Caleb Williams’ NFL future could depend on whether the Bears land Jim Harbaugh as head coach

If the Bears can’t get Harbaugh, they will probably stick with Matt Eberflus, which would point to retaining Justin Fields.

The speculation surrounding the 2024 NFL draft is revving up now that the draft order is official and the regular season is over. Teams are making head coaching and staffing decisions while beginning to plot their moves for the draft in the spring.

If you’re in Chicago as a member of the Bears’ ownership group or front office, what are you thinking right now? No one ever said the Bears are a well-run organization, but if you’re trying to be logical about improving a bad team, you would agree with this basic point: If you’re going to fire your head coach, you should probably start over at quarterback. If you’re going to retain your head coach, you should probably try to give the head coach what he needs to repair and improve his relationship with the quarterback he already knows.

Should the Bears retain head coach Matt Eberflus? Probably not. Eberflus has shown nothing to indicate he will take this team to a higher level. However, the word on the street in Chicago is that the front office will stand by Eberflus … unless the Bears can bring in Jim Harbaugh, who is widely expected to leave Michigan for the NFL.

Harbaugh is seen as a favorite to become the next coach of the Los Angeles Chargers, but if the Bears can somehow convince Harbaugh to come to the Windy City, everything changes.

If Harbaugh goes to Chicago, then the Bears would naturally want to start fresh at quarterback as well and take Caleb Williams. If Chicago fails to get Harbaugh, though, that means Eberflus likely stays. In that case, sticking with Justin Fields makes more sense. Trusting the head coach for one more year should lead the organization to ride with the quarterback one more year. Give the coach and quarterback the groceries, the list of ingredients they need in order to cook.

If Caleb Williams does get picked by the Bears, it’s more likely to be under Jim Harbaugh than Matt Eberflus.

Then again, the Bears aren’t a well-run organization. They could keep Eberflus and still pick Caleb Williams, entrusting the star quarterback to a mediocre and unproven coach they might then fire one season later. It wouldn’t be the right way to do things, but then again, the Bears usually don’t do things the right way.

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