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Money comes and money goes, which is cool when you’re talking about $5 or $10. But these stars made millions and millions of dollars and somehow managed to spend even more.

For more on megastars who went broke, check out Moguldom’s latest documentary, When The Checks Stop Coming In.

Allen Iverson

When Allen Iverson stepped into the NBA, he was nicknamed “The Answer.” Although he never won an NBA championship, he will go down as one of the greatest point guards to ever dribble a basketball. But Iverson has always made as many headlines off the court for his legal woes and financial difficulties. Even though at one point he was making $20 million per season, Iverson has spent up much of his money. He frequently traveled with an entourage that rivaled MC Hammer’s crew. In 2012, he admitted in court documents that he pulled in $62,500 a month but had to shell out $360,000 in expenses, with most of it going to creditors and mortgage payments.

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