The spectacularly inconsistent Bears quarterback was a source of hope and despair during his eight seasons with the team, representing the best and worst qualities of a franchise that has been unable to find much, if any, success during that time. In an NFC championship game at home against the Green Bay Packers, Cutler was knocked out with a knee injury. The Bears haven't returned to the playoffs since. Bears 7-3 with Cutler, fall to 8-8 under Caleb Hanie.
The final pass of Cutler's career was an interception on a comeback attempt to beat the Giants. Plus, Cutler for years has had a reputation as a locker room malcontent. It may stem from the amount of money he's expected to be given, because that vitriol got cranked up again on Thursday morning with a report of an impending contract with Chicago.
Cutler is the Bears' all-time leader in completion percentage, passing yards and touchdown passes, but he also led the league in interceptions twice - one more time than he's led Chicago to the postseason.
What's next for the Bears?
Look, Glennon has the size and the strong arm going for him. Hopefully, Glennon will be good enough to keep the boat afloat while Chicago's potential rookie quarterback is learning the ropes. The Chiefs are paying Alex Smith an average of $17 million per year, and Andy Dalton is getting $16 million per year from the Bengals.
But he lacks mobilitiy. As a result, Glennon was extremely limited in action.
Cutler, who turns 33 in April, was the 11th overall pick in the first round by the Broncos in 2006.
Bears fans are also taking this in stride and in no way comparing Glennon to Osweiler.
However, the desire to start and promise of more money certainly weighed heavily on his decision to decline the generous offer, and has ultimately lead us all to this place.
Buffalo is another possibility, based on prior connections at least. Cutler has only been selected to one Pro Bowl in his career - and that came in 2008, when Bates was his QB coach in Denver.
There is no simple, black-and-white answer to the Cutler signing question, because it all depends on the contractual commitment the Jets make to Cutler.