Former Chicago Bears quarterback Jay Cutler last played pro football in 2017, but the Pro Bowler hasn't stayed out of the limelight in retirement. From his high-profile marriage to Kristin Cavallari to his 2024 DUI arrest, Cutler is one of a handful of athletes who has become a household name beyond the NFL. Cutler and Cavallari began dating in 2010, early in his Bears career, and got engaged in 2011. "Jay is a good Midwestern boy; he's a gentleman," Cavallari exclusively told Us Weekly ahead of their engagement.