7 questions for Bears amid pivotal offseason search for coach, general manager

George McCaskey’s press conference was:
Inconsistent. He couldn’t seem to decide whether he was the tough, buck-stops-here type of owner or the aw-shucks-regular-guy who just so happens to own a team. He didn’t see anything “magical” about having a football czar, but basically just hired one in Bill Polian to help make two enormous decisions for the franchise.
What lesson should the Bears learn from the Ryan Pace-Matt Nagy pairing?
That they’re overly patient and lenient. It’s great that Pace and Nagy were nice guys and collaborated so seamlessly with each other, but it should’ve been obvious at least a year earlier that the combination wasn’t working. Even after that, the Bears should’ve done what any other team would’ve done in their position and fired both in November so they could begin the process of replacing them with no delay.
Rank the Bears’ coaching job against other NFL openings:
Fourth out of eight, behind the Jaguars, Raiders and Dolphins. Beyond the organizational concerns about the Bears, those three teams offer very enticing opportunities to win quickly. The Jaguars believe they have a franchise quarterback in Trevor Lawrence, tons of salary-cap space, the No. 1 pick in the draft and play in a manageable division. The Raiders are already a playoff team. The Dolphins went 9-8, are projected to have the most cap space in the NFL and have three first-round picks over the next two years.

Should the Bears prioritize an offensive coach?
No. That’s shortsighted. Hire a coach who knows what he’s doing and could hold the job for a decade. Period. Bill Belichick is a defensive genius, and the Patriots have been a top-10 scoring team in 19 of his 22 seasons. Hire the right coach and he’ll hire the right coordinators.

The head coach candidate that intrigues me is:
Brian Flores. There’s no way he should be available. He seemed to learn plenty from his 11 seasons with the Patriots and inherited a much more challenging situation with the Dolphins than what the Bears present. He made mistakes that he needs to learn from, but still went 19-14 over the last two seasons.

The general manager candidate that intrigues me is:
Omar Khan. The Bears think they’re the Steelers. They clearly aren’t, but Khan could teach them if they’re willing to listen. He has spent 21 years with the Steelers and had tremendous success. The best thing the Bears could do is hire him and do whatever he says, leaving him in charge of resetting their “culture” to build an organization that insists upon excellence in every aspect.

How long will it take for the Bears to be good enough to win a playoff game?
It’s looking like 2024 if things go well. The upcoming season is a sunk cost, then maybe there’s progress in 2023 and a chance to legitimately compete in 2024. The biggest factor in that won’t be the coach or general manager, though. That plan hinges largely on quarterback Justin Fields growing into a star.