Allen Iverson $200,000,000
No player in NBA history did the “live fast and go broke” thing better than Allen Iverson. But Iverson had a very unique way of spending his cash. Few athletes in sports history were as generous, yet totally reckless as “The Answer.” There were numerous stories of Iverson giving homeless people in Philadelphia large wads of hundred dollar bills, because he said he’d likely be one of them if not for basketball. But he also foolishly bankrolled his entire entourage whenever and wherever they were. Including insane amounts of money spent at casinos. Of course, there were the usual “bling” purchases too. Iverson and all of his buddies had plenty of flashy jewelry, fancy cars, and expensive clothing. He then spent $4.5 million on a gated estate in Atlanta that spanned almost 10,000 square feet, featuring a gourmet kitchen (which rarely got used), a massive bar, and gutters made from pure copper. Iverson refused to employ any financial advisors after he became wealthy. Instead he remained loyal to his “first-day friends,” for better or for worse. He’d rack up enormous debt on credit cards, then simply stop paying for most of the purchases. At a divorce hearing in 2012, he told the court he didn’t even have enough money for a cheeseburger.