2. Ian Cunningham, assistant general manager Bears
The Chicago Bears have consistently found themselves watching other NFC North teams thrive while they remain in the cellar of the division. It's been a while since they made noise. Sure, they made the playoffs in the distant year of 2018, but they've been irrelevant for the most part. Then again, the Jaguars know that feeling way. Until recently, they were the laughingstock of the league, and if they got the spotlight it was because of Urban Meyer's shenanigans.
Fortunately, things have changed for Jacksonville since Doug Pederson became the head coach, putting together winning seasons in back-to-back years. Having said that, you could make the case that Trent Baalke is holding them back, and if they ever decide to make a change, the Jags should take a look at Bears assistant general manager Ian Cunningham, a widely-respected figure around the league.
Even though hiring Cunningham could be met with a shrug, he's been one of Chicago's bright spots in recent years. A former player, he worked in various roles for the Baltimore Ravens and Philadelphia Eagles before joining the Bears as their assistant general manager in 2022.
Cunningham learned from the likes of Howie Roseman (Eagles) and Eric DeCosta (Ravens), and has interviewed for openings in the past. Maybe he hasn't garnered much attention because Chicago has been messy the past two years but a club in need of a general manager will eventually poach him and find itself with an outstanding talent evaluator.