Fresh off his defeat in the Olympics, Mayweather started boxing professionally. Although he was a highly touted prospect, he began his career like almost every other professional boxer–fighting on smaller cards for low pay. He signed with Bob Arum’s promotional company, Top Rank to manage him. After a couple years where he beat every boxer he faced, he signed an HBO contract paying him hundreds of thousands per fight.

By the end of 1999, he attempted to negotiate a new contract with HBO, but referred to the seven-fight, $12.5 million deal he was offered as a “slave contract.” His final fight on his original HBO contract paid him $750,000, but he ended up negotiating a deal with HBO that was similar to the company’s original offer.

With an impressive victory over Diego Corrales in early 2001, Mayweather got a new contract with HBO, this one a six-fight, $15 million deal.

While Mayweather was now making millions for each fight, he had a few problems. He wanted to be making more, but his popularity didn’t match his ambitions, as he wasn’t even cracking 400,000 buys as a pay-per-view headliner. And his management received a sizable cut of everything he made.