Building a New Path: Rick Gray’s Journey from Incarceration to Empowerment

Okay Nightmare Success lifters, we are back, and I’ve got Rick Gray with me today. Rick’s story hits different because he’s not just talking about reentry, he’s actually doing something about it. For 22 years now, he’s been going back into prisons, and he’s built a nonprofit called Constructing Futures that takes guys fresh out and teaches them carpentry while they get their lives together.

But Rick’s path to helping others started in the worst possible way.

From 16 to 30: Living in the System

“From about the age of 16 to 30 I was either in jail, on probation or I had a court date,” Rick told me. That’s a 14-year span of constant trouble. He wasn’t the only guy in his friend group going through this, he was the one guy who kept getting caught.

Rick traces it back to insecurity and his relationship with his father. “I just was so acutely insecure,” he said. His dad had done 18 months in Hutchinson, Kansas when he was 16 for breaking into houses. When his father sat him down in fourth grade and told him about his own prison time, Rick had a strange reaction: “I knew from that moment forward I was going to prison.”

The drugs started as a way to not feel that insecurity. Rick got into cocaine, and his pattern became writing bad checks to support his habit. “I would go out at night trying to you know in my insecurity trying to feed that. I’d end up drinking. Which then you know turns that all the decision makers off. And then we’re doing drug before long and now I’m writing bad checks.”

Making Kansas City’s Most Wanted

Rick’s wake-up call came in the most unexpected way. He was at a golf course, taking steroids, got into it with another player who was too slow. Rick shoved the guy hard enough that he fell down and did a somersault. By the time Rick got to the clubhouse, there were 20 cops in the parking lot.

He went through multiple court dates for battery. The older guy showed up to every single one, wanting Rick’s behind. At the final court date, Rick got probation. “That little door. That little turn style that you walk through. That wasn’t even close behind me. When I heard the prosecutor lean over to the guy and say don’t worry about it. We’re going to charge him with felony forgery today.”

They’d connected the dots on his bad check scheme. Rick ended up on Kansas City’s top 10 most wanted list for a probation violation. “Sounds a lot scarier than it is,” he laughed.

After getting pulled over going 100 mph down Manchester at 10 p.m. to buy crack, Rick fled from police, made it home, and thought he’d gotten away. But they waited outside his apartment for hours. Somehow, he walked out the next afternoon and drove away. “To this day I don’t know how that happened,” Rick said. He was on the run for 14 months.

The Moment Everything Changed

Being on the run wore Rick down completely. After staying up for two nights straight on drugs, hearing paranoid voices outside that weren’t real, he couldn’t take it anymore. He turned himself in that Monday.

After six months in county jail and four months in work release, Rick got out and was placed in an Oxford house. Within two weeks, he was using again. But this time felt different when he got caught.

“My sobriety date is December 30, 1994,” Rick told me. Two days later, he got called in for a surprise drug test and failed it. When his parole officer asked when he was going to get honest about his drug use, something clicked.

“It was like the scales fell from my eyes. I couldn’t believe that I had risked this, that I knew these judges wouldn’t give me another chance. And I did it anyway.”

In county jail, waiting for his revocation hearing and looking at four years in prison, Rick went to an AA meeting. When he got back to his cell, he saw his reflection in the little glass window. “It struck me the difference between how smart I was, thought I was, and how nothing I had ever done had worked.”

He fell to his knees, but this time was different from all his previous “foxhole prayers.” “This was, you know, a give, a surrender. My way is not working. I admit it. I’m an alcoholic ad. I admit it to you, to my God, to me. And I said, I need a miracle. And I will do the footwork.”

Rick did four months on a four-year sentence. All his other cases went away. All the restitution disappeared. He got a fresh start.

Building Constructing Futures

After 18 months of solid recovery work, Rick got asked back into the family furniture business and moved to St. Louis. He’d been going to county jails to speak, but couldn’t get into prisons until he was off paper.

The idea for Constructing Futures came during Hurricane Katrina relief work. Churches would ask who was a contractor, and those guys became team leaders. “Very quickly, I saw, I’m teaching like Banker’s Housewives, Car salesman, how to do, how to tape and mud. I thought, I could do this with guys coming out of prison.”

Rick started small, calling probation and parole officers, the same people he used to fear. “I got 15 of them in my phone, which is so ironic,” he said. Now he calls them when he needs someone for his program.

The Three Types of Men

After 22 years of going into prisons and hiring guys coming out, Rick has developed what he calls his pie chart. There’s a small percentage who have no interest in changing. “One, they’re not in my meetings. So that’s the first giveaway.”

There’s another small piece who say they want to change but are really looking for a handout. “These are guys that have this victim mentality, which I had. Everybody else’s life. I had this too. It takes all your strength away.”

But the majority are guys “who, if someone would just come alongside them and show them that they believe in them, not hand them any things, right? I hand them anything.”

Rick tells the same story every time about a guy who didn’t have a tape measure. Rick had an extra one he was never going to use again, sitting in the bottom of his toolbox. He gave it to the guy but took $5 out of his paycheck. “I don’t need the $5, but the principal there is in the game.”

That’s the difference Rick is making, not handouts, but hand-ups. Teaching skills, providing structure, and showing guys that someone believes they can do better. After being on the wrong side of the system for so long, Rick found his purpose on the other side of those prison doors.