In George McCaskey's tenure overseeing the entire operation of the Chicago Bears, the cycle has made all hope dead on arrival every time this team was ready to reset under a new regime.
Whether making decisions retroactively instead of proactively, firing coaches and general managers one year too late, or conducting a head coaching search alongside a general manager search, thereby handicapping their new general manager by assigning them their first head coach, the Bears just never got it right.
Eventually, the general manager tries to scapegoat the head coach, who tries to scapegoat the quarterback, and two of the three move on, only for one to be left behind to reboot everything and then join them in the wind one year later. The cycle.
The fear is that the cycle is now repeating itself once more, this time though, potentially hindering the development of the Bears' biggest source of long-term hope in at least 30 years.
If Caleb Williams does not get to a second contract with the Chicago Bears, it will be the greatest failure in the organization's 100-plus-year history.
With the Bears' head coach already gone, the team president vocally saying he will be involved with the next head coach search, and the general manager entering 2025 on the proverbial hot seat, it is easy to see how the cycle repeating itself is inevitable.
However, there are two key distinctions that separate this situation from situations past. The first has nothing to do with the Bears and everything to do with sheer luck. I.e., Caleb Williams flourishing play in the midst of all this chaos will attract the best coaches to the job, and if the Bears can find the right coach and success is had, then stability will ensue.
The second distinction has to do with the potential to hire a coach with cache, something the Bears have not been able to successfully do in the past. With reports floating out there that the Bears may have a path to inquire about established head coaches like Kyle Shannahan and other, currently employed, coaches reaching out anonymously asking why their name is not being linked with the Bears' job, there is a strong chance that the Bears end up with a coach that comes in with an existing reputation and nothing to prove.
The value of this type of coach is that this coach is too proven to have their job security be at the mercy of the general manager's ego. Typically, general managers like to pick their coaches, and if Ryan Poles is let go by the Bears in a year and replaced by someone new, the worry would be that the Bears' second-year head coach would then be on the hot seat.
However, in this instance, If the general manager has to be let go, the Bears already have a coach who has enough respect and connections around the league that the Bears could hire a skilled general manager to go along with their head coach and stability can be maintained. It's why it didn't affect Andy Reid when the Chiefs moved on from John Dorsey as GM and hired Brett Veach because no one in their right mind would fire Andy Reid over their ego.
Hypothetically, consider if the Bears traded for a Kyle Shanahan, Sean McVay type, or if the Bears signed a Mike Vrabel-type. This coach is going to command the type of respect and receive a contract with the type of money that it frankly doesn't matter if Ryan Poles is on board with the hiring or if. That's how the Bears and Kevin Warren can avoid the consequences of a mismatched timeline by acing their head coaching hire.