Stewart began his CFL career with the Edmonton Eskimos in 1984 and played there until 1990. He then moved on to BC and Saskatchewan where he finished his CFL career in 1993. Stewart was a Western Allstar 5 times and a CFL Allstar 3 times. He was the runner up for both the 1984 CFL Rookie of the Year and 1990 CFL Outstanding Defensive Player of the Year and won a Grey Cup in 1987 with the Eskimos.