Why Jaelan Phillips Would Be A Sneaky-Good Free-Agent Signing for Bears

What if I told you the Chicago Bears could potentially upgrade significantly at defensive end this offseason without having to break the bank with a Trey Hendrickson or Maxx Crosby signing?

With the Bears hoping to capitalize on a possible Super Bowl window with Caleb Williams on a rookie contract, a lot of Bears fans want to see the team go all-in on to shore up the pass rush, either by signing Hendrickson, who led the league in sacks two seasons ago, or trade for Crosby, who is among the most disruptive players in the game and has apparently grown tired of the Las Vegas Raiders.

But there’s a middle ground that could save the Bears some money, upgrade the position, and allow them to focus their draft capital and resources on other spots.

ESPN’s latest rankings of top free agencts naturally listed Hendrickson as the top get this offseason. But a few spots below that at No. 5 was a very curious name who quietly had a really good season in 2025: Jaelan Phillips, who finished last season with the Philadelphia Eagles.

A former No. 18 overall pick in the 2021 NFL Draft by the Miami Dolphins, the 6-5, 266-pound pass rusher had slowed down significantly due to injuries after starting out hot with 15.5 sacks in his first two seasons, leading Miami to trade him to Philadelphia in 2025. The change agreed with him, as he posted 41 pressures and 15 stops in his eight games with the Eagles, according to Pro Football Focus.

With the Eagles paying a whole lot of people big money and more to come, they’re highly unlikely to retain Phillips. Assuming that’s true, the Bears need to be one of the first teams on his call list when free agency opens in March.

Newly-acquired #Eagles pass-rusher Jaelan Phillips tonight:

6 total tackles
1 forced fumble
1 fumble recovery

The trade is paying off for Howie and Philadelphia: pic.twitter.com/7uzVwv1Os7
— Arye Pulli (@AryePulliNFL) November 11, 2025

When healthy, Phillips has rare explosiveness as a pass rusher and can also stand up strong against the run, making him a true three-down player on the outside. On top of that, he’s used to playing in the four-man fronts Chicago likes to employ under Dennis Allen, having just excelled in one with Vic Fangio and the Patriots. Chicago even got a close look at him in that Black Friday win in Philadelphia, giving them a chance to scout him a little extra this offseason.

Though he plays more as a stand-up outside linebacker than a hand-in-the-dirt guy, there’s no doubt he can play in Allen’s system as an edge.

On top of that, he’s young (26) and might not be nearly as expensive as the other options listed. Some agents view his potential contract as being closer to the one Josh Sweat signed with the Arizona Cardinals last year (four years, $76.4 million; 41 million guaranteed), which would be far less than the $25-$30 million Hendrickson will probably want or the $30M+ Crosby is already making.

If you do that deal, you can more easily afford to re-sign Kevin Byard and can then spend draft capital on other positions of need, like defensive and offensive tackle. Plus, you’d then have Austin Booker, who emerged as a threat in the playoffs, playing a more situational pass-rush role or as a swing guy who can play both spots.

He might not be the flashiest option on the list, but a healthy Phillips, like the one who finished last year with Philadelphia, is one the Bears can definitely use.

More Chicago Bears News:

Which Current Bears Could Make The Hall Of Fame One Day?

Why Drake Maye’s Super Bowl run doesn’t hurt Caleb Williams

Colston Loveland, Joe Thuney Crack Sports Illustrated's List Of Top 100 Players In 2026

A New Defensive Lineman Enters Chat For Bears In PFF Mock Draft