Jay Cutler stands among the best quarterbacks in Chicago Bears history. That may not be saying much in a wider context. However, there is no denying it was never boring to watch #6 on Sundays. As it turns out, it also wasn’t boring whenever people managed to get a microphone on him. The guy was notorious for being surly and somewhat standoffish, but there was a sharp wit about him and a dry sense of humor that one couldn’t help but love.

He still has plenty of fans in Chicago even to this day. They believe he wasn’t the perfect quarterback, but he was perfect for this city. That might be why he lasted as long as he did despite long bumps along the road. It also might be why the NFL saw fit to honor him as one of the greatest characters in league history. He comes in at #99 overall, trailing right behind Jerome Bettis and Terrell Suggs. Not bad company to keep all things considered.

Jay Cutler might’ve been higher had he won more

One would imagine characters aren’t judged on wins but this is the NFL. Of course they are. Terry Bradshaw is the highest-ranked quarterback thus far on the list (#32). He won four Super Bowls so it’s only natural he’d earn such a spot. The bottom line is Cutler would’ve been so much more appreciated as the character he was had he been able to win more games. Unfortunately, he and the Bears just couldn’t quite get it done.

There were opportunities. They had winning seasons in 2010 and 2012 and reached the NFC championship. Sadly an aging defense and mismanaged offense led to him running out the final four seasons of his time in Chicago in mediocrity.