Changemaker Spotlight: Jesse Crosson on Why Redemption Is a Practice

August 24, 2026

By Robert Roche, VP of Marketing at The Last Mile.

Jesse Crosson was barely an adult when his life collapsed into a prison sentence measured in decades.

After years of insecurity and substance use, he committed a robbery and an unrelated nonfatal shooting. A judge sentenced him to 138 years, with 106 suspended. His active sentence was 32 years. Jesse would spend 19 years incarcerated before receiving a conditional pardon.

How does someone build a future from that trajectory?

For Jesse Crosson, the answer came through years of work, education, relationships, mistakes, and repeated choices. Our conversation kept returning to one central idea: redemption happens through practice.

“No-one Is Just One Thing”

Jesse traces his early struggles to a feeling that something was wrong with him.

“I felt like a mistake,” he has previously written. “I can’t explain why, but I just never felt like I belonged or was good enough.” Drugs and alcohol eventually seemed like an answer.

During our conversation, Jesse described a similar pattern.

“I didn’t know how to deal with difficult emotions or social pressures,” he told me. “So I ran away.”

He found substances, activities, and people that could temporarily make those feelings disappear. Then he found cocaine.

“I went from this guy teetering on a tightrope to just falling directly toward the ground,” Jesse said. He committed serious crimes and eventually received a 32-year sentence.

Jesse takes responsibility for the damage he caused. At the same time, his experience taught him something fundamental about people.

“One of the things that I learned in prison is that no one is just one thing,” he said.

How Jesse Crosson’s Work Began on the Inside

Jesse used his years inside to build skills and examine the patterns that had shaped his life.

He earned a bachelor’s degree, became a journeyman electrician, mentored other incarcerated men, and wrote for publication.

When I asked about a defining turning point, Jesse resisted the idea that transformation happened in one dramatic moment.

“I don’t think there was a single moment,” he said. “I think it was a lot of steps forward and backward.”

One experience stayed with him: Jesse helped another incarcerated man earn his GED. The man had struggled for years and became emotional when he finally succeeded. “It was significant to one person in a small way,” Jesse said.

That experience helped Jesse recognize something about himself. “I like this feeling,” he remembered thinking. “I want to do this thing. I want to help people.”

Later, a career course asked Jesse to identify his core values and design a life around them. “I built on paper the life that I have today,” he said. “I just didn’t believe it could be possible.”

No one is just one thing. We have the choice to work within what is or not, and the unpleasant work of working within systems we don’t like or with people we don’t agree with is how we get things done in the real world.”

Jesse Crosson

Redemption Is A Practice

That gradual process shaped one of Jesse Crosson’s most powerful ideas.Redemption, he believes, requires daily action.

“I think we have this idea that we’re trying to get to an end point,” Jesse told me. People imagine becoming “educated enough,” “redeemed enough,” or “smart enough.” His experience taught him something different.

“If we’re working to make up for the harm we’ve done in the past, that’s the thing we do every day,” he said. “That’s how we show up with the people around us. It’s in how we spend our time and spend our energy.”

That philosophy connects closely with our work at The Last Mile. Education and career preparation give incarcerated people practical tools. They also create space to build habits and develop confidence before release.

Jesse described the value of that opportunity directly. “When you have time, when you have the opportunity, you can focus on really growing in that area that allows you to succeed when you get out,” he said.

Finding The Best Part of Prison

Jesse eventually turned his experiences into a memoir, The Best Part of Prison.

He knows the title can provoke a reaction. “I called it that specifically because it’s kind of controversial,” Jesse explained.

He does not describe prison as enjoyable or defend the way prisons operate. His title refers to what he chose to do within the circumstances he faced. “The best part of prison for me was that it forced me to stop,” he said. “It forced me to have time and do things differently.”

About 16 years into his sentence, another experience helped shape the book. For the first time, Jesse watched a formerly incarcerated man return to speak at the prison.

The man had spent 22 years fighting to get home. Then he used part of his freedom to come back. Jesse recalled his words perfectly: “You have a future and it starts today.”

Jesse remembers the room breaking down in tears. Someone who had lived their experience stood before them and offered proof that another future existed. “That was the intention behind the book,” Jesse said.” I want readers to know there’s a hand reaching down to help them across the mountain.”

Creating Second Chances for Others

After 19 years incarcerated, Jesse received a conditional pardon and returned home. He then founded the Second Chancer Foundation.

When I asked what people need after incarceration, his answer was simple. “We need pretty much everything that a person in the world needs.”

The foundation works across education, reentry, parenting, employment, and relationships. Jesse also works with young people in juvenile detention.

He noticed that many young people immediately excluded themselves from opportunities. “This college thing is great. This vocational thing is great,” Jesse recalled them saying. “But, not for someone like me.”

The organization began bringing in speakers with similar backgrounds and experiences. “All of a sudden you see that light switch,” Jesse said. “‘Maybe I do belong. Maybe there is a place for me.’”

That line carries particular weight coming from Jesse. The young man who once felt like a mistake now spends his time helping others see a place for themselves.

Your Future Starts Today

Near the end of our conversation, I asked Jesse what he tells incarcerated people who have run out of hope. He starts by rejecting comparisons.

“Your story is probably not going to look like mine or like this other person’s,” Jesse said. “We all have our individual journeys.”

People run out of energy. They lose hope. Jesse even tells people it is acceptable to feel miserable for a while. “Just put a time limit on it,” he said.

“It really and truly does start today,” Jesse told me. “It starts with what you do right now, what you do in an hour, what you do tonight before you go to bed, what you do when you wake up in the morning.”

Those patterns, he explained, eventually determine where someone goes.

“If you keep showing up over and over and over, you’re gonna start catching the bus,” Jesse said. “You’re gonna start getting to places you’ve never been before. You’ve probably never imagined before.”

We Are More Than Our Worst Moments

Jesse Crosson cannot undo the harm he caused as a young man. His work now asks what responsibility can look like over a lifetime.

That practice carried him through 19 years of incarceration. It helped him build an education, a trade, a book, a nonprofit, and a life centered on creating opportunities for others.

His story also reflects a line Jesse has used to describe his larger philosophy: “We are, all of us, more than our worst moments.” That belief leaves room for accountability, growth, and the possibility of a different future.

Jesse’s message remains remarkably consistent: decide where you want to go, start building today, and extend a hand to someone coming behind you.

To learn more about Jesse Crosson, read The Best Part of Prison and explore the work of the Second Chancer Foundation.

About Changemaker Spotlight

Changemaker Spotlight is a recurring series from The Last Mile highlighting the people, organizations, and leaders driving meaningful change across the criminal justice system. From advocates and researchers to employers, educators, and those with lived experience, we feature individuals whose work is creating opportunity, restoring dignity, and building a more effective path forward.

Know someone whose story deserves to be shared? We’d love to hear from you. Send your nominations to robert.roche@thelastmile.org with a brief description of their work and why they should be featured in a future Changemaker Spotlight.