Wilson played for ten seasons with the Bears, compiling overall record of 111 pass receptions, 1,342 receiving yards, and fifteen touchdowns.

After just two seasons with Chicago, Wilson left in 1949 for another assistant coaching position with the Detroit Lions, a division rival of the Bears.

Shortly after the season ended, Miami Dolphins owner Joe Robbie hired Wilson as the first head coach of the new AFL franchise in 1966.

After being fired as head coach of the Miami Dolphins, Wilson retired from football and entered the construction and real estate business in South Florida.

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.

[2] In the 1943 NFL Championship Game, Wilson caught three passes for 29 yards in the club's 41–21 defeat of the Redskins.

[5] 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.

[7] Wilson instituted an 11 p.m. curfew for his team while issuing $50 per hour fines for violators and doing bed checks at training camp.

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 NFL championship game, still the most recent league title for the Lions.

[12] In 1960, Wilson hired Don Shula as the defensive coordinator, who later succeeded him as head coach of the Miami Dolphins.

[9] He resigned on December 23, two days after his five assistant coaches were fired by ownership,[15][16][17] and was succeeded by former Lions player Harry Gilmer.

[18] Upon his resignation from the Lions, Wilson had compiled a 53–45–6 (.538) record; only Wayne Fontes had more wins as head coach of Detroit.

[19] On January 29, 1966,[20] Joe Robbie named Wilson the first head coach of the American Football League's first expansion franchise, the Miami Dolphins.

"[29] However, the Dolphins regressed to 3–10–1, worst in the AFL; Wilson was fired two months later on February 18, 1970, and was succeeded by Baltimore Colts' head coach Shula.

In criticism directly aimed at Shula, Wilson remarked, "I also helped him get the Baltimore Colts head coaching job (in 1963).

In 1978, Wilson moved back to Michigan and intended to eventually live in a house he built in Howell, but died before doing so.

On November 23, 1978, Wilson Sr. suffered a heart attack and died at Sinai-Grace Hospital in Detroit at the age of 64.