Stewart played college basketball for the University of Southern California, where he left as the school's all-time leader in three-point field goals made with 245.

He later signed an Exhibit 10 deal with the Indiana Pacers, which included Summer League and training camp.

[7] He was subsequently added to the Fort Wayne Mad Ants training camp roster.

[8] On January 22, 2019, the Fort Wayne Mad Ants announced that they had traded Stewart to the Wisconsin Herd with the returning player rights to Alex Hamilton for Jordan Barnett and Ike Nwamu.

[12] Stewart was named league player of the week on November 10, after contributing 30 points, six rebounds and two assists in a win against Wilki Morskie Szczecin.