Caitlyn Jenner – $100 Million

The world fell in love with Jenner while still a male and named Bruce Jenner. Jenner took the Olympic gold for decathlon not once but twice, in both 1975 and 1976. The Mount Kisco-born all-American hero exploded into popularity after transitioning to female. She underwent a complete gender reassignment surgery procedure in 2015, as per Hello!

Jenner had lived life as the male celebrity Bruce Jenner, but at 39, Jenner first started becoming a woman. Today, the 71-year-old Caitlyn Jenner is worth $100 million and is one of the world’s foremost transgender community activists.