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. He played in all 48 games for Detroit in 1939–40; his lone goal on the campaign was the first of his career. Stewart and the Red Wings reached the Stanley Cup final in both 1941 and 1942, but lost to the Boston Bruins and Toronto Maple Leafs, respectively. 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. Reaching the final for the third consecutive season, Detroit defeated Boston to win the Stanley Cup. Stewart scored one goal, added two assists and had 35 penalty minutes in ten playoff games.