Floyd Mayweather has beaten Canelo, Oscar De La Hoya and Manny Pacquiao in lucrative fights to retire with 50-0 record, but journeyman boxer nicknamed ‘The Drunken Master’ gave him his toughest fight

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Floyd Mayweather has fought and beaten a plethora of boxing superstars, retiring with millions of dollars in the bank and a 50-0 record.

Oscar De La Hoya, Ricky Hatton, Canelo Alvarez, Manny Pacquiao and a host of other world champions couldn’t beat him, but none of them earned his respect like a journeyman nicknamed ‘The Drunken Master’ who bloodied Floyd’s nose, yet eventually retired with a 38-34-6 record.

Even Canelo couldn’t beat Mayweather as he bulldozed his way to greatness

2013 Golden Boy

Even Canelo couldn’t beat Mayweather as he bulldozed his way to greatness

However, it was Augustus who made him sweat the most

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However, it was Augustus who made him sweat the most

“I’m going to rate Emanuel Augustus first compared to all the guys that I’ve faced,” said Mayweather in 2012 when asked to name his toughest opponent. By that stage, ‘Money’ was 42-0, a multi-weight world champion and the sport’s pound-for-pound king.

“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.”

When Mayweather is making excuses about why a fighter had success against him, you know that boxer did well. What’s incredible is that Augustus fought Mayweather, in 2000, at the peak of his physical powers.

The very bout after that hard-earned win, Mayweather put in what most critics still regard as his most punch-perfect display: when he scored five knockdowns against previously unbeaten danger man Diego Corrales in January 2001.

However, when Mayweather fought Augustus, he had to deal with a rival who blew kisses at him mid-round and showboated as no other foe would have dared.

Born Emanuel Burton, Augustus was one of those boxers where – like a real-life Rocky Balboa – the record does not tell you the full story.

Several of his defeats were controversial decisions or outright robberies. Several more were due to his taking fights at a few days’ notice or his refusal to take the sport seriously; clowning and playacting during fights and winning over a cult following but few favours from the judges.

Augustus was an American TV staple for years but watching him could be a surreal experience. None more so than when he took on ‘Pretty Boy’ Floyd in 2000. The fight took place on one of HBO’s short-lived KO Nation shows that mixed live hip-hop with boxing (Triller eat your heart out).

Going in, Mayweather had won six successive world title fights in dominant fashion. Augustus on the other hand had lost four of his last six fights, including defeats to the likes of Teddy ‘Who?’ Reid and Allan ‘Why?’ Vester.

Safe to say that few were expecting anything other than a showcase for Mayweather’s sizzling skills.

Augustus’ record – 38-34-6 – reads slightly different to Mayweather’s who appeared impressed with him nonetheless when they met

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Augustus’ record – 38-34-6 – reads slightly different to Mayweather’s who appeared impressed with him nonetheless when they met

Mayweather certainly won the early rounds but the 26-year-old Augustus fired back in the fourth, catching him with punches along the ropes, before damaging his nose in the fifth and getting the crowd on their feet.

Augustus was famed for his jerky, unorthodox ‘string-puppet’ style of fighting: raised knees, dipped shoulders and unusual punch sequences. But Mayweather was still banking rounds and, in the ninth of the scheduled 10 rounder, Augustus’s corner decided to pull their fighter out: a wise move, even if he was never off his feet in the contest.

“He’s a true warrior, a true champion,” said Mayweather in his post-bout interview. “Before the fight, I heard he had got robbed [by bad decisions] a lot of times – and I believe that’s true.”

Even to his own corner, Floyd could be heard lavishing praise on Augustus in the immediate aftermath of the contest being stopped. “Good fight – he’s a tough motherf***er,” said Mayweather, while shaking out his injured right hand. “I had to dig deep.”

Fighting Mayweather has proven to be big business as Conor McGregor found out in 2017

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Fighting Mayweather has proven to be big business as Conor McGregor found out in 2017

He is regarded as the one of the greatest ever and retired with a perfect 50-0 record – and millions of dollars in the bank

Chris Farina/Top Rank

He is regarded as the one of the greatest ever and retired with a perfect 50-0 record – and millions of dollars in the bank

Mayweather would go on to win another 26 pro fights out of 26 after defeating Augustus. But the impressive outing did little for his opponent’s career.

Augustus would go on winning and losing in almost equal measure, including a famous 10-round war against ‘Irish’ Micky Ward in 2001 (Ward would later claim Augustus was, alongside Arturo Gatti, one of the toughest men he took on).

Augustus last fought in 2011 and somehow survived a bullet to the head in 2014, the victim of a random shooting. The 46-year-old has suffered health problems since, but has shared his memories of the Mayweather fight with Boxing News magazine.

When it’s brought up that Mayweather often namechecks him as his toughest opponent, Augustus remained modest. “But he still won,” the ex-fighter replies. “That’s like an ant telling a bird, ‘Boy, you’re bad’ – but he’s already in the bird’s mouth going down the stomach.”

Truthfully, Mayweather probably is being kind in naming Augustus as his toughest fight, rather than what it really was: simply a tougher than expected fight.

Jose Luis Castillo came closest to beating Mayweather during their first fight in 2002, while De La Hoya or Miguel Cotto probably took more rounds off Mayweather than Augustus did.

To this day, many believe Castillo was robbed in his first fight against Mayweather

Getty Images – Getty

To this day, many believe Castillo was robbed in his first fight against Mayweather

De La Hoya pushed Mayweather close in 2007

Getty Images – Getty

De La Hoya pushed Mayweather close in 2007

But Mayweather is choosy when doling out compliments to opponents. Notoriously thin-skinned, he could sneer and cruelly tear into rivals he disliked. But he could also treat with dignity opponents he respected, such as Genaro Hernendez – whom Mayweather defeated for his first world title and whose funeral expenses he would later pay after Hernendez died from cancer in 2011.

Mayweather’s inclusion of Augustus on lists of his toughest opponents is actually an act of generosity and acknowledgement. Perhaps, deep down, the man who masterfully managed his own career had some sympathy for a boxer on the other side of the coin: one who had an abundance of talent but zero direction in terms of plotting a serious career path.

‘The Drunken Master’ never fought for a world title but, in going toe-to-toe with a peak Mayweather and actually winning his respect, Emanuel Augustus arguably achieved something far more rare.





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