Kristin Cavallari & Jay Cutler – $60 Million

Next up, we have another marriage cross-over from the sports industry and Hollywood. We’re talking about no other than Kristin Cavallari and her NFL other-half, Jay Cutler. The couple met ten years ago when Jay Cutler was still playing for the Chicago Bears. Since the two lived in two different states, making their relationship work was initially a struggle. At first, Kristin wanted to pass on Jay’s invitation for a date since her schedule in California was jam-packed. Fortunately, The Hills star came around, and the two ended up getting engaged a year later.

Their relationship still had its ups and downs, though, as Jay found it challenging to cope with Kristin’s fast-paced life. In 2012, the two welcomed their first child together and followed it up with a wedding in 2013. Since getting married, Kristin and Jay have shared several memories and investments that gave them a combined net worth of $60 million. Sadly, the couple decided to end their decade-long relationship in 2020. Hopefully, the two maintain a good relationship with each other despite going their separate ways.