How the Chicago Bears can land the franchise's best head coach since George Halas
Star players are a good thing.
Draft capital is a good thing.
Or maybe not. Y’see, the Chicago Bears had plenty of both heading into the 2024 season, and it didn’t do much for their winning percentage, did it?
For better or worse, the summer of 2025 looks much the same in Bearsland. Chicago boasts top-shelf players like D.J. Moore, Jaylon Johnson, and, of course, Caleb Williams, along with a treasure trove of draft picks—eight in total, four of which fall in the top 75.
The big difference between the ’24 and ’25 offseasons? The Bears don’t have a head coach.
Given that, might it be worth sacrificing some of those assets—be it players, or picks, or cash, or all of the above—to acquire a high-end sideline general?
Been There, Done That
We’ve seen ten HC trades in NFL history, some of which were brilliant, and some of which were, oh, let’s be polite and say misguided.
New Orleans trades Sean Payton to Denver (2023)
- Compensation: 2023 first-round pick, 2024 second-round pick
Arizona trades Bruce Arians to Tampa Bay (2019)
- Compensation: Sixth-round pick
New York Jets trade Herm Edwards to Kansas City (2006)
- Compensation: Fourth-round pick to the Jets.
Oakland trades Jon Gruden to Tampa Bay (2002)
- Compensation: Two first-round picks (2002, 2003), Two second-round picks (2002, 2004), $8 million to the Raiders.
New York Jets trade Bill Belichick to New England (2000)
- Compensation: 2000 first-round pick
Green Bay trades Mike Holmgren to Seattle (1999)
- Compensation: Second-round pick
New England trades Bill Parcells to New York Jets (1997)
- Compensation: 1997 third- and fourth-round picks, 1998 second-round pick, 1999 first-round pick
Baltimore Colts trade Don Shula to Miami (1970)
- Compensation: 1971 first-round pick
Boston Patriots trade Lou Saban to Buffalo (1962)
- Compensation: Cash
Kansas City trades Hank Stram to New Orleans (1976)
- Compensation: Cash and/or draft picks
Belichick crushed it in New England, Gruden delivered a Super Bowl in Tampa, and Payton looks promising in Denver, while the Hank Stram and Herm Edwards deals were epic busts.
So history tells us it's a crapshoot, but maybe the Bears should give it a shot. After all, what we’ve seen on the Chicago sidelines in the post-Lovie Smith era hasn’t been great.
Trade #1: Mike? Check!
Chicago Receives: Mike Tomlin
Pittsburgh Receives: 2025 third round pick, WR Keenan Allen, cash
The Skinny: Tomlin is a culture-builder, he has a career winning percentage of .630, and he’s the proud owner of a shiny Super Bowl ring. The 52-year-old's last few years, however, have been a tad wobbly—he hasn’t won a playoff game since 2016—so Pittsburgh ownership might be happy to let him go for a Day Two pick, a Hall of Fame receiver, and a bit of scratch.
And if the Steelers don’t feel like foraging for a coach, they have Arthur Smith on their staff…the very same Arthur Smith whose name, along with everybody else’s in the football world, is on the Bears’ head coach interview list.
Trade #2: Planting the Shanahan Tree
Chicago Receives: Kyle Shanahan
San Francisco Receives: 2025 second round pick, WR D.J. Moore
The Skinny: Kyle Shanahan is an innovative sideline general who has won 70 of his 132 games. But Kyle Shanahan is also an innovative sideline general who hasn’t won a Super Bowl. Last season, the injury-riddled Niners saddled Shanahan with his first sub-.500 record since 2020, and the vibe in the Bay wasn't what you'd call optimal.
Shanahan might welcome a change of scenery, and the Niners would definitely welcome Moore, who would be an ideal replacement for the likely-soon-to-be-waived Deebo Samuel.
Trade #3: Go Fish
Chicago Receives: Mike McDaniel
Miami Receives: 2025 second round pick, 2026 third round pick
The Skinny: This might be a hard sell to the fan base, as McDaniel’s Dolphins stumbled in 2024, missing the playoffs after a regression in his third year. But the sardonic 41-year-old is Shanahan Lite (except way nicer and way way funnier), an original thinker who has the potential to evolve and grow with Caleb Williams.
McDaniel may not be Ben Johnson, but he’s not not Ben Johnson.