The Chicago Bears already have an extra second-round pick in the NFL Draft due to their Bryce Young trade with the Carolina Panthers. However, the Bears can earn an extra third-rounder depending on how the Jacksonville Jaguars’ general manager search plays out.
Current Chicago assistant general manager Ian Cunningham is a finalist for the Jacksonville GM role. If he were to get hired, the Bears would receive a compensatory third-round draft pick in 2025 and 2026 due to the Rooney Rule. The Jaguars are planning to hire a GM before the NFL Draft, via John Shipley of Sports Illustrated. So, the Bears will know if their draft plans are altered sooner rather than later.
Cunningham is one of five finalists for the job, joined by Jon Eric-Sullivan of the Green Bay Packers, Josh Williams of the San Francisco 49ers, James Gladstone of the Los Angeles Rams and current Jaguars interim GM Ethan Waugh, via Brad Biggs of the Chicago Tribune. So it isn’t a guarantee that Cunningham leaves Chicago for Jacksonville. However, the fact he is still in the hunt is significant.
Ian Cunningham’s run with the Chicago Bears

The assistant general manager has been with the Bears since 2022, joining forces with Ryan Poles. He has been coveted by teams around the league ever since. Cunningham was a finalist for the Washington Commanders GM job before it went to Adam Peters. He actually turned down the same role with the Arizona Cardinals before Monti Ossenfort was hired.
Clearly, the Bears and almost everyone around the league know what Cunningham brings to the table. The Jaguars are trying to reshape their vision under Liam Coen, and a mind like Cunningham’s might be the perfect fit. If he does end up leaving, it’d be a major blow to Chicago’s front office.
Chicago Bears preparing for 2025 NFL Draft

But there would be a silver lining. Not only would the Bears get two third-round picks, but there’s a chance their 2025 selection falls within the first 100 picks. Chicago already has four picks within the top 100. Adding another one gives new head coach Ben Johnson and company a grand opportunity to shape the roster in their vision.
The Bears are entering the NFL combine looking to craft the future of their franchise. But another high draft pick at their disposal would alter those plans, for all the good reasons. Chicago certainly wants to keep Cunningham in their front office, but with so much interest over the years, a promotion almost seems inevitable. At least if it were to happen entering 2025, the Chicago Bears would be compensated.
For More Great Chicago Sports Content
Follow us on Twitter at @chicitysports23 for more great content. We appreciate you taking time to read our articles. To interact more with our community and keep up to date on the latest in Chicago sports news, JOIN OUR FREE FACEBOOK GROUP by CLICKING HERE