How the Chicago Bears can land the franchise's best head coach since George Halas

Three stunning trade scenarios that would deliver the Bears and Caleb Williams a sideline general for the ages
Mike Tomlin would look pretty good in a Chicago Bears baseball cap, wouldn't he?
Mike Tomlin would look pretty good in a Chicago Bears baseball cap, wouldn't he? / Amber Searls-Imagn Images
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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!

Mike Tomlin
Barry Reeger-Imagn Images

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

Kyle Shanahan
Cary Edmondson-Imagn Images

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

Mike McDaniel
Paul Rutherford-Imagn Images

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.


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Alan Goldsher
ALAN GOLDSHER

Alan Goldsher has written about sports for Sports Illustrated, ESPN, Apple, Playboy, NFL.com, and NBA.com, and he’s the creator of the Chicago Sports Stuff Substack. He’s the bestselling author of 15 books, and the founder/CEO of Gold Note Records. Alan lives in Chicago, where he writes, makes music, and consumes and creates way too much Bears content. You can visit him at http://www.AlanGoldsher.com and http://x.com/AlanGoldsher.