In the aftermath of Israel Adesanya’s stunning knockout of Paulo Costa at UFC 253 on Fight Island, President Dana White will have allowed himself a wry smile.
After watching another successful main event in Abu Dhabi, with a world champion cementing himself as a superstar, White had every reason to be optimistic.
Yet the 51-year-old’s face contorted into an uncomfortable grimace when one of the first questions posed to him at the press conference was about a retired fighter more than 3,500 miles away in Ireland.
Conor McGregor was once again the main topic of conversation amongst members of the media in the United Arab Emirates after ‘The Notorious’ released screenshots of Instagram conversations between the pair.
White described the Irishman’s plan as ‘one of the dirtiest things you can do’ and accused him of breaking ‘man code’.
The latest instalment of this complex, love-hate relationship appears to have thawed somewhat with McGregor ending his fourth retirement to fight Dustin Poirier at UFC 257 on Fight Island.
But how has the golden boy of the UFC fallen so foul of the company’s president and where did their seemingly unbreakable relationship begin to deteriorate?
When McGregor became the Cage Warriors featherweight champion in 2012, he sent his first ever Tweet to the UFC president in the hope of getting noticed.
It wasn’t until 2013 when the UFC finally signed the Irishman, who had destroyed Ivan Buchinger to become a two-weight world champion with Cage Warriors.
His featherweight bout with Marcus Brimage lasted just 67 seconds as McGregor displayed incredible movement and power to send the American crashing to the canvas before winning the hearts and minds of fans everywhere in his post-fight interview.
“Dana, 60 G’s baby!”
“This is the best moment (of my career) so far,” said McGregor in the post-event press conference. “I didn’t have money before this. I was collecting €188-a-week off the social welfare, and now here I am with a 60 G’s bonus and then my own pay.”
After suffering a torn anterior cruciate ligament in 2013 against Max Holloway, McGregor was ruled out for almost a year and returned to action in sensational style.
White witnessed the superstar potential of his newest protégé first hand when, in front of a raucous, sold-out 02 crowd in Dublin, McGregor stopped Diego Brandao in the first round. After confidently predicting when the fight would end, he introduced the world to ‘Mystic Mac’.
The Irishman was pushed through the 145lbs division at a rapid pace to continually generate publicity and controversy in equal measure.
It led to a monstrous new deal with the UFC in 2014 which was agreed with former co-owner Lorenzo Fertitta and effectively set the Dublin-native up for life.
He wrote on Instagram: “Lorenzo brought me into his office, myself and my manager Audie Attar, and placed a contract down in front of me with numbers I’d never seen before in my life!”
Victory over Poirier in September of that year also led to a big-money deal with Reebok, a massive UFC partner.
By now, White and McGregor had developed into more than just business partners. When he was scheduled to face Jose Aldo at UFC 189 in 2015, the boss visited the infamous ‘Mac Mansion’ and told him Aldo had dropped out just two weeks before the July date.
Instead of baulking, McGregor simply asked who he would face instead, forever earning the boss’ respect.
Becoming interim champion at UFC 189 was just the beginning, with McGregor proceeding to knock Aldo out cold at UFC 194 in their rearranged bout a few months later in July.
However, the cracks soon began to show between him and White. When Rafael dos Anjos pulled out of UFC 196, McGregor faced Nate Diaz in March 2016 instead and was handed his first ever loss.
Sensing a lucrative rematch, White tried to sanction an instant sequel, but McGregor baulked at the extensive media duties he was being forced to perform to promote the fight.
In April 2016, he retired from the sport of MMA for the first time and duly pulled out of UFC 200.
Speaking on the Dan Patrick Show, White insisted the pair had not actually fallen out and they were planning on meeting to resolve their differences.
“Conor and I have been talking every day,” White said. “We’re going to have dinner next week.
“Our relationship is great, and we’re going to put the little speed bump in the road that happened there behind us and move forward. So everything is great.”
After successfully avenging his loss to Diaz at UFC 202 in August 2016, White pitted his superstar against Eddie Alvarez for the UFC lightweight title and McGregor claimed his second UFC belt to become the first ever simultaneous world champion.
It seemed as though everything was rosy between the pair, especially when White gave McGregor the green light to drift from the UFC entirely and fight Floyd Mayweather in a boxing match.
Not only did White allow the Irishman to leave the company and not defend either of his titles, he vociferously promoted it and also acted as a hype man during the build-up to his professional boxing debut.
However, as McGregor’s star threatened to burn brighter than the UFC once again, it took an inevitable toll on the pair’s relationship again.
After not hearing a single word from the superstar about his potential return in 2018, White told reporters on the Wednesday before UFC 223 in April that he expected ‘The Notorious’ to fight again.
By the Thursday evening, the New York Police Department had issued a warrant for his arrest after he attacked a bus carrying fighters, including bitter rival Khabib Nurmagomedov.
“This is the most disgusting thing that has ever happened in the history of the company, and there is a warrant out for Conor McGregor’s arrest,” he said. “And they’re looking for him right now.
“His plane cannot take off, he cannot leave the state of New York with this warrant. He’ll be grounded, and I’m assuming eventually if they don’t catch him, he’ll turn himself in. You can imagine he’s going to be sued beyond belief and this was a real bad career move for him.
“I don’t know if [McGregor is] on drugs, or what his deal is. But to come and do this and to act like this — you’re talking about a guy who had a baby,” White added. “He just had a kid. This is how you’re acting? You have a son at home.”
When the fight with Khabib was booked for UFC 229 in October, there was no suggestion the pair had made amends. Although the atmosphere between the two was cordial and even friendly once again, the most lucrative fight in UFC history was tinged with violence and hatred.
McGregor’s insults and trash-talking went too far at times, with White having to defend the Irishman after the press conference and suggesting he was simply engaging in trash talk.
He said: “It was the darkest press conference I’ve ever been a part of. But Conor McGregor is the master of mental warfare.
“I’ve said it before, and I’ll say it again: He’s better than anybody. Even [Muhammad] Ali. You don’t want to say anybody’s better than Ali, but I think when it comes to the mental war game in this sport, or any other sport, Conor McGregor is the best ever.”
The loss to Khabib and subsequent brawl at the T-Mobile Arena sparked yet another retirement from McGregor in March 2019 as he walked away from the sport for the second time in third years.
Yet, unlike his first retirement after UFC 196, White did not pander to his star. With Khabib, Jon Jones, Jorge Masvidal and Israel Adesanya emerging as genuine PPV stars for the company, he simply wished his former employee all the best.
“It totally makes sense. If I was him, I would retire too,” he told MMA Junkie. “He’s retiring from fighting, not from working. The whiskey will keep him busy, and I’m sure he has other things he’s working on.
“We really have never had a bad conversation since Conor has been in the UFC,” White added. “You know how I feel about retirement: If you are saying it, you should probably do it.”
When he did finally make his comeback, the world was plunged into chaos with the outbreak of COVID-19. Yet another retirement for ‘The Notorious’ was met with disdain by his former employer, who simply insisted he would return.
Despite the rematch with Poirier finally being confirmed last month, the relationship between White and McGregor, which seemed to more closely resemble a genuine friendship appears on ice.
The pair will surely continue to generate millions of dollars, but the relationship they once enjoyed appears fractured beyond repair.