He attended and played football at Northwestern University. Wilson was a member of the 1936 Wildcats team, which won the Big Ten Conference championship. After going undrafted in 1937, he was signed by the Chicago Bears later that year. Although Wilson participated in all eleven games of his rookie season, he started only two games. He recorded just one reception for 20 yards in 1937. The following season, Wilson recorded his first career touchdown. From 1940 to 1942, he was selected for the NFL All-Star Game, today known as the Pro Bowl, and was First-Team in 1942. Wilson was a member of the Bears during their five appearances in the National Football League championship Game from 1940 to 1943 and in 1946, with the team winning in all but 1942. Listed as a starting right end for the 1940 NFL Championship Game, Wilson threw a tremendous block which took out two Redskin defenders as Bill Osmanski broke away for the Bears first score during their historic 73–0 rout of the Washington Redskins.