Hulk Hogan

Hulk Hogan was the biggest star in professional wrestling during the 1980s and 1990s, headlining 12 WrestleMania events and becoming the most recognized wrestler in history. He earned tens of millions from WWE and WCW contracts, merchandise royalties, and pay-per-view bonuses. His peak annual income in the late 1990s with WCW was reportedly $10 million per year, making him the highest-paid wrestler of that era.

Hogan's financial story is one of extremes. He earned over $100 million in his career but lost much of it through divorces, bad business deals, and a lavish lifestyle. His $31 million legal settlement against Gawker Media in 2016 -- funded by Peter Thiel and resulting in Gawker's bankruptcy -- was one of the most consequential media lawsuits of the century. However, legal fees and prior debts consumed much of the award.

Hogan has rebuilt through his Hogan's Beach Shop restaurant and bar in Clearwater, Florida, a reality TV career, and ongoing WWE appearance fees and merchandise royalties. His net worth of $25 million is far below his career earnings, making him an example of how even the highest-earning athletes can see their wealth erode without careful financial management.