11. Booker T
Given that Booker T has had such a successful career in the world of professional wrestling, it can be easy for fans to forget that he was not always as well to do as he is now.
As a youth, Booker, who is now a millionaire, was flat broke and struggling to get by. In an attempt to get some money in his pockets, the future WWE World Heavyweight Champion got together with some friends to hold up the Wendy’s in which he worked.
Because Booker T was not an experienced criminal, he made a number of errors during the robbery which easily led police to him. He was sentenced to five years in prison, though was released after serving one third of that term.
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