How Greg Fleming overcame insurmountable odds to become One of Chicago’s youngest varsity basketball coaches

By Luke Elder

Greg Fleming standing outside the "Row", the only remaining buildings of the Cabrini Green projects.
Photo Courtesy of Luke Elder/The Elder Sportsman

Greg Fleming, Roberto Clemente’s boys basketball coach, leads with intensity. Making mistakes results in an earful full of rhetorical questions and curse words. From the outside looking in, he’s just another young coach with a chip on his shoulder, but Greg Fleming’s bearing the weight of his community. The famous Cabrini Green community, known as well for Candyman as it is for gang violence. A place imagined cinematically for the American public.

“I’ve met a lot of people who look at Cabrini as if it’s a bad place,” Fleming said. “Me on the other hand, on the inside, growing up here, it made me who I am. It’s a project, so we get looked at ten times worse than the average place. The older guys were always in my ear, constantly, you know, reminding me keep going, keep going. They’d threaten me, saying ‘if I catch you on drugs I’ll kick your ass.’ I really think that helped me. So many people pushed me, and I could thank so many people. What I do, I do for my community. I try to represent my community in the best way that I can, try to show people outside Cabrini that there are good people from here.”

Amongst the crowd of supporters is Fleming’s cousin, Kenneth Hammond. Wearing a toothy grin and diamond earrings while he cooks sloppy Joes for his family, Hammond remembers Greg’s time in Cabrini as a boy, as well as his own. 

“Lil’ Greg is one of the special ones in the family, we don’t have a lot of successful athletes,” Hammond said. “So he was the oldest kid in his family, and he became a real, responsible mentor young– taking care of his younger siblings in the household. So that right there, put Greg at a whole different standpoint from a lot of us coming up, you know, I was raised in a house with six other siblings with just my mom.”

Hammond sees a great deal of himself in Fleming, sharing far more than just similar family upbringing. Violence is something Hammond and Fleming saw plenty of growing up. It’s an unfortunate–and inevitable–aspect of their community.

“Greg and his little brother were really close, like ‘yin’ and ‘yang’, and his brother was also a guy who had a chance to lead the community, and make something of himself.” Hammond said. “Unfortunately he was lost to gun violence. My oldest son was recently lost to gun violence, too. The temptation is so strong once you leave your house out here, and I know, because my brother was a notorious gang leader.”

Though Fleming was surrounded by shootings and gang activity, he worked hard to avoid what felt like the only path for young men in his community. Though later success was found in basketball, baseball was Fleming’s first love. Fleming would later be introduced to Roberto Clemente Community Academy as a baseball prospect.

“During the summer when I was a kid, we’d have baseball games in the morning.” Fleming said. “We’d come back to Cabrini, with our uniform still on, and play ‘til it got dark.”

Greg was in fourth grade. At the time, his cousin was working with the Chicago Park District, who ran a program to help keep young students off the streets. Some kids came to get a meal if they couldn’t get one at home, but most came as a place of shelter–of solace.

Fleming alongside his cousin, Kenneth Hammond.
Photo Courtesy of Luke Elder/The Elder Sportsman

“When lil’ Greg was coming up, and someone wanted to be rough or not follow the rules of the park, we’d say, “we’ll give you two, three days up out of here and see how you want to act.” Hammond said. “Because we all knew, at a certain time of the day, no matter if you were an athlete or just hanging out, you wanted to be in the park. We’ve been surrounded by this all of our lives, so you need to have a strong mentality to want something more in life than just this. To want something for the future.”

Athletics was a helpful incentive to keep Fleming away from the violence-laden streets, but he attributes his avoidance with Cabrini’s drug trade to his mentor, Deepak Devaraj. In 2004, Devaraj was struggling to find fulfillment beyond his workplace in trading. Blindly, Devaraj was exploring Catholic charity programs and stumbled upon one called “Cabrini Connections”. Knowing nothing about it, he searched online and found that it was a mentorship program, on Wednesday nights. 

“We were sitting in a classroom, and there's probably 15 or 20 of us up front, that were kind of adult-ish. There's probably, you know, 25 or 30 kids in the room,” Devaraj said. “So the administrator of Cabrini Connections gave a speech, and as soon as he's done, Greg looked straight at me. He points to me and he goes, “I want you to be my mentor.””

It was through seeing Greg’s background and beginning to understand his struggles that Devaraj found purpose in their partnership, and the two quickly formed a tight bond that would last a lifetime. Devaraj said the two were a perfect pair, because Fleming was in need of love, and he had love to give.

“I realized, like, this can go beyond  just learning how to read and solve math problems. So while it started in the classroom, it kind of morphed into him actually just becoming part of my family. And I always say it's like he's the oldest child I never had and he's the younger brother I never had.”

Devaraj was quick to note Fleming’s confidence and outgoing nature from an early age, but was sure to imbue a sense of hard work while showing Fleming other options in life; other cultures and neighborhoods.

“He always tells me, “dude, if it wasn't for you, opening my eyes to what really existed in the world.” Devaraj said. He's like, “there's no shot in hell I would ever be doing any of this. But once he saw what was on the other side, once he saw a functional family eating dinner together, a functional person getting up every morning at 4:30 to go to work, it showed him like, I'm not afraid to put in the work. So once he once all that clicked, it was kind of game on.”

Devaraj remembers being thrown first hand into Cabrini Green’s projects, when a young Greg found it all to be too much. 

“I’ve had to go to the projects to go find him because sometimes he would kind of disappear a little bit. Then I would have to go up to his house–going up to the eighth floor of the [Cabrini] towers. It's not such a welcoming site, when you're an outsider. It was one of those things where he’s just a part of my family and, and he will always be.”

Through a difficult upbringing, Fleming was molded into a mature young man and gifted athlete. So much so, that he was offered a basketball scholarship to attend Grand Rapids Community College.

“They were a powerhouse at the time. I kept my head down in the classroom and had a good ass season. I ended up picking up like six offers after that,” Fleming said. “Afterwards, I ended up at Lourdes University, had one of the toughest coaches ever. Coach Smith. He was this big black dude, and when I had just met him, I had lost my brother. I didn’t even know if I wanted to take the scholarship, but signed the letter of intent, and then a month later my brother is murdered. I was excited to go to school, but at the same time I just lost my brother.”

Fleming finished just short of a degree due to personal reasons, but was thankful for the chance to experience life outside of his hardened upbringing.

“It was fun. Being able to play ball, go to school for free,” Fleming said. “Just opened my eyes to a different viewpoint. Made me a better person, being around all these positive people.” 

Devaraj was confident that Fleming could still find a way to finish the last few credits of his college degree. He wondered if Fleming might’ve finished if he were closer to his support system. 

“He'd always come to eat dinner and hang out. We were together all the time,” Devaraj said. “When he moved to college, then it was more of like we would talk on the phone, you know, once a month kind of thing, maybe a little bit more often if there was some trouble going on. But you know, it's just hard when you're not in the same city. Like, I went and watched his first game of the season, and we’d talk on the phone once a while, but it was much easier when he was in the city.”

Finishing aside, the opportunity to have a basketball scholarship and “make it out” of Cabrini was exceptional, and Fleming’s community noticed. Now, as one of Chicago’s youngest head basketball coaches, Greg is presented with a task not too dissimilar to the one his cousin and mentor had managed all those years ago. 

“Greg is doing the same thing, now, but it might take a village to do that with the way things have changed,” Hammond said. “Greg is future representation for our family. A lot of things might happen, but he’ll be a successful man. Maybe he’ll buy me lunch. He don’t owe me nothing, but he knows I love to eat.”

The love and care shown by Fleming’s supporters is an unquestionable product of the community, but also, the life experience Fleming has overcome to become a mature leader. 

“One of the reasons he's going to have a tremendous amount of success is, there's no high school or junior high kid that's going to be able to bullshit him, right?” Devaraj asked. “I mean, the guy has seen it all his brother was murdered. You know, he's seen the gangbanging and seen the drugs, he's seen everything firsthand. So it's like, you know, he knows what happens when you become a product of the system. And I think in a weird way, I think the players respect that and look up to him for that.”

Fleming with his mentor, Deepak Devaraj
Photo Courtesy of Luke Elder/The Elder Sportsman

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As a first-year varsity coach given the job just before the season, Fleming was left with few opportunities to prepare and recruit players before the preseason’s start in the fall. Fleming is not a stranger to being left with few options, so a positive outlook was his natural inclination.

“It was definitely frustrating. I had to kick a few kids off the team for grades, not being coachable or undisciplined,” Fleming said. “I laid down the expectations that this is what it’s gonna be. We struggled, but it was a learning experience for me and my team, so I feel blessed for that. I learned a lot.” 

Fleming knew that giving back to his community, one way or another, was always the goal. 

“I think I wanted to help kids my whole life,” Fleming said. “I had a chance to play [basketball] overseas, but I turned it down. I came back home, and the Clemente coach at the time reached out to me and asked me if I wanted it, and I said yes. I wanted to help kids, kids like myself that were unfortunate, that didn’t have the best resources. Kids that had single moms, that don’t got a lot. I figured out quick that it was my purpose, my why. I think God brought me back to Chicago. I’m just trying to do a good job. I think I’m doing a good job.”

“A great job”, Hammond added with a smile and a hand on Fleming’s shoulder. “Lil greg plays a big part in our community, our neighborhood. I know that I appreciate it, and that others appreciate him. It’s important to our community, because our future is our kids. Greg’s playing a big part of that, helping them come up. There aren't a lot of lil’ Gregs over here, still. He stayed connected to where he’s from.”

If Greg’s coaching career were over tomorrow, he’d still have a community of people to back him. Proud of their roots, Cabrini Green’s residents wear their hardships like a badge of honor.

“The temptations are really hard to fight, and the expectation is so high once you come up out of the inner city. Especially from Cabrini, famous Cabrini,” Hammond said, “We’ve had actors, singers, athletes come from here.”

No stranger to the difficulties faced by those he now mentors, Greg Fleming is working to be enshrined amongst the Cabrini success stories. His tool? A basketball. It was his way out, and he hopes it’ll be a chance for others like him. ​