Stewart played
junior hockey with the Portage Terriers of the
Manitoba Junior Hockey League in 1935–36 and 1936–37, where he was discovered by a
Winnipeg businessman who suggested that
James Norris, owner of the
Detroit Red Wings, sign him. He was sent to play his first season of professional hockey for the team's minor league affiliate, the
Pittsburgh Hornets of the
International-American Hockey League (IAHL). He recorded one assist in 48 games in the
1937–38 season. Partway through his second season with the Hornets, the Red Wings recalled Stewart as part of a bid to shake up their team which had been struggling. He appeared in 32 games in his NHL rookie season of
1938–39, and immediately established himself as a physical presence. In his fifth season,
1942–43, Stewart was named to the
NHL first All-Star team on defence and helped lead the Red Wings to the NHL regular season title. Stewart scored one goal, added two assists and had 35
penalty minutes in ten playoff games. Upon his return to the NHL, Stewart was paired up with
Bill Quackenbush on the Red Wings defence. Following the championship, the Red Wings dealt Stewart to the
Chicago Black Hawks as part of a nine-player trade that was, at the time, the largest in NHL history. Stewart,
Harry Lumley,
Al Dewsbury,
Pete Babando and
Don Morrison were sent to Chicago in exchange for
Metro Prystai,
Bob Goldham,
Gaye Stewart and
Jim Henry. Doctors diagnosed his injury as a ruptured disc and urged him to retire. He was told following the injury that he was lucky he could still walk without a cane and not to risk further damage on the ice. Instead, Stewart had the disc removed and after completing what Black Hawks' team doctors described as a "most remarkable" recovery, he opted to continue his career and signed with Chicago for the
1951–52 season. Early in the season, Stewart suffered a minor skull fracture after colliding with teammate
Clare Martin, an injury that forced him out of the lineup for several weeks. Stewart spent two weeks in hospital, after which he announced his retirement, but he again shocked observers by returning to the ice. However, by mid February 1952, his injuries led Stewart to ask the Black Hawks for his release so that he could seek a minor league coaching position. ==Coaching career==