Herb Simon

Herb Simon is a basketball hall of famer who is married to Miss Universe. No, we don't have him mixed up with Wilt Chamberlain (he never married any of the women he shtupped). Believe your eyes: it's the Jewish man on the left. That's Herb Simon. We repeat: basketball hall of famer, married to Miss Universe!

No, Herb did not exactly excel on the basketball court. Together with his brother Mel, he founded a real estate development group that became the largest mall owner in America. (If there is still a mall next to your town, odds are that it's owned by the Simon Property Group.) Mel and Herb bought the Indiana Pacers in 1983, and Herb is currently the longest-tenured owner in the NBA. That's because Mel passed away in 2009; he wasn't alive for Herb's induction to the Basketball Hall of Fame in 2024 in the contributor category. (Justice for Mel!)

From here, you can pretty much figure out the Miss Universe part. Par the course for these billionaire types, Herb divorced his first wife to marry a daughter of an Indiana politician... and then divorced her to wed Porntip Nakhirunkanok, a Thai beauty queen who is 35 years his junior. (That's love!) Porntip (that's her real name!) was crowned Miss Universe in 1988.

So, no, your eyes weren't deceiving you...