Antoine Walker – His story is maybe the most tragic of them all. He lost all of his $110 million fortune to generosity. Or stupidity, depending on how you look at it. He financed the lifestyle of an entourage of over 70 family members and friends, including the infamous gold digger Evelyn Lozada. When he tried to gamble alongside the likes of Michael Jordan — and live like MJ — he lost his entire estate, as well as Lozada’s “love.” Then he was arrested in Las Vegas for writing 10 bad checks, a felony.