Trade Pitch Has Bears Acquiring $60 Million Superstar Edge Rusher

Getty Bears potential trade target Trey Hendrickson, a three-time Pro Bowl defensive end.

The Chicago Bears could not land veteran pass rusher Matthew Judon in a trade and may have a difficult time plucking Haason Reddick from his contentious situation with the New York Jets. If they are willing to make a big play, though, they may have one more target to pursue: Cincinnati Bengals superstar Trey Hendrickson.

Hendrickson requested a trade out of Cincinnati earlier in the 2024 offseason after the team declined to give him more security in the form of a long-term contract extension. The 29-year-old signed a four-year, $60 million contract with the Bengals in 2021 and, last summer, added another year onto his deal to tie him to the team through 2025.

Hendrickson, however, recorded a career-high 17.5 sacks in 2023 and has been one of the NFL’s top pass rushers over the past three seasons all while playing on a contract that does not compensate him like one of the league’s best. His contract has an average annual value of $21 million, putting him outside the top 10 highest-paid at the position — and incentivizing him to request a trade after the Bengals refused to sign a new deal.

Now, Hendrickson has participated in the majority of workouts for the Bengals since requesting a trade on April 24. He showed up for voluntary workouts in the spring and remains an active participant at the team’s training camp this summer, telling media in May that playing for the Bengals during the 2024 season is a “no-brainer.”

Nevertheless, Hendrickson also said he and his agent approached the team about either a trade or a contract extension and the front office’s response was “pretty firm.” And if the sense is the Bengals won’t budge on their stance, the Bears could have a golden opportunity to trade for a premier defensive talent.

Bears Have Extra 2nd-Round Pick to Offer in Trade

If the Bengals are open to trade offers for Hendrickson, acquiring him would not be a cheap endeavor for the Bears. Hendrickson is already making more than $20 million per season on his current deal and wants greater security, which would likely mean the Bears would have to add at least one more year onto his deal and up his annual pay.

The Bears would also have to give up significant draft capital to acquire Hendrickson. Chicago offered a third-round pick to New England for Judon, but Cincinnati would presumably need more — at least a second-rounder — for their superstar edge rusher.

A realistic trade pitch for Hendrickson would look something like this: The Bears would hand over the better of their two 2025 second-round picks — presumably the one they acquired from Carolina with the higher projected value — in exchange for the superstar pass rusher and the right to sign him to a long-term extension beyond the 2025 season.

The Bengals may insist on getting a first-rounder from the Bears or any other team that inquires about Hendrickson, but Chicago could sell them on how valuable Carolina’s pick could become. The latest ESPN power rankings project the Panthers to finish dead last in 2024, which would make their second-rounder the 33rd overall pick.

The Bears can afford a lucrative extension for Hendrickson with the right structure. Per Over the Cap, they are projected to have roughly $37.3 million in effective cap space for 2025 and will only see that number skyrocket in 2026, depending on future moves. The question is, would such a high-cost trade be in the Bears’ best long-term interest?

Would Trey Hendrickson Trade Cost Bears Too Much?

Figuring out how to pay Hendrickson would be a significant obstacle for the Bears. It is unclear exactly how big of a raise Hendrickson is seeking, but his production suggests he is deserving of money similar to 30-year-old Danielle Hunter — who signed a two-year, $49 million contract with the Houston Texans during 2024 NFL free agency.

If $24.5 million annually is an accurate estimate, the Bears would have a tough time justifying such a cost for Hendrickson. After all, they are already paying star Montez Sweat that much annually over the next four seasons after signing him to a $98 million contract last November. Double-dipping at the same price point is nearly impossible.

The Bears may also prefer to keep both of their second-round picks for 2025. The Panthers’ pick could be a pseudo-first-rounder if Carolina hits rock bottom again in 2024, while their own selection would be a top-50 pick based on the same ESPN power rankings that have the Bears at No. 17 overall. For a team that just landed its franchise quarterback, it could be more advantageous to use those picks instead of trading them.

The Bears might feel differently closer to the 2024 NFL trade deadline on November 5, though. If they are desperately in need of pass-rushing reinforcements at the season’s midpoint, they could feel better about using one of their two second-rounders to add another veteran to the mix, even Hendrickson under the right circumstances.

Bears general manager Ryan Poles has traded second-round picks at each of the past two trade deadlines, dealing away one for Chase Claypool in 2022 and another for Sweat in 2023. If an opportunity arises, don’t expect Poles to sit on his hands.