There’s No Reason Bears Can’t Keep Keenan Allen Beyond 2024

That is a good point.  Maybe one more year would be nice though (2025) for continuity for Caleb.  Maybe pass rusher will get attention in next year's draft with 3 picks in the first two rounds of the draft.  Pass rusher and OL.

I'm probably being delusional but I keep hoping Allen might be willing to work with the Bears on a somewhat reasonable extension like that... so he can end his career here with Caleb and this offense.  At the end of this year, it is reported that his career earnings will be a bit over $133 million dollars.  I could see him wanting to max out his earnings for retirement... or he could be a bit less aggressive if he doesn't want to move on again at this point at the end of his career.  He is 32 years old now.  A two year extension would keep him here through 2026.  But the Bears will need to extend D.J. Moore for 2026 and beyond, so maybe they go for just the Allen extension for 2025 and put that WR money into the new DJ contract for 2026.  And after 2027 the Bears will ideally extend Odunze... that will be a whopper cost.

I totally see your point.  Regarding 2027, you're right that the roster will have aged.  A good GM should make certain that there isn't a doomsday point where the team is back to where it was when Poles inherited the financial and age mess here... the Bears will (hopefully) have people in the draft pipeline that will be ready to replace players we jettison each year.  It's an ongoing process so the team can sustain winning, like the better NFL franchises do, like the Chiefs.  Once you have an elite QB1 you have the opportunity to reload the roster like this.  It doesn't mean you win super bowls every year, but it means you have a winning team most years (like the Chiefs and the better winning franchises of the past).  Sustained winning.  Not a flash-in-the-pan year where you may be super bowl ready but not actually win the super bowl that year (things like injuries can derail that pretty quickly for that season).  Sustained winning is a better way and this is the model Poles has outlined from the beginning as his focus.  Yes, there are lots of moving parts here, and things can go wrong... but I do like the Poles' model for sustained winning.  I guess a way to look at it is a "super bowl ready" team that spans a decade rather than 1 season or two.  Doesn't mean you win 10 super bowls, but rather you have that caliber of team most years for a long time.  If Caleb is the real deal we may have that opportunity.