Carlos Rebollo: From Prison to Purpose

When a 15-year-old gets sentenced to 45 years in adult prison, most people would assume that story ends in tragedy.

I just finished talking with Carlos Rebollo, and I’m still processing everything he shared with me. Twenty-four years behind bars, starting as a kid who could barely understand what a 45-year sentence even meant. But Carlos didn’t just survive those years – he used them to completely rebuild himself from the ground up.

Getting Handcuffed While Taking a Shower at 15

Carlos walked me through his entry into the system, and honestly, some of it shocked even me. This was supposed to be a juvenile facility, but the reality was brutal. Twenty-three hours locked in a cell, one hour out. And when shower time came? They handcuffed him.

“I remember that you’re supposed to have, you know, like Carlos, I’ve never even heard of you because I’ve heard a lot of different guys, go into the hole and then they get to take a shower like three times a week or whatever and I’ve never heard of people being handcuffed while they’re taking their shower,” I told him. That’s a whole different level of dehumanization for a 15-year-old kid.

The breaking point came when Carlos couldn’t advance to the next phase of the program. The reason? He didn’t smile enough. When he challenged this, staff told him it wasn’t a joke – his attitude needed improvement because he wasn’t smiling. At 15 years old, in solitary confinement, he was expected to smile his way to better treatment.

The Mentors Who Saw Through the System’s Lies

Years into his sentence, Carlos met some men who changed everything. These weren’t your typical prison success stories. These guys had been locked up for decades, but they were different. They were reading, writing books, challenging policies. And they told Carlos something that rocked his world.

“Carlos, you’re a criminal, you still have criminal tendency,” they said. But here’s the key – they didn’t stop there. They showed him that all the certificates and programs he’d been completing were just setting him up for failure.

“The problem with that, is that that information is not connected. It’s not integrated at all,” Carlos explained to me. “If I had a drug problem, all that was required for me was to address my drug problem and I’d be great. If I was a bad dad, all I had to do was become a great parent. If I had an anger issue, all that required for me, was to deal with my anger issues and I’d be great.”

But these mentors pushed him deeper. They made him ask the hard question: What does it actually mean about me that I tried to take an innocent person’s life? Not what society says, not what the programs say – what does it mean about who Carlos really was?

Breaking Down the Real Criminal Thinking

This is where Carlos’s story gets powerful. Instead of just going through the motions of prison programs, he started doing the real work. He identified his actual criminal thinking patterns – like his need to feel powerful, his victim stance, and his mental laziness when presented with challenging information.

“I was never the problem. It was always somebody else,” Carlos told me. But even as a kid, he remembered other children his age telling him he was out of his mind, that they were going to focus on school and their futures. He had examples all around him showing a different path, but he chose to ignore them.

The breakthrough came when Carlos stopped chasing freedom and started focusing on becoming someone worthy of freedom. “I’m going to focus on actually making Freedom significant by developing myself into the kind of person that can appreciate Freedom once I’m placed in the position to fully take advantage of it.”

That shift changed everything. Opportunities started presenting themselves. He began reaching beyond the walls, making connections, preparing for a life that mattered. And ironically, the same system that was supposed to help him started fighting him every step of the way.

When HBO was there filming his parole hearing, Carlos wasn’t celebrating. His response? “This system is so twisted that I wonder how much of you guys being here influenced that decision.” Even in that moment of victory, he was thinking about the broken system and the work still ahead.

Carlos has been out for three months now. He’s a full-time student pursuing journalism, and HBO is making a documentary about his life. But what struck me most was his approach to the future: “No matter where I end up, as long as I hold on to the idea that whether there’s failure or challenge, or what may have you may be presented to me, that I’m capable of coping with the basic challenges of life and that no matter what happens, I can deal with it.”

That’s not just surviving your nightmare. That’s turning it into your foundation for success.