Here's my theory on the Bears organization, after growing up in the area, and living there unti 2015:
The McCaskey family somehow built an incredible team in the mid 80s. OK, Jim Finks built it but they had to hire him. It was an incredible defense, a legendary RB, and a quarterback who wouldn't lose the games for them.
Fast forward, all the rule changes since the mid to late 80s have favored the offense. The Bears are still focused on a dominating defense first. The 2006 team in some ways, resembled the mid 80s team. No not as dominant, but a great defense and got to the Super Bowl with a mediocre QB. The 2018 team was fraudulent; some top line defenders but they relied on gimmick plays offensively.
The McCaskeys are still living in 1987. The game has changed; they haven't adapted. They clearly do not have the right people in place to judge quarterbacks. Rick Mirer? Then the one year guys like Kordell Stewart and Chris Chandler. Rex Grossman in the first round? THey trade a couple number 1s for Jay Cutler. Cutler wasn't horrible but if he holds all your franchise passing records, its not good. Then the 3 number ones to move up 1 spot to draft a guy (Trubisky) that San Francisco had no interest in. Now they move up to draft an OSU quarterback who's biggest questions were about progressing thru his reads. Ever think anyone questioned Brady, Peyton or Brees progressing thru reads? Of course not, as that should be a huge factor in judging a QB.