Whatever the outcome of the much-hyped big fight against Conor McGregor, the 40-year-old has earned his status as the finest boxer of his generation

Lou DiBella was near the end of an 11-year run as an executive at HBO when a young fighter walked into his office looking to renegotiate his contract with the network. The year was 1999 and Floyd Mayweather was the 22-year-old super featherweight champion of the world.

The offer on the table was a four-fight, $5m extension. It was, HBO insisted, one of the best contracts any young fighter in the world had been offered. But for the Olympic bronze medallist who had signed with Bob Arum’s Top Rank Promotions, it was a non-starter. Or, as he put it at the time, “slave wages”.

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“I’m not any young fighter,” Mayweather told the room. “I’m not like the rest of those guys. I’m going to be the greatest. I’m never going to lose.”

And here we are. Nearly two decades on, Mayweather is widely recognised as the finest boxer of his generation, unbeaten in 49 professional fights and 26 world championship contests with titles in five weight classes. He will surpass $1bn in career earnings whether he wins or loses in Saturday’s 12-round boxing match against Conor McGregor, a two-division UFC champion who is making his professional boxing debut.

But as the 40-year-old from Michigan prepares for what appears to be his final ring outing, he remains a figure with a complex legacy that can only be drawn in shades of grey. He overcame a chaotic upbringing filled with drug abuse and violence to rise to the 1% but in turn has been dogged by allegations, and a conviction, of domestic abuse. As the frontman for his nascent promotional company, he speaks passionately and credibly about advocating on behalf of fighters but when I asked him last week about his thoughts on Charlottesville, he pirouetted from the query with the elusiveness he’s shown for years. Ali on Vietnam this was not: states are neither red nor blue on Floyd’s map, only green.

Behold Mayweather at the peak of his promotional heft: now he will earn a nine-figure guarantee fighting a non-title bout against an opponent with no boxing experience on the pro or even senior amateur level.

DiBella, who opened shop as a promoter in New York after departing HBO in 2000, remembers the young Mayweather as “a star in terms of ability but not in terms of popularity or recognition” – a precocious talent frustrated with the lack of traction he’d made after signing with Arum. As the network and fighter dug in over the contract extension, DiBella suggested they could walk down to Times Square, a one-avenue jaunt from HBO’s midtown Manhattan headquarters, and if people started stopping Mayweather on the street then the network would renegotiate.

Mayweather never did sign the extension but the implication was clear: there is a difference between an elite boxer and an attraction. Just being good at what you do is not enough. One can only speculate where that demonstration fits into the origin story of Money Mayweather, the pantomime-villain persona that Floyd launched after buying himself out from Arum in 2007 for a lump sum of $750,000 and has since leveraged to untold riches.

There is something to be admired about Mayweather’s ascent in a business that has traditionally conspired to exploit and defraud fighters for as long as anyone can remember, in the way he has leveraged his success to rewrite the rules for himself. Nearly all other boxers receive a contracted purse, with their promoters pocketing the rest. Not Mayweather, who has worked with an enigmatic adviser named Al Haymon – a Harvard-educated former concert promoter who obsessively keeps to the shadows – to develop a unique financial structure based on the exchange of upfront risk for back-end profit.

Of course if it was that easy, everyone would do it. Some, such as Adrien Broner, have tried. But Mayweather did not hack the sport because he was brash or cocksure. It happened because he works harder than anybody else, from his impossibly rigorous training sessions to those famous 4am runs. Unlike so many of his fistic brethren who balloon up and down in weight between fights, Mayweather stays in fighting shape all year round; his is a deceptively monastic lifestyle.

So much of Mayweather’s allure hinges on the zero in his loss ledger, that he has never been down or seriously hurt so much as lost a fight as a professional. Not until he turned heel eight years ago did the eight- and nine-figure paydays become the norm. The fact is, more fans will plunk down $99.95 on Saturday night to watch him lose than to watch him win.

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They are almost certain to come away disappointed. Mayweather spent his boxing career so far ahead of everyone else it was embarrassing. The proverbial “puncher’s chance” that is McGregor’s best hope is never less meaningful then against a slippery technician such as Floyd.

No, this is yet another first for Mayweather: a valedictory lap for a fighter. Happy endings such as these are as rare as it gets in this cruel trade. As goes the timeworn chestnut: you don’t retire from boxing, boxing retires you. The decline is almost never gradual. The night when it becomes evident that a fighter no longer has what it takes to compete at the highest level it is often wildly brutal and dramatic, it is not signified by something as harmless as shooting 20% from the field or completing 10-of-35 passes with four interceptions.

When it’s gone for a fighter, they find themselves positioned across from a very dangerous individual who is trying to hurt them. It is a life-threatening situation.

Perhaps that is the fate that awaits Mayweather on Saturday night but the possibility is so astronomically remote that it is barely worth discussing. Instead, even if you despise the man and what he represents, it is time to doff your cap and send him on his way. The last laugh is Floyd’s – and surely he has earned it.

“I still find it remarkable that this cocky little fucker, he was right,” DiBella said, with a laugh. “It’s nearly 20 years later and this kid still hasn’t lost and he’s amassed the biggest fortune that any fighter ever has in boxing.”