Chicago Bears fans held out hope for weeks that the team might swing a deal for star pass rusher Maxx Crosby. He wanted out of Las Vegas and reportedly loved teh idea of joining the organization, being a big admirer of head coach Ben Johnson and quarterback Caleb Williams. The Bears were involved in talks up to the end, but their offer wasn’t strong enough. The Baltimore Ravens proved the big winners, giving up two 1st round picks to bring the five-time Pro Bowler to the east coast.

Then the bombshell dropped.

Less than 24 hours before the new league year opens, Baltimore announced it had rescinded the trade due to a failed physical. Crosby had just had knee surgery in January.

This is an unprecedented development. Trades have been voided for medical issues before, but never one of this magnitude. Suddenly, the Raiders get Crosby back, along with his massive contract, right after they agreed to several expensive free agent deals. Unless they withdraw some of those offers, they have to find a new trade partner for the defensive end or risk dealing with serious cap problems. What makes it worse is that their original asking price is now out the window.

The Bears can now make another run at Maxx Crosby.

This time, they might be able to land him at a far more palatable price. They have two 2nd round picks this year. That might be a good starting point. As for the contract, they still haven’t restructured any current deals. They should be able to do a few of those and find the necessary cap space to bring Maxx Crosby aboard. He is the last piece they’re missing. They’ve already added a quality safety (Coby Bryant) and a linebacker (Devin Bush). Crosby would provide the pass rush element they’ve been missing.

Getting a player of his quality without truly mortgaging the future is a dream scenario for the Bears. The tricky part will be whether they’re willing to pass him medically after what happened in Baltimore. We already know general manager Ryan Poles has failed players in the past. See Larry Ogunjobi. However, this case feels different. The Bears knew Crosby was recovering from surgery when they engaged in trade talks. His knee not being fully recovered shouldn’t be a shock to anybody.

The risk could be worth the reward.

The Bears have the ammunition to get Crosby.

They have four picks in the first three rounds of the upcoming draft. Perhaps they could offer the 25th overall pick and get it done. That would still leave them with two 2nd-round picks and a 3rd-round pick the following day to add more young talent to their roster. In addition, they wouldn’t have to give up any future picks. Everything depends on how aggressive Poles and Johnson wish to be. If they’re comfortable with the medical risks, it’s a no-brainer. Crosby plugs the last major hole on defense.

It’s not like Baltimore hasn’t failed players before. Michael Brockers signed a free agent deal with them in 2020, but failed the physical. He went on to have a really good season that year and didn’t miss a game in 2021 as well. Ogunjobi failed the Bears’ physical, signed with Pittsburgh, and remained a solid player. Presuming the knee recovers as it should from surgery, Crosby should remain a productive player for at least a few more years.

The Chicago Bears had a busy first day of legal tampering. Three fresh faces were added to the defense in the form of safety Coby Bryant, defensive tackle Neville Gallimore, and linebacker Devin Bush. However, it wasn’t limited to that. The Bears also retained some of their own free agents with linebacker D’Marco Jackson, special teams ace Daniel Hardy, and left tackle Braxton Jones. However, the most interesting move might’ve been the return of backup quarterback Case Keenum.

On the surface, that doesn’t sound odd at all. Keenum was a tremendous part of the Bears quarterback room in 2025, serving as a sounding board and mentor for Caleb Williams. His motivational skills and intelligence were on full display during several moments last season, including some of Williams’ epic comebacks. Bringing him back isn’t the interesting part. It is how much they paid. Keenum returns on a two-year deal worth up to $8 million. For those who don’t know, third-string quarterbacks almost never make more than $1.5 million for a season. The fact that Keenum is making around $4 million should not be brushed aside.

It could signal something else is going on.

The Case Keenum raises alarms about Tyson Bagent.

Right now, the young quarterback remains firmly entrenched as the team’s #2 quarterback. Head coach Ben Johnson loves him. However, it’s no secret the 25-year-old has been surrounded by trade rumors for weeks. The weak state of free agency and the draft at quarterbacks makes the idea of trading for an intriguing backup more palatable. Johnson’s nod of approval certainly helped his case. If the Bears are getting trade offers they feel might be difficult to turn down, then working to retain Keenum makes more sense.

He is a proven player with several years of experience and can still throw the ball. He now has a strong understanding of Johnson’s offense and is a firm ally of Williams. It’s an obvious move. Don’t forget the Bears have also been quietly sniffing around potential late-round quarterbacks in the NFL draft. They wouldn’t be doing all of this unless there was a chance they might trade Bagent. They could only be waiting to see what happens with notable veterans on the market like Kyler Murray and Daniel Jones.

The Bears may feel Bagent’s market will develop.

Right now, teams seem happy with settling for veteran journeymen. Arizona is moving forward with Jacoby Brissett and Gardner Minshew as its options. The Jets just traded for Geno Smith despite a horrendous season in Las Vegas last year. While there is definite interest in Bagent to this point, the Bears’ asking price hasn’t been met. They’ve made it clear they have no desire to get rid of the backup. They love him and believe he is a huge asset to the team. So if another team wants him, they’ll have to pay.

It seems unlikely an offer will happen right now. There are still some free agents out there who haven’t found homes. However, as the draft gets closer, those who don’t get anyone will be left with a choice.

1. Gamble on a rookie in what is viewed as a weak draft class
2. Flip a day two pick for Bagent, who is young, cheap, and developed

Desperation often leads to aggressive decisions. The Bears are likely banking on that. Locking up Case Keenum now to a two-year deal means the Bears have an insurance policy in place should that offer come. It is the only explanation that makes sense for the pay raise he just got. Not that he doesn’t deserve it.

The Chicago Bears kick-started their turnaround last year when they won the Ben Johnson sweepstakes, luring the Detroit Lions’ offensive coordinator to take over as their new head coach. The impact was felt immediately by both sides. The Lions’ offense lost much of its identity, forced to change playcallers midseason as a result. This contributed to their disappointing 9-8 finish. Chicago became one of the league’s best rushing attacks, had their first top 10 offense since 2013, and won the division at 11-6.

It was a bitter pill to swallow for Detroit, which knew it had been on the cusp of a Super Bowl over the past two years with Johnson on the staff. It appears that the connection remains alive as the Bears brought another name over from the Motor City.

Kalif Raymond is a quality addition for the Bears. Not only does he bring an element of vertical speed the team needs, but his value as a punt returner can’t be overstated with All-Pro nods in 2022 and 2024. Yet it might be his leadership and locker-room presence that Detroit will miss the most. Amon-Ra St. Brown made that pretty clear.

The Chicago Bears continue to show a sharpening sense for quality.

This 2026 free agency period is revealing that. Their first big move was safety Coby Bryant. While not the star of that Seattle Seahawks defense, he was a top playmaker and revered as one of its core leaders. Linebacker Devin Bush soon followed, a vocal leader since his days at Michigan and somebody who plays with violence, speed, and intelligence. Raymond is another step in that direction. Not only is he dynamic with the ball in his hands, but he’s also a central presence that others look to for help.

It isn’t surprising. Raymond had to battle his way up the mountain from Holy Cross into the NFL as an undrafted free agent. He endured some dark years in Denver and New York before turning the corner in Tennessee. This is what led to Detroit having interest, and he quickly carved out a role as their third wide receiver and return specialist. He was a central part of their successful playoff runs in 2023 and 2024. Only the rise of Isaac Tesla made it difficult for the team to keep him.

Their loss is the Bears’ gain.

Chicago already had their top two guys in place with Rome Odunze and Luther Burden. However, the exit of D.J. Moore via trade to Buffalo opened a void in the receiver lineup. Jahdae Walker could certainly step up to fill it. Still, they might prefer somebody with more proven experience. Raymond checks that box while also filling the punt returner spot at the same time. Getting that level of stability is well worth the $5 million the Chicago Bears are paying.

This, together with the Braxton Jones and Garrett Bradbury moves, should settle most of the immediate issues on offense. GM Ryan Poles should be able to focus on retooling the defense all the way through the draft. While the money involved won’t show it, the importance of this addition is clear. Raymond gives them much-needed explosive playmaking while also adding more leadership to the locker room. Those are two things an NFL franchise can never have enough of.

When it was revealed that the Detroit Lions were releasing longtime left tackle Taylor Decker, everybody expected the Chicago Bears to be a prime destination. It made sense. They needed a stopgap at left tackle with Ozzy Trapilo likely to miss most of 2026 with his knee injury. Decker had deep ties with head coach Ben Johnson from their time together in Detroit. Both sides felt like a great match. Unfortunately, it appears things didn’t develop as hoped. Chicago made their decision pretty clear when news broke that Braxton Jones was returning on a one-year deal worth $5 million with another $5 million in incentives.

Before Decker became available, the prevailing assumption was that bringing Jones back might be the Bears’ best option short of drafting somebody in the 1st round. That was never palatable because the team doesn’t have a high enough draft slot. Keeping Jones would give them someone with starting experience who knows the offense. It isn’t the splash Decker would’ve been, but it gives the Bears some stability at a crucial position as they try focusing on improving their 29th-ranked defense.

The Taylor Decker situation isn’t difficult to decipher.

Usually in situations like this, the determining factor is always the same: money. Chicago had probably hoped the former Pro Bowler might be willing to play at a reasonable rate. However, his market value was set at $21 million per year after the news of his release broke. If that is the range he is indeed looking for, it made the hopes of signing him almost impossible. Chicago was already limited on cap space when free agency began. They would have to significantly restructure multiple contracts on the books to find the space necessary for what Taylor Decker wants.

Poles’ track record made it clear such a strategy was something he wanted to avoid. Decker is a good player, but he’s also in his 30s. Sacrificing future financial flexibility for a player who is on the downside of his career isn’t smart business. If he is chasing one last big payday, that is perfectly fine. Let somebody else pay him. The Bears should be fine with Jones and could bring in some competition in the draft. While disappointing, there isn’t much use in brooding over it. These things happen in free agency all the time.