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No, I'm thinking he's like the ten guys in that Time's article I linked to, all of which made more than GSP has, who share with him a lack of any other money making skill to fall back on, and a lack of any previous money handling skills.
If it was just Iverson then yeah, its one guy being an idiot. But its so frequent in sport that its more like a large group of people who suddenly started making a lot of money without any of the skills it takes to not waste it away. Lottery winners fall into the same group - a large percentage of them end up broke within a few years. You are poor, you suddenly make a lot of money and start living the high life, and then continue living that life when the money stops coming in, until there's no money left. At which point you have nothing left.
Read up on it, its very common among athletes (and lottery winners). People think they can always make money other ways (coaching, endorsements etc), but the reality is being a great athlete typically is a very different skill set than coaching, and few athletes can make money via endorsements after retirement. Jordan and Gretzky still make a bit, but far less than they used to. Most make nothing at all, advertising companies are even more fickle than Sherdog fans - what you did five years ago means nothing to them.
Dude these guys make 10s of millions of dollars and you're saying they don't make enough? It's a lack of money management skills, not anything else.