When Trey Hendrickson first joined the Bengals in 2021, he wasn’t just another free-agent signing—he was a seismic shift in Cincinnati’s defensive identity. But for all the pressure he applies on opposing quarterbacks, it’s the Bengals’ front office now feeling the heat. Last year’s league-leader in sacks is suddenly at odds with the very franchise he helped power to playoff relevance. And just as it seems Hendrickson might want out, a $6.3 billion heavyweight from the NFC North is circling.

It’s been a turbulent offseason in Cincinnati—and things just got stormier. A few months ago, the Bengals were already catching flak for slow-rolling contracts with Tee Higgins and Ja’Marr Chase. Now, the organization faces fresh criticism for its handling of star defensive end Trey Hendrickson, who’s coming off a monster season and demanding a new deal.

And right on cue, a new player has entered the chat. According to multiple reports, the Chicago Bears are actively engaged in trade talks for Hendrickson, signaling a potential blockbuster move. The Bears, now armed with a high-powered roster and aggressive front office, appear willing to make a major splash as they hunt for postseason relevance.

Trey Hendrickson isn’t just a big name—he’s big production. Originally drafted by the New Orleans Saints in 2017, he signed a four-year, $60 million deal with Cincinnati in 2021. Since then, he’s become a cornerstone of the Bengals’ defense, earning multiple Pro Bowl nods and racking up numbers most edge rushers would envy.

In 2024, Hendrickson logged:

• 17.5 sacks (highest in the league, second consecutive season with same stat)
• 46 total tackles
• 6 pass deflections
• 2 forced fumbles

Despite signing a $21 million extension last offseason to stay through 2026, the 30-year-old wants a raise—and given those stats, he’s got a compelling case.

Trey Hendrickson’s rift with Bengals grows

The drama escalated at the NFL’s annual league meetings when Bengals Executive Vice President Katie Blackburn downplayed Hendrickson’s extension demands. “I think he should be happy at certain rates that maybe he doesn’t think he’d be happy at… It takes him to say yes to something,” Blackburn remarked. That comment didn’t sit well with Hendrickson, who publicly fired back on The Pat McAfee Show, saying: “That was a little disappointing. Communication has been poor over the last couple of months.”

Hendrickson later elaborated during a post-practice interview: “The offers before the draft didn’t match the vision we had or what was promised last offseason if I kept playing at a high level… Instead of working together to get me back on the team, they’ve just stopped communicating.”

Even Steelers veteran Cameron Heyward couldn’t resist a jab: “They don’t have enough money. I dare you to go pay him,” Heyward said, referring to the Bengals’ notorious frugality. For a team as stacked with talent as Cincinnati, the optics aren’t great. First, it was the Higgins drama. Then the Chase uncertainty. Now, with both the WRs finally paid, their defensive anchor is publicly calling out leadership for ghosting him after promises were made.

The Bears have cap space, a revamped roster, and a win-now mindset. Adding Hendrickson to a front seven that already includes Montez Sweat would give Chicago arguably one of the NFL’s most disruptive edge tandems. And with the NFC North suddenly wide open, a move like this could signal serious playoff intent.

The Bengals are now on the clock—not for a draft pick, but for a decision. Do they pay Hendrickson what he’s asking, or trade him before the tension turns toxic? At 30, Hendrickson is in his prime. But his public frustration, coupled with suitors like the Bears showing interest, means this situation may not simmer down anytime soon.

From sack leader to trade bait, Hendrickson’s offseason arc is suddenly the league’s latest cliffhanger.