The Jim Harbaugh connections were there. Michigan's national-championship winning coach had spent years playing QB for the Bears, and rumors of the two sides being mutually interested in one another have been around Chicago for years. The Bears also love bringing in alumni based on what they did for the team in the 80's, which makes even more sense why the two would have been a good fit. And yet, while Harbaugh's spent the last 2-3 years interviewing with half the teams in the NFL, the Bears have kept to themselves, opting to keep Matt Nagy and Matt Eberflus in seasons when Harbaugh – and other, arguably-better coaches – were theoretically available. But now that Harbaugh's going to the Chargers, the dream is officially dead. So did the Bears make a mistake by not hiring Harbaugh when they could?
Why the Bears will regret not hiring Jim Harbaugh?
The short answer is yes. The slightly-longer answer, which you'll run into here in a moment, is still yes. Everywhere he goes, Harbaugh wins. He won at San Diego St., he won at Stanford (Stanford!), he won in San Francisco, and he certainly won at Michigan. There's plenty of reason to be skeptical about college coaches making the jump to the NFL, but when you've already successfully done that – like Harbaugh has – it's hard to bring up that point. Outside of all the pomp and circumstance that would have surrounded a Harbaugh return to Chicago, it would have just been a smart move.
Instead, the Bears are stuck with a (semi?) lame-duck coach who will probably go into 2024 on the hot seat. What makes that even worse is the fact that the Bears, more than likely, will be heading into said lame-duck season with their new franchise quarterback that they used the first overall pick on. So instead of getting Caleb Williams (or Drake Maye, I guess) in the building with one of the best head coaches – which is not even mentioning his skill at developing QBs – in football, they're going to try and make it work with a defensive-minded coach that has almost no job security, and an offensive coordinator who comes to Chicago with mixed results on his resume. Even outside of the specific people involved, that's just a bad process, and the fastest way to continue being mediocre at best.
And yeah, maybe Harbaugh to the Bears wasn't ever as realistic as the radio callers in Chicago suggested. He can reportedly be tough to work with, and will presumably want control of a ton of organizational decisions with the Chargers. Maybe that's more than what Bears president Kevin Warren, and GM Ryan Poles, were comfortable giving up. The Bears showed encouraging signs of growth in the second half of the 2023 season, so it's at least understanable that the shot-callers would want to see how the rest of that process plays out. But still: when you have Harbaugh – or any of the other half-dozen coaches that are still available – out there, and you stick with the guy that hasn't done a whole lot yet, it's a tough look.