Stewart's NHL career was interrupted by the Second World War in 1943. He remained in Canada, serving as a Leading Aircraftman in the Royal Canadian Air Force and playing hockey for the Montreal RCAF and Winnipeg RCAF teams between 1943 and 1945. Upon his return to the NHL, Stewart was paired up with Bill Quackenbush on the Red Wings defence. He went on to earn four additional all-star selections: he was named to the second team in 1945–46 and 1946–47, and to the first team again in 1947–48 and 1948–49. Additionally, he played in the first four National Hockey League All-Star Games, held between 1947 and 1950. Not known for his offence, Stewart never scored more than five goals in a season, and his career high of 19 points was set in 1947–48. He won his second Stanley Cup with the Red Wings in 1950 as they defeated the New York Rangers in double overtime of the deciding seventh game.