Kristin Cavallari and Jay Cutler flipped their roles as breadwinner for their family prior to getting divorced in April 2020 - but where do their finances stand now? When Cavallari and Cutler began dating in 2010, to many, Cutler was the bigger name because of his career as an NFL quarterback. Although Cavallari came from a reality TV background, Cutler was one of the highest-paid quarterbacks in the league during the 2014 season, one year after they tied the knot. The pair, who share sons Camden and Jaxon and daughter Saylor, had a bit of a financial role reversal by 2017.