 Growing up, Stewart became friends with fellow Toronto native hockey player Wayne Simmonds, currently of the New Jersey Devils, and they return to Toronto as house-mates during the NHL off-season.Prior to the 2004–05, Stewart's older brother Anthony, who was the captain of the Kingston Frontenacs, put his reputation on the line when he asked Frontenacs General Manager Larry Mavety to give Chris the chance to try out with the Frontenacs as an undrafted free agent.Mavety complied, and Stewart made the team in training camp, allowing the brothers to play together on the same team.