How Lost Boyz are finding a home on the field in Chicago’s South Side

America’s Pastime has also been a key to its progress

As a bastion of social progress, there are few arenas in American culture that can boast the same success as the baseball diamond. When Jackie Robinson put on Dodger blue, the ripple effect of both his inclusion and his excellence as a ball player extended well beyond the field. And while there’s still a long way to go, with new and familiar challenges facing our society, we are all equals between the lines.

That sense of American history—how intertwined baseball is with fight for social equality in the United States—is one thing among many that inspired LaVont’e Stewart, a native of Chicago’s South Shore, to start Lost Boyz, Inc., a youth baseball and mentoring program built to help bridge gaps inside and outside the community where he first laced up his cleats.

“[The inspiration behind Lost Boyz] was twofold,” explains Stewart. “On one hand, it was about being proactive in refurbishing the community—helping to be a part of building something down the road for my children (because they were babies when it started). Looking at the direction the community was going, as a lifelong member of that community, I wanted to put my fingerprints on something, and help build the kind of environment that would be conducive to raising my children.

“So thinking that, of course, it meant I needed to think about something that would help other children, because that would more than likely get at the root of whatever obstacles or challenges my kids might face in the community.”

But there was also reason for urgency—a successful, local baseball league in which Stewart served as a coach announced that it would be folding at the end of the season.

“Hands down, [sports] have been the greatest tool for equality.”

“I was running a practice in the summer time,” he says. “I had to let my athletes know that we were going to disband—I was going to help them get into an adjacent league in a different district—when we witnessed something very traumatic.”

What was it?

“There were two assailants chasing another guy across the field, with guns out in the middle of the day,” he remembers.

“I’m kind of old school, so I just hit the ground—I’m from a generation that lived by a motto where bullets don’t have a name. But this newer generation of kids still have this kind of ‘I’m invincible’ attitude, so they were just standing around, unaffected. They were just really desensitized to the violence—for them, it had become normal.

“That really, really affected me. It was an epiphany for me I guess—it was a reflective moment, thinking about what type of destructive behavior I may have engaged in when I was a teenager, and in what ways I might have contributed to that environment. And then I felt like I had this onus, as an adult in that community, to contribute in a positive way. So, that was really the start of it.”

Drawing from the athletes he coached in the previous, but now defunct, league, Stewart put together what he calls a ‘barnstorming’ team of about 15 kids. Now, Lost Boyz offers programming year round, including spring and summer leagues, fall ball, and winter training, as well as softball programs for girls.

“Baseball was one of my two favorite sports,” Stewart says. (He was also a football player in both high school and college). While he says he may have had more natural talent in football, his love of baseball led him to coaching, and he enjoyed immediate success—in his first year coaching youth baseball, his team won the league title. “That was really fun—I was hooked.”

But it goes way beyond winning and losing.

“From an intellectual perspective, I have such a great regard for sports, and the individual and collective impact that they have on people. And, historically, the collective impact that they’ve had on this country.

“Hands down, [sports] have been the greatest tool for equality. They really have. If you step back and look at it from a historical perspective, baseball has opened the door for all kinds of marginalized groups. So, without Jackie Robinson, there’s no integration of baseball—if there’s no integration of baseball, you could argue that there would have been no integration of the military, or other areas of civic life.

“I didn’t want any kid to make the mistakes that I made,” he says. “I wanted to be that consistent voice, that person in their corner (in addition to family or whomever) that’s saying hey, you can do great things. Stay on track. Stay focused.”

“Baseball gives you that moment—that window in time,” he says. “Baseball gives you that two and a half to three hours, where nothing else matters. It doesn’t matter what your socio-economic background is, race, ethnicity, gender, orientation, level of education—nothing matters. You can sit right next to a billionaire and you can be best buds for three hours. The sport allows people to be seen. It gives them their humanity. And for people who may be looked at with a certain bias—it casts them in a new light.

“Jackie Robinson became this beacon—this hero—to many people. People who were diehard Brooklyn fans, for whom at some point it no longer mattered that he was a colored boy—all that mattered was that he was a Dodger, and he was going to get them to the ‘ship.

“There was that phenomenal moment on the field, with Pee Wee Reese, that’s included in the movie ‘42’—little things like that, that shifted the thought pattern of people. Just something that little.

“And if it did, or didn’t happen exactly that way, doesn’t matter. It’s the fact that these guys, and that team, with deep, Southern cultural roots, were able to embrace a black man like they would any of their brothers.”


As is the case with most things that Stewart takes up, his interest extended beyond what was immediately in front of him. In talking about baseball, Stewart shows his appreciation for its position in history. And in talking about coaching, he reveals a similar appreciation for the broader opportunities it presents.

“Part of my personal story—and I’m not ashamed of it—is the block of time where I really put myself on a bad path,” he explains, “in that 18-, 19-year-old range, when you think you can conquer the world, and you’re off to college, and getting a taste of living on your own. I ended up getting myself incarcerated—I spent four years in prison on my first offense in Missouri, while I was off at college.

“That, coupled with all of my experiences growing up in my community had kind of skewed me toward that behavior pattern—it was a kind of ‘survival of the fittest’ mentality.”

All of the above served as a background for Stewart’s decision to do more with baseball.

“I didn’t want any kid to make the mistakes that I made,” he says. “I wanted to be that consistent voice, that person in their corner (in addition to family or whomever) that’s saying hey, you can do great things. Stay on track. Stay focused.”

“Basically, it grew from a model that’s called ‘Positive Youth Development’ — that’s how the mentoring, cultural enrichment, and social engagement components emerged.”

Through that commitment to helping his young student-athletes stay on the right path, Stewart also began to realize just how significant the challenges facing them at home were.

“I found myself being a disciplinarian,” says Stewart. “But then, as I began to discover through talking to these kids as a group or one on one, I just started to realize how many of them had messed up situations they were dealing with, where you have mom or dad scrapping and working all kinds of hours to provide for their children, which takes away from the quality time that those parents can invest with their child. So, I saw that pain. I saw with some of the kids, the absentee father part, and how significant that was. And again, the environmental pressure that they had to face—the circumstances in the community.

“Given all of that most of them couldn’t even focus on baseball. I thought, how can I make use of the sport in a positive way, and avoid having it backfire and have the opposite result—if the team did terribly, then the kids would get discouraged and not think that much about baseball. It would just be another failure, or challenge, to add to this big bucket they’re already carrying.”

Fortunately, Stewart found that he had a natural knack for coaching. The next step was to become a non-profit, which also forced Stewart to ask himself some difficult questions.

“I didn’t have a mission statement. I hadn’t identified this greater mission clearly.”

The process of becoming a non-profit, as well as earning his masters degree at DePaul University, helped him to think about how all of the individual pieces fit into the larger puzzle. “Basically, it grew from a model that’s called ‘Positive Youth Development’—that’s how the mentoring, cultural enrichment, and social engagement components emerged.”

Stewart studied what had worked well for him and those around him, and applied that experience to the above framework. The result was a baseball program that had a strong mentoring component, as well as important facets off the field. A recent example was a trip last year to a local Jewish Community Center, getting Stewart’s student-athletes out of their neighborhood and engaged with both a culture and people outside their normal experience.

“It creates connections, empathy, and competence,” Stewart says.

Hard to argue with that.


The first year that Lost Boyz began to offer programming for girls, there was something like a 3:1 ratio of boys to girls. But now, four years later, that ratio is looking more like 2:1. “Their numbers are quickly climbing in terms of the percentage of kids we serve,” he says.

The opportunities to grow go beyond the field, not only through mentoring and tutoring, but also through Lost Boyz’ SYL, or Successful Youth Leaders program.

“It’s the same model, but it’s more advanced. So, for example, instead of tutoring kids as the academic component, we’re focusing on ACT prep. We’re focusing on college research. Helping them apply, and fill out the financial aid paperwork. And we’re hoping soon to be able to pay to send them on college visits,” outlines Stewart. There are also roles for ‘Sports Journalist’ and ‘Statistical Analyst’ that kids can take on, gaining experience working for a program they love, which they can apply to other areas of their life.

Since the program has been growing for some time now, Stewart has been able to enjoy seeing the success of his former players through high school and on up into the college ranks. That success has come from the grassroots level, literally.

“We’re on public property—the Chicago Park District owns that property,” says Stewart. “But they have hundreds of baseball diamonds, if not thousands, across the city, and the crew that maintains them is less than 10 people. So the odds of always having your dirt turned and fields chalked for a game are not great—lots of people are trying to figure out solutions, but that’s where this program meets a lot of needs. It’s much easier to have the kids help out than it is to hire a landscaper.”

The kids get the benefit taking ownership of the field they use, and the skills that go along with that, while the community benefits from its upkeep at minimal cost. In other words, it’s a win-win.

And, it’s the kind of team we can all root for. //

Story by Bryan Kitch, for UpMetrics Data for Good.

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