TERRY BRADSHAW – $45 MILLION

He retired decades ago, but Terry remains one of the most iconic NFL athletes. Before retiring, he played a total of 14 seasons as quarterback for the Pittsburgh Steelers and surprised fans of the sport when he decided to call it quits early on. He wasn’t left bankrupt after doing so, however. Terry found a career as a presenter and even as an actor! Later on, he signed with CBS as a game analyst and guest commentator.

His eyes are always on the prize, proven by his keen sense for business. In 2008, he became the first footballer to receive a star on the Walk of Fame. It was known that during the early part of his career with the Steelers, Bradshaw was a used car salesman during the off-season. He even sold peanut butter just to supplement his income. But as his career progressed until he retired from football, he found a new interest in broadcasting and television work.