Joe Francis
Also known as "America's biggest scumbag," Francis was the sleazy mastermind behind Girls Gone Wild. As it turns out, Francis never asked his subjects what their age was, and he ended up distributing explicit material of underaged girls. He did a brief stint in prison and came back to find that he was in massive debt. He borrowed money here and there until he found out that there was a warrant out for his arrest due to tax evasion. He purchased a plot of land in Mexico and has become a resort owner for celebrities like Kim Kardashian and even Donald Trump.