There's been a lot of debate in recent years about whether Tiger Woods has permanently lost his sparkle out on the golf course, and if his best years are behind him. If they are, he'll be walking away with more money than any other pro golf player in history. Whether he's the greatest of all time is subjective, but he has spent more time ranked as world #1 than any other player in history and has 14 Major championships to his name.
As the new poster boy of golf, Woods was the most marketable sports star in the world in the early 21st Century, signing endorsement deals with Nike, American Express and many other big companies. He's designed a golf proof watch with TAG Hueur and licensed his name to EA Sports for a series of video games, all of which sent his cash reserves through the roof. Back surgeries may have slowed him down, but the money keeps on coming.