1. Jay Cutler
Would you truly pick anyone else other than smokin' Jay Cutler to put atop this list? It's impossible to do so. The easy answer as to why Cutler is the greatest quarterback in Bears history is because he owns the record for most passing yards (23,443), touchdowns (154), wins (51), game-winning drives (18) and games started (102).
Cutler had one of the most naturally-gifted arms this league has ever seen, and that's a fact. The way he could sling it downfield, effortlessly, is what drew scouts and coaches to him out of Vanderbilt in the first place.
Now, say what you want about Cutler as a person, but from the outside, nobody really knew the guy. He kept mostly to himself. We only saw what he portrayed to the media. But, if you ask plenty of his ex-teammates, most of them will tell you he was a great guy to have around the locker room.
Cutler does a ton off the field for underprivileged kids and children with diabetes, which is something he's dealt with himself. He still loves the city of Chicago, today, and it's pretty safe to say the city loves him back. As many of those "Oh no" throws he made, he also made plenty of great plays during his time in Chicago.
He's still the greatest quarterback this franchise has ever seen, so we've got to respect that and keep the jokes in good taste, right?