There's nothing quite as unique as the Chicago Bears' quarterback experience. And when I say unique, I mean "miserable" or "depressing" or "bleak." They're the only team – literally the only one – without a single-season 4,000 yard passer, and the long line of mistakes they made at the position would be, frankly, a more interesting listicle to put together. It doesn't help that recent high-profile decisions to draft Mitch Trubisky and Justin Fields have backfired spectacularly, but that's kinda par for the course in Chicago.
But now it's Caleb Williams' turn to try and break the cycle. If he ends up like Trubisky or Fields, maybe they should just try playing football a different way. At that point, it couldn't hurt. But while we all wait to see whether Williams is finally the guy that the Bears have been waiting 100 years for, let's look back on who's been kinda good for them in the past. These are the 5 best QBs in Chicago Bears history. It was supposed to be 10, but I couldn't find enough.
The top 5 quarterbacks in Chicago Bears history
5. Mitch Trubisky (sorry)
This is how bleak things in Chicago are. And if you wanted to put Erik Kramer here, I wouldn't stop you. Yet, somehow, Trubisky ranks 5th in yards (10609), 5th in total record (29-21), 3rd in completions (1010), and 8th in QB rating (87.2) despite being universally panned by every single Bears fan at some point in the last half decade. The trade up to get him doesn't help his case, nor does the fact that a very certain QB was taken a few picks later. He was plenty capable during that magical 2018 season, and he even played pretty well during the biggest game of his career – it certainly wasn't his fault that the game ended with not one, but two doinks. He's also the inaugural Nickelodeon's Valuable Player award winner. Still, he wasn't particularly good, and it speaks more to the Bears' bleak QB history that he makes this admittedly subjective ranking.
4. Jim Harbaugh
Harbaugh has the wonderful distinction of being one of the few QBs on the list who actually has a winning record with the team. The Bears! He went 35-30 over 89 games played with the team, all from 1987-1993. During that time, Harbaugh threw for over 11,000 yards, 1,000 completions, and 50 touchdown passes. As of this year, he's 3rd all-time in passing yards, 8th all-time in touchdown passes, and 2nd all-time in completions. He also had the distinct honor of being the latest former Bears player to be seriously considered for a head coaching position, a tale as old as time in Chicago. (Although he was, admittedly, a much stronger candidate than a lot of other options that popped up in rumors.)
3. Jim McMahon
Maybe the most beloved QB on this list? Even if he wasn't good, being the QB of the Super Bowl winning 1985 team was always going to get you free drinks in Chicago for the rest of your life. Fortunately, McMahon was also pretty damn good: he was the NFC Offensive Rookie of the Year in 1982, made the Pro Bowl in 1985, and won Comeback Player of the Year in 1991. On the team record board, McMahon ranks 6th in completions (874), 4th in touchdown passes (67), 2nd in QB record (46-15), and 4th in total passing yards (11,203). He's an icon in Chicago, and the headband routine was an all-time great bit. He's also the most entertaining Twitter follow of anyone on the list, for what it's worth. He's one of the NFL's great characters, and the Bears would be a much less interesting franchise without him.
2. Sid Luckman
It's hard to compare most of the quarterbacks on the Bears' QB Football Reference page with Luckman, mostly because Luckman's the only guy towards the top who played in a totally different era. He played so long ago that Football Reference doesn't even have a record for him, which is really saying something. But he still – somehow – ranks 2nd in total passing yards (14,686), touchdown passes (137), and 5th in completions (904). On the Bears' single-season passing record boards, Luckman's 1943 season (sigh) is tied for 2nd all-time in touchdown passes (28). He's the franchises' one real historically great QB, and if you put his stats on any other team, that probably wouldn't quite be the case. But he's the base that radio hosts use to complain about the Bears' QB history, which is an important role in the sports discourse ecosystem.
1. Jay Cutler
It brings me no joy to admit this, because Cutler's schtick isn't nearly as charming as he and his supporters pretend it to be. But there's no denying that Cutler was a star for the Bears – after eight years of being QB1 in Chicago, Cutler finished 1st in touchdown passes (154), 1st in passing yards (23,443), 1st in completions (2020), and 1st in game winning drives (18). He's a bit of a cult hero in Chicago, if only because he played during a time where everyone was online and knew how to photoshop cigarettes into pictures. But Cutler was the QB behind some of the better teams in modern franchise history, and he brought a physical toolset that Bears fans hadn't really ever seen before. He's also 2nd all-time in franchise history for interceptions, which is partly due to the amount of passes he threw, but also speaks a little to the style of quarterback he was. Caleb Williams, you're Chicago's only hope.