Best: Chicago Bears – Sid Luckman
Though the Chicago Bears franchise has had some of the most iconic names in NFL history on its roster, including Walter Payton, Dick Butkus, and Mike Singletary, they haven’t had anything close to that at the quarterback position. The franchise forever known for its “Monsters of the Midway” defense haven’t boasted a truly elite NFL quarterback since Sid Luckman played under center for them in the 1940’s, under legendary coach George Halas.
Though Luckman’s passing yardage and touchdown pass totals were eventually surpassed by Jay Cutler, the latter is not — and will never be — a five-time All-Pro selection and Hall of Fame inductee like Luckman.
Worst: Chicago Bears – Bob Avellini
For all the glory the Chicago Bears have had on the defensive side of the football (and at the running back position), that hasn’t been shared at the quarterback spot. The history of the Bears franchise is filled with guys like Bob Avellini, who had one winning season during his first four years in the NFL.
Avellini finished his nine-year career in Chicago with more than a 2:1 ratio of interceptions to touchdowns (throwing 69 interceptions to only 33 touchdowns).