Jermaine Wilson: From Juvenile Hall to the Mayor’s Office

From Five Years Old to the Streets

When I talked with Jermaine Wilson, I couldn’t get over how young he was when everything started. Five years old. That’s when he and his seven-year-old brother started sneaking around their neighborhood in Leavenworth, Kansas, getting exposed to drugs, gunshots, and violence. His mom had moved them there from Kennett, Missouri (Sheryl Crow’s hometown, as Jermaine pointed out) looking for something better. She was twenty years old with four kids, working two jobs, trying to make ends meet.

“Every time she would leave, you know, my brother and I, you know, we snuck around the neighborhood. And that was the time that we got exposed to what drugs were, gunshots, violence. And so we were accustomed to that. And it became our norm every single day,” Jermaine told me.

What struck me about this part of his story wasn’t just the exposure to violence at such a young age. It was how he described feeling like an outsider everywhere else. Short for his age, always trying to fit in, moving schools every year because his mom couldn’t afford rent. The streets became the one place where he felt accepted.

Four Years Lost in the System

By twelve, Jermaine had committed his first breaking and entering. He got diversion that time. But the attention from his peers at school, the acceptance from older kids, kept pulling him back. At fifteen, he committed robbery and got sentenced to two years in juvenile corrections. Then he tried to escape.

“I started thinking about the movie Escape from Alcatraz. I thought it was a good idea to try to escape. I tried to escape, failed in the attempt, and was sentenced to an additional two years. So, from 15 to 19 years old, I gave up my entire juvenile teenage years just because I wanted to fit in and be part of the popular group,” he said.

Four years. That’s a lifetime when you’re a teenager. Jermaine described juvenile corrections as a bunch of teenagers with chips on their shoulders, testosterone through the roof. He learned to fight immediately because he knew his size would make him a target. His fears turned into aggression, and that aggression built a reputation that protected him.

Eighteen Months and Back to Leavenworth

When Jermaine got out at nineteen, he lasted eighteen months before getting arrested again. This time it was federal drug trafficking charges that would send him to Leavenworth Federal Penitentiary. The same town where he grew up.

“When I came home, I had made up in my mind that I was going to become one of the biggest drug dealers because I felt like that time that was given to me and juvenile those four years I felt like my time was robbed from me. I felt like I didn’t deserve it,” Jermaine explained.

He had a son now with his childhood girlfriend. In his mind, he was hustling to give his son a better life. But his girlfriend kept telling him his son needed his time, not his money. Jermaine wasn’t mature enough to understand what she meant. The investigation eventually caught up with him, and when they pulled him over, they found everything in his vehicle.

The Moment Everything Changed

Here’s the part of Jermaine’s story that really got to me. He ended up in Lansing Correctional Facility, the maximum security prison in his hometown. He knew everybody there. The negative thoughts started flowing. But then something happened while he was sitting in his cell.

“I was sober minded to realize while I was sitting in my cell one day, if I don’t change my life, my son’s going to follow in the same footsteps. The legacy that’s been handed down from generation to generation within my family has always been crime, drugs, and incarceration,” he told me.

That’s when it hit him. Kids don’t do what you tell them to do. They do what they see you do. If he wanted to break the cycle for his son, he had to be the example. He started hanging out with the older inmates, many of them lifers who saw something in him and shared their wisdom. He stopped using profanity, started going to church, reading self-help books. His thinking changed, then his outlook, then his outcomes.

From Ex-Con to Mayor

After his release in December 2010, Jermaine hit the ground running. Day one: parole officer, workforce development, food stamps, all the resources available. Day two: job hunting. Three weeks later, he found work. But more importantly, he started sharing his story at the same juvenile facility he’d tried to escape from years earlier.

The speaking led to community work, which led to an idea about unity. Jermaine went to the police chief with a proposal for a basketball game between youth and police. The chief was skeptical at first, but they tried it. Over 200 people showed up from all parts of the community. No violence, no problems, just people coming together.

That’s when people started asking if he’d ever thought about politics. His friend Sean planted the seed about maybe becoming mayor someday. When Jermaine called his wife to tell her about the conversation, she said maybe he could. Two years later, he decided to run.

The Campaign and the Attacks

Eleven people ran in the primary for mayor. When the results came out, Jermaine was in first place. That’s when the attacks started. People dug into his background, wrote negative articles questioning whether someone with a criminal record could lead effectively. Would he be biased? Could he support law enforcement?

But something interesting happened. The newspaper had already published Jermaine’s story years earlier when he was doing community work. People started asking how you can attack someone for being open and honest about their past. His criminal record had been expunged, and some people even questioned whether he was making up his prison story to get votes.

Jermaine won with the most votes. He became the mayor of the same town where he’d grown up on the streets, been arrested, and served time in the federal prison.

What Comes Next

Jermaine’s book, “From Lawbreaker to Lawmaker,” comes out this summer. The title came from a news anchor who covered his story. But his real focus is on touching hearts and opening eyes about second chances. His message is simple: we all fall short, we all need each other, and we all have to be united to create positive change.

Listening to Jermaine’s story reminded me why we do this podcast. Sometimes the people who’ve been through the worst are exactly the ones we need leading us forward. They’ve earned the right to speak about change because they’ve lived it.