Mayweather-McGregor: How five years and fate led to the biggest fight in history


Floyd Mayweather was but 10 days into a 90-day jail sentence, yet the desperation had become real. He feared for everything – his health, his sanity, his career. He was left begging for mercy from officials disinclined to provide any. For a man who had known nothing but victory in the ring, nothing was assured.

“I’m just hoping this time [doesn’t] have an [affect] on my career,” Mayweather wrote in a letter to Clark County Detention Center officials on June 9, 2012.

That career likely culminates Aug. 26 when he puts his 49-0 record on the line to fight mixed martial arts star Conor McGregor in what may be the richest prize fight in history.

The concept of such success was a fading vision back in the summer 2012, as Mayweather sat in a tiny jail cell in downtown Las Vegas. Full of anxiety, he scratched out letter after letter to officials, pleading for better treatment. He was serving a three-month stint as part of a guilty plea on misdemeanor domestic violence.

Mayweather took the deal to avoid a trial on a slew of felony charges for assaulting his then-girlfriend and mother of three of his children in 2010. He could have been hit with 34 years for that, ending what was already a rich career. Now he wondered if this was going to finish him anyway.

Jail was never going to be easy. He was trading his 22,000-square foot mansion for a 6-by-10 foot cell. Mayweather expressed outward confidence however, displaying the unflappability that has helped him dominate in the ring.

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Reality was different. Jail officials placed him in protective custody, arguing that his fame and fortune would have made him a target by fellow inmates. That meant solitary confinement, on the first floor of the jail’s 2M unit. Monday thru Friday he spent 23 hours a day in his cell. On weekends it was all 24. There was little to no interaction with others for a man long accustomed and comfortable being the center of attention.

Floyd Mayweather Jr. (L) and Conor McGregor face off during a news conference on July 14. (AP)
Floyd Mayweather Jr. (L) and Conor McGregor face off during a news conference on July 14. (AP)

Mayweather complained vehemently about his treatment in a letter included in his Clark County inmate file, obtained via open-records law. He argued that considering his misdemeanor plea, he shouldn’t be “treated like a murderer or a child predator.” He begged to be moved to general population or out to a separate facility in suburban Henderson, Nev.

“Out of 168 hours in a week, I only get five outside my cell,” Mayweather wrote. “It’s not fair.”

He refused the jail food, subsisting on commissary items – mostly candy bars, beef jerky, Chili Cheese Fritos and soda. He saw his weight drop and his blood pressure rise. He bristled at being cooped up, a stunning change for an elite athlete.

At one point, in a jail letter, he claimed he’d busted up a rib when he heard “something pop” while reaching for a bottle of lotion that had rolled under his bunk. He said he needed surgery and promised a lawsuit.

Mainly, he was just losing it.

“I’ve lost weight,” Mayweather wrote. “Mentally, my mind is not the same. I’m stressed out. I can’t work out and I need some type of exercise.”

Jail officials were unimpressed, promising to refer him for medical and psychological assistance but little more.

“You will not be moved,” a Sgt. Neville wrote back, nearly a week later.

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At the same time, early June 2012, Conor McGregor was teetering through mixed emotions. Just a few days prior he’d won his first championship belt – in the featherweight division of the Cage Warriors MMA promotion – yet with the hardware came little else.

There was almost no fanfare and even less respect. Cage Warriors, especially then, was a local outfit, mostly running cards in McGregor’s native Dublin, Ireland, in London and occasionally the Middle East. It paid little.

McGregor was about to turn 24 but stuck in a painful reality. He was a plumber by trade; an aspiring, long-shot fighter by dream. The training for the latter took too much time to do the former. He could only survive financially by signing up for the Irish welfare system, marching down to the government offices and standing in a queue each week to get a check for roughly $200.

Week after week McGregor needed to show his ID, show he had no job, show his face to whomever else was in there or walked by, shaking their head at an able-bodied man who apparently couldn’t support himself. This wasn’t the poverty of youth, the poverty of circumstance. No one blames a kid for growing up like that.

This was different. This was poverty of choice, and no matter how many times McGregor tried to talk up the possibility of being a big-money fighter, telling people that this new sport would one day make him internationally famous, he noticed most people’s eyes just glaze over. If he were such a big deal, then why, four-plus years into his MMA career, entering his mid-20s, was he still fighting for peanuts?

In Crumlin, a tough, tightly packed neighborhood southwest of Dublin, where he was raised as a child and walked as a young man, they saw it as an excuse for laziness. Or maybe procrastination built on delusion. He and his own father, a longtime factory worker, had, at one point, a falling-out over the career path. He used to have to borrow his girlfriend’s car to get around.

He could feel the condescension. It haunted him.

“That can drain a man’s mind,” McGregor said a couple years back.

He was in his own solitary confinement, if you will.

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That was Floyd Mayweather and Conor McGregor five years ago.

One in the hole. One on the dole.

There are no similarities to the paths each took to that spot. Mayweather committed a crime. Violence against women is a particularly pathetic act. McGregor simply hadn’t gotten his break yet, just another hungry athlete.

Yet career-wise, there was a similar unease. Nothing promised. Nothing guaranteed. Each saw their confidence challenged in those lonely days.

Part of the appeal of this fight is that this is a clash of opposites – most notably a boxer fighting a mixed martial artist. There’s more though. Black and white, American and European, “old” (40) and “young” (29).

Mayweather’s jail stint was a darker place than McGregor’s and was borne of inexcusable actions.

While he’d already earned millions, he’d also spent millions and long-term economic stability was not assured. He was 35, and even under the best of circumstances, age comes quickly in boxing – speed and reflexes fade fast. Here in the worst of situations, a health nut unable to care for himself, there was no guarantee for millions more to be had.

He was at risk of losing everything.

McGregor did nothing wrong in not yet becoming a rich and famous star. He was not a criminal. He enjoyed freedom and possibilities. Yet he says he held shame from that weekly welfare check – shame that was compounded by the doubt that it would never amount to anything; shame that he’d just wind up another broken-down Irish fighter; shame that fitting pipe on construction sites was his real destiny. Few in MMA make truly big money, let alone a guy outside of the U.S.-focused UFC.

He was at risk of never getting anything.

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Mayweather learned to grind out his time. It wasn’t easy. There were clashes with guards and continued protest. He countered with a lot of pushups. He played cards by himself, read fan mail and as motivation browsed magazines geared for the wealthy, such as Robb Report. He also found a way to make the jail work for him, with officials suspecting he was paying other inmates in exchange for favors.

That included, according to Mayweather’s jail files, officers overhearing Mayweather shouting to an inmate named Paul Lopez, “I am putting $500 on your books [which is used for supplies or commissary]. Thanks for looking out.” Indeed, a third-party soon put that sum on Lopez’s account, just one such incident. Lopez is now serving two life sentences in the Ely State Prison for first-degree murder.

Mayweather eventually made it out, rehabbed his rib and regained his strength. He returned to the ring in May 2013 and is 6-0 since that fateful summer, including a massive, 2015 payday victory over Manny Pacquiao. His debt to society paid, he hasn’t been in trouble with the law since (though he does allegedly owe the IRS a considerable sum).

He rarely discusses that time, although once, when asked by columnist David Mayo of his hometown Grand Rapids Gazette if anything positive came from it, Mayweather declared, “nothing.”

“I did all my time in the hole,” Mayweather said. “It was tough.”

As for McGregor, he also found a way to grind his way up and out, using the pain of the old days as fuel.

“I’ll never forget being on the dole, standing there,” McGregor said. “I’ll never forget those times.”

When he finally got to the UFC in 2013, he made sure not just to win fights, but do it in thrilling fashion. All eight of his bouts since 2014 have been named either performance or fight of the night.

Following Mayweather’s blueprint, he doubled down on impossible-to-ignore antics, trash talk and bold plans. “I’m running things now,” he’d crow. “I’m never going back,” he’d promised. His goal was to make as much money as possible, as quickly as possible. He soon became the UFC’s most bankable star. Along the way he broke Dana White’s supposed ironclad rules by becoming the first to ever simultaneously hold title belts in two weight classes and now the first to crossover and compete in boxing.

In the end, a meeting of these two was probably inevitable. A boxing match against one another is worth 10 times more than anything a UFC card (for McGregor) or anything else (for a retired Mayweather) could produce.

“The biggest fight in sporting history,” McGregor said during the London portion of the fight’s promotional tour last month.

That the once-impossible is upon him was not lost on McGregor.

“[Five] years ago, I fought in London…in front of about 500 people,” McGregor continued. “Now here I am, about to quadruple my net worth…I’m in shock every day I wake up.”

The crowd on hand roared… a five-year ride from the bottom to the top.

Floyd Mayweather, sitting there as McGregor worked the mic, listened and no doubt understood the sentiment.