OJ Simpson

OJ Simpson is, to a huge degree, as talented as he was controversial. He is a football player, a sports commentator, and an actor. He was first known in 1969 as the number one draft pick by the NFL team Buffalo Bills. During that time, he demanded what was then the largest contract in sports history: $650 thousand for five years (around $4.5 million today). He played in six Pro Bowls and was inducted into the Pro Football Hall of Fame in 1985. However, it was his stint as an actor that propelled him into international stardom. He appeared in films such as The Klansman and The Naked Gun series.

His net worth isn’t that substantial due to the several court cases he was involved in. He is, however, still eligible for an NFL pension, from which he started to get about $10,000 every month. He also has a fully funded personal pension that is worth anywhere from $2-5 million depending on how the assets were invested.