How Will the Bears Handle Their Franchise-Defining Moment?

Warren would be wise IMO to let Poles know he's safe for the foreseeable future. 

First off, he's done a pretty damn good job for a rookie GM taking over an absolute dumpster fire left to him by the previous regime.  Not perfect--no GM is--but pretty darn good job of getting the ship turned around.
Secondly, he didn't draft Fields so I wouldn't be looking to fire him next year even if he keeps JF and JF flops badly.  Poles should be able to set himself up with extra 2025 draft capital to move on if needed.
Thirdly, most GMs get a 2nd HC hire and at least one shot at drafting a new QB if the team needs one.

Point is, I want him to make the difficult personnel choices he has to make the next few months based on the coaches and players involved, NOT on concerns for his own job security.  Cuz yeah for his own selfish purposes, drafting Caleb is by far the safer choice.  He would reset the contract clock and buy himself several more seasons while a rookie QB gets up to speed.  

Make the decision on the MERITS, not on saving your own ass.  

+1

The more I think about this, the more I agree with you.  I think it will come down to the outcome of that game.  I am seeing lots of activity on social media that George McCaskey really, really wants to see us win that game.  If Flus, Fields and the rest of the team can pull it off, it will be basically impossible to do anything else than keep Flus and Fields (and maybe even Getsy, as disgusting as that though is).

It will be interesting to watch how this all goes for the Bears at QB.  Watching Caleb this year I thought he was not the guy for us even if we do draft a QB from this class.  But it's on the Bears to figure this all out, and I admit I could be wrong about Caleb.  If we do draft him I will be 100% cheering for him to do well here.  

Exactly

This should be obvious -- Management 101 stuff here -- but the Bears have been inept at these things before so it's hard to trust them.  

At the very least, give Poles full assurances that his job is not at stake.  Remove all extraneous factors from the decision.