Ranking the Top 3 Edge Rushers The Chicago Bears Need To Target in Free Agency
The 2025 Chicago Bears pass rush was about as intimidating as a soggy Portillo’s bun. While the rest of the team was busy fighting for a playoff spot and watching Caleb Williams transform into a franchise savior, the defensive front — aside from Montez Sweat — spent most of the year doing a whole lot of nothing.
Watching our pressure rate hover at a pathetic 27th in the league while the secondary got hung out to dry was like watching a slow-motion car crash in the middle of a blizzard. It was ugly, it was predictable, and it was entirely avoidable. Montez Sweat shouldn’t have to play hero ball on every single snap just because his supporting cast is MIA. Dayo Odeyingbo? A $32 million guaranteed mistake that ended in a Week 9 Achilles tear. Austin Booker? A fun developmental story, but he’s not ready to be the Robin to Sweat’s Batman.
With Dennis Allen now at the helm, the mandate is simple: get long, get mean, and get to the damn quarterback. We need a “juice” player opposite Sweat, and we need him yesterday.
The good news? Ryan Poles has played the cap like a fiddle. While the “accounting experts” on Twitter will tell you the Bears are $9 million over the 2026 cap, the reality is that a few simple restructures could open up $85.9 million in cold, hard cash. Poles is sitting on a war chest, and it’s time to spend it on someone who can actually bend the edge without needing a GPS.
Here are the top three free-agent edge rushers the Bears must target to fix this mess in 2026.
The State of the Pass Rush: By the Numbers (2025)
Before we look at the targets, look at this carnage. This is why we can’t have nice things.
| Category | Stat | NFL Rank |
|---|---|---|
| Team Pressure Rate | 28.6% | 31st |
| Total Sacks | 35 | 25th |
| PFF Pass-Rush Grade | 64.2 | 25th |
| Montez Sweat Sacks | 10.5 | (Alone on an island) |
| Rest of DE Room Sacks | 5.5 | (Pitiful) |
1. Trey Hendrickson: The Certified Mercenary
Age (2026): 31 | 2025 Sacks: 4.0 (Limited by injury) | Projected Cost: 2 years / $48M
If you want a guy who eats, breathes, and sleeps quarterback souls, you call Trey Hendrickson. He is the best pure pass rusher on the market, period. I don’t care about the age, and I certainly don’t care that he only played seven games in 2025.
Before his hip and back started acting up, Hendrickson was coming off back-to-back 17.5-sack seasons. Do you know how hard that is? Only five dudes in the history of the league have done that. He is a technical savage with a motor that makes Brian Urlacher look like he was napping.
Why he fits Dennis Allen’s vision: Allen loves a 4-3 front that creates pressure without needing to send the house every play. Hendrickson is a power-based rusher who wins with violent hands and elite leverage. He is exactly the kind of force multiplier that makes everyone else better. If you put Hendrickson opposite Sweat, offensive coordinators are going to have a mental breakdown trying to figure out who to double-team. You can’t tilt the protection both ways, and that’s when the magic happens.
The “Catch”: He’s 31. He just had core muscle surgery in December. He’s looking for one last bag. But here’s the thing: we don’t need a five-year commitment. We need a two-year window where Caleb Williams is on his rookie deal and we are aggressively hunting a Super Bowl. Hendrickson on a high-AAV, short-term deal is the ultimate “fuck it, we’re winning now” move.
The Verdict: Grade: A- He’s the highest-ceiling option. If he’s healthy, our defense goes from “pretty good” to “nightmare fuel” overnight.
2. Odafe Oweh: The High-Octane Breakout
Age (2026): 27 | 2025 Sacks: 7.5 | Projected Cost: 4 years / $77M
Odafe Oweh is the guy you sign if you want to pair Montez Sweat with his younger, more explosive twin. Oweh was a “traits” guy in Baltimore who finally put it all together when he got traded to the Chargers mid-season. He basically went supernova in LA, recording 7.5 sacks in 12 games and absolutely terrorizing the Patriots in the Wild Card round (3 sacks in one game!).
Why he fits Dennis Allen’s vision: Oweh is 6’5”, 250+ lbs, and runs like a gazelle. Dennis Allen has a documented obsession with length and “get-off.” Oweh has both in spades. He can flatten his path to the QB better than almost anyone in the league, and his ability to win with speed-to-power is exactly what you want in a modern DE.
The “Catch”: Consistency has been the boogeyman for Oweh his entire career. Before 2025, he was the king of “almost sacks.” He’d get the pressure, but he couldn’t finish. He finally learned how to close the deal in LA, but you’re betting nearly $20 million a year that the lightbulb stays on. Also, the Chargers have $100 million in cap space; they aren’t going to let him walk without a fight. We might have to overpay.
The Verdict: Grade: B+ If you want the long-term solution — a guy who can be here for the next four or five years — Oweh is the choice. He gives us the most physically imposing duo in the NFC.
3. Jaelan Phillips: The “Prove-It” Powerhouse
Age (2026): 26 | 2025 Sacks: 5.0 | Projected Cost: 1 year / $15M
Jaelan Phillips is the ultimate wildcard. If you looked at his talent in a vacuum, he’s a $25 million-a-year player. He is 6’5”, 266 lbs, and has the most polished technique of anyone on this list. But his medical chart is longer than a CVS receipt. Between the Achilles tear in 2023 and the subsequent recovery issues, he hasn’t been able to stay on the field.
Why he fits Dennis Allen’s vision: Phillips is the biggest body of the three. He is a stone wall against the run and a technical surgeon as a rusher. Allen likes ends who can play “heavy” and set a physical edge. Phillips does that better than Hendrickson or Oweh. He also spent time in Philadelphia under Vic Fangio, so he knows how to function in a high-IQ, gap-disciplined system.
The “Catch”: Can he play 17 games? That’s the only question that matters. He managed it in 2025 (Miami + Philly), but the production was modest (5 sacks). You’re signing him on a “prove-it” deal hoping he hits his 12-sack ceiling.
The Verdict: Grade: B This is the low-risk, high-reward play. If Poles wants to save money for a big-time Left Tackle or Defensive Tackle, signing Phillips to a one-year deal is the smartest move on the board.
The Poles Masterplan: How to Pay for It
I hear the cap casualties screaming already. “But we have no money!” Shut up. Seriously.
Ryan Poles is a wizard when it comes to contract structure. By doing “simple restructures” — basically just turning base salary into signing bonuses—the Bears can create a massive amount of breathing room without actually cutting anyone we like.
Potential Cap Savings via Simple Restructure:
- Montez Sweat: +$15.7M
- DJ Moore: +$17.9M
- Jaylon Johnson: +$11.1M
- Joe Thuney: +$12.1M
- Dayo Odeyingbo (If kept): +$11.8M
Total potential space: $85.9 Million. Poles isn’t aiming for the full $85M — he’ll likely target about $40M in active space for free agency. That is more than enough to sign Hendrickson and add a veteran safety or another piece on the interior.
Final Verdict
If I’m Ryan Poles, I’m not overthinking this. We were one defensive stop away from the NFC Championship game in 2025. One stop. Our window is wide open, and Caleb Williams is the truth.
The Move: Go get Trey Hendrickson on a 2-year, $50M deal. Front-load the guarantees while Caleb is cheap. Let Hendrickson and Sweat spend the next two years making life a living hell for Jordan Love and Jared Goff.
Then, use your first-round pick (No. 25) on a young, high-upside edge like Zion Young or Dani Dennis-Sutton. Let them learn behind two of the best in the business.
The time for “bridge” players and “flashes” is over. We have the quarterback. We have the offensive identity. Now, give Dennis Allen the predator he needs to finish the job.
Because if we roll into 2026 with Austin Booker as our primary pass-rush answer again, we deserve exactly what we get.
Bear Down.