After Life

Chris Wilson was sentenced to life in prison for first-degree murder. Today he's making deals with celebrities and Fortune 500 companies. This is the story of a man who saved himself...

CONTENT WARNING: This interview contains disturbing facts.

Breaker Chris Wilson often begins his speeches with Plato’s allegory of the cave. The Cave was Plato’s way of describing the blindness with which citizens are forced to view society, chained to a wall where only shadows of the truth are visible. Only through an awakening of the mind can citizens free themselves from the cave, and see things for how they really are.

The Cave may be an even better allegory, however, for Wilson himself, a man who spent sixteen years in prison for first degree murder. It was his mind, a decision made within himself, and a plan to overcome, that set him free.

In our interview with Chris, we learn the devastating and incredible story of how a man saved his own life through planning, perseverance, and a poster of the Paypal Mafia…

So, how did you end up with a life sentence?

I grew up in Northeast Washington D.C. In the early 90's there was a crime spike in D.C, and it became the murder capital of the world. My mom started dating a crooked cop, sort of like Denzel in Training Day. Needless to say he hated me, and one day he knocked me out and raped my mom in front of me and bashed her skull in with his service weapon. She survived, but she became depressed and got addicted to booze and prescription pills. She could never work after that.

The cop did eighteen months in prison, and when he got out he started stalking us, so my family started carrying guns. My cousin didn’t bring a gun one day when he went to the store, and they found both my cousin and brother shot—my brother seven times and my cousin seventeen times in the face. My cousin died and my brother miraculously survived. I was seventeen.

A short time later, I was approached by some men, asking if I was Chris Wilson, saying they’d been watching me. They circled me and made threats. At that point I pulled out my gun and opened fire. Unfortunately, I ended up taking a man’s life.

While we were awaiting trial, people came to my father’s house, where my brother was laying low. They carved up my brother with a butcher knife, robbed the house, tied everyone up, and cut my father’s throat, where he bled out on the kitchen floor.

At trial, I was found guilty and sentenced to life in prison.

Wilson giving one of his famous speeches in Baltimore

Wilson giving one of his famous speeches in Baltimore

How did you get out after only sixteen years?

It was a long process, but it started with a flash. I’d been depressed. I was told that since I was serving life, that this is where I’d die, and I believed it at first. So I was smoking a lot of weed, which was easy to find in prison, and being depressed. But one day I just snapped and said, “there’s no way I’m going out like this.”

So I started writing a list of the things I wanted to do with my life, things I was going to commit myself to every day. Things like getting my high school diploma, going to college, learning Spanish, writing a book, and getting a black Corvette convertible. Most importantly, I wanted to help impoverished communities, like the one I grew up in, and give back by creating opportunities. 

So I set to work on the list. I ended up getting my high school diploma, my college degree, learning several foreign languages: Spanish, Italian, a bit of Mandarin, I started a book club, a self-help group, a career center, and became a gang mediator.

For 10 years straight, I worked on my plan. Every year, I sent updates on the plan to a new judge on my case.

At the time I had started talking to God, praying mostly although I did speak out loud to Him, hoping He would send me a sign. Two weeks later, my lawyer came to see me and said that he didn’t know why, but the judge had a change of heart and wanted to see me. I stood in front of the judge and told her of not only my remorse and the events that led up to the charges, but of my self-education and the plans I would carry out if given a second chance. The judge said that what I’d done in prison was nothing short of amazing. She offered me a second chance, but only if I did everything that was in my Master Plan. She agreed to resentence me to life all suspended by twenty-four years, which meant I could get out for good behavior in sixteen. And that’s what happened.

What did you do when you got out?

I left with nothing more than $50 and my Master Plan. I went to Baltimore because I saw it as a place where I could grow and give back.

I knew a few people, people that would buy me books while in prison, and they asked me what I needed to get on my feet. I told them $500 and they laughed! But they loaned it to me. I took $300 of that and bought a lawn mower and a gas can from Home Depot, and a $10 phone from Radio Shack.  I took over my whole neighborhood by doing lawn mowing and landscaping.

After I got stable, I reached out to the University of Baltimore, and they accepted me. That started me on the path to where I am now, running two businesses, being a community organizer and speaking. Oh, and of course driving my black corvette convertible!

So it was smooth sailing from then on?

No not at all. It was still very, very hard. When I went to prison, my mom had to finance the house, and it quickly went into foreclosure and she became homeless. She ended up moving, of all places, to a Native American reservation in South Dakota. When I got out I called her and she thought I had broke out of prison. We talked on the phone for awhile, but she sounded odd, she was apologizing a lot… something just wasn’t right. After we hung up, she wrote a letter and committed suicide.

I used the pain as motivation. Fifty-two days later, I found a job at Strong City Baltimore in Community Organizing and Work Force Development—a job I had always dreamed of.  But I still needed more to move along the Master Plan, so I raised some money and started a furniture and restoration company called The House of DaVinci. I borrowed money, which was very expensive at a 20% interest rate, and made $30,000 in 30 days working with some very wealthy and upscale clientele.

Then I started another company Barclay Investment Corporation that works with people in extremely impoverished and violent neighborhoods, providing contracting jobs. We’ve been doing that for around two years now, working all over the city with some of the big contractors, big developers, putting in art installations, you name it. We go into neighborhoods that need work and invest in them; get them I.D.s if they need them, give them clothes, and they produce a return by paying back their taxes, and saving their wages by staying out of prison. We met recently with Bob Embry from the Abell Foundation—and he’s agreed to give us a $100,000 line of credit guarantee for our operations. We also have a grant from Bill Clark at the OSPREY Foundation and he’s giving us a few thousand dollars for some trucks. And, every month, he’s going to give us $1500 for insurance costs and upkeep on the trucks/equipment.

We want to be comfortable, hire more people, and grow steadily…and that is the Master Plan.

Wilson and ex-offender advocate Alicia Keys

Wilson and ex-offender advocate Alicia Keys

What else do you think Baltimore needs right now to grow in the right way?

There are so many Chris’s, people like me out here, and what we need is a low tech incubator. I mean, the kind of work we do is dumb in the sense that it’s not hard, it’s fairly simple, but it’s very profitable and has good margins. We just need a chance to get them up and running.

You’re also a major speaker, telling your story at big conferences and events. What sets you apart from other speakers? What is your unique message?

Usually, folks just want me to tell my story, but if I meet with businesses, I give them my side of things and try to inspire change. It’s important that I remind them I’m not an exception to the rule—I’m not special. Again, there are a lot of Chris’s all over the city. I advocate to give ex-offenders a chance—to be patient with us, because we know that we need a job and want to get back to living a normal life.

But not all of those ex-offenders are Chris’s. What have you learned that’s made you so much more successful than most who leave prison?

You have got to be patient. Pride is going to mess you up when you get out. There’s going to be opportunities for quick hustles that will end you back in jail. Whereas I wasn’t going to let that happen. I knew I wasn’t going to do a quick hustle, that doesn’t work. I created a very “dumb” small-time business mowing lawns and had to do that for a long time before I started to get my feet under me. Then I was fortunate enough to have a few people call me and see what I needed to go further and made sure I was doing the right things. It’s all about starting small.

And now you’re working on mega projects with Under Armour’s Development firm Sagamore, Howard Shultz and Alicia Keys?

Haha, yeah well that’s in the works. Sagamore has expressed interest in supporting my company.  I was asked to set up a meeting with Alicia Keys, Kevin Plank, and Howard Shultz (Starbucks) after working with Alicia’s We Are Here campaign and Cut50, both organizations that work towards criminal justice policy reform. So, I knew it would be a tough thing to do, but I reached out to the Under Armour people and they agreed to talk. We think that the next step is to change HR policy to better foster opportunities for ex-offenders.  These three people coming together could make a huge difference in so many peoples' lives just by using their influence. So my fingers are crossed.

Having literally gone from mingling with those at the very bottom to those at the very top, is there anyone you really look up to?

I still idolize the "PayPal Mafia.” [The group of ex-paypal employees that went on to change the world of tech]. I remember in prison, my cell buddy and I hung that up that photo of them, all dressed up like mobsters, in our cell and said that that is what we’d look like one day. Out, and successful.

Wilson's "Master Plan" from prison.

Wilson's "Master Plan" from prison.

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