CHICAGO — Four years ago, Chicago Bears general manager Ryan Poles was reflecting on the timing of the NFL’s free-agent negotiating window and the emotions required to renege on a three-year, $40.5 million agreement with defensive tackle Larry Ogunjobi.

“I almost feel like the process is flawed a little bit where I wish we could have some of these images and some of the physicals done before,” Poles said at the NFL owners meeting in March 2022. “That’s going to (require) some type of rule change. I don’t know the process in getting that done. It’s probably something (to be discussed) at a meeting like this in the future. Yeah, I think a lot of people were hurt with the whole timing of it.”

Ogunjobi was the most damaged. The Bears failed him on a physical because he had suffered a Lisfranc ligament injury in his foot in the 2021 playoffs. He wound up with a one-year, $8 million prove-it contract with the Pittsburgh Steelers.

It was notable Wednesday, a day after the Baltimore Ravens scuttled a blockbuster trade to acquire defensive end Maxx Crosby from the Las Vegas Raiders in exchange for two first-round draft picks. The Ravens reportedly failed Crosby on a physical two months after he had surgery to repair a torn meniscus in his left knee.

The Ravens pivoted quickly to sign defensive end Trey Hendrickson. While some have speculated they got buyer’s remorse, they were within their rights to conduct a physical and have a change of heart based on medical findings.

The Ravens have played things close to the vest on medicals in the past, especially with free agents. Offensive lineman Roberto Garza eventually landed with the Bears in 2005 after Baltimore walked back a three-year, $7 million offer when a physical revealed he was missing an ACL in his right knee.

Now Crosby is back in Las Vegas, where the Raiders have just enough salary-cap space for him after they blitzed the market when the negotiating window opened Monday. They secured deals for center Tyler Linderbaum, linebackers Quay Walker and Nakobe Dean, defensive end Kwity Paye and wide receiver Jalen Nailor, among others.

The Raiders can imagine a future with Crosby wearing silver and black, or they can explore what a new trade market looks like. It’s highly unlikely to be what it was last week, when they believed they had a deal with the Ravens. Some teams that might have been in the mix have since committed resources to other players. There’s an even bigger “buyer beware” tag on Crosby now too.

It’s unknown whether the Bears are intrigued by the possibility of acquiring Crosby at a price tag lower than two first-round picks. They’ve used a good chunk of their available cap space in agreeing to terms with safety Coby Bryant, defensive tackles Neville Gallimore and Kentavius Street, linebacker Devin Bush, wide receiver Kalif Raymond and defensive back Cam Lewis, plus re-signing left tackle Braxton Jones, defensive end Daniel Hardy, linebacker D’Marco Jackson, safety Elijah Hicks and quarterback Case Keenum.

The only moves the team announced when the new league year started at 4 p.m. ET Wednesday were two trades: the acquisition of center Garrett Bradbury from the New England Patriots and the second-round pick received from the Buffalo Bills for wide receiver DJ Moore.

The Bears could restructure enough contracts to carve out space for Crosby, but a lot of calculus would need to be done in weighing the price of a trade, the cost of the player and the projected health of a guy who turns 29 in August and is signed through 2029.

It’s hard to say what can be done in the future to avoid hang-ups like this that clearly put a team — the Raiders in this instance — in an absolute bind. The league instituted the negotiating window (a 52-hour period this year) in 2012 to level the playing field for unrestricted free agency and curb what had become rampant tampering.

One partial solution would be if the league permitted trades to be finalized before the new league year starts. That wouldn’t have changed the circumstances of the Ogunjobi situation, but an earlier timeline — if the league allowed trades to be executed beginning the week after the scouting combine — could have allowed everything to play out with Crosby before this became the ultimate bad beat for Las Vegas.

The Bears were an injured party after the Ogunjobi situation. They lost out on other free agents while the resources committed to him were tied up in a deal contingent on medical information. That’s a rare but likely unavoidable pitfall in free agency.

“From the business side, it was very clear: I’m going to listen, we have a process, I’m going to listen to our doctors,” Poles said in 2022. “I’m going to look at the evidence and go with what I think is right again for the organization. The toughest thing I’ve had to go through — it was emotionally draining — was to deny someone an opportunity when you have this verbal agreement that that’s what’s going to happen.

“That tore me to pieces. I sat in the back of the car and I had a conversation with the kid and let him know, just from what my job was and from my perspective, what we had to do. That was hard. Really hard.”

Whether the Bears or another team finds a way to benefit from the Raiders’ misfortune remains to be seen. Poles, in one of his first significant moves on the job, traded defensive end Khalil Mack to the Los Angeles Chargers in 2022 for a second-round pick that turned into safety Jaquan Brisker and a 2023 sixth-round pick. That sixth-rounder was then shipped back to the Chargers for two seventh-round picks in 2022 that turned into Hicks and punter Trenton Gill.

In light of what the Bears paid the Raiders to acquire Mack in 2018, it was a small return, but Poles knew the team was entering an arduous rebuilding process.

“It comes down to a lot of things with analytics, age, play time — we put all of that together and there’s a timing mechanism as well,” he said. “If you wait, what does that look like? If you do it now, what does it look like? We just thought right now it would allow the Bears to have more ammunition to add more players.”

Mack was entering his ninth season then, and he has 361/2 sacks in four seasons with the Chargers, a half-sack more than he totaled in four years with the Bears. Crosby is preparing for his eighth season, and with the money and trade compensation involved, the pressing question for any team considering making a move for him is how he projects over the next three seasons. His salary is $30 million this season, and his $29 million base salary for 2027 becomes fully guaranteed Friday.

The Ravens, obviously, didn’t get a satisfactory answer to that question at the price tag of two first-round picks, and they’re not escaping without damage. Their roster has been raided for free agents, a few of whom you’d imagine they would have made an effort to keep if they didn’t believe they were landing Crosby. Perhaps another club, with its own team of medical experts, will feel comfortable if the asking price is somewhat reduced, but it’s folly to think the Raiders simply would give him away.

The Bears have added defensive parts, with Bryant a replacement for All-Pro Kevin Byard III — who reached a deal Wednesday with the New England Patriots — and Bush and Jackson in place to stabilize things at linebacker after the release of Tremaine Edmunds. Raymond could effectively replace both third receiver Olamide Zaccheaus and returner Devin Duvernay, and Gallimore and Street are depth pieces at defensive tackle.

Poles can weigh the analytics and medical prospects of taking a plunge with Crosby, or he can focus on the draft with the Bears owning four picks in the top 89 selections, including two second-rounders.

For what it’s worth, Ogunjobi played in 48 games over three seasons for the Steelers after the deal fell through with the Bears, who liked him as a disruptive three-technique. After recording seven sacks for the Cincinnati Bengals in 2021, he totaled six in three seasons in Pittsburgh before playing sparingly last season for the Bills. In hindsight, Poles probably feels like he made the right call.

The process and timing mechanisms in place are flawed. Maybe a team will emerge as a winner from the whole mess. The proof will be in how Crosby performs over the next several seasons, and that’s a hard projection to make — maybe as difficult as it was for Poles to tell Ogunjobi sorry.

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