Easy to forget that people who make a lot of money tend to spend a lot of money. When the money you make is because you own as well run business, fine, that money will probably continue to rolk in. But when your income is purely for the contract work you do (esp. sports or entertainment), awful lot of people don't plan as if they will ever be unpopular or unfit for that work down the road.

Can't speak to his personal situation, but there are an awful lot of broke former athletes and entertainers out there.