Stewart attended Manley Academy in Chicago, Illinois, where he played basketball under head coach Bo Delaney. He was a teammate of future NBA player Luther Head.[1] His playing time increased after Head left the team.[2] Stewart was known for being a strong ball-handler and became Manley's top point guard heading into his senior season.[3] As a senior, he averaged 16.2 points, 12.1 assists and 4.9 rebounds, winning all-sectional honors. Stewart also earned All-Chicago Public School accolades two times.[1]
Stewart was born on September 5, 1983, in Chicago, Illinois to mother Cassandra Stewart. 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. He taught pre-kindergarten at Sherman Elementary School.[5]