Oh come on lol..
If you had made Sheen dollars and failed to diversify enough to account for a divorce, or other unfortunate turn of events, then you deserve to be broke. You're certainly not WINNING, as Charlie is wholeheartedly claiming to be.
I don't see how income matters, and I don't see how bankruptcy is even applicable. Besides, going bankrupt and being broke are two completely different things.
Trump went bankrupt, remember? He sure as fuck wasn't broke.
Stop apologizing for this behaviour. If you're a multi-millionaire, don't complain about money. Ever. Complain about the carpet stains on your nephew's yacht or something.