It took 10 years of prizefighting, but in 2006 Mayweather made a big move that would end up being the smartest of his career. His contract with Top Rank had an opt-out clause that he exercised by paying the company $750,000. This left him free to start his own promotional company, Mayweather Promotions.

Leonard Ellerbe, longtime Mayweather confidante and CEO of Mayweather Promotions, told Forbes back in 2015 that Mayweather “envisioned himself as a headliner who could make nine figures in one night. Floyd wanted to take his career in a new direction [so] Floyd walked into Top Rank’s office, handed them a check and the rest is history.”

His first fight after opting out was against Carlos Baldomir. It only sold 325,000 pay-per-views, but Mayweather made $8 million, by far his largest purse up to then. That set him up for a career-changing fight against Oscar De La Hoya.

mayweather de la hoya magazine
Image via Getty/The Ring Magazine

Mayweather’s original nickname was “Pretty Boy” because his defensive abilities led to him taking little damage in most of his fights. Before fighting De La Hoya, one of boxing’s biggest stars, he changed his nickname to “Money” and adopted a more abrasive, villainous persona.

His timing was perfect, as HBO debuted a new series, 24/7, to promote the Mayweather-De La Hoya fight. Mayweather had gone from a skilled fighter who attracted little attention to someone people loved or hated. Either way, they were tuning in. The fight served as a turning point in Mayweather’s career.

As Todd Duboef, President of Top Rank promotions, told to the NY Daily News back in 2007:

"He felt his abilities made him the best in the sport. You don't get paid by ability. You get paid by marketability. He saw Oscar making $20 million to fight Felix Trinidad and he couldn't believe it because he didn't think Oscar was that good in the ring. That was Floyd's nemesis when he was with us. His marketability hadn't caught up to his talent. He didn't have patience to wait for it.”

MORE IMPORTANT, HE SIGNIFICANTLY BOOSTED HIS POPULARITY, AND FOR ALL HIS FUTURE FIGHTS HE WOULD BE THE 'A-SIDE,' THE FIGHTER WHO EARNS THE LARGER PAYCHECK.

De La Hoya was the more popular fighter and earned $52 million, but Mayweather won the fight and earned $25 million. More important, he had significantly boosted his popularity, and for all his future fights, he would be the “A-Side,” which is the fighter who earns the larger paycheck.

Mayweather earned around $25 million in his next fight against Ricky Hatton, who was also undefeated at the time. He then retired from boxing, although he would return almost two years later. In his first fight back, against Juan Manuel Marquez, he earned $10 million. His pay steadily increased, and in 2012, he earned $45 million in his fight against Miguel Cotto.

For comparison, Manny Pacquiao, whose rise as one of the best pound-for-pound boxers in the world coincided with Mayweather’s, was guaranteed $26 million in June 2012 in a bout against Timothy Bradley and another $26 million later in the year against Marquez.