#2-Edward “Dutch” Sternaman
Tenure: 1920-1927
Not only was “Dutch” a player, but he was also an integral part of bringing the team to Chicago as a co-owner with George Halas. The two were teammates at Illinois and along with being players, the two men co-coached the team for a number of years. He was part of the controversial NFL champion team in 1921, earned All-NFL honors in 1923, and became a part of the Chicago Bears Ring of Honor in 2009.
Runner-up: Paul Edinger
And don’t yell at me for Doug Flutie. He was in Chicago for a year and played four games.