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Floyd Mayweather Jr. fought some of the greatest boxers in his career, including Manny Pacquiao, Oscar De La Hoya, and Shane Mosley. He never lost a single bout. According to Mayweather, those big-name fighters don’t register as his toughest opponent. Mayweather said that fight happened in 2000, during the height of his career, against a boxer nicknamed The Drunken Master.

Floyd Mayweather’s toughest fights

Floyd Mayweather achieved an unblemished record of 50-0 in his boxing career from 1996 through his last bout in 2017. While his record is perfect, that doesn’t mean he didn’t have a few bad rounds, or even a few bad fights.

In fact, of Mayweather’s 50 fights, his opponent took him the distance 23 times or just under half the time he stepped into the ring. One of the first times Mayweather was really challenged came in 2007 against Oscar De La Hoya. The six-division champion battled Mayweather and at the halfway point judges had the fight even. In the last half of the bout, Mayweather was the better fighter and won in a majority decision.

Mayweather also endured tough matchups with Canelo Alvarez and Marcos Maidana, both of those fights ending with Mayweather earning victory by majority decision. Many boxing experts think the closest Mayweather ever came to losing was in April 2002 when Jose Luis Castillo took Mayweather the distance. Many of those ringside and in the crowd thought the Mexican actually won the fight. The judges, however, disagreed and Mayweather maintained his perfect record at 28-0.

Who is Emanuel Augustus?

Emanuel Augustus turned professional in 1994. He won his first fight. Then, he lost the second. Those two fights would ultimately sum up the level of success in his career. He would win a fight or two, only to lose the next several fights. 

Augustus’s success, or lack thereof, wasn’t necessarily a reflection of his own skills, as much as those he stepped in the ring to fight. Augustus never backed away from a fight even if it was on short notice, and he knew he was outclassed. In his career, he fought the likes of Jesus Chavez, Micky Ward, and of course, Mayweather. He always entered the ring with two prevailing thoughts: win and entertain, and he delivered on the second with regularity. 

His unorthodox style included a wild array of dipping shoulders, raised legs, and punch sequences, unlike the sport had ever seen. Augustus appeared to be part boxer, part string-puppet. His herky-jerky style earned him The Drunken Master nickname. 

Floyd Mayweather says Emanuel Augustus toughest opponent ever

On October 21, 2001, Mayweather got introduced to The Drunken Master. Mayweather entered with a 24-0 record while Augustus came into the fight with an unimpressive 22-16-4 record. No one expected it to be close. 

Mayweather got off to a quick start in the early rounds, only to be answered by the underdog with a rally in the fourth and fifth rounds. In the fifth, Augustus landed a flurry of punches that bloodied Mayweather’s nose and brought the crowd to its feet. In addition to his boxing skill, Augustus entertained the crowd with his trademark showboating, which included grinning and blowing a few kisses to the super-featherweight champ.

As expected, Mayweather took control in the closing rounds of the fight and in the ninth round, Augustus’s corner threw in the towel. In the post-fight interview, Mayweather talked about his opponent.

“He’s a true warrior, a true champion. Before the fight, I heard he had got robbed [via poor judging decisions] a lot of times—and I believe that’s true.”

Years later, with time to reflect on his career and the many fighters he battled in the ring, Mayweather returned back to that October 2001 fight against The Drunken Master.

“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 said in an interview with “He didn’t have the best record in the sport of boxing, he has never won a world title. But he came to fight and, of course, at that particular time I had took a long layoff.”

Emanuel Augustus retired from boxing in 2011 with a career record of 38-34-6. Unfortunately, he was the victim of a random shooting to the head in 2014, but survived. While he may not be a household name and remembered for achieving boxing greatness, Augustus did achieve one thing that October night in 2001 that will last forever—respect from one of the greatest boxers of all time.