“It’s Never Too Late” is a series that tells the stories of people who decide to pursue their dreams on their own terms.
It was nearly 4 a.m. one Wednesday in May 1999 when Devon Simmons came home to find some acquaintances gathered outside his home in Harlem. They fell into an argument. Mr. Simmons was 17, set to graduate from high school in three weeks.
The argument escalated, and as he would later tell authorities, he thought he saw a gun. He drew his own. In a flash, one person lay mortally wounded and another injured. Mr. Simmons was convicted of first- and second-degree assault, as well as criminal possession of a weapon. En route to Coxsackie Correctional Facility, he felt a grimly familiar narrative close around him: another poor young Black man in handcuffs.
“Once you’re arrested as a young person, it’s like a pathway,” he said.
Mr. Simmons spent 15 years in prison. Since 2014, he’s been a free man — one whose trajectory was dramatically rerouted not once, but twice. As a reader and writer in prison, and then the first graduate — summa cum laude — of the John Jay College of Criminal Justice’s Prison-to-College Pipeline program, he broke free of that dark narrative. In the years since, he’s devoted himself to rewriting it altogether.
At 40, Mr. Simmons has been named a 2017 David Rockefeller Fund Fellow, a 2019 Soros Justice Fellow, a Senior Atlantic Fellow and vice chair of the Canary Impact Fund. He’s a father now, too, and he’s made it his mission to remake not just his own life, but to change the educational and career opportunities afforded to incarcerated and formerly incarcerated people, and the way society thinks about that population in the first place. (The following interview has been edited and condensed.)
What were you like as a kid?
I always thought I was a good kid. I wanted to go to college, though not for the right reasons — I wanted to sell weed to white boys. But I was a good kid, didn’t want to do harm to anyone.
I’d say I got a passion for education when I was young, because my mom used her work address so I could go to a better school rather than in our own district in Harlem, which was horrible. I got to leave the neighborhood every morning to go to school. I saw all the great architecture, saw there was another world, two train stops away.
What was that first year in prison like?
I got my G.E.D. my first year, but there was no higher education after that, because of the  crime bill, which canceled Pell grants for people in prison. So I just started reading. I don’t think I ever read an entire book until prison. I began to read autobiographies. “The Autobiography of Malcolm X.” I was trying to see a world outside prison.
I was starting to change. I would take new words and try to use them — I’d be in the yard and be like, “Why you so loquacious?”
What was it like trying to change while also serving time?
Reading a lot of books helped with that. I went to South Africa in my head before I actually went there, years later.
I had to be really intentional about what I thought about, and talked about. I had to not engage with who got stabbed last week, or who’s selling drugs. Those thoughts aren’t positive. I was trying to have a positive mind-set.
What did you think when you heard about the Prison-to-College Pipeline program?
It was intimidating — I hadn’t been in a school setting for 12 years. But I was already litigating, because I had to file for my appeal. Being a jailhouse lawyer kept me sharp academically.
A lot of people in jail or prison have to learn the law as a means of representing themselves — writing briefs, submitting motions. But when they come out, they’re not able to utilize those skills. It’s a missed opportunity for us as a society.
What was it like pivoting from prison life to student life?
Being a student gave me agency. Like before, if I was just a parolee complaining about stop-and-frisk, people would be like “chill out.” But if I said those same things in school, as a student, I’d be commended for it, and it’s considered critical thinking.
Do you remember your first day out?
The day of my release I was shot twice and left for dead — it was the guy involved in what sent me away back in 1999. You’d think it’d be the greatest day of my life, but it didn’t turn out that way. I stayed in the hospital about a week, got a plate in my right arm.
I think the world anticipated me focusing on the shooting. I chose to focus on school instead. I had a special pen that would record the lecture, because I couldn’t write. I decided it’s up to me to choose my narrative. Is it that I was shot immediately upon my release? Or is it graduating summa cum laude, and trying to change the criminal legal system?
How did the world respond to you in general?
You’ve got to find a way to reinvent yourself and promote yourself to the world.
But there’s a stigma. For a long time, for example, any application for school, housing, a job, you needed to check the box saying you’re formerly incarcerated. The disenfranchisement pushes a lot of people into the informal market — selling drugs, for example.
That’s why I’m trying to change not just the education opportunities for formerly incarcerated people, but public perception. That stigma — it shouldn’t be that a bad choice you make at 15 follows you the rest of your life.
What’s it like being asked about what got you arrested?
There’s a dignity piece. I wasn’t a bad kid. I was in a bad situation. It’s definitely part of my journey, but I don’t feel it speaks to who I am today. I’d hope people would reassess whether that information is actually relevant to how they understand me today.
What’s your focus now?
I cocreated the Paralegal Pathways Initiative, at Columbia Law School, to help those jailhouse lawyers find a way into the legal field. It’s a 14-week training course that teaches tech skills, legal ethics, soft communication skills, a little legal history — all the basics that would allow you to be a paralegal. After the course, our participants either get a fellowship or job placement, or move on to law school.
I’m also trying to create more pipeline programs like John Jay’s around the world. As global ambassador for the Incarceration Nations Network, I’ve traveled to South Africa, Cuba, Jamaica and the U.K. I’m also working to change thinking about parole, too. I’d also love to help law firms diversify better, too. I wear a variety of hats.
What does the future look like for you?
That’s challenging for formerly incarcerated people. I struggle with that. I try to live in the moment. I would love to continue the work I’m doing. And maybe one day I’ll write a book or do a documentary. But I’m always cognizant that tomorrow is not promised.
Any words of wisdom you’d like to share?
I try to contribute to rewriting my eulogy every day. I think I got that out of “The 7 Habits of Highly Effective People.”
Also, I’ve come to the realization that people are flawed. That got me to learn empathy over the years.
What is your takeaway from your experience?
I’m blessed. The universe wasn’t supposed to let me live to see 40. I’m a formerly incarcerated person and I can never take that away. But if I can use my platform to create change, that’s a blessing.
We’re looking for people who decide that it’s never too late to switch gears, change their life and pursue dreams. Should we talk to you or someone you know? Share your story here.