Windy City Gridiron
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.
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.
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...
