Floyd Mayweather Jr.
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His nickname was literally money. And he lost a lot of it. Floyd Mayweather Jr., the controversial boxer, earned money that would set most folks for life just for showing up to fights. But he couldn’t hang on to it for long, regularly buying cars, jets, and jewelry — $7 million of which robbers stole from him in 2008. After a nearly two year retirement, Mayweather Jr. returned to the ring — primarily in order to refill his empty wallet.