When Conor McGregor arrived at Fight Island on a massive yacht for his UFC 257 main event against Dustin Poirier, it was yet another illustration of a career that has reached unprecedented heights for an MMA fighter.
It wasn’t always this way. McGregor’s coach, John Kavanagh, remembers a time in 2013 when McGregor thought he needed a new line of work. He was competing in the minor leagues of MMA and was making so little he survived on welfare checks.
During the course of the next eight years, McGregor’s storyline — and bank account — have taken dramatic turns. He has enjoyed historic success in the Octagon, countered by defeat disillusionment and several temporary retirements.
His rise in fame also brought trouble, and while his successes have been caught on camera, so have some of his transgressions. He attacked a bus of UFC fighters in New York and punched a Dublin bar patron. He’s been arrested a number of times, and there have been reports of sexual assault allegations in Ireland and France.
Away from the limelight, those who have known McGregor from the beginning, and those who crossed his path along the way, tell the behind-the-scenes stories of the highlights of McGregor’s journey. They describe what it was like to stand next to McGregor as his group entered Jennifer Lopez’s private residence for a party, only to find a quiet, mostly empty apartment. Rosie Perez describes what she was thinking when McGregor gave her a “Who the f— are you?” look during the wild media tour for his boxing match against Floyd Mayweather in 2017. And Bruce Buffer remembers meeting a young man in Ireland who made an astonishing prediction that he ultimately backed up.
Editor’s note: Some content was edited for brevity and clarity.
How to purchase UFC 257
Irish roots: Meeting Chuck Liddell, facing self-doubt
‘The Crumlin shots’
Phil Sutcliffe Sr. was McGregor’s boxing coach from 1998 until 2005, and after time apart, he rejoined McGregor’s camp in 2019.
The first time I met Conor was when he came into the gym when he was only 10 years of age. He was out playing football [soccer], out in the Crumlin ground. The Crumlin football team trains behind our gym. He was training there and he came in with his football boots, and Stephen Kavanagh, one of my other coaches, told him, “Get the boots off, son. You’re not allowed into the gym with them football boots.”
So, he took them off and gave them to his mother. He came back in and started punching the bag. Stephen sent him over to me and told him he had to get his mother’s permission or his father’s permission to officially join the club. He was just a kid — we get a lot of kids.
He was always diligent. He put a lot into his training.
He was very good. He would have been a [boxing] champion, but he started mixing with the martial arts at about 15. I didn’t really watch him [in MMA] until he said, “Phil, watch this fight, watch that fight.” And then I look at his fights and what do I see? I see him stepping back and throwing his back hand, I see him reading. All the Crumlin shots. He’s knocking these guys out with the shots he learned as a boy, from 10 years of age. He went back to his fundamentals in his cage, which was fantastic.
‘What’s his problem?’
Petesy Carroll is a longtime MMA journalist in Ireland.
It was about 2009, and I was at my first-ever regional MMA event. I was with my brother, and he was training jiu-jitsu at SBG [where McGregor trains]. I was writing for some fan magazine, and I was doing my best to kind of look like I belonged in the community. My brother knew all these guys. He’d been at many fights. He was telling me, “Every time I’m at one of these cards, some d—head is shouting s— from the front row, shouting all these instructions that don’t even make sense. Everyone in MMA hates those kind of guys.”
If I knew nothing else, I knew I wasn’t to do that. So the main event came on and Paddy Holohan is fighting. And we’re seated cageside. All of a sudden this guy starts screaming all this s— into the cage. He’s on his feet, he’s the loudest person in the room. He’s just about trying to jump over the f—ing fence and get in there with the fighters. I saw this and I see an opportunity to look cool, to look like an experienced head. I turn around to my brother and say, “Look at this dude, what’s his problem?” My brother looked me dead in the eye and said: “Shut the f— up! That’s Conor McGregor. If he hears you saying that, he could beat the s— out of both of us without breaking a sweat.” And that was the first time I met Conor McGregor.
‘That man is special’
Paddy Holohan is a former UFC flyweight and longtime McGregor training partner.
Conor had a tough fight against a guy named Artur Sowinski, a really tough Polish fighter, in 2011. It was going to be in a hostile environment, because there’s a massive Polish following over here in Ireland as well.
I was getting ready to get my tickets, and someone said, “Conor is already here.” I was thinking he’s gotta be a little bit nervous maybe. I looked around, and over in the crowd Conor was there, wearing this three-piece track suit with the bottoms tucked into his socks, shades on, arms over each sofa and as cool as you like.
I just knew at this moment, I was like, that man is special. This is an incredibly tough fight, and to be that cool about it is absolutely incredible.
McGregor knocked out Sowinski in the second round.
‘I started fighting because of you’
Chuck Liddell is a UFC Hall of Famer.
Conor posted a picture last year on Twitter of me and him from 2008. I didn’t know who he was at the time, he was a kid. He must have just jumped into the picture.
Five years before he was in the UFC, Conor McGregor watched his first UFC event in 2008 and took this photo with Chuck Liddell as a fan.
In 2020, the second photo was taken with Chuck Liddell in the crowd watching McGregor. @espnmma
— ESPN (@espn) April 13, 2020
He’s one of a few guys who has said, “I started fighting because of you.”
Having that legacy where you have someone like him come out and say, “You inspired me to start this, to try this” — that makes it amazing for me. That’s the ultimate compliment. If I inspire someone to get in there and chase their dream and fight and be in the sport I love, that’s gratifying to me. I can look back and say, “I did something.”
‘Answer your bloody phone’
John Kavanagh is McGregor’s longtime coach and owner of Straight Blast Gym in Dublin. This item originally ran in an oral history of McGregor’s first UFC fight.
Conor had kind of drifted away from the gym because he just didn’t seem to be getting anywhere. It wasn’t long after he won the second world title with Cage Warriors [on Dec. 31, 2012], so he had two belts, and I think he was fighting for between $500 and $1,000. You’re getting enough money to pay for your training. He was saying, “Well, I guess I better try something else.”
I had been harassing [UFC matchmaker] Sean Shelby, and eventually he replied late January — I still have that email. He said, “Look, there’s a fight April 6.”
I was in Iceland and very excited, and I started ringing Conor, and he wouldn’t answer. I heard he wasn’t showing up in the gym to teach his class. He thought I was ringing him to give him a hard time about that. Eventually, I had to text him and say, “Answer your bloody phone. The UFC has been in touch.”
So he picked up the phone, and you know how Conor is, very calm and calculated, doesn’t get hyper or excited? I could almost hear him screaming all the way to Iceland without needing a phone.
Getting noticed on the way up
Sunglasses and shopping bags
Megan Olivi is a UFC broadcaster who remembers seeing McGregor before he beat Max Holloway by unanimous decision on Aug. 17, 2013, in Boston. That was McGregor’s second UFC fight.
He came into the hotel lobby, and when I say he had a lot of shopping bags, I mean he could not carry them all. He had sunglasses on, he had all these shopping bags, and he had some friends with him. It was just kind of a spectacle. He was still relatively new to the UFC scene, and I think some people maybe had pessimistic ideas about how he was conducting himself or spending his money.
But I just remember thinking, wow, this is cool — somebody is really into style, shopping and fashion. Because obviously that was relatively unheard of in the organization among fighters for the most part. That was the first time I remember him — outside of his fights — where there was something special about how he was conducting himself and how people were observing him.
What’s wrong with your face?
Tristin Kennedy, who is now McGregor’s nutritionist, met him randomly as a college student looking to take a picture with a celebrity.
I was outside the Dublin Institute of Technology at the time, and he was just walking the streets of Dublin. There were a lot of students around, and he was giving a lot of photographs.
I shook his hand and said, “What’s up, man? Can I get a photo with you?” He goes, “What the f— happened to your face, man?” I said, “I got sunburned skiing.” He said, “You got sunburned skiing?” He started laughing. He threw up his hand [in a fight pose for the photo], then he goes, “Throw up your hand there and pose for the photo.” That photo is actually up on my Instagram.
It’s crazy, because then several years later we took a photo in the dressing room after his [Jan. 18, 2020] win over Donald “Cowboy” Cerrone.
When I first started working with him, I told him about the old photo and he started laughing. I don’t think he remembered. But when I put up the post after the Cerrone fight, and you can see the sunburn on my face, we had a right laugh over that.
Daniel Cormier, a former UFC champ and current analyst for ESPN and the UFC, recalls the news conference on Aug. 4, 2014, when he and Jon Jones started jostling on stage, and the fighters tumbled into the crowd. McGregor and Poirier were on that card and had faced off earlier.
Jon and I start fighting and fall off the stage at the MGM Grand. If you look closely at the video, there’s Conor McGregor in the back, taking selfies with the fans.
That’s probably the thing that stands out the most to me. Him and Dustin Poirier went face-to-face before Jones and I, and then Jones and I started fighting out there. Conor just stood there in the midst of all that chaos and managed to take some photos.
Superstardom: J.Lo’s party; dinner with Bono
‘I don’t know if she knows me’
Colin Byrne is McGregor’s conditioning coach, and he recalls a night when he drove McGregor and his fiancee, Dee Devlin; John Kavanagh and his wife, Orlagh; and MMA fighter Dillon Danis to a private party.
We’re in Vegas training for the second [Nate] Diaz fight in 2016. Conor gets a message from [soccer star] Cristiano Ronaldo, and Ronaldo comes down to the gym. Conor said to him, “What are you doing in Las Vegas?” Ronaldo says, “I’m going to Jennifer Lopez’s birthday party tonight.” And then Conor just says jokingly, “Can we go?” And Ronaldo says, “Sure, no problem.” Then he bounced and sent Conor a text to where it was.
We get to the hotel, and inside Caesars Palace there’s another private hotel, and it’s where she has her suite. We go to the concierge, but he won’t let us in. All of a sudden, the lift opens up and this guy comes out in a suit. He’s like, “Hey, Conor! Where are you going, man?” Conor said, “I’m going to Jennifer Lopez’s birthday party.” The guy says, “OK, come with me.”
We get in the elevator, it goes up and the doors open. We walk out, and it’s her apartment. On the wall, it says “J.Lo” in flowers. It’s quiet. There’s six of us in her house. We’re like, what do we do now? We started walking. There were about eight people on an L-shaped sofa, and one of them was Jennifer Lopez. But there’s no sign of Ronaldo — and we weren’t invited. Conor is going, “What do you think I should do?” We were like, “You better go up and say hello.” Conor’s like, “I don’t know if she knows me.” He waves, and she’s like, “Oh my god, Conor!” She jumps up, grabs him by the hand and runs out with him toward the patio.
On the patio, there’s a whole dance thing going on. There’s a deejay. Fat Joe is there. Ronaldo is out there. It was just absolutely brilliant. And she was such a pleasure. Conor got a selfie with her. I didn’t.
At the end of the evening, we were gonna leave. Conor wanted to train. It was one of the only times where I was like, “Can we stay a little bit longer?” Usually, I’m on him like, “Let’s go, we’ve gotta get out of here, we’ve gotta train in the morning.” J.Lo was like, “Hey Conor, just hang on. My band is gonna play some songs.” They had her band with a keyboard in the sitting room. We stayed for two songs. I would have stayed all night. It was one of the best experiences ever.
‘Bigger than Beatlemania’
Tim Simpson is the director of MMA management at Paradigm Sports Management, which represents McGregor. He remembers the reaction in England after McGregor beat Eddie Alvarez on Nov. 12, 2016, in New York to become the first UFC fighter to hold belts in two different weight classes simultaneously.
Conor had a major promotional event in Manchester, England. New York was crazy, but this trip it really dawned on me how big of a star this guy was.
It was bigger than Beatlemania — we literally couldn’t go anywhere. There were hundreds of people — no joke, hundreds — outside of our hotel 24 hours a day. We had a full security escort just to get out to the shops. Screaming fans — men and women in tears trying to meet him.
On the night of the actual event, two cars were run off the road by fans chasing our vehicles en route to the venue. At the event, I had kids coming up to me in tears asking for a chance to see him in person. The barriers at the after-party got knocked down with crowds trying to get to him. There were no injuries, thankfully.
Me and Bono pic.twitter.com/tPWV7HEzij
— Conor McGregor (@TheNotoriousMMA) September 11, 2016
‘Two kids in a candy store’
Audie Attar is the CEO of Paradigm.
Conor was out in L.A. with me for a few days handling some business, and we were invited to a Drake concert by record executive Jimmy Iovine and his son Jamie. They had us over for dinner at their home beforehand with their family and a couple of close family friends.
One of the guests was Bono. Sitting down over a nice intimate meal, we got to know Bono and hear some amazing stories.
The part that resonated with me most was when Bono started to sing us his new album that hadn’t even dropped yet. I remember Conor and I looking at each other in disbelief. I remember communicating with our eyes and no words, and it was as if we were two kids in a candy store.
The MayMac press tour: Loud suits and louder fans
McGregor boxed Mayweather on Aug. 26, 2017, in Las Vegas. There was a press tour to promote the event with stops in L.A., Toronto, Brooklyn and London.
‘Give me that suit’
David Heil is the owner of David August Inc., a luxury men’s clothing line. At the request of former UFC owner Lorenzo Fertitta, Heil made McGregor an ivory suit before McGregor faced Poirier on Sept. 27, 2014. Heil then made another one before the Mayweather news conference in Los Angeles.
When I did the “F— You” suit, that was a big surprise. I actually made about 10 yards of fabric of that for myself and for him. It was more of a joke, just for Conor and I. I brought him four suits to look at when he was going to do the press conferences with Floyd Mayweather, and he looked at them all and said, “I love it.”
Then I pulled out this last one and said, “Or you can wear this one.” And he looked at it and said, “Oh, that’s just a pinstripe suit.” I told him to look closely. He looked at it closely and saw it said “F— You” in the pinstripes, and he grabbed it and said, “Give me that suit!”
We put it on him, he was so excited. So, he walks out on stage, and Dana White introduces him and the first thing he says is, “How do I look? If you look at my pinstripes closely it says exactly how I feel about the Mayweather camp.”
That suit went viral. We put it out as a limited edition, just a very select group of fans, we put out 30 suits, they sold out overnight. We sold them for $11,995. We get constant requests for a rerelease, and we probably will, but we like to keep it a limited thing.
‘I couldn’t stop laughing’
Actress/activist Rosie Perez and radio host/entertainer Sway attended the news conference for McGregor vs. Mayweather on July 14, 2017, at the Barclays Center in Brooklyn. They were asked on stage before the fighters arrived.
It was packed, and Ray Flores was the emcee of the night. Ray asked who did we think would win. I was going to say Mayweather, but before I could say it, I said, “All I have to say is it’s a boxing match.” I got booed. I never got booed like that in my life. [Laughing] I was like, “Oh, my god, this is crazy.” I thought it was supposed to be fun.
Everybody from Floyd’s camp was waving hello to me, I’m waving hello back to them, and Conor McGregor, with his infamous swagger walk, is going back and forth across the stage. At one point, he’s staring at me as he’s walking in my direction, and he gives me the most smug, pathetic look, like, “who the f— are you, and who the f— do you think you are?”
And I went, “Oh, my god.” I actually said that out loud. And in a very slow, dramatic fashion, he looks at me as his body goes to turn in the opposite way, he’s still facing me, and then he rolls his eyes with disdain and then turns and starts walking the other way. And everybody went, “Oh, my god, did you see him look at you like that?”
It was exhilarating. I was shook, I’m not going to lie, but at the same time, I couldn’t stop laughing. I thought, “All this to promote a fight, wow. OK, I applaud you guys. I have to give it to you.”
Meeting Cowboy’s grandmother and playing the Garden
‘I’ve always wanted to meet you’
Jerry Cerrone is the grandmother of UFC star Donald “Cowboy” Cerrone.
I was in the Octagon after my grandson’s loss to Conor in January 2020. When I saw Conor go over and give “Cowboy” a kiss on top of the head, I knew he had recognized “Cowboy” as a legend.
Conor looked up at me, and I motioned for him to come to me. So, he came over. I told him it was a good fight and thanked him for being so respectful to “The Cowboy.”
He said, “I’ve always wanted to meet you.” He said it was an honor to meet me, which was kind of surprising. He said something about me being the steadfast person of the UFC, which is kind of an exaggeration, but a great compliment. I hugged him, and he hugged me back. I was just so touched by the respect that he showed Donald. I wanted to let him know I recognized that.
During Conor McGregor’s workout at Madison Square Garden in preparation of UFC 205, McGregor banks in his jump shot just beyond the foul line.
Julian Dalby is McGregor’s exercise physiologist.
This was in Madison Square Garden in November 2016. Conor was due to fight Eddie Alvarez. It was the first-ever UFC event to be held in New York City. They held an open workout where fighters display their skills for fans. Conor was punching pads, he was kicking, he was boxing, he was grappling around on the ground. Overly energetic stuff.
At the end, he stood up. He was out of breath, panting, covered in sweat. And somebody produced a basketball and pointed at the hoop. I think it might have been Dillon Danis. So Conor, he stepped back, threw the ball. It went up in the air, hit the rim of the hoop, rolled around a bit and it went in. And the crowd went nuts, everybody started yelling and shouting. This was the Knicks’ home arena. People just couldn’t believe it.
An offer he can’t refuse
Michael Conlan is an Irish boxer.
Conor was in Belfast for a paid appearance at a local bar to speak to the fans in a sit-down chat with a speaker, and he told me to come and meet up. So I was there with my brother and a few of our friends.
He invited me to the stage to chat. With a few drinks in my system and feeling confident, I asked Conor — in front of a few thousand who were there — would he walk me out for my Madison Square Garden debut on March 17, 2017, knowing it would be hard for him to say no.
He agreed and said he’d be honored. After the event, we ate, then went and partied all night in Belfast. Good times.
‘Remember my name’
Bruce Buffer is the UFC’s top Octagon announcer, and he met McGregor in 2009 at a UFC event in Dublin, four years before McGregor would debut with the UFC.
This young man came up to me and said: “My name is Conor McGregor, and I’m going to be a UFC champion someday. Remember my name.”
I was very impressed by that, and then when I saw him first walk in the Octagon on April 6, 2013, I remembered that moment. I realized he had this amazing foresight and intestinal fortitude to fulfill his goal.
And we all know what happened from there.
Contributing: Andrew Feldman, Andres Ferrari, Ariel Helwani, Roman Modrowski, Brett Okamoto, Marc Raimondi