transformation happened because Kerwin made “the main thing the main thing.” He stayed away from substances and anything he saw as potential downfalls. He connected with resources and people around him. Within a few years, thousands were following his work. The governor asked him to join a criminal justice reform commission. He became a lobbyist, got bills passed, spoke at bill signings.

“Never give up on yourself. Never count yourself. Never count yourself out,” Kerwin told me. “Never think you’re not good enough. Never think you don’t belong in these spaces because you do belong. And just because you made a mistake or a bad decision, it does not amount to your life, your total life sum. It is an opportunity for redemption.”

From beer runner to prison owner. That’s what happens when someone decides the main thing is the main thing.