Dennis Rodman's life is spinning out of control. After appearing in court, and avoiding jail time for his failure to make child support payments, Rodman's "advisors" are trying to help him restructure his life.
This speaks to a need to create an annuity program (also mentioned by Atrios) for professional athletes. It is simply impossible to understand how anyone payed tens of millions of dollars could possibly be broke, but that is becoming the normal situation for professional athletes from all walks of life. Setting aside a portion of contract salary for an annuity makes total sense, provided the annuity cannot be sold off.
What is hurting Rodman is the fact that he had to cash out his NBA retirement for pennies on the dollar; what should be keeping him afloat right now is, essentially, gone. He didn't do that because of greed. He did it because he was behind in his taxes. And taxes are what is hurting Rodman in the cash flow department. Poor management has left him with a string of unpaid tax bills. That sort of thing can undermine any effort to make good on obligations.
Couple all of that with Rodman's alcohol problems and you can see where this sad story is headed.