Ryan Poles’ history puts Trey Hendrickson trade right in Bears crosshairs

The Bears general manager has already made two trades before the new league year began. Could he pull off another one involving one of the top pass rusher in the game?
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The Chicago Bears' needs this offseason are simple. They need to upgrade the trenches on both sides badly. Offensive line in particular needs at least three new starters after giving up almost 70 sacks in 2024, which nearly derailed Caleb Williams' rookie season.

With the hiring of former Detroit Lions offensive coordinator Ben Johnson as their newest head coach, Poles is not messing around after wasting three years with Matt Eberflus, who became the first head coach in franchise history to be fired mid-season.

Last Wednesday, he acquired guard Jonah Jackson from the Los Angeles Rams for 2025 sixth-round pick and guard Joe Thuney from the AFC Champion Kansas City Chiefs for 2026 fourth-round pick the next day. The Bears immediately filled two huge holes without giving up much although their effort to fix the offensive line should not stop.

Another area of need for the Bears is upgrading the defensive line. There are plenty of options available for the Bears after the recent release of Harold Landry, Jonathan Allen and Joey Bosa, as well as free agents like ex-Chicago Bear Khalil Mack and Josh Sweat from the Philadelphia Eagles. You can add Trey Hendrickson from the Cincinnati Bengals to the list of available pass rushers after the Bengals announced he can seek a trade.

Bears can fill pass rush need with Trey Hendrickson trade

Hendrickson led the league with 17.5 sacks last season despite playing for a bad defense. However, he is 30 years old and wants a contract extension, which could cost a new team a lot of money in terms of annual salary. Hendrickson to the Bears has gained strong traction as new defensive coordinator Dennis Allen coached him when they were together in New Orleans from 2017-2020.

Although the Bengals want a first-round pick or a big Day 2 trade haul in return, his age (30) would probably make it difficult for the Bengals to get what they want. But since Poles became a general manager in 2022, the Bears have history of giving up draft picks for veterans with mixed results. Here are the list of players Poles have acquired by trading away their draft capital before recent acquisition of Jonah Jackson and Joe Thuney.

Player

Draft Capital Traded

WR Chase Claypool

2023 2nd-round pick

DL Montez Sweat

2024 2nd-round pick

C Dan Feeney

2024 6th-round pick

DT Chris Williams

2025 7th-round pick

OL Ryan Bates

2024 6th-round pick

DL Darrell Taylor

2025 6th-round pick

WR Keenan Allen

2024 4th-round pick

WR N'Keal Harry

2024 7th-round pick

The ones that can be called successful are Montez Sweat and Keenan Allen. The rest are nothing more than backup players that Poles may have overestimated their value. Despite receiving praise for adding Jackson and Thuney, I do not blame some Bears fan shaking their head as Poles gave up more draft capital to add more veterans considering his dubious trade history.

Will desperation lead Poles to trade more draft capital for Trey Hendrickson? Or will they settle for a free-agent veteran like Mack, who played for the Bears from 2018-21? The Bengals are probably hoping that they can dupe the Bears into giving up one of their second round picks (39th or 41st) for Hendrickson. And if recent history is an indication, they just might.

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