Stewart attended Manley Academy in Chicago, Illinois, where he played basketball under head coach Bo Delaney.

[2] Stewart was known for being a strong ball-handler and became Manley's top point guard heading into his senior season.

After his freshman season in the NJCAA, he averaged 14.3 points, 6.1 assists, 4.1 rebounds and 3.3 steals, and he shot 60% on field goals.

He has three brothers in Anthony, Darnell, Amir, and Jamil, and three sisters in Gabrielle Jayla, and Jessica.

[1] In early 2013, Stewart had a hiatus from professional basketball, leaving the Island Storm, to pursue a career as a teacher in the Chicago school system.