Jay Cutler
A wise man once said that Chicago is where NFL quarterbacks go to die. The Bears traded for Cutler in 2004 after he showed promising signs in Denver. Cutler occasionally threatened greatness but never fulfilled expectations. It’s wrong to call him a total failure but Chicago didn’t progress the way that they expected.

They thought that they were getting an elite star after he made the Pro Bowl for the first time in 2008. But that was the only selection of his confusing career. Arguably, the Bears clung to Cutler for too long and should have moved on quicker. It’s difficult to pick an actual highlight from his time in the Windy City (via Sports Illustrated).