How Conor McGregor and Floyd Mayweather Made the Impossible Fight Happen

Chad DundasMMA Lead WriterAugust 21, 2017

B/R

The weekend after Conor McGregor knocks out Floyd Mayweather Jr., he's going to Ibiza and he's going to rent a yacht.       

McGregor's childhood buddy is getting married, and the fighter wants to get together on this 100-foot boat. He can picture them all cruising along the eastern coast of Spain, surrounded by travel-brochure sunshine and technicolor water. Call it a cross between a wedding reception and a victory party.

"We're just going to have fun," McGregor says. "Celebrating that knockout. Enjoying life—and I'll be silked-up from head to toe."

Of course, this is just a dream for now. As he visualizes the celebration during an interview with Bleacher Report, the fight is still 15 days away.

It's a muggy Las Vegas evening in mid-August, and McGregor's open workout and media day at the UFC Performance Institute have been running characteristically late. After abusing a series of heavy bags over the course of 12 three-minute rounds, he disappeared for more than an hour, leaving gathered reporters milling around an empty microphone setup, waiting to ask him questions. When he finally did show back up—cradling his infant son like a football in one arm and having exchanged his personalized Versace fight robe for a skin-tight white shirt and pink paisley pants—he made it worth everyone's while.

LAS VEGAS, NV - AUGUST 11:  UFC lightweight champion Conor McGregor carries his son Conor McGregor Junior during a media workout at the UFC Performance Institute on August 11, 2017 in Las Vegas, Nevada. McGregor will fight Floyd Mayweather Jr. in a boxing
Brandon Magnus/Zuffa LLC/Getty Images

McGregor held court for nearly 40 minutes on every topic from his chances against Mayweather to his public feud with sparring partner Paulie Malignaggi. In the end, everybody seemed to go home happy. In that way, the media day was a classic McGregor experience: He's going to give you a great show, but he's going to do it on his own terms.

Now, he's squeezing in a few last one-on-interviews before his private training session begins at 11:30 p.m.

As is almost always the case, he's having a blast. He thrives on this, McGregor keeps reminding us. He lives to be under the lights.

"I take a step back every day and just kind of relish it all," he says. "I never look to let things pass—to live it and not actually feel it. I always want to feel where I am and acknowledge it, so I can truly enjoy it and embrace it."

Part of McGregor's Ibiza dream is certain to come true. The trip is booked, and he's estimated to make between $75-150 million versus Mayweather, so he can afford to rent or buy any yacht he wants, any time, for the rest of his life.

The celebration, though, is more speculative. McGregor is going off as close to a 4-to-1 underdog against Mayweather, according to OddsShark, and even that line seems generous. The only people truly expecting a KO win are McGregor, his close-knit team and his legion of Irish fans. Nearly everyone else forecasts a lopsided victory for Mayweather.

Yet here in the interview room, McGregor is deadly serious about his dreams. He possesses them with an unwavering, full-fisted confidence. He believes in them completely, and then forces the rest of the world to believe through sheer strength of will and the power in his Mack truck left hand.

In a few minutes, he'll breeze out of the room, drop his baby boy off at home and return to work out and spar until well after midnight. If he's feeling pressure, or nerves or the grind of a fight camp, it doesn't show. Perhaps he even has a bit more bounce in his step these days. Perhaps the glint in his eye is a tad keener as he discusses his hopes and dreams.

He might get badly beaten on Aug. 26, but the truth is he's already won. The swaggering, 29-year-old Dublin native has succeeded in pulling off one of the greatest coups in combat sports history.

He's already convinced his UFC bosses to let him do something they have never allowed before. He's already talked the greatest boxer of his generation into meeting him in the ring. He's in the process of luring in an audience many expect will break the all-time pay-per-view buys record—all for a fight where he'll step into the ring with a 0-0 professional boxing record.

How did McGregor do it?

That's a great question.

For a long time, a matchup with Mayweather was thought to be impossible—too out there even for a guy occasionally called "Mystic Mac."

Somehow, though, here we are.

The story of how it all came to be is a meandering one. It's part verifiable fact, part rumor and part recollection—often vague—from the people who built it.

We don't really think about things that can't happen. When we dream and we have certain ambitions, we just work hard and we go get it. — Audie Attar, Conor McGregor's agent

Even in the final days leading up to this fight, there's still a surreal quality to it. But McGregor has already turned many of our doubts to dust.

"We don't really think about things that can't happen," explains Audie Attar, McGregor's agent. "When we dream and we have certain ambitions, we just work hard and we go get it."

 

"I would kill him in less than 30 seconds."

The first time McGregor publicly uttered Mayweather's name was on a frigid day in New York City in early 2015.

McGregor and longtime girlfriend Dee Devlin were touring the city with Esquire writer Chris Jones for a profile that would run in the publication's May issue. This was a big deal for McGregor. After jetting to a 5-0 start in the UFC, he was well-known in MMA circles and beginning to come into his own with the mainstream. The Esquire story would be some of his first real crossover exposure, and his unique cocktail of machismo and sartorial flair figured to play perfectly to the magazine's male-dominated readership.

"It was an interesting time because he wasn't really famous yet," Jones says. "We walked around New York, and he got recognized a couple of times ... but [mostly] nobody looked twice at him."

Problem was, the weather was too cold to spend the day exploring NYC. The trio retreated inside for lunch, where Jones ended up asking what he thought was one of the more innocuous questions of the day-long interview.

"This is going to sound stupid in retrospect, now that it's become this big deal," Jones says, "but at the time, I didn't think much of it. I think I just asked him: 'How would you do against Floyd Mayweather?'"

McGregor's answer, delivered in the fighter's trademark emphatic brogue, would land him on the map in a way he hadn't previously experienced.

"If I fought Floyd, I would kill him in less than 30 seconds," McGregor told Jones. "It would take me less than 30 seconds to wrap around him like a boa constrictor and strangle him."

At first, Jones says he failed to separate this over-the-top declaration from the torrent of other vehement proclamations McGregor made that day. But when the story came out online in April, the Mayweather quote broke big. Suddenly, platforms that hadn't paid any attention to McGregor before were scrambling to write UFC Fighter Calls Out Money Mayweather stories.

"I was shocked," Jones says. "That quote went everywhere."

It got so much attention that Mayweather responded, telling TMZ Sports: "I don't take that dude seriously. He's just trying to get himself some publicity."

This wasn't the first time the boxer had jawed with an MMA fighter. During Ronda Rousey's unbeaten UFC run from 2013-15, she and Mayweather intermittently swiped at each other in interviews. In a way, the budding Mayweather-McGregor beef picked up where the bad blood with Rousey left off.

In July 2015, McGregor appeared on the Conan O'Brien show and again fielded questions about Mayweather.

In December, the boxer took shots at McGregor and Rousey in an interview with FightHype.com, and McGregor clapped back on Instagram.

Still, no one was seriously entertaining the idea of a bout between the two. McGregor fought three times in the UFC in 2015, winning the interim featherweight title and then unifying the belt by knocking out perennial world No. 1 Jose Aldo in 13 seconds at UFC 194. Meanwhile, Mayweather finally had his long-delayed superfight with Manny Pacquiao in May, shattering the all-time pay-per-view buys record. In September, he beat Andre Berto via lackluster unanimous decision and announced his retirement.

If anything, Mayweather and McGregor appeared to be drifting in opposite directions. In May 2016, an article by the UK Sun's James Beal and Matt Heath-Smith claiming the two were "on the verge of [a] billion-dollar mega-fight" elicited only snickers. UFC President Dana White poured cold water on the report, telling Yahoo Sports' Kevin Iole it was "just a tabloid story."

A curious thing began to happen, though, amid all this public bluster. Each time the fighters tweeted or Instagrammed at each other, internet traffic went crazy. Everywhere they traveled, fans asked about the beef and the media lobbed questions, even if some of it was tongue-in-cheek. For a couple of consummate self-promoters like Mayweather and McGregor, this didn't go unnoticed.

"Social media played a vital role in getting this fight done," says Mayweather Promotions CEO Leonard Ellerbe. "All the enthusiasm from the fans—from the MMA fans to the casual fans to the boxing fans—who want to actually see this fight take place. It's been a global interest. You've got two worlds clashing."

McGregor is often lauded as a visionary, but it was Mayweather who first began to believe their fight could be a real thing. As the boxer eased into retirement, he saw the MMA champion becoming the biggest story in combat sports. Maybe, just maybe, Mayweather reasoned, there was something substantive brewing.

In the days following the UK Sun report, McGregor took more potshots at Mayweather during a "Sunday Conversation" with ESPN's Kenny Mayne. Dana White went on the Dan Patrick Show and said if Mayweather wanted to fight McGregor, he should "call me."

Later that month, Mayweather tweeted a fake fight poster teasing a bout with McGregor. Along with an interview he gave to FightHype.com around the same time, the boxer started putting it out there he would come out of retirement to fight McGregor—in a boxing ring, of course. Skepticism still loomed, but now both principals had gone on record saying they were game. The discussion began to become something more than purely hypothetical.

"Give credit to Floyd Mayweather," says Stephen Espinoza, executive vice president of Showtime Sports and a longtime Mayweather partner. "He's the one who saw this as a real opportunity—as something that could happen and could be huge—way earlier than anyone else did."

Give credit to Floyd Mayweather. He's the one who saw this as a real opportunity—as something that could happen and could be huge—way earlier than anyone else did. — Showtime Sports VP Stephen Espinoza

Still there was one big obstacle: McGregor was locked into one of the UFC's notoriously rigid exclusive contracts. He'd need the company's blessing before he could move forward, and almost nobody thought that was possible.

"It became clear very quickly that this was not something the UFC was in support of," Espinoza says. "... So, Floyd kept [things] alive, but a lot of us were skeptical because we didn't think there was any point at which UFC would actually agree to cooperate with it."

"You gotta stay open-minded in the fight business."

It's a few days after McGregor's open workout and Q&A, and Dana White is in a Las Vegas Champ Sports looking at shoes. A kid who works there approaches him.

This isn't unusual for White. After nearly two decades as the face of the UFC, he's used to getting pulled aside in public, taking pictures with fans and signing autographs. This time, though, the kid doesn't want White's signature. He wants to talk about Mayweather-McGregor.

"The kid who was working there comes up to me and says, 'Dana, I bought a brand-new, massive TV just for the McGregor fight,'" White says. "He said, 'I swear to God, I'm throwing the biggest party ever.'"

After leaving the store, White gets another message from a fan who's pumped to watch the fight. This time it's Robert Downey Jr., texting to say he's also planning the biggest party ever, on the set of the next Avengers movie.

So you might say there's interest here from a broad range of demographics.

"It's incredible how big this fight is and how far it spans with people," White says. "We're already breaking records."

Even the brash UFC boss can't conceal a note of wonder that he's about to co-promote a boxing match with Mayweather. White says he originally counted himself among those who thought this fight was a pipe dream. The fact it's really happening seems to amuse him.

"The one thing I've learned in this business, there's a lot of crazy things that happen," he says. "You gotta stay open-minded in the fight business."

It's incredible how big this fight is and how far it spans with people. We're already breaking records. — Dana White

People expected that open-mindedness to be tested by this booking. With the exception of a foray by Chuck Liddell into the Pride FC middleweight grand prix in Japan in 2003, UFC fighters have always remained exclusive to the Octagon. When Randy Couture attempted to free himself from his UFC contract to chase a dream matchup with heavyweight legend Fedor Emelianenko in 2007, the company took him to court. During 2008, the UFC also publicly squashed the notion that boxer Roy Jones Jr. might fight middleweight champion Anderson Silva.

Conventional wisdom said McGregor's attempts would suffer the same fate. The relationship between the UFC and its all-time biggest PPV draw was already running hot and cold, after all. The organization had pulled McGregor from its gala UFC 200 lineup in April 2016 after the two sides couldn't agree on his press obligations. Though the following year UFC brass allowed him to move up in weight to fight lightweight titleist Eddie Alvarez at UFC 205—in McGregor's successful bid to become a two-division champ, another first for the promotion—it stripped him of the featherweight title just 15 days later.

A potential fight against Mayweather felt like just another opportunity for McGregor and his bosses to butt heads, and some of the fighter's initial public moves indicated that's exactly what was happening.

Just a few days after the UFC stripped him of his 145-pound belt, news broke that McGregor had obtained a boxing license in California. This only fueled internet conspiracy theories he might be on the verge of challenging his UFC contract in court. Some thought McGregor could potentially cite the federal Muhammad Ali Reform Boxing Act, which forbids boxers from signing exclusive deals with promoters but doesn't extend to MMA fighters.

Two months later, in January 2017, McGregor said as much during a pay-per-view interview with journalist Ariel Helwani in London, emphatically stating his next fight would be in boxing and against Mayweather. While McGregor noted he'd rather have the UFC's blessing, he said he was willing to go it alone.

"With the Ali Act, I believe I can [do it]," McGregor said. "... I think it's smoother if everyone just gets together and gets involved, but, again, everyone's got to know their place."

The same night, at a UFC event in Denver, Colorado, media asked White to respond to McGregor's comments.

"You know how I feel about Conor," White said. "I've always shown Conor nothing but respect. If he wants to go down that road with us, it'll be an epic fall."

Even now, McGregor's team implies things with the UFC got off to a rocky start, though it's unclear how much actual back-and-forth was going on.

"If I were to go and look at some of the public statements that were made, I don't think they were necessarily on board initially," Attar says. "But, look, credit to Dana and the UFC for recognizing a serious opportunity—and recognizing that they had a special athlete and a special individual in Conor that could potentially pull something off that nobody has ever pulled off in the history of sports."

The bad feelings—if indeed there were any—were fleeting. That contentious contract negotiation many people expected? White says it never materialized. Even during the time he warned of an "epic fall" for McGregor, he insists they were always on good terms.

TORONTO, ON - JULY 12:   Conor McGregor speaks with UFC President Dana White during the Floyd Mayweather Jr. v Conor McGregor World Press Tour at Budweiser Stage on July 12, 2017 in Toronto, Canada.  (Photo by Vaughn Ridley/Getty Images)
Vaughn Ridley/Getty Images

"There was never anything where we were battling back and forth," he says.

When asked if the Ali Act ever came up during the deal-making process, White says: "Not even a little bit."

For his part, Attar says McGregor received that California boxing license merely as another way to gauge interest in his boxing career. They were hungry for more data supporting the idea that McGregor could be a draw in the sweet science, numbers underscoring his market viability. A slightly less jargon-filled way to say it might be that it was at least partially a publicity stunt—and it sure worked.

"When that news hit of us filing for the license, it almost broke the internet," Attar says. "Nobody was talking about whatever the most recent current event [in MMA] was. Nobody was talking about that. This became international news."

Once it was time for the posturing to stop and the haggling to begin, Team McGregor and White did it in friendly territory, meeting in the office of recently departed UFC co-owner Lorenzo Fertitta. Fertitta had exited the company not long after he and his brother Frank sold it to WME-IMG in July 2016 for a reported $4.2 billion. Long seen as a calming presence, Fertitta is regarded as something of a mentor to McGregor. White says it made perfect sense to call him in for this negotiation, despite the fact the former top boss is no longer involved in the day-to-day operations of the UFC.

"Even when he's out, he's in," White says. "He's my best friend and my partner for 17 years, and he helped build this thing. Conor loves and trusts the guy, too, so we all went and met at his office."

Whatever the secret ingredient was, the meeting was fruitful. Perhaps what observers expected to be a complicated deal turned out to be more straightforward—just a matter of the company agreeing to let McGregor fight Mayweather in exchange for a cut of the earnings. Most of the concrete numbers involved in Mayweather vs. McGregor are protected by confidentiality agreements, so no one can say exactly what that split is—but it's clear that everyone is happy with the terms.

"For the most part this came together quickly," Attar says. "You're always going to have challenges in deals of this magnitude—it's expected—but, again, I'm proud and honored that everybody allowed their cooler heads to prevail and everybody saw that this was a great opportunity."

On May 18, 2017, White announced McGregor's side of the deal was done. With the biggest apparent obstacle to the fight cleared, the once-impossible fantasy matchup had begun to feel more like an inevitability.

Fast forward to August, and McGregor says all parties are better off for working together.

"To do it without [the UFC] and not have them on board—it probably could've been [that way], but there was no need for it," McGregor says. "I'm very happy with how it all played out. The relationship has only gotten stronger through this. It has gone to a different level now. We are partners now, true partners."

"I was cheesing, man. I was like, yeah!"

The enormity of the accomplishment is just starting to sink in for Attar when he runs into Fertitta at what will become an infamous sparring session in early August.

The former UFC owner has stopped in to check out McGregor's training, and at one point Fertitta pulls him aside for a chat. He confides in the agent that on the drive to the workout he passed a Mayweather-McGregor billboard and had to pinch himself to make sure it was real.

You know you're involved in a pretty big deal when even the billionaires can't quite believe it. Attar says he knows the feeling.

"I had my little ah-ha moment, too," he says. "When I got to Vegas and came into the baggage claim at the airport, it says 'Welcome to Las Vegas' and in the background you could see: 'Mayweather vs. McGregor.' I was cheesing, man. I was like, yeah! But at the end of the day, you have to shake it off and get back to work, because it isn't over yet."

Attar is right to be proud that his team at Paradigm Sports Management landed this deal. In many ways, it represents the biggest business win ever achieved by a UFC fighter.

"Audie has been instrumental in the growth of my entire business game," McGregor says in praise of his longtime agent. "He knows [our] worth. That's rule No. 1: Know your worth. Know the numbers, know what you deserve and then seek to get that. If it's not got? Well, then you leave it sit and that's it—there's no rush, no panic. I think his patience is one of his best attributes."

While Mayweather has long been in McGregor's sights—telling friends he wanted to box the legend as far back as spring 2015—Attar says McGregor didn't start to think seriously about chasing the bout until after he'd defeated Alvarez at UFC 205 in November. Following that win, McGregor paused from his breakneck UFC schedule to announce a lengthy paternity leave. He and Devlin welcomed their son Conor Jr. in May, just around the time Mayweather talks started to heat up. That makes these heady times, even by McGregor's standards—starting a family while simultaneously tumbling into the biggest opportunity of his professional life.

Or, perhaps more accurately, willing it into existence.

Even after McGregor and the UFC reached their deal, White still had to hammer out an agreement with Mayweather. Luckily, it sounds as though that was as close to a formality as any deal of this size could be. White sat down with Ellerbe and promoter Al Haymon and, while there were stipulations and hang-ups and confidentiality agreements to work out, each man emerged from the experience offering raving reviews.

"It was a joy to work with those guys," Ellerbe says. "They have some excellent leadership and they have a great understanding of how to make deals. Everything was really smooth."

Compared to the marathon slog of the Pacquiao negotiations, Mayweather-McGregor proceeded in record time. It took just a couple weeks for the formal agreement to be reached. First targeted for September 16, the bout actually had to be moved up after it lost its proposed date to the Canelo Alvarez vs. Gennady Golovkin fight.

Frank Franklin II/Associated Press

"Late August is, speaking candidly, probably too soon," Espinoza says. "But November or December seemed like a lost opportunity and too long. Faced with those two choices, I think everybody said let's jump into it and get it done—strike while the iron is hot."

This means the lead-up to the biggest bout in history has been a little like "assembling a moving car while you're in it," Espinoza says.

Both the production side and the fighters have likely been scrambling to get ready. The madcap nature merely adds another layer to the already crazy mix. It's still hard to fathom that in less than a week, these two men will climb into a ring and fight each other. It still doesn't seem possible and yet it will be.

In the middle of it all sits McGregor, decked out in his paisley pants, dreaming of Ibiza and dreaming of shocking the world.

The nature of the triumph he's already scored is in no way lost on him.

"Everyone involved was just intelligent and understood everyone else's position," McGregor says. "It happened seamlessly. Good business is good business. You've got to put your hands up to good business."