LaVonte Stewart Believes In The Transformative Nature Of Sports
Written by Vocalo Radio on September 8, 2023
LaVonte Stewart knows there’s no such thing as a “bad kid.” With his organization Lost Boyz Inc., he works to help Chicago kids heal trauma through sports-based development.
As the founding executive director of Lost Boyz Inc., LaVonte Stewart, Sr., provides Chicago youth with a constructive environment to express themselves through sports — and set them up on a positive life trajectory.
A former athlete, Stewart has felt passionately about sports his entire life. He recalls becoming enamored with Chicago sports throughout his childhood, playing little league and idolizing Sox players. In his early 20s, he also helped establish prison athletic programs while incarcerated.
“[I brought] cultural enrichment, sports programs, football and baseball to the prison that wasn’t happening prior to my incarceration,” he noted.
Emerging from prison at 25, Stewart became a little league coach. He led his team of 12-year-olds to victory in the first championship and was hooked on coaching.
“I still had this craving, this yearning, this itch to be a part of sports, but it wasn’t working out for me to play,” he said. “Living vicariously through other youth became a new thing, a new way of life.”

When the league was dissolved by its founder, Stewart took matters into his own hands and started a nonprofit so his team could keep playing. What began as the league’s continuation grew into observing youth behavioral patterns, and Stewart decided to begin Lost Boyz to address developmental needs as well as recreation.
“That really piqued my interest and led me down a path of Socratic questioning,” he said. “Why do children act the way that they do? Why do we write them off and say that they’re ‘bad’?”
Founded in 2009, Lost Boyz Inc. has grown from just boys programs to both boys and girls in the South Shore neighborhood ages 4 to 24 and has won multiple national, global and local awards. Stewart feels most rewarded, though, by making an impact in his community, especially seeing alumni return to become coaches and mentors for future generations.
For this segment of “This Is What Chicago Sounds Like,” LaVonte Stewart discusses how he created Lost Boyz Inc. and the importance of sports recreation on childhood development.
Introduce yourself and your work in a few words.
I’m LaVonte Stewart, Sr., founding executive director of Lost Boyz Inc., located in Chicago’s South Side.
What is Lost Boyz Inc.?
Lost Boyz Inc. is a sports space youth development organization based on the South Side. So what we do is we center our work on baseball and fast-pitch softball. With that, there is supplementary programming that is focused on human development. I mean, sport as well. But then there are about five to seven developmental areas that we’re focused on. Social-emotional learning, academic enrichment, cultural awareness, civic engagement, community service-slash-service learning, health and wellness, nutritional, sexual health, our programs kind of center in on all of these different aspects of development that are needed for young people. Ultimately, our goal is to increase protective factors for youth, and to decrease risk factors.

Where are you from?
I’m from the South Side, from South Shore. I grew up in the late ’80s, early ’90s. I’m in my late 40s. And so it was a different community then. It was more of the village, more like the “Wakanda” of all Black people’s imaginations, where your neighbors knew you. The neighbors owned the businesses. It’s just an amazing community. There was a lot going on. And then something… things changed. I would say it changed with the crack pandemic. We all know that played a big role in the decline of Black communities across America. And so, I think I witnessed it, and I didn’t really realize what I was witnessing. I was this really bubbly, nerdy kid. Book fairs were like, to me, the Taste of Chicago.
Then I got into sports. Sports became a great outlet. I started with little league baseball, we had South Shore Little League. A love of sports, I think, naturally came with being a Chicagoan. Initially, when I was a little kid, we weren’t winning any championships in Chicago, but we had some of the best names in the game. I mean, Michael Jordan, right? We’re still talking about “23” to this day, people are still wearing the shoes, generations that have never seen him play, other than in the video. Sweetness, Walter Payton, one of the greatest running backs to ever touch the football field. Bobby Hall, and the Blackhawks, you had all these amazing stars that were in Chicago. I was growing up watching sports, and I think just Chicago is a sports town. Sox, Cubs. Ozzie Guillén was my favorite baseball player, Harold Baines. On the other side, you had Shawon Dunston and Andre Dawson, Ryne Sandberg.
I mean, I don’t know how you avoid sports in Chicago, because there’s just no way you’re not gonna be down for tha Bears. Baseball, I think there was a particular love for it because it was the first sport that I played. It was the first sport that I was exposed to, I kind of grew that love of sport from the city itself.

How did you start Lost Boyz Inc.?
I ended up in prison while I was in college, it was really just young, dumb decisions. Little bit of unfairness played a role in it. But even still, then, while I was incarcerated, I was creating programs at the prison I was at, around all types of stuff. Cultural enrichment, sports programs, football and baseball to the prison that wasn’t happening prior to my incarceration. By the time I got home, I was 25 years old. And I was trying to figure life out. I started a family. My children’s mom, she came across a flier in a corner store for a little league, and they were looking for coaches, and it was the name of the league I grew up in. And so that kind of brought back some nostalgia. So I’m like, “Yeah, I’ll give it a shot. I want to coach.” Won the league championship with the 12-year-olds the first year and I was kind of hooked into coaching.
I couldn’t play anymore, and 25 is relatively young to stop playing sports. I still had this craving, this yearning, this itch to be a part of sports, but it wasn’t working out for me to play. I needed to work and make money and take care of children. Living vicariously through other youth became a new thing, a new way of life. I always figured I’d end up working with kids and coaching sport in some capacity, but I never thought I’d make a complete career out of it.
This guy decides, for whatever reason, he folds his league, and so now it leaves a lot of kids without a baseball league to belong to. I didn’t know what the other teams were going to do, but I wanted to keep mine going. So I started the paperwork to create a nonprofit. But in the process of doing that, in those first three years of coaching, it gave me an opportunity to really observe the youth. I’m seeing some common repetitive patterns of behavior. That really piqued my interest and led me down a path of Socratic questioning. Why do children act the way that they do? Why do we write them off and say that they’re “bad”? My immediate answer, as a Christian, was, “No, God didn’t make anybody bad. We learn to be bad.”
I wanted to really investigate that and dig deeper into that question, but also wanted to provide a high quality service built back around sport. So I had to expand what we were doing, it became more than the sport, because you’d have kids show up to practice and they’re angry or they’re not engaged. And so I’m just wondering, okay, what’s going on. As I start peeling back the layers and learning to talk to children and learning to be more observant about their home environments, their school environments, community environments, then I started seeing that children were impacted mostly by trauma. I set out on a path to become an expert in human development, behavior and trauma. I think I kind of hitched my life to trauma for the last decade and a half, just kind of trying to understand it and trying to apply the lessons learned in the environment here. What it led us to was becoming what’s called a sport space youth development organization.

What does that mean exactly?
Basically, what that is, from a social scientific perspective, is simply a theory that says, if you intentionally use sports, in connection with other OSTs, out-of-school time activities, and you create this positive environment and experience for youth, it places them on a very positive trajectory in life. And so this is what the science finds, right? There’s a lot of research around it. That was the path that I continued down with Lost Boyz. Two of my friends, we started it out, one of them was my high school teammate. We played baseball together, football, after high school. And he was shot when we were 17 and paralyzed, so he was confined to a wheelchair for the rest of his life. Joe Stewart, with Monty Edwards, good friend, former baseball player, we’re now into our 16th year. May of every year is kind of the anniversary of it.
I didn’t think that I’d be doing this, this long, but I’m really proud of the work. Our organization has won multiple awards for this type of work, national awards, global awards, local awards. I think, more importantly, though, than the awards is the impact that we know we’re having on our community, and the youth and the families that we serve. And that shows itself by the young people that come back as alumni. And they come back and they become staff, and they become the coaches and the mentors, all of that good stuff. I think, for me, that let me know that my time has been appreciated and used very wisely.
Since 2016, we have been profiling people who give their all to Chicago and enrich us socially and culturally by virtue of their artistry, social justice work and community-building. Take a listen. Read their words. Become inspired.

Interview and audio production by Ari Mejia
Written introduction and transcription by Morgan Ciocca
Photos by Ari Mejia, edited by Morgan Ciocca
More from Vocalo: