Charles Barkley – $50 Million

If we were to ask a basketball fan who some of his favorite players are, it wouldn’t be too surprising to see Charles Barkley make his way into that list. Like many of his colleagues, Barkley began his journey into the sport during his years in school. Although he initially played as the team’s reserved, he eventually played a more significant part not long after. Suffice to say; this gave him the chance to shine on the court.

Well, who would’ve thought those earlier years in the sport would become the first few investments he made for his eventual career. By 1984, Barkley made his way to the big leagues. From then to his final year in 2000, he played for NBA teams Philadelphia 76ers, Houston Rockets, and the Phoenix Suns. Now often regarded as one of the NBA’s all-time greats, Barkley is now making a splash as a sports analyst.