(BALTIMORE – September 4, 2026) – Kaii Gilliam doesn’t fit the mold of the typical Baltimore basketball legend piece — he’s only 27, still playing, still climbing. But his path from a sixth-grader who landed in Baltimore from the Bronx to a professional point guard hoisting a championship trophy in Colombia is exactly the kind of story that belongs alongside the city’s playground legends.
Finding Baltimore
Gilliam wasn’t born here. He was raised in the Bronx before his family moved to Baltimore when he was in sixth grade. He attended Woodlawn Middle School — now known as Southwest Academy — before attending Milford Mill Academy for high school.
At Milford Mill, Gilliam played behind Justin Jennifer, a Division I recruit, learning the game from the bench before it was his turn to lead.
I got connected to Kaii through Brian Hatcher of the OOH Foundation. Opportunities Over Handouts. Brian’s grandmother also organized in the community. While OOH has hosted the Sandtown’s Legends Game and Cookout for 21 years, Ms. Alma Tucker was organizing beach trips at the Odyssey since I was a kid. That went on for at least 30 years. So, Brian’s work is no surprise. In fact, he’s carrying on a family legacy.
So, if Brian thinks highly of Gilliam, I trust his word. The more I learned about his path, the more it felt like a story worth telling — not just as a basketball story, but as a story about persistence.”
First Witnessed at McAbee’s
I first witnessed Kaii Gilliam play in person at the 2026 Legends Game in Sandtown, presented by the OOH Foundation, at McAbee’s — right across from the former Gilmor Elementary. Gilliam has known OOH Foundation founder Bryan Hatcher since childhood, and coming back to Sandtown to play was never a burden for him — it felt natural, like coming home.
His team took home the trophy that day. It wasn’t the first time — his team also won back in 2016, a full decade earlier.
Building a Career, One Stop at a Time
Gilliam’s path to professional basketball wasn’t a straight line. He played junior college ball before landing at Wilberforce University in Ohio for a season, then transferred to Wilkes University in Pennsylvania. It was at Wilkes where things clicked — Gilliam earned All-Conference and All-American honors, helping lead the team to the NCAA Division II Final Four.
He graduated in 2022 with a bachelor’s degree in business administration, concentrating in marketing management. Off the court, Gilliam has his sights set on graduate school — he’s expressed interest in eventually pursuing a master’s in psychology.
Family Roots
Basketball and education run in the family story. Gilliam’s parents met at Shaw University — his father’s family has roots in the Bronx, his mother’s family in North Carolina. He has an older sister, four years his senior.
Turning Pro — and Winning a Championship
Gilliam’s most recent stop took him well outside the United States: playing for Girardota Storm in the Copa Elite league in Medellín, Colombia, where he helped the team win its first championship. He’s now working with an agent to find his next opportunity overseas.
Coming Home for the Legends
That return trip — from a kid new to Baltimore, to a national college standout, to a champion overseas, and back to Sandtown for the Legends Game two decades of trophies later — is the arc that makes Kaii Gilliam’s story worth telling now, while he’s still writing it.
This profile is part of BMORENews.com’s “Legends of Baltimore: More Than a Game” series.
