7. Ric Flair
It doesn’t need to be said that “The Nature Boy” Ric Flair is one of the most highly revered individuals in the rich history of professional wrestling. Before Hulk Hogan was taking WrestleMania into the mainstream spotlight, Ric Flair was wrestling classic matches and winning World Championships.
This high profile career would go on for decades and it was only a few years ago that Flair finally hung up his wrestling boots for good. Truth be told, if Ric Flair still wanted to wrestle today he could probably school WWE’s entire roster.
Though he’s been in the spotlight again lately due to the great successes of his daughter Charlotte Flair, it has been said that Ric has been in some major debt for years now and doesn’t actually have much in the way of cash these days. Years of alcohol abuse and personal issues have not helped his situation, but if anyone can work his way out of a situation like this it’s the Nature Boy.