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Ranking 4 loaded Bears trade proposals by the best deal to land a pass rusher

The Chicago Bears have to be urgent in addressing their pass rush deficiencies and these four options are all in play.
ByWynston Wilcox|
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The Chicago Bears have to be urgent in addressing their pass rush deficiences and these four options are all in play.
The Chicago Bears have to be urgent in addressing their pass rush deficiences and these four options are all in play. | Chris Unger/GettyImages

Key Points

Bullet point summary by AI

  • The Chicago Bears are evaluating trade proposals to address a critical pass-rusher need on their defense.
  • Maxx Crosby requires significant draft capital while Josh Sweat offers strong immediate impact with less upfront cost.
  • The final two options present varying levels of risk and reward as the Bears aim to boost their playoff chances this season.

The Chicago Bears have a lot of work ahead of them if they want to keep pace with the rest of the NFC this season. The recipe seems to be finding that elite pass rusher that will change the trajectory of your defense. That’s the one position that has a question mark for the Bears.

So who could that actually go after in training camp and ahead of Week 1? Well believe it or not, there’s a lot of options out there for them. Maxx Crosby is the name that keeps coming up, but he’s not the only one. If the Bears are serious about wanting to be playoff contenders, here’s what it would take to land one of the big names on the trade market.

1. Maxx Crosby

Maxx Crosby is going to be the most expensive by far for the Bears to land. The Las Vegas Raiders originally asked for two first-round picks for the 29-year-old pass rusher. While rumblings about what it’s going to cost to land him haven’t really changed, it’s likely the Bears could get away with just one first round pick. They’ll have to still give up more draft capital, but they could at least retain at least one first round pick in this deal. 

The Raiders don’t need player compensation. They need as much draft compensation as possible. When you look at Austen Bundy’s breakdown of what potential Maxx Crosby’s suitors would have to give up on FanSided.com, you see the Bears will have to be very aggressive. Especially if teams like the San Francisco 49ers are looking to land him as well. The 49ers have every easy to be aggressive for Crosby when you look at the rest of the NFC West division. 

Chicago can’t be complacent at this point. Montez Sweat is a good option, but they need a better primary option, if nothing more, to instill fear into other offenses. That what going after Crosby would do, not just for the NFC North division, but the NFC as a whole.

2. Josh Sweat

Like the Raiders, the Arizona Cardinals need draft compensation badly. They’re undergoing a massive rebuild and truthfully, Josh Sweat is more valuable as a trade piece than as a roster piece. The Cardinals may not be as greedy as the Raiders are with Crosby, but the Bears will have to give up decent draft capital. I settled on a first round pick and a 2028 third round pick for a couple of reasons. For one, Arizona is going to want a really good pick to add to their 2027 allotment. 

Sweat is good enough to yield multiple picks in any deal. A third rounder seems fair because Sweat is worth two top 100 picks in the NFL Draft. If you’re the Bears, you’re not worried about filling out your roster with young draft picks that may or may not work out. The Bears’ biggest concern needs to be about winning now, not preparing for the future. Chicago went on a miracle playoff run that came up one score short of a potential spot in the NFC title game. 

Draft picks are obviously important, but it shouldn’t be a priority for the Bears. When it comes to anybody on this list – especially Crosby and Sweat – the Bears can’t get wrapped up in how much draft capital they're giving up when they know they’ll be getting instant help on their defensive line. 

3. Alex Highsmith

It’s hard to find pass rushers like Myles Garrett, who are good enough to get 20 sacks in a single season. But if you can have a pass rush tandem that’s good enough to produce 20-plus sacks, it’s a win. That’s what a move for Alex Highsmith would be for the Bears. Between Montez Sweat and Highsmith, the Bears would have had 19.5 total sacks last season. That’s something you can’t ignore if you’re Chicago. 

After Sweat’s 10 sacks last year in Chicago, the second most was six and then the second most for a pass rusher was 4.5. They totaled 35 sacks all of last season and if you add Highsmith’s production, that’s nearly 45 sacks. That makes this team much better, defensively, than if he wasn’t there. Highsmith probably won’t be their top priority with Josh Sweat and Maxx Crosby still in play (for now), but Highsmith isn’t a bad backup option at all. 

4. Kayvon Thibodeaux

This would be the cheapest trade most likely and could be either a move that yields a lot of results or ends Kayvon Thibodeaux’s potential. The New York Giants drafted him top five back in 2022 and aside from a strong second season, hasn’t really turned into the elite pass rusher the Giants thought he would. That’s why they added Abdul Carter and then landed Arvell Reese in April. Maybe Thibodeaux needs a new home to tap back into his potential. 

The biggest risk for the Bears is going after Thibodeaux right now is he doesn’t look like a player that’s going to drastically change this defense. Then again, we’ve seen quarterbacks move on from the team that drafted them and end up better so Thibodeaux could need a new system to finally find his role.

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