The Bears head into the 2025 NFL trade deadline on a high note, having defeated the Bengals 47-42 on Sunday in one of the craziest matchups in the team’s recent history. Now that they sit at 5-3 coming
out of Week 9, they’re well positioned for what should be a competitive playoff race for the remainder of the season.
It feels cliche or even reactionary to say, but the season genuinely felt on the line in the Bears’ rollercoaster game against Cincinnati. Given how difficult the NFC North figures to be – and considering Chicago has four more divisional matchups this season – every win they can get outside of the division gives them more leeway for the playoff race. Now, if the Bears defeat the Giants and Browns, they’d only need to go 2-5 the rest of the year to finish above .500. A 3-4 record in those remaining games would put them at 10-7 and likely get them into the postseason.
In order to win those games down the stretch, the Bears may want to make upgrades before the trade deadline on Tuesday at 3 p.m. CST. They certainly trend towards buyers than sellers, though they could always make a move dealing a backup for additional draft capital. Should they make a trade before the deadline, these are six players they could identify as targets.
Seahawks CB Riq Woolen
Sunday night saw the Seahawks obliterate the Commanders, and they did so with Riq Woolen on the bench for a solid part of the game. Woolen is having a down year, and Seattle fares well enough with Josh Jobe and either Shaquill Griffin or Derion Kendrick out wide, with Devon Witherspoon shutting things down in the slot. The 2022 Pro Bowler has been the subject of trade rumors as of late and is arguably the top cornerback on the market.
The 6’4”, 210-pound Woolen meets the size and length criteria that Dennis Allen seems to like in his cornerbacks. He would fit right in alongside Tyrique Stevenson in the Bears’ cornerback room, with C.J. Gardner-Johnson likely to hold down the nickelback position until Kyler Gordon comes back. Coming off a game in which Chicago allowed 42 points and saw players like Nahshon Wright and Nick McCloud struggle in coverage, it’s clear the secondary is a weakness. Woolen would be an upgrade, even if it’s just for one year.
Dolphins EDGE Bradley Chubb
Having missed the 2024 season with a torn ACL and now playing for a lackluster Dolphins team, it’s easy to forget about Bradley Chubb. He’s quietly been decent this season, though, having tallied four sacks in nine games for Miami. A Pro Bowler during his time in Denver, he’s a crafty edge defender with a good power game and a diverse arsenal of moves to shed blocks, even if he’s a step slower than he was in his rookie deal.
What would make Chubb an enticing trade target is the cost, both in terms of cap space and draft capital. Compared to the already traded Jaelan Phillips (he’s Philly bound for a third), Chubb would require much less value in terms of draft picks in a trade due to being three years older. The Bears would also take on just under $1.8 million of cap space this year by acquiring him, meaning they wouldn’t have to pull any strings in the accounting department to get the deal to work. He could be a solid veteran option to rotate along the defensive line.
Saints CB Alontae Taylor
Another talented cornerback in the final year of his rookie deal, Alontae Taylor offers intriguing inside-outside versatility at corner and has been a solid starter for a Saints team that’s had little to celebrate this season. He’s played in eight games and started in seven, tallying four pass deflections and a sack in the process. His 68.8 PFF grade in coverage is the best of his career so far, and it’s a better coverage grade than any healthy Bears cornerback not named Tyrique Stevenson.
Like Gardner-Johnson, Taylor would be a good fit from a schematic perspective, having played under Bears defensive coordinator Dennis Allen for three seasons in New Orleans. I’d consider Woolen a more valuable trade asset, so Taylor could be a good stop-gap option in the starting lineup who wouldn’t break the bank in terms of draft capital this season.
Jets EDGE Jermaine Johnson II
With a 1-7 record coming out of their Week 9 bye, the Jets should be firmly thinking about selling at this year’s trade deadline. Breece Hall would’ve been a great potential target if I wrote this article a few weeks ago. However, Kyle Monangai’s breakout performance against the Bengals and D’Andre Swift’s improved play in recent weeks has me thinking the Bears don’t need to trade for a running back this year. Instead, they should look at one of New York’s defenders.
Jermaine Johnson II was a Pro Bowler in just his second season in the NFL in 2023, but he played in just two games in 2024 due to injury and has rotated into the Jets’ defensive line since then. The financial cost to acquire him would be cheap, but Dianna Russini of The Athletic indicated the Jets want a second-round pick in return for him. It feels unlikely they’d receive that much in a deal for Johnson, but if the Bears can talk them down to a conditional fourth-round pick with the ability to become a third, it could be something to consider.
Bengals EDGE Trey Hendrickson
I almost didn’t want to include Trey Hendrickson in this article, because I don’t really believe the Bengals will ship him out this year. That said, they’re now 3-6 after losing to the Bears on Sunday. Their chances of making the playoffs are slim, and given how ugly contract negotiations were between the two sides this offseason before settling on a raise on a one-year contract, a long-term deal might be tough to reach.
If the Bears traded for Hendrickson, they would surely give him a contract extension. They’d also take on a cap hit of $8 million this year, which is slightly more than the $7.8 million in cap space that OverTheCap has for them. They’d have to make some slight adjustments, but it’s worth it for an edge rusher who’s made the Pro Bowl each of the last four seasons. He would instantly be the best defender on Chicago’s roster, and his sheer presence would elevate the other defensive linemen rushing alongside him.
