The Bears' Trey Hendrickson Dilemma

By Clete Campbell Windy City End Zone Staff Writer

There is a Pros and Cons List every NFL general manager has at the ready when considering adding to their team a marquee player with a lucrative salary cap hit number.

The latest Scouting reports. Player ratings. Performance trajectory charts. They have everything at the ready to make an X-Factor decision that could change their teams’ fortunes in both the short and long term.

In the NFL, they analyze everything right down to if a player is a Kendrick Lamar or Drake fan and their fast food preference (Chipolte and Subway guys get higher points). And when it comes to salary cap busting moves, you study everything 12 ways from Sunday.

So with the Chicago Bears’ 2025 season a must playoff season, not just for the team’s on-field fortunes but momentum for its forever-gestating new stadium project, general manager Ryan Poles is weighing the Pros and Cons of acquiring a game-changing talent like Cincinnati Bengals All-Pro pass rusher Trey Hendrickson 53 ways from Game Day Sunday.

The Bears have already added a complementary pass rush piece to Montez Sweat this offseason in Dayo Odeyinbo, who joined the team on a three-year, $48-million pact with $30 million guaranteed. Adding Hendrickson would be legit pass rush gravy.

Alas, now come the cons. Hendrickson, who the Bengals are set to pay a base pay rate of $15.8 million in 2025, is threatening to hold out, saying he won’t play on his current deal.

(Trey has definitely studied and passed NFL Economics. His thesis paper was: “Be Sure to Get Your Fair Market Value.”)

Hendrickson has statistically been the best pass rusher in football over the last two seasons, totaling 17.5 sacks in 2023 and 2024 and coming second in Defensive Player of the Year voting last year behind Denver Broncos standout corner Patrick Surtain II.

The Bears-Hendrickson rumors are now whipping up like a 50-mph wind gust off Lake Michigan. The Tribune’s Brad Biggs vetoed any serious chance of Hendrickson donning a Bears jersey come the team’s Sept. 8 Monday Night Football season opener against the Minnesota Vikings.

“If the Bengals explore the possibility and are seeking a first-round pick in exchange, I’d be stunned if the Bears had any interest,” Biggs wrote on May 14. (Bears Insider Gives Update on Trey Hendrickson Trade Rumors )“That would be a steep asking price because any team that acquired Hendrickson would have to give him an expensive extension as he’s entering the final year of his contract at $16 million.”

Brad doubts the Bears would deal for Hendrickson even if the Bengals were willing to reduce their asking price to a second-round pick.

The reason? Simple NFL salary cap math, Biggs says.

“The Bears have been entirely too dependent on free-agent and trade acquisitions to bolster their pass rush,” Biggs added. “They’ve simply struggled to draft and develop pass rushers. They currently have $38.1 million in salary-cap space committed to edge defenders, ninth-most in the league, according to OverTheCap.com. Trade for Hendrickson and sign him to an extension, and the Bears would zoom to the top of that list or very near it.”

Plus, Odeyingbo is already here and already prepping to do the job Hendrickson would be asked to do: Flank Sweat on the rush. The 6-foot-6, 286-pounder has 16.5 sacks, 21 tackles for loss, five forced fumbles and three fumble recoveries to his name.

Then again. He’s no Trey Hendrickson. The Draft Network’s Justin Melo reports adding Hendrickson is an aggressive move the Bears need to make.

"Other offseason acquisitions include Colston Loveland and Luther Burden III,” The Sporting News’ Dharya Sharma notes. (Bears trade proposal lands Bengals projected $62 million All-Pro in Chicago | Sporting News) “On the defensive line, Grady Jarrett and Dayo Odeyingbo were added to help support Montez Sweat. Odeyingbo is a stellar three-down defensive end, but the aggressive Bears would really elevate the d-line by pairing Sweat with Hendrickson. Trading for Hendrickson would serve as the cherry on top of what's been an outstanding offseason," Melo wrote.

How serious is the 30-year-old Hendrickson about going to the team who can pay him what he believes he’s worth? Let’s let Trey tell us.

"No communication has taken place between my camp and the organization post draft," Hendrickson said in a statement to ESPN on Monday. "The offers prior to the draft did not reflect the vision we shared and were promised last offseason if I continued to play at a high level. Coaches are aware of these past conversations. Rather than using collaboration to get us to a point to bring me home to the team, THEY are no longer communicating. I have been eagerly awaiting a resolution of this situation, but that's hard to do when there is no discussion and an evident lack of interest in reaching mutual goals."

Will a Hendrickson-to-the-Bears deal happen? Only the NFL future knows. And it won’t tell us until it happens. But we can understand why Ryan Poles is studying a Trey Hendrickson deal harder than he studied the fine print of his mortgage.

Because his NFL team’s playoff future may just depend on it.