Wilson began his coaching career with the Bears in 1947, when he became an assistant coach to George Halas. He spent just two seasons with Chicago, before taking an assistant coaching position in 1949 with the Detroit Lions, a division rival of the Bears. Before the 1957 season began, he succeeded Buddy Parker as head coach. In his first year as head coach, Wilson guided Detroit to an 8–4 season and a 59–14 victory over the Cleveland Browns in the 1957 NFL Championship Game, to date the most recent league championship for the Lions. For his efforts, Wilson received the Associated Press NFL Coach of the Year Award, being the first recipient of the award. During the post-1957 season, he also served as the Western Conference head coach for the first nationally televised Pro Bowl, while Parker, then head coach of the Pittsburgh Steelers, coached the Eastern Conference. The Western Conference defeated the Eastern Conference by a score of 26–7.