1. Allen Iverson – $200 Million Lost

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As is often the case with sports stars, Iverson ended up supporting an entourage 50 deep. This ¬†was a massive drain on his resources, and he’s also thought to be banned from some Casinos across the US. That’s gotta hurt!

2. David Harrison – $4.4 Million Lost

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Harrison ended up working in McDonalds five years after retiring from the NBA.