30 Years Incarcerated: Dialo Orr’s Journey from Destruction to Redemption

I'm sitting here at Stanley Correctional Institution in 2025, 30 years deep into what was supposed to be a 120-year sentence, and I need you to understand something: the man talking to you right now isn't the same boy who walked through these doors in 1995. That young fool was angry, scared, and stupid. This man? I'm positive, mature, and sure. There's a difference between existing and living, and it took me three decades to figure that out.

My name is Dialo Orr, number 304958. I been locked up since '94, sentenced in December, ’95. I was convicted of felony party to felony murder, armed robbery and attempted armed robbery. When that judge handed down 60 plus 40 plus 20 years, I thought my life was over. In some ways, it was. But in other ways, it was just beginning.

The Making of a Criminal

See, I came up hard in Racine, Wisconsin, then Joliet and Chicago. Single-parent household, mother who had me when she was sixteen. Never knew my father. Mom worked two jobs sometimes, trying to keep us fed and housed. When she wasn't working, she was resting or with the boyfriend she had at the time. We lived in decent neighborhoods, but decent neighborhoods don't raise children, people do. And the people raising me were either working themselves to death or focused on their own survival.

My mother was a no-nonsense disciplinarian, but discipline without direction is just punishment, and I was drowning in a world I didn't understand. From age 10 to 16, we moved constantly, two different states, three different cities, four different middle schools, two different high schools. No roots, no consistency, no sense of belonging anywhere. You try being the new kid that many times. You try walking into classrooms where everybody already knows each other, where the teachers look at you like another problem to deal with.

When I was 17, Mom passed away from what we know now was Lupus. She was 32 years old, younger than I am sitting here talking to you right now. When you lose your anchor that young, you either learn to swim or you sink. I sank, sank deep.

I went to my grandparents in Racine. That's when everything started falling apart. My grandparents were good people, but they were old-school, set in their ways. They tried, but they didn't know how to handle a grieving, angry 17-year-old who'd never learned how to process pain in a healthy way.

I had this uncle, Uncle Jay, who could’ve been my example of what a real man looked like. He had his head on straight, carried himself with dignity, showed me what it meant to stand for something. But he was gone too early, and my know-it-all teenage self went looking for father figures in all the wrong places.

I started hanging with men who saw me coming from a mile away, young, desperate, no direction, carrying pain I didn’t know how to handle. They used me to serve their purposes, pretended to be friends until it was too late for me to see the game. These weren’t necessarily bad dudes, understand. Some of them were just as lost as I was. But lost people leading lost people is how you end up in a ditch.

I stopped going to class, started hanging in parking lots and cafeterias. School didn't make sense to me anyway. What was the point of algebra when I couldn't even figure out how to get through a day? Eventually, I got kicked out of school altogether. No real work skills, but I expected to achieve success with nothing. You probably know that old song: "Nothing from nothing leaves nothing, you got to have something." But I wanted something, and I wanted it now. I was like 18 years old, watching other guys my age driving nice cars, wearing hip clothes, having folding money. I didn't want to wait.

So I tried to get something the fast way, the wrong way, and landed myself in prison with nobody to blame but myself. I could give you all the reasons and excuses for my situation, and they'd all be true, but they don't bring back the life that was lost in that bank robbery. They don't give me back thirty years of freedom. They don't undo the pain I caused.

Now, finally, I understood I had to accept responsibility for developing my mental, emotional, educational, and spiritual capacity. Reasons, blame, excuses, anger, hatred, and ignorance, none of those existed anymore. They were negative luxuries I couldn't afford if I wanted to become a different man.

The Day Everything Changed

One day in ‘95, me and another guy tried to rob a bank, but the whole thing went sideways, and somebody died. Somebody's father, husband, son gone because of decisions I made. I was convicted of armed robbery and as an accomplice to murder. Just like that, my life was over before it really began.

When I first got to Green Bay maximum security, we called it “gladiator school,” I was scared and angry. They threw me in segregation, "the hole," and I stayed angry. For years, I'd drink and get in fights, blame everybody but myself for where I was at. The system, the lawyers, the judge, society, my mother for dying, my father for never being there in the first place. Blame everybody except the man in the mirror.

By 2004, I was doing my fourth stint in the hole, and I was thirty-three years old, the oldest man in segregation. And you know what I was doing? Leading other men in negative ways. I was teaching them how to be angry, how to blame everybody else, how to make their time harder than it already was.

But there was this man named Munson. Older guy, been down longer than me, but he carried himself different. Munson kept coming at me with the Gospel, with positive words from scripture. At first, I wasn't trying to hear it. I'd curse him out, tell him to keep his Jesus to himself, that I wasn't interested in fairy tales and false hope.

“Man, where was God when my mom was dying?” I’d say, “Where was God when I was bouncing from school to school, house to house? Where was God when I was sitting in that courtroom getting sentenced to die in prison?” But Munson, he was patient. He'd just keep talking, keep sharing, keep planting seeds even when I was throwing them back in his face.

You know how it is when you're holding a grudge? You’re the one carrying the weight, you're the one losing sleep, you're the one eating yourself alive while the person you're mad at is probably somewhere living their life, not even thinking about you.

The Dream That Changed My Attitude

Then I had this dream. I'd been having it since ’96, someone screaming for help like they were about to die, this desperate, terrified voice crying out in agony. I kept thinking, “I wish they would shut up.” The screaming would wake me up, leave me shaking and angry. Many nights, same dream, same voice, same helpless screaming.

But in 2004, when I had that dream again, something made me decide to help the guy instead of just wishing the screaming would stop. In the dream, I followed the voice through dark corridors, up stairs, down hallways, searching for whoever was in trouble. Finally, I walked into a bathroom, looked in a mirror, and saw my own face staring back at me, eyes bugged out, mouth open, lips moving. The person screaming for help was me.

I woke up that night different. Something had shifted, something had cracked open inside me. I told Munson about that dream the next day, and he just nodded like he'd been waiting for me to figure it out.

"That's God calling you," he said. "You have to let go of all that pain and anger. Your inner soul is screaming out for help, and you're the only one who can answer."

Right then and there, in that box they called a cell, I gave my life to Jesus Christ. Not because I suddenly believed in miracles or because I thought religion was going to get me out of prison early. I did it because I was tired of drowning. I did it because I was tired of being angry.

“Listen, Jesus,” I said, “if there's a better way than what I'm doing right now, and you can give it to me, then I need it. Because I'm already in hell." And I was.

That moment in 2004, that was my rock bottom. But sometimes you got to hit rock bottom before you can push off and swim back to the surface.

Anger Almost Ate Me Alive

God blessed me with two books that prepared me for the next stage of my life: Houses of Healing: The Prisoner's Guide to Inner Power and James Satterfield's book about retraining your state of mind. Those self-help books saved my life, literally. Without them, I probably would've died in that hole, either by violence or by letting the anger eat me alive.

Here's what's backward about the prison system: they don't give you anger management courses until six months before your release. Think about how ass-backwards that is. They got a man who's clearly got anger issues because that's why he's in segregation in the first place, but instead of helping him deal with those issues, they just lock him up until he's a short hair from release. They should start these programs when guys enter prison, give them two or three years to learn while they're in a protected environment. Let them fall down, get up, fall down, get up, and learn from their mistakes without those mistakes costing them their freedom. Let prison be the training ground, the place where you practice being better. That way, you’ve had years to practice, years to develop good habits and become the kind of person who can succeed.

Instead, they wait until six months before your release, hand you a bunch of tools you've never used before, then put you out on the streets expecting you to build a whole new life. It's like teaching someone to drive by putting them behind the wheel of a car on the freeway during rush hour. When you crash, they act all surprised and then lock you back up.

What made me change was getting tired of self-inflicted wounds. The guards went home to their families every night. The warden slept in his own bed. The judge who sentenced me was living his life. But I was in that cell, stewing in my own rage. It's like holding a burning log, waiting for your enemy to come so you can hit him with it, but the enemy isn't even there yet, and you're standing there burning yourself up. The people I was trying to hurt with my anger couldn't even feel it, but I was destroying myself every single day.

I had to accept that the only change was going to come from me, because the prison system sure wasn't helping much. The system is designed to warehouse bodies, not transform lives. If you want to become a better person, that's on you. If you want to educate yourself, that's on you. If you want to develop coping skills and emotional intelligence and spiritual strength, that's all on you.

This Knowledge Will Set Me Free

When I got out of solitary for the last time, I met Rudy Bankston in the library. He’s a well-known author now, published several books, made something of himself after getting out. He saw me checking out a psychology book, a sign language book, and a self-help book on depression. 

I told him, “This knowledge is going to set me free, not free from prison necessarily, but free from the ignorance and anger and self-destructive patterns that landed me here in the first place.” Rudy encouraged me, told me to keep reading, keep learning, keep growing. That's how I obtained all the knowledge I have, understanding that my freedom was only going to come from me.

I had to learn about empathy and good character. See, when you grow up like I did, bouncing around, losing people, protecting yourself by not caring too much about anything, you develop emotional walls. But empathy isn't weakness. Caring isn't weakness. Being able to put yourself in someone else's shoes, to understand their pain and their struggles, that's strength.

When you take classes in prison, math, reading, writing, nine times out of 10, a guy inside is the tutor. The system uses prisoners to teach other prisoners because we understand each other in ways the staff never could. We know what it's like to struggle with learning, to feel stupid, to be ashamed of not knowing things.

So why not do the same thing with life skills? Instead of making these programs so hard to get into, so restricted, why not give a man a book to read by himself? Most men doing time are illiterate, but some are not. Use the literate ones as tutors, same way they do in education. Set up study groups in the day rooms. Create mentorship programs where older guys teach younger guys.

You have older men like me who've been locked up for decades. We know how to do time. We know how to stay out of trouble, how to make the best of a bad situation, how to use incarceration as an opportunity for growth instead of just punishment. When a young man comes in wild, making all the same mistakes I made, what do they do? They cell him up with seasoned men who can teach him how to conduct himself, how to do time smart instead of hard.

I had a 3rd-grade Reading Level and 6th-grade Math Level

I'm proud of improving my mental and emotional skills, which made me more productive, more valuable to myself and to the people around me. When I got locked up, I had a 3rd-grade reading level and 6th-grade math level, barely literate. That's what happens when you move around as much as I did, when you're more focused on survival than on learning.

But I earned my high school equivalency degree in here. Took me longer than it should have, but I got it. Then I achieved higher degrees in vocational training and Microsoft Office. Computer skills, business skills, practical knowledge I could use on the outside. Most importantly, I got my degree in Biblical Studies from an outside Christian college.

College was difficult, harder than anything I'd ever attempted. I almost gave up multiple times. At first, I was nervous, wondering if I could really do it, if my mind was capable of that level of work. As I started working through the material, reading the textbooks, writing the papers, I realized I could. My brain wasn't broken. I wasn't stupid. I'd just never been taught how to learn properly.

When I didn't understand something, I buckled down. I focused. I disciplined myself. I asked for help when I needed it. I stayed up late reading and rereading until concepts clicked. I'd sit down, meditate, clear my mind of negative noise, then reread the materials until I understood. Sometimes it took three or four times. Sometimes it took a week. But I stuck with it. I plan to go into Christian counseling, to use everything I've learned and experienced to help other people navigate out of their own darkness.

The Most Gratifying and Peaceful Time of my Incarceration

In 2013, another incarcerated guy, Shannon Ross, and I developed the first Coping Skills program for the incarcerated - how to cope when in prison, including mental health and meditation techniques. We developed it right here at Stanley Correctional Facility, two men who'd been written off by society creating something that could help others transform their lives. Let me say this as well, that Shannon Ross was an inspiration to me. He was always doing projects including a newsletter going out to prison institutions.

It was the most gratifying and peaceful time of my incarceration. Working with Shannon, researching, reading, putting together curriculum that addressed the real issues men face in prison. Not just the obvious stuff like violence and drugs, but the psychological challenges, the emotional trauma, the spiritual emptiness that drives so much destructive behavior.

That program is still being taught in prisons and even mental health institutions throughout Wisconsin. It addressed real needs with practical solutions. Shannon was released in 2020 after 17 years inside for a violent crime when he was a teenager. He now captains The Community, a nonprofit dedicated to helping people with criminal records reintegrate into society. He shows them opportunities.

I had to learn empathy and compassion not just as nice ideas, but as practical skills. Nobody wants to be around a man who doesn't have empathy and compassion. You'd be a loner, brushed off, denounced. People can sense when you don't care about anyone but yourself, when you can't connect with their experiences or understand their struggles.

I’m a Man of Faith Now

I'm a man of faith now, and that faith isn't just Sunday morning religion or jailhouse conversion that disappears when times get tough. It's the foundation everything else is built on. I want God's will, not my will, because my will got me a 120-year sentence and thirty years of my life gone.

Following Him made me the man I am today. Walking with God, I encountered miracles and blessings. I felt hope, truth, and love in my life and saw them in other men's and women's lives too. Doors opening that should have stayed closed. People coming into my life when I needed them.

When I step out of prison, I'm going to have roadblocks. Life on the outside isn't going to be simple, especially for a man who's been locked up for over three decades. The world has changed. Technology has advanced. Social norms have shifted. I'm going to be starting over at 55 with a felony record and a huge gap in my resume.

But this higher power got me past so many roadblocks while incarcerated. Now I'm strong like iron, strong like a diamond, and I shine like a diamond because I've been under pressure long enough to know what I'm made of.

Helping and Mentoring Men to be Better

I'll be prepared when that day comes because God has prepared me mentally, physically, and emotionally. I've matured in ways I never could have imagined when I first walked through these doors. There's one thing I always tell people: men who have been incarcerated for a long time are not the same people they were when they entered prison. Either you got worse throughout that period, or you got better. There's no staying the same.

I told the post release corrections officer, “Listen, I haven't received a conduct report in nine to ten years. You shouldn't be offering me programs like I'm still the same man who used to get in fights and tear up cells. You should be asking me what I've done that kept me out of trouble, that kept me working and developing good work habits.”

I've had a job ever since I've been incarcerated, through every transfer, every classification change, every shift in my circumstances. Working isn't just about the small paycheck or the way it makes time pass faster. It's about developing habits, learning to show up even when you don't feel like it.

You might ask what I did to maintain myself in this structured environment, in the worst conditions you can imagine. What helped me get through all this time without losing my humanity? What tools did I develop to share with other men who are still struggling? But that's not how the system works. They see the conviction, they see the sentence, they see the number of years, and they assume that's all there is to know about who you are and what you're capable of becoming.

I found myself always focused on two things: helping and mentoring men to be better while they're incarcerated and pointing them toward education and employment preparation. Those became my missions, my reasons for getting up every morning and trying to make something positive out of an impossible situation.

For myself, I want to get out, get employment, get housing, and then just live life. Not survive, not just make it through each day, but actually live. I want to get out and live as a man who's in tune with who he is and what his responsibilities are.

I want to be a productive man in society because that's the only way to have a good life, the only way to contribute something positive to the world instead of just taking from it. I want to help free people trapped in the walls of their own thinking.

Developing my Work Ethic

I have a degree in Christian counseling because I've walked in the shadow of death, and I've found my way back to the light. If I can use that journey to help someone else find their way, then maybe all of this suffering will have served a purpose.

I'm constantly working on developing my work ethic because that's crucial when you get out. I've taken all kinds of jobs in here, morning shifts, afternoon shifts, all-day shifts, kitchen work, maintenance, library assistant, whatever they needed. I did it to prepare myself so when the time comes, I can take any job, start at the bottom and work my way up. I'll work at McDonald's, I'll clean floors, I'll do whatever needs to be done. I know that with my work ethic, wherever I go, I'll advance. Maybe not fast, maybe not as far as younger men without my background, but I'll advance because I know how to work hard and be reliable.

I do workouts to keep my body in shape, keep my mind sharp, maintain the discipline that's gotten me this far. Physical fitness isn't just about looking good or staying healthy, though those matter. It's about proving to yourself every day that you can do difficult things, that you can push through discomfort, that you can maintain standards even when nobody's watching.

And I stay reading to keep learning, keep growing, keep expanding my understanding of the world and my place in it. I picked up The 7 Habits of Highly Effective People again and reread it. Love that book. Choice Theory too. I'm rereading all the books that helped me to retool myself. That's beautiful because a lot of times we get wrapped up trying to do new things and learn new stuff, but we don't go back to the basics and fundamentals of how to live life peacefully, how to build meaningful relationships, how to contribute something positive to the world around us.

In 2024, I got my certificate from the U.S. Career Institute for Accountant Specialist. Practical skills, marketable skills, something I can use to support myself when I get out. It's summer 2025 now, and I hope to be released by 2027. Thirty-two years will be enough. More than enough.

The System is Backwards in Many Ways

Prison is like having cancer, and the institution has treatments, but they make you suffer longer before you get the cure. The difference is, I found the cure myself through books, through faith, through the mentorship of men like Munson and the partnership of men like Shannon Ross. I found it through accepting responsibility and refusing to let reasons become excuses.

The system is backwards in many ways, and that frustrates me because I see so much wasted potential in here. Young men who could be doctors, teachers, entrepreneurs, leaders if they just had the right guidance and opportunities at the right time. Instead, they're warehoused, forgotten, written off before they've had a chance to show what they're really capable of. But that doesn't mean change is impossible. It just means the change has to come from within. Every man in here has a choice: get worse or get better. Get bitter or get better.

When I walk out of here, I’ll be a different man. Not perfect, because perfection isn't the goal. That's the real transformation: understanding that freedom isn't just about being outside these walls. It's about being free inside your own mind, your own heart, your own spirit.

I'm Dialo Orr, number 304958. I've been incarcerated for over three decades, but I've been free for the last 15 years. The difference between those two statements is everything. The difference between existing and living, between surviving and thriving, between being a victim of your circumstances and being the architect of your own transformation.

That's what I want people to understand when they hear my story. Not that prison is a good place or that suffering is noble or that everything happens for a reason. But that no matter how far you've fallen, no matter how much you've messed up, no matter how hopeless your situation looks, you still have choices. You still have the power to become better than you were. You still have the ability to contribute something positive to the world, even from the darkest places.