Eleven kids with ten different women? That’s a recipe for financial disaster. Worst yet, Henry who enjoyed a relatively short NFL career from 2001 to 2007, never made superstar-type money, only amassing about $20 million during his career. His lawyer estimated in 2009 that Henry owed about $170,000 per year in child support. Things went from bad to worst over the course of Henry’s year as well. He was indicted on federal drug charges for distribution of cocaine and spent two years in prison.