Even 65 games (63 starts), 104 solo tackles, and 57 sacks over four seasons couldn’t convince Mike Brown to grant Trey Hendrickson an extension. The star defensive end has made his stance clear: he’s not suiting up for the Bengals in 2025 under his current deal. Scheduled to make $16 million this season, Hendrickson is holding out unless Cincinnati steps up. The team hasn’t blinked. And now? They may be preparing their next move: the five-day letter.

Just to be clear, the Bengals did crack open their vault, but Trey Hendrickson isn’t budging. And neither is Mike Brown. At first glance, it seems like Cincinnati finally blinked. Multiple reports, including one from Albert Breer, suggest the Bengals’ latest offer to Hendrickson comes with an average annual value “well into the $30 million,” putting him near the Nick Bosa ($34 million AAV) and T.J. Watt ($41 million AAV) tier. But the number was never the sticking point. Hendrickson wants guaranteed money beyond year one—something Mike Brown, one of the league’s most fiscally rigid owners, has consistently avoided.

Sure, Tee Higgins (4-year, $115 million) and Ja’Marr Chase (4-year, $161 million) got their deals, but they play positions the Bengals prioritize. Pass rushers don’t get the same grace. This negotiation is less about value and more about precedent. The front office explored softening their stance with minor second-year guarantees, but Hendrickson’s camp hasn’t moved. Word is, a $10 million gap in guaranteed money remains. But, as revealed by former NFL agent Joel Corry, the Browns could send the five-day letter— rarely used, borderline nuclear option under the NFL Constitution and Bylaws. 

It’s a procedural hammer that can ultimately place a player on the reserve/left squad list, stripping him of pay, play, and any semblance of a 2025 season. Once on that list, a player is persona non grata, no meetings, no practices, no games. Just silence. Corry also talked about how Micah Parsons and the Cowboys are in the same situation, and so are the Commanders and Terry McLaurin.

But to let a star walk away? Yeah, only Cincy could, realistically speaking. Corry wrote on his CBS column: “Out of the three teams, the Bengals appear to be the most likely to go to the nuclear option first with a player walking out.”

The clock starts with a letter. And if Trey Hendrickson doesn’t return within five days? That’s it. The Bengals would freeze his deal, tolling it to 2026. No paycheck, no accrual, and no credit toward free agency. It’s not unheard of, but it’s close. Only a handful of players have received the five-day letter over the last two decades. Kentwan Balmer, Su’a Cravens, Percy Harvin, Richard Seymour. That’s it. The tool exists, but teams rarely pull it out of the toolbox.

So why would the Bengals? Because, frankly, they’ve done it before. Carson Palmer ring a bell? Cincinnati didn’t flinch when he walked away in 2011. Mike Brown let him sit in retirement for half a season before sending him to Oakland, only after the Raiders lost their starter. That’s who the Bengals are. Principles over panic. Patience over pressure.

So, when Hendrickson threatens to leave if they don’t pay? History says Mike Brown is fully capable of calling that bluff. The closest historical parallel might be Terry Glenn. In 2001, after a suspension, Glenn left Patriots training camp. New England hit him with a five-day letter too. His camp scrambled to set up a meeting with the team. Didn’t matter.

The Pats still put him on the reserve list, and Glenn filed a grievance. Fast. Arbitrator Richard Bloch sided with the player, not because of the letter itself, but because the team shut the door while Glenn’s camp was actively trying to re-engage. Could Hendrickson’s agent, Harold Lewis, try a similar play if the Bengals follow through? Maybe. But unless Lewis has some tightrope negotiation ready, the team doesn’t seem likely to cave. The tension is real. So, what happens next?

If this drags into the season, trade noise will start creeping in. Quietly, a few AFC teams have already poked around. For now, that core philosophical gap, guarantees vs. tradition, isn’t going away without someone blinking.