Should (and could) the Chicago Bears Trade for Trey Hendrickson?

Trey Hendrickson has reportedly refused to report to Bengals training camp as contract talks between the star defensive end and Cincinnati have broken down over guaranteed money. Hendrickson has now indicated that he left the state of Ohio:

Should the Chicago Bears Trade for Trey Hendrickson?

The biggest weakness on the Chicago Bears roster right now is at the edge position, as my colleague Aaron Leming noted in his recent article outlining Five Questions Surrounding The Chicago Bears Heading Into Training Camp. According to PFF, the Chicago Bears have the 54th and 55th ranked defensive ends in the NFL right now in Montez Sweat and Dayo Odeyingbo. Of course, Sweat is coming off of a down year. Still, the Chicago Bears has had some of the worst edge production on defense in the league the past few seasons. According to Fox Sports, the Bears had the 27th-ranked total defense, and a big part of that was their lack of pass rush. Per ESPN, the Bears ranked 16th in total sacks in 2024, with just 40 sacks total the whole season. That’s certainly not going to cut it for any defense, let alone a disruptive attack like the one that Dennis Allen runs. Bottom line: YES, the Chicago Bears need more pass rush help.

If you look up the definition of “pass rush help” in the dictionary, you will find a picture of Trey Hendrickson. Hendrickson has recorded 77 sacks in his eight year career. Hendrickson has been incredibly durable: since 2020 he has never played in less than 15 games. His last two seasons he played in 17 games each. And speaking of the number 17, Trey Hendrickson was second in the NFL in sacks in 2023 and he lead the league in sacks last year, posting 17.5 sacks in both seasons. Trey Hendrickson is a sack machine. If sacks are what you need, sacks are what he’s got.

Could the Chicago Bears Trade for Trey Hendrickson?

As Aaron notes in his article, according to Over The Cap, the Bears currently have $12 million in cap space, and that amounts to about $4 million in effective cap space for moves. However, the Bears could restructure DJ Moore’s contract, cut Chris Williams, and perhaps make another move or two to open up somewhere between $10-$15 million in available space for this season. Obviously, the Bears would need to offer Trey Hendrickson the new contract that he wants but has not been able to get out of the Bengals. What would that look like? According to reports, Hendrickson wants multiple years of guaranteed money akin to what Maxx Crosby and TJ Watt received. Those players received three years of guaranteed money. So let’s look at the Crosby and Watt contracts along with Myles Garrett, who is an older player like Hendrickson and also recently got a contract extension, again using Over The Cap’s contract numbers:

As we can see, Watt substantially jumped the Garrett and Crosby guarantees. While Garrett and Crosby both have little over half of their contract guaranteed, Watt got nearly 90% of his massive new contract guaranteed. So what would the Bears need to guarantee in order to get Hendrickson to sign? If it is a four-year contract, and Hendrickson wants three years guaranteed, then that would be approximately 75% of the contract guaranteed. That would be just a bit north of the median guarantees between the Crosby contract and Watt contract. Let’s do a bit of back-of-the-envelope figuring and think about what a reasonable offer from the Bears would look like:

Contract length: 4 Years

Total Value: $148,000,000

APY: $37,000,000

Total Guaranteed: $111,000,000

% Guaranteed: 75%

Could that get it done? Yes – I think so. Certainly, something in that neighborhood should appeal to Trey Hendrickson – it would secure him through his age 36 season, would guarantee him more money than Crosby, but a little less than Garrett. Can the Bears fit that into their cap structure? As of now – yes. But there are too many variables to consider whether it would be feasible given future moves they will have to make over the next several seasons. However, this does have the benefit of guaranteeing all of Trey’s contract during Caleb’s rookie contract.

Now, let’s talk about what a trade for Trey Hendrickson might look like. The obvious comparison to make is, of course, the last time the Chicago Bears traded for a star defensive end: the Khalil Mack trade in 2018. Let’s outline that trade first:

Raiders to Bears: Khalil Mack, 2020 2nd round pick, 2020 5th round pick (conditional – eventually becomes 2020 7th round pick)

Bears to the Raiders: 2019 1st Round Pick, 2020 1st Round Pick, 2019 6th round pick, 2020 3rd round pick.

A significant difference between trading for Mack and trading for Hendrickson is the age gap between the two players. Mack had just turned 27 years old in 2018, while Hendrickson will turn 32 years old in December. That should substantially reduce the draft compensation required to acquire him from the Bengals. Of course, there are a number of variables that come into play with such a trade, including competition from other teams, the Bears expected win totals going forward (and thus draft position), etc. etc. The Bengals are likely to argue (to the Bears) that the Bears will be drafting in the later half of the draft in the next few seasons. For argument’s sake, let’s assume the Bears are smack dab in the middle (16th pick). So what might a reasonable trade look like here?

Bengals to Bears: Trey Hendrickson, 2026 4th round pick

Bears to Bengals: 2026 1st round pick, 2026 5th round pick

Should the Bears do that trade? I would. Absolutely. If you get two great seasons and one or two good seasons out of it – I think you win that trade hands down, and that is a reasonable expectation for what Hendrickson could produce. And he would complete this Bears defense in much the same way that Mack completed the 2018-19 Chicago Bears defenses. Could the Bears get away with not offering a 1st round pick? I doubt it. But either way, my answer to the question is a resounding YES – the Bears should absolutely trade for Trey Hendrickson if this is the contract, and this is the trade compensation. Or something along these lines.

But what do you think? Tell us in the comments below!