Eh I don't really feel bad for him, he had his time to shine and he made plenty of money. It was his responsibility to save it, he didn't and now he's in debt (as heard from the news outlets). He can always try to play basketball overseas in China if anything, there are plenty of ex NBA players over there.
After all his appearances on radio shows etc on how to manage your money when you make it to the NBA, he still doesn't get it, but if I were in his shoes would I have done the same? Maybe.