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The Bears have retired fourteen uniform numbers, which is the most in the NFL, and ranks fourth behind the NBA's Boston Celtics (21), MLB's New York Yankees (20), and NHL's Montreal Canadiens (15) for the most in the four major professional sports leagues in the United States and Canada.
Justin Fields (2021–2023) Mitchell Trubisky (2017–2020) Jay Cutler, who holds multiple Bears franchise passing records [1] (2009–2016) Kyle Orton started 15 games in 2008 Rex Grossman, who played for the Bears in Super Bowl XLI in 2006 (2003–2008) Jim McMahon, who won the Bears' only Super Bowl in 1985 (1982–1988)
On later date, Chicagobears.com released a list titled "Top 10: Best of the rest", that featured the top 10 snubs from the centennial list. The players include (in a following order): Alex Brown , Thomas Jones , Dave Whitsell , Curtis Conway , Tim Jennings , Leslie Frazier , Roberto Garza , Marty Booker , Nathan Vasher and William Perry .
Here's a look at some of the names connected to the job thus far. Bears head coach rumors While plenty of names will eventually fill out the list, the Bears look ready to prioritize an offensive ...
Longest run from scrimmage – Bill Osmanski rushed 86 yards vs. the Chicago Cardinals, 10/15/39. Longest pass from scrimmage – Bo Farrington caught 98-yard pass at the Detroit Lions , 10/8/61. Longest play in Bears history – 108 yard missed field goal return , Nathan Vasher , vs. San Francisco 49ers , 11/13/05; Devin Hester , at New York ...
Now in the single digits of the 30 Most Important Bears, at No. 9 is Trevis Gipson, who is primed to become a breakout star this season.
Chicago Bears fans, take a deep breath. Yes, drafting Mitchell Trubisky over Patrick Mahomes is Da Bears' most painful what-if of the 21st century. But this one might be a close second.
The most recent Bears to be inducted were Devin Hester and Steve McMichael in 2024 (primary contributors) and Jared Allen (minor contributor) in 2025. In addition, Ray Bray was enshrined in Helms Athletic Foundation Pro Football Hall of Fame , which was established in 1950 and preceded the Pro Football Hall of Fame.