Biggest Winners and Losers from Bears 2026 Offseason Includes Both Playcallers

The long NFL offseason is finally over, and Chicago Bears football is back. Next Sunday, they'll take on the Carolina Panthers in their regular season opener, a game that the Bears are expected to win. But before we get into the regular season, let's take one last look back at what proved to be an eventful seven months.

From the shocking retirement of Drew Dalman to Ozzy Trapilo's historic recovery from a ruptured patellar tendon, here are the biggest winners and losers from the Bears' offseason. I limited myself to just four apiece for this exercise, for brevity's sake.

WINNERS

Ozzy Trapilo

Cole Kmet and Ozzy Trapil — Chicago Bears TE Cole Kmet celebrates a touchdown with OT Ozzy Trapilo. Mandatory Credit: Eric Hartline-Imagn Images | IMAGN IMAGES via Reuters Connect

The biggest winner by far this offseason has to be Ozzy Trapilo. The left tackle's improbable return from injury last month shocked fans and analysts alike, many of whom had expected Trapilo to miss most or all of the 2026 season after he ruptured his patellar tendon in January. He still has to prove that he can play at the same level he was at the time of his injury, but being in the mix for a Week 1 start proves that Caleb Williams' Avengers-inspired nickname for Trapilo was spot-on.

Ben Johnson

The rich get richer, and Ben Johnson continues to collect electric weapons for his offense from the NFL draft. The Bears surprised their fans when they selected two pass catchers in the third round of the 2026 NFL draft, tight end Sam Roush and receiver Zavion Thomas, but both have already shown early promises of a strong R.O.I.

Roush looked like a Cole Kmet clone during preseason games, which is a tremendous compliment for any rookie tight end. If his development continues on into the regular season, trade talks around Kmet will reach a fever pitch next offseason. As for Thomas, he only played in one preseason game due to injuries, and he proved unstoppable. He caught all five of his targets for 140 yards, including a show-stopping 97-yard catch-and-run touchdown.

The Bears' defense may be a major question mark heading into the season, but Ben Johnson's offense has to be driving defensive coordinators insane trying to come up with counters.

Caleb Williams

You'd be hard-pressed to find anyone in the league whose arrow is pointing higher than Caleb Williams' is after this offseason. From landing on the Madden 27 cover to earning his place as a Top 10 NFL quarterback, the Iceman stands on the cusp of superstardom, and it seems like everyone except for rival fanbases of the NFC North believe he's going to make that leap in 2026.

Of course, those are just off-field wins. What really matters is what happens on the field, and in that regard Williams is still a winner. According to most reports, Williams is in full command of Ben Johnson's offense and is miles ahead of where he was at this time last year. His breakout season in 2025 is expected to lead into an MVP-caliber season in 2026, and so far it doesn't look like he'll disappoint.

Jaylon Johnson

The Bears as a whole enjoyed a successful season in 2025, but it was hardly a banner year for the longest tenured member of the defense. Two-time Pro Bowler Jaylon Johnson missed almost the entire season with a nagging injury he suffered in July, and even when he was healthy enough to take the field again, he was clearly nowhere close to his usual self.

The 2026 season is already off to a much better start for the two-time Pro Bowler. Johnson has been as healthy as a horse throughout training camp and appears to once again be the kind of cornerback who locks down his side of the field. With contract talks once again on the horizon, that makes Johnson a big winner this summer.

LOSERS

Dennis Allen

Immediately following the 2026 NFL draft, Dennis Allen looked like a winner thanks to the Bears pulling off the biggest Round 1 heist of the draft with their selection of safety Dillon Thieneman. It's all been downhill for Allen since then. He lost his key free agency acquisition, safety Coby Bryant, for most of the season after Bryant had to undergo knee surgery. The Bears failed to add a playmaking pass rusher to his arsenal. Kyler Gordon started training camp on the PUP list and hasn't practiced at all.

Allen is once again being asked to deal with a revolving door of backups and depth pieces thanks to a string of injuries to likely starters, and he still doesn't have a star pass rusher. That makes him a loser for the offseason.

Fans who wanted to attend training camp practices

A Chicago Bears fan reacts after a Bears touchdown at Soldier Field. Mandatory Credit: Matt Marton-Imagn Images | IMAGN IMAGES via Reuters Connect

The weather just didn't cooperate with training camp this year. Only a handful of practices are made open to the public every year, and three of them were moved indoors due to inclement weather, which meant the fans were not allowed in. Even worse, some fans had already made the trek out to Halas Hall and had to be turned away. While not a big deal in the grand scheme of things, it was still a frustrating few weeks for fans who'd been hoping for a first-person view of practice.

Gervon Dexter Sr.

Whatever you think of Gervon Dexter's level of play on the field during his three years in Chicago, it sucks to see him go right as the Bears were hitting their stride. Just seven months after Dexter finally got to be part of a playoff win, the Bears traded Dexter to the Atlanta Falcons. He's going from a team that has an elite, franchise quarterback, a team that many expect to become a legitimate Super Bowl contender in 2026, to one that may very well be competing for the No. 1 overall pick in the 2027 NFL draft. That's got to sting.

Kyle Monangai

Caleb Williams and Kyle Monanga — Chicago Bears QB Caleb Williams hands the ball to RB Kyle Monangai. Mandatory Credit: Kamil Krzaczynski-Imagn Images | IMAGN IMAGES via Reuters Connect

The Bears are counting on Kyle Monangai to once again play the part of thunder to D'Andre Swift's lightning in the running game this year, but that plan has already gone off the rails. After participating in the first practice of training camp, Monangai missed the next three with an injury. Then, he went down with another injury on August 16th and hasn't practiced since. As of the latest injury update on Monangai, his availability for Week 1 is still in doubt.

Monangai posted an exciting rookie season, especially for a seventh-round pick, but he still has a long way to go in his professional development. Missing half of training camp and the preseason will almost certainly set him back a ways.

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