When is a “debt to society” fully paid? When can we move beyond the choices made by a child to see that, maybe, their “choices” were inevitable?

Stephen spent upwards of 23 years in prison. He was inside for most of his 20s, all his 30s, and a lot of his 40s as well. He doesn’t deny the necessity of that time. He doesn’t make excuses for the crimes he committed, nor does he downplay them. He did bad things. He knows it.

But today, even now, this Turning Leaf graduate is dealing with the consequences of those actions. He was just let go from a job at which he was excelling after failing a background check. His crimes were committed two decades ago.

This is Stephen’s story.

* * * *

To understand Stephen’s story, you need to know the setting. Stephen was born in 1973 in Overtown, a historic district in Miami that was known as Colored Town during Jim Crow. One of the oldest Black settlements in the country, it was once a thriving part of the city. Visionaries like  Ella Fitzgerald, Count Basie, Billie Holiday, and Cab Calloway stayed in Overtown when playing in Miami. They couldn’t stay in white districts.

Overtown had its own theater – the Lyric – and a vibrant social and economic lifestyle. Good Bread Alley, with its well-kept row houses and bakeries, was the yeast-scented hub of the neighborhood.

But by the time Stephen was born Overtown was, in his words, a ghetto.  He lived in a 2-bedroom garden apartment just outside the “official” neighborhood projects.  Behind his apartment was an empty lot where they’d throw bottles and cans. Nearby stood an empty field where they kept stolen cars. And, as he says, “A ghetto is a ghetto. It doesn’t matter how high the apartment is. The neighborhood is just as rough.”

“Growing up in Overtown was never scary, though,” he says. “You see so much violence and death and everything every day. It’s everywhere you go.”

One memory sticks out. Stephen was 11 or 12, walking through the projects at night. “In the projects they shoot out all the lights and you’ve got trees everywhere. It’s dark. If you really don’t live there, you shouldn’t walk through the projects,” he says. “Guys sit in the dark, and in the little bit of light they can see you coming. They say, when they see you, ‘Oh, that’s what’s-his-name coming through.’ They know. But in the middle of the projects, it gets real, real dark.”

That night, in the distance, a door opened. “There was light from the door,” he says. “I see this lady, for a brief moment, and then this dude shot her, right in the head. Boom. I heard the gunshot. But I didn’t even really know she was shot until the ambulance came and put a sheet over the body.”

Just another night in Overtown.

On some levels, Stephen knew he had it better than others. They weren’t in the projects, after all. Their apartment was decent, and although he was the youngest of nine children (six boys and three girls), the older siblings were encouraged to move out as soon as possible, which helped with overcrowding. His mom cleaned houses for rich Miami families. She’d bring home bags of designer hand-me-downs for the children, many of which still had tags. While the kids in Stephen’s class wore Converse All Stars and corduroy pants, he was in Izod and Polo. When he complained to his mother about dressing different, she asked how the girls treated him.

“I said, ‘They love me,’ and she said, ‘Well, there you go. If it’s a woman you want to impress, a guy has to know how to dress.’” That was the end of that discussion.

Stephen’s father was a longshoreman, gone from 5 a.m. to 5 p.m. every day. Together his parents made enough money. They could have moved out of Overtown had they chosen to. Instead they stayed. Their neighborhood was historic, inexpensive, and everything they needed was within walking distance. “My mother never drove a car in her life,” says Stephen.

Unlike the majority of their classmates, Stephen and his siblings didn’t qualify for free school lunch. And while his father was liberal and generous with Stephen’s sisters, Stephen had a different experience. “One day, I asked my father for some money,” Stephen says. “He’s like, ‘I’ll be glad when you get older and can take care of yourself.’ I was eight years old.”

That stuck with Stephen. Already a bit of a wild child, he became fiercely independent.

Stephen committed his first robbery when he was nine years old. Yes, that’s correct. Nine. While other boys his age were playing He-Man and GI Joe, he and his fourteen-year-old godbrother robbed a Circle K. From there, all bets were off. Stephen was running the streets, dealing drugs, robbing. He fit in with his brothers; they were already doing the same. “I didn’t have to go in the streets to get the drugs to sell,” he says. They were right there in his own apartment.

“I got a lot of beatings,” he says. By the time he was eleven his mother was so frustrated with his behavior – staying out all night, selling drugs, robbing – that she moved him into an efficiency across the street from their apartment. He lived in that room, alone, while his mother kept watch from afar to make sure he went to school every day.

Which he did. He liked school. He sold drugs there. “I made a lot of money at school,” he says, laughing. “It was the 70s, you know? Still a little like hippie days. We were all smoking dollar joints.”

He did his schoolwork, often during quiet points of a night on the streets, even if he didn’t make it to class. Sometimes he had his sister turn in the work for him. He made Bs and Cs, mostly, with an occasional A.

At school Stephen was well-known for his generosity. “Sometimes the school would call my mother,” he says, “saying, ‘do you know this boy got thousands of dollars in his pocket?’” He used the money to take are of everyone around him. “I’d buy my sisters lunch and treats for everyone else. It was like, I’d see chocolate chip cookies, and I’d say, ‘Gimme all them cookies right there. I want every last one of them.’”

When he was twelve he bought a car from a local dealership for a thousand dollars and drove himself to see his grandparents in Harleyville, South Carolina. He didn’t know the way, couldn’t even see over the steering wheel, but he made it.

Stephen’s first arrest came in 1985. He was twelve, selling crack on the street one evening, when he saw police watching him. “The dude I was serving didn’t see them. He was trying to pick what crack he wanted,” Stephen says. He rushed the guy along, pointing out the cops. “He put his little four rocks in his mouth and we both ran.”

Stephen knew if he could make it to the projects he’d be safe. They had him in their net, but he escaped.

They caught him a day or two later at his mother’s house. He had a pocketful of cash, and they pinned a lot of other things on him, too. “They found a big old bag of crack that was not mine,” says Stephen. “And a couple of pounds of marijuana that was not mine…and about a half a kilo of cocaine which wasn’t mine.” The judge tried to throw the book at him, but a technicality with a gun’s serial number got him released instead. Stephen, still only thirteen, asked the judge if he’d get his pocketful of confiscated cash back. The judge told him he could sue for its return, to which Stephen replied, “Don’t worry, I’ll just get more on the streets.” The judge threw him out of the courtroom.

“And that,” says Stephen, “was the last time I sold drugs. From then on I had people working for me.”

Throughout his teens he lived in Florida and South Carolina, hustling, with a staff of dealers working for him. In 1993 he went to prison for trafficking cocaine and was released in 1994. His first real stay in prison came in 1996 when he served four years for assault and battery with intent to kill. His mother died while he was inside. He wasn’t able to attend her funeral.

But, he says, “I never stopped hustling in prison.” When he got out in 2000, he went right back to robbing. This time it was grocery stores, jewelry stores, and even banks. The only thing he knew, and the most unsustainable life imaginable.

By 2001 he was back in prison on racketeering and armed robbery charges. He served 18 and a half years of a 20-year sentence. This time it was his father and his grandfather who passed away while he was inside. Stephen finally realized things needed to change.

“Prison doesn’t rehabilitate you,” he says. “You got to rehabilitate yourself.”

He enrolled in every program that came along, from janitorial certifications to culinary arts. He worked with two women in the kitchen who had a big impact on him, teaching him how to cook while imparting him life lessons. “They told me, ‘Don’t be scared. Sometimes you’re going to mess up, even in life,’” he says.

Stephen found Turning Leaf through a friend at the halfway house after his release. At 48 years old, he’d missed so much of his life, he knew he could never go back to prison. As soon as he got here, he knew he wanted to stay. To learn. To change.

“I learned a lot from Joe,” he says. Joe was the Classroom Facilitator at the time. “He taught me how to deal with pride, and about the Man Box and how to get out of it. Society tells us what we think a man should and shouldn’t be. It’s not always right.”

He also learned the difference, as he puts it, “between a citizen of a community and someone like me, doing crime. I shouldn’t expect a person that’s a law-abiding citizen to feel and think the way I do.”

“Turning Leaf is like a family,” he says. “Growing up, everybody loved me. I was always loved. When I had all the money I shared it with everybody, but then, in my time of need, I never had anybody there for me. Until Turning Leaf. In my time of need, they supported me. They said, ‘Okay, man, we’re gonna give you all the tools to succeed.’ They helped me find the path out.”

After graduating Stephen was hired by a global company pending his background approval. He was crushing it at work and his manager loved him. But the background check went deep and found the extent of his crimes, so he was let go. His manager fought for him but was overruled. “It was big for me, to have a GM fight for me the way he did,” says Stephen. “He let me know I was doing the right thing. He told me I could call him anytime.”

“But it makes me wonder. Even with all the time I did, when will I have paid my debt to society. I feel like no matter how much time you did and how hard you worked to rectify the situation, you’re still in debt.”

“I was young and made wrong choices. But I did my time. When will it be enough?”

* * * *

At Turning Leaf, we believe it’s more than enough already. He’s back with us while we work to find another job placement. We will never turn our back on you, Stephen. Like you said, Turning Leaf is family, and we’re your family now.