Year: 2002
Net worth: -$1 Million ($30 Million Reebok trust fund, which can't be accessed until 2030)

Allen Iverson is no stranger to financial issues. And according to one server at a Philadelphia area restaurant, those issues were front and center at The Answer’s bachelor party a few years back. Apparently, Iverson and 25 of his closest friends ran up a bill of X amount of dollars on food and drinks, which was subsequently paid for by his mother upon her departure from the party. Cool, right? Well, Iverson and a few others kept turning up, but refused to throw down once they were done. They attempted to walk out on a $200 bill all together—forget the tip—and when confronted by the manager, AI allegedly threw two bills on the floor and stormed out. Damn.

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