Floyd Mayweather Picks Lesser Known Fighter As His Toughest Opponent

But 'Money' believes Emanuel Augustus - called Emanuel Burton at the time - gave him the most difficulty inside the squared circle and even outdid him when it came to showboating antics.

Augustus, nicknamed ' the Drunken Master' thanks his bizarre punch sequences and unique puppet-like approach, retired with a record 38-34-6 record.

Coming into the bout in October 2000 in Detroit, he had 22 wins and 16 defeats in his professional career but he gave Mayweather, who had been super featherweight world champion for two years at the time, some serious trouble.

He was eventually pulled out of the fight in the ninth round yet earned the respect of Mayweather, who had his nose bloodied by him in the fifth after some combinations.

"If I was rating certain fighters out of every guy that I fought, I'm going to rate Emanuel Augustus first compared to all the guys that I've faced," Mayweather stated.

At the very end of the fight, where he suffered an injured right hand, Mayweather called Augustus a "tough motherf***er" when speaking to his corner and later showered him with praise in his post-fight interview.

"He's a true warrior, a true champion," Mayweather said.

"Before the fight, I heard he had got robbed [via poor judging decisions] a lot of times - and I believe that's true."

As the undefeated Mayweather continued to ascend, breaking numerous pay-per-view records and making millions, Augustus' topsy-turvy, inconsistent career lasted for another 11 years.

Six years ago, he was the victim of a random shooting where he was hit with a bullet to the head but somehow survived and lived to tell the tale.