The Bears took players who turned out to be underachievers and made them much, much worse. They ruined Trubisky's career, and may have done the same to Fields.
That's speculative as, unfortunately, there is no way to prove or disprove that anyone's career can be ruined by an organization. The only real barometer we have is performance; in the case of Trubisky, you have an additional data point of performance in two different organizations and offenses: Bears and Steelers. There's examples of players moving on to different teams and revitalizing their careers (or at least, improving significantly) such as Geno Smith, Baker Mayfield, Drew Brees, Ryan Tannehill. However, in the case of Tannehill, he regressed back to mean over time (and most would agree he isn't a franchise qb). There's also cases of QBs going elsewhere and ultimately failing or worsening such as Russel Wilson and Carson Wentz (though Wentz definitely went downhill while still in Philly - his precipitous degradation in performance is still bogglingly enigmatic to me).
To take a big swing, though, you need to wait for the right pitch. The Bears always seem like they're trying to outsmart somebody (trading up for Trubisky, taking Fields even when he mysteriously fell down the board on draft day). They end up outsmarting themselves.
That's a bit of revisionist history though. Calling Trubisky, who was the #1 QB on lots of media draft boards at QB (won't speculate on teams' draft boards as those are publicly published), not the 'right pitch,' seems obvious in retrospect, but wasn't so at the time of the draft because of the aforementioned draft pundits analysis of QB prospects at the time. Fields, also at the time he was drafted, was touted as 'QB1-B' behind QB1A, Trevor Lawrence, and held that position since really high school. Some claim the revelation of Fields' epilepsy might have contributed to his draft fall, but I'd say, most other teams that drafted other QBs before Fields were the ones that tried to outsmart everyone (and thus, outsmarted themselves). Wilson and Trey Lance were surprise picks over Fields and I don't think anyone is disputing which of the three are better - it's Fields and it isn't close.
Now here's Caleb Williams widely touted as the #1 quarterback in this draft in this "generation," (whatever that means). I'm not necessarily a Williams guy (there's someone else I'm intrigued by), but it would seem to be a no-brainer for the Bears to draft Williams, as it appears to be for everyone else. But the Bears are arrogant. Will they outsmart themselves yet again? Will Virginia get involved and start pulling King George's strings?
Hyperbole aside, I think implying something that is widely debated here on the forums, in the media, amongst active players, and throughout the general online community a "no-brainer" makes it decidedly not a "no-brainer" decision. That only serves to denigrate anyone with an opposing viewpoint to the one you're positing, but ultimately undermines your position as it's a clear fallacy to label something so widely argued as clear-cut as you assert. The prominent illeist himself, Shoopster, often touting his own sensible pragmatism, should be capable of rationally conceptualizing both sides of a pervasive debate, no? I'd argue they never did outsmart themselves in either swings for first round QBs they just simply made the wrong pick - not due to arrogance, but rather because of the uncertainty that any draft prospect presents. The was a thread not too long ago that listed a bunch of first QBs in the draft taken and the hit rate was less than 50%. Now, that either speaks to the vast ineptitude of scouting within organizations of the highest echelons of football (only 32 NFL scouting teams and GMs) or that these draft picks are anything but assured. Implying, it takes a combination of luck along with competence simply to have a greater chance of striking gold on your next field general.
The wildcard here is Poles. I don't think he'll puppet himself to bend to the McCaskey/Accorsi/Polian/any-other-NFL-veteran-we'll-be-surprised- to-hear-is still-alive-when-we-hear-the-Bears-are-consulting-them recommendation. Can he hit on a Super Bowl coaching staff and franchise quarterback in one off-season and write his ticket for another 10 years? He has a tremendous opportunity and I find it difficult to believe he is going to settle for retreads in either direction if he doesn't believe in them, and neither Everlose nor Fields has given him enough reasons to believe in my opinion. Poles has to go for it . . .
Drafting itself is a wild card among a deck of uncertainties that the prognosticator of prognosticators can't augury. We don't know what Poles will do, we don't know what input Kevin Warren has, we don't know what input Kevin Warren would give...we just don't know.