The 40-year-old has a connection to Ryan in Bears GM Ryan Poles, who was one of Ryan's teammates at Boston College. Cunningham, formerly with the Ravens and Eagles, has worked under Poles in Chicago since 2022. He has interviewed elsewhere for several promotions since then, including the Commanders' president of football operations gig in January 2024. Cunningham was a finalist for that opening, but the Commanders hired Adam Peters instead.