4. Gilbert Arenas

-cash blown: $111 million

Gilbert is not yet bankrupt, probably because he is still being paid even though he hasn’t played since 2012. He signed a six year contract of 111,000,000 dollars with the Wizards in the year 2008 and later on he was traded to Orlando Magic.

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He still continues to live a life of luxury even though he’s no longer playing for the NBA, this is all thanks to his contract. However, he’s learning that money can quickly disappear. He has a personal shark, over two thousand pair pairs of shoes, massive gambling activities and a seven bedroom mansion all of which he can barely afford.