Winning in Chicago: Why Bears Should Swing Big in 2022

Let’s turn the clock back to 2011 — October, to be exact — when the culture of Chicago swung in a new direction with the weight of 108-year-old pendulum. The Cubs hired Theo Epstein: Breaker of curses in Boston, baseball genius, most sought-after front office executive in modern-day baseball. Everything changed on the North Side, and for good reason. Ownership took a Vlad Guerrero-sized swing to transform the franchise from a laughing stock of ineptitude to eventual world champions.

Their risk/reward should be a model for Chicago sports ownership, and what George McCaskey should keep in mind as the Bears decide their next era of front office jobs and coaching assignments. To quote Bulls forward DeMar DeRozan: “Imagine going there and winning in Chicago, oh my God.”

Winning one here means a lifetime of respect.

As the Bears approach “Black Monday” in the NFL season, it seems likely Matt Nagy is gone. Ryan Pace is still a mystery, and that might be about right. Pace has proven a solid late-round draft general manager, finding extreme talents of David Montgomery and Darnell Mooney, to name a few with more possible to emerge.

What the McCaskey family needs to realize from here on out is that the Bears are a destination. Chicago is a destination. Winning in Chicago is a lifetime of adulation among the fans. It’s ultimately why Epstein came to the Cubs — to break another curse — why DeRozan might lead a new era of free agents to the United Center and why a Blackhawks dynasty stuck together.

Fact is, the Bears can have whatever the franchise needs if ownership is willing to open the pocketbook. In addition to the Bears’ rich history — even if it’s little more than laurels for the organization to rest upon — Chicago itself carries prestige matched by precious few cities. If fans and players accept anything less than a major effort by ownership to leverage these things, then shame on them.

Shame on us.

I don’t want to turn this into a “hire this guy” post. That’s not the point. I have dream scenarios for the Bears, yes. A president of football operations that include the names of Tony Dungy, Ozzie Newsome, or Chris Ballard. A head coach that starts with Jim Harbaugh. Coordinators that start with Joe Brady and Vic Fangio.

It is all possible.

The Bears and the McCaskeys can make the wildest dreams of Bears fans come true, even if they retain Pace in some capacity. The Chicago Bears are a destination — so long as they aren’t run like a country club where membership more or less expires rather than being revoked — meaning hard decisions from the very top are necessary.

Epstein came to the Cubs with far fewer resources than the Bears currently possess. He didn’t have a Justin Fields or Darnell Mooney, much less a rejuvenated Robert Quinn or an emerging superstar like Roquan Smith.

The Cubs were Old Mother Hubbard and Javy Baez in the cupboard. That’s it. The Bears have building blocks, some salary cap issues to limbo around, and the most talented quarterback in Bears history if they can develop him.

George McCaskey has never been in a better position to build sustainable success than he is now, and that should be the goal. Epstein and the Cubs did so for a long time — the best stretch in Cubs history. The Bears can do the same if they want to, and that should be the model.

I believe the McCaskeys want to win. Do they know how to get there? It’s up to them.

Point is, the Bears can hire whomever they want if the pocketbook is opened up, if roster control is opened up, if a forward-looking view is taken to managing the team and if Fields is viewed as the guy. This team can reshape itself in a matter of time.

Why can’t Dungy or Newsome take control? Why can’t Sean Payton, Mike Tomlin, or Jim Harbaugh be a head coach in Chicago?

The answer is the Bears breaking the cycle of running as a family business and a country club, and taking advantage of the city, the prestige, and the Halas lineage to bring another Super Bowl to Chicago.

Fans here have held the 1985 Bears in the highest regard for more than 30 years. The 2005 Bears as the next best. It isn’t good enough for this storied franchise, in the end.

The blueprint for sustained success is everywhere in Chicago — Cubs, (current) Bulls, Blackhawks and White Sox — except the Bears. That’s the goal. Enough trips to the dance, the team will score the big one. Develop the franchise quarterback, and everything possible.

It’s not a pipe dream to think the Bears and McCaskeys can do this. Especially if they cut off the spigot of the wrong pipeline of talent. If there’s an NFL white whale like Epstein (hell, maybe it is Epstein), the Bears can land them if they want.

If not, the clock will only turn back to 1985 in memories. Not in actuality, which is the only thing that matters in the end.