Derek Jeter – $185 Million
When Derek Jeter exploded onto the baseball scene in the 1990s, he made a huge wave. In 1996, he won Rookie of the Year; and in 1999, he signed a huge contract with the New York Yankees for about $119 million. It was a brand new age for the Yankees’ dynasty, and Jeter was the star, winning five World Series Championships. He was famous for his partying ways and his dating lifestyle as well. Eventually, he married model Hannah Davis, and together, they own a $14.7-million deluxe house in New York.