CAMBRIDGE, Mass. — Since its inception in 2015, Kyle Umemba has turned the Let It Fly Classic into a summer basketball fixture in Boston.
AJ Dybantsa and the late Terrence Clarke are among the names who have participated in the event that now attracts some of the best talent in the region for a fun and competitive tournament at Chelsea High School. Umemba, a former player at Buckingham, Browne & Nichols, partnered with his friend Cesar Castro, a former Chelsea High standout and now the program’s head coach, to give back to the community with the event. And the two have continued to look for ways to grow it.
They did that this year, by expanding their tournament to South Africa and London in June and July, respectively. But Umemba had always wanted to find a way to add a development piece for the star-studded talent that they bring in. He markets Let It Fly as street ball-style basketball that can get intense, but he believes it’s crucial to hone in on players’ skills, especially in this age of social media where he thinks it’s getting overlooked.
“It can still be fun, but developing is the key to unleashing the players’ real capabilities,” Umemba said.
Fortunately for Umemba, he knew the perfect guy to help him.
Nick Friedman, a friend and former AAU teammate with NBA coaching experience, had long admired Let It Fly from afar. And after spending the last five seasons as an assistant coach with the Charlotte Hornets, he had an opportunity to get involved this summer. Friedman connected with Umemba in June, and last Friday – a day before the marquee Let It Fly tournament – he held an invite-only workout billed as an NBA developmental experience called “The Preparation” for some of the top prospects in Massachusetts.
Sebastian Wilkins (Canton, Mass.), Alex Wilkins (Charlestown, Mass), Warren Keel (Springfield, Mass.), Sam Fleming (Springfield, Mass.), Xavier Abreu (Lynn, Mass.) and Jaylen Hunter-Coleman (Charlestown, Mass.) – six of the best recruits from the 2025 and 2026 classes – were among the participants in Friday morning’s workout led by Friedman and a collection of coaches at Cambridge Ringe and Latin School. Friedman put them through a two-hour experience designed to simulate an NBA pre-draft or practice workout, including film study, conceptual group skill work and live game simulation.
For Friedman, it was a special opportunity for him to return home to Cambridge and lead a workout at his alma mater, but it went even deeper. Friedman has recognized that there’s a large presence of New Englanders in the NBA – from players to coaches to front office members – but there hasn’t necessarily been a lot of giving back and improving the basketball culture back home, and it was important for him to do that.
Friedman has also had the chance to coach at Chris Paul’s elite camp – where some of the best high school recruits in the country are invited – for the last six years, which has informed his understanding of what the top prospects know about what it takes to be successful at the next level. As someone with coaching experience at the NBA, G-League, college and international levels, Friedman wanted to use his unique platform for good.
“The biggest issue is how these kids struggle to know how to play the right way and understand the pace at which it takes to play, and so if I have the opportunity to come back to Boston specifically and provide that knowledge and context of what it takes on the court, I was just kind of blown away with that opportunity to do so,” Friedman said.
“For me to be able to provide context of where I’ve been and use that context to help improve a life, that’s what we do. It made perfect sense as soon as we talked about it.”
Friday’s workout was all-encompassing, with three periods of film breakdown scheduled around on-court drills. They talked about spacing principles, making quick decisions, how to properly switch defensively and how to attack them offensively. They went into everything that would make them successful at the NBA level – which is obviously years away from being a possibility, but will make them better and prepared in the meantime.
“I really wanted to make it a high processing environment where kids may struggle, but the whole point of the exercise is how you maintain your joy, how do you maintain your focus and competitiveness and how do you move on to the next play all within a highly demanding environment and that’s what the NBA is,” Friedman said. “Getting these guys used to that environment early and getting a taste of that I think could be tremendous for an Alex Wilkins, a Sebastian Wilkins, a Warren Keel and these guys that are talented and have been talked about a ton.”
Sebastian Wilkins, a 6-foot-8 wing who plays at Brewster Academy and is one of the top recruits nationally in the Class of 2026, has NBA dreams and savored the opportunity to be involved in Friday’s workout. He had several takeaways from the experience, including learning more about the sharpness, short-term memory and quick decision-making it takes to be successful at the next level.
“I think it’s going to be very valuable,” he said. “Being able to take what I learned and mix it in between what I already do, and just like when I get to that level, being maybe a step ahead of some of the other people who didn’t get to experience that.”
The hope is for this development workout to continue and grow alongside the Let It Fly Classic, which has firmly established itself as a community staple over the last decade with fun and entertaining basketball featuring local stars that’s completely free for the community. The event has raised more than $60,000 to allocate more than 60 scholarships – which are in Terrence Clarke’s name – for Chelsea High School students since it began.
Continued expansion of Let It Fly is in the works, and Umemba wants to see it travel to Africa, Europe and Latin America. “We’re literally going to chase the sun,” Umemba said. Growing Friedman’s workouts are in their plans, too.
Friedman said he wants to see this become a two-day event where they bring in a group of New England-based prospects and another group from outside the region. He believes being exposed to players from other parts of the country and the world is paramount to growth as these kids see what different talent and playing styles look like.
“My ultimate goal is to make this a platform of growth for years to come,” Friedman said. “Kids come in here, some of the highest level kids in the state and region of New England, we get them in the gym and we put them through two hours of what would be a pre-draft style, training camp style type of workout environment where it’s quick hitting, fast developing, we hit them at all angles. …
“It’s an activity of growth, and that’s what we’re here for.”
