For all intents and purposes, NFL free agency starts on Monday, when the early negotiation window opens. But if we’re really being honest, there have already been initial inquiries made between teams and agents through various channels for weeks, if not months, because once that window is cracked (11:01 am CT), the league insiders will unload their reports they’ve had saved in their drafts.
The Chicago Bears are coached by a former Lion, the defense is run by a former Saint, and there are also former Jaguars,
Cowboys, and Dolphins on staff, plus the GM came from K.C. That’s just naming a handful of obvious connections they have around the league.
Looking at the needs the Bears currently have and the free agents looking for a place to play in 2026, a few have ties to Chicago’s current regime. And yes, most of these are on the back nine of their career, but the Bears need to fill roster spots with some vets while they draft and develop.
Cameron Jordan, DE – The longtime New Orleans Saints defensive end will be 37 in July, but he can still get it done. He had 10.5 sacks last season on a 6-win team, and Pro Football Focus gave him an overall grade of 76, which was 24th among EDGEs. He knows he’s nearing the end, which is why his last two years, he’s only in on about 50% of the snaps on D. A similar part-time role in Chicago while he tries for a ring could be a nice way to close out a career.
Taylor Decker, LT – Head coach Ben Johnson knows him well from their time together with the Detroit Lions, and while the soon-to-be 33-year-old wouldn’t be the long-term answer at left tackle, he’d give the Bears a serviceable stopgap until they can reassess Ozzy Trapilo.
Alonte Taylor, CB – While Taylor is known for playing nickel with the Saints, he has played outside and even lined up like a safety at times. His versatility is a plus for helping disguise coverages, and pairing him with another versatile corner who can play slot, outside, or safety (Kyler Gordon) could be fun.
Alex Anzelone, LB – Not only did Anzelone cross paths with Johnson in Detroit, but he started his career in New Orleans with Dennis Allen as his defensive coordinator.
Demario Davis, LB – Another veteran defender with ties to Allen is the 37-year-old Davis, who is coming off a career high 143 tackles with the Saints. Even after 14 years in the NFL, he’s still playing at a high level, and PFF had him as their 6th highest graded linebacker.
Alec Ingold, FB – The Bears didn’t have a fullback on the roster last year, but they would often line one of their tight ends up in the backfield. Ingold can line up on the wing, go in motion, wham block a defender, and play in the third phase. He was a cap casualty by the Dolphins, where he spent four years being coached by current Bears’ running backs coach Eric Studesville.
Khalil Mack, DE – Yes, another player in his 30s (Mack just turned 35), but he’s a complete defensive end who can set the edge and play in Allen’s scheme. Which he already did as a rookie when he was drafted by the Raiders and their head coach at the time, Dennis Allen. I think Mack would benefit from a reduced role à la the aforementioned Cam Jordan. If Mack could get his snap count around 50%, you could save him and deploy him on critical drives during the game.
It depends on the money they’re after, but I’d love the idea of Mack and Jordan to pair with Montez Sweat and Austin Booker in 2026. Last year’s second-round pick, Shemar Turner, can give some inside-outside flexibility, and then, if the NFL Draft falls just right, maybe you draft an EDGE, and now you have a solid rotation at defensive end to keep everyone fresh.
Are there any free agents with connections to the Bears that you’d like to see them sign?
