Floyd Mayweather has faced some of the biggest names in boxing — from Manny Pacquiao to Canelo Álvarez — but he says his toughest test came early in his career against Emanuel “The Drunken Master” Augustus.
The two fought on October 21, 2000, when a 23-year-old Mayweather was still a rising star. Augustus, despite his modest record of 22-16-4, was known for his unpredictable, showboating “drunken” style that baffled opponents.
Mayweather started strong, using his trademark speed and precision to dominate early rounds. But Augustus made it a war, smiling through heavy shots and taunting Mayweather throughout. At one point, he even blew Mayweather a kiss after the first round, igniting the young champion’s competitive fire.
Though Mayweather largely controlled the bout, Augustus’ toughness forced him into one of the bloodiest fights of his career — leaving the future legend with a bloodied nose before Augustus’ corner stopped the fight in the ninth round.
Afterward, Mayweather praised his opponent, calling him “a true warrior” and later describing him as the toughest fighter he ever faced. “Emanuel Augustus was my toughest opponent,” Mayweather told Fight Hype years later. “His record didn’t show his skill set, but the guy was unbelievable.”
Now retired from professional boxing, Mayweather is preparing for another high-profile exhibition in 2026, when he’s set to face Mike Tyson — a matchup already stirring major controversy in the boxing world.
