What It's Like to Be in Mayweather's Entourage: Behind the Scenes with Triple H

Jonathan Snowden@JESnowdenCombat Sports Senior WriterApril 23, 2015


On the evening of May 5, 2012, Floyd Mayweather was in pure relaxation mode. Chilling on the couch, the Oklahoma City Thunder in the midst of sweeping the Dallas Mavericks, the best pound-for-pound boxer in the world was in his element.

"I'm sure he had money on the game," WWE superstar and official Friend of Floyd Triple H said. "You know how Floyd is."

As the two sat and chatted, it was easy to forget what brought them together. In minutes, Mayweather would be in the ring, facing arguably the biggest challenge of his career: Puerto Rican banger Miguel Cotto.

"Here's this guy about to fight this massive fight, and I don't want to be in his way," Triple H said. "I'm in his world now. So, the second there is a lull in conversation, I try to make my exit. 'All right man, we're going to let you do your thing.'

Mayweather dispatched Cotto by decision.
Mayweather dispatched Cotto by decision.Eric Jamison/Associated Press/Associated Press

"Floyd looks at me and says, 'If you want to hang out, man, I'm not doing nothing. I'm just watching TV.'

"I said, 'Floyd, I just don't want to be in your way. You've got some stuff to do to get ready for this fight.' And he said, 'I've done everything I'm going to do. Nothing I do in the next little bit is going to change anything, so ain't no use getting worried about it. I'm going to watch this game for a little bit, talk with you if you want, and then I'm going to go win my fight.' He's so calm. It was unbelievable."

When the champ wants to hang, you hang. And while you do, you take in a who's who of the entertainment and combat sports worlds.

"There's always people coming out of Floyd's room," Triple H remembered. "Lil Wayne is in there. The next thing you know, Adrien Broner is in there. [Oscar] De La Hoya drops by. There's a lot of people coming in and out. There's a lot of traffic. Especially as it gets closer to the fight.

"He's not worried. He's not nervous. He's not wasting any energy. Now, the room picks up tempo as he's warming up, but it's a much calmer environment than you'd imagine."

And when the champ wants you to walk him out to the ring, alongside Canadian pop star Justin Bieber and rap mogul 50 Cent? Well, you walk.

Triple H does entrances big.
Triple H does entrances big.Jonathan Bachman/Associated Press/Associated Press

In the boxing world, though tame compared to Triple H's own Terminator-inspired ring walk this year against Sting at WrestleMania, Mayweather's entrances are considered top of the food chain. Whether he's putting on a sombrero as the first of many jabs landed against Oscar De La Hoya or walking with a wrestling legend, Mayweather knows how to get fans going.

There's always a method to his seeming madness. What appeared to be a random collection of disparate stars, the collision of worlds that don't normally interact was, in fact, quite purposeful. He and Triple H, more than friends, had done serious business together when Mayweather main-evented the 24th WrestleMania against Big Show. It turned out 50 Cent was gearing up to take his shot as a boxing promoter.

And Bieber?

"He came to the ring with us and then sat with Floyd's daughter Iyanna at ringside," Triple H remembered. "She was a big fan."

Mayweather, as always, had his bases covered. Even on the night of his biggest professional challenge, the fighter had made sure to take care of his young daughter.

"It's a little bit of a statement to who Floyd is as a person outside of the persona he puts on in the media," Triple H said. "He's the kind of guy, when you treat him well, he's going to treat you well in return. He's very loyal, and he doesn't forget. Everything with him is just first-class."

For Triple H, son-in-law of WWE owner Vince McMahon and millionaire many times over, first class isn't necessarily about the finest accommodations or the most expensive steak. It's about taking care of people, a trait he's learned as a senior executive and sees reflected in Floyd.

"You're just well taken care of. Does he put you up in a nice suite at the MGM? Yeah. But that's not what impressed me," he said. "What impressed me was that he knows what time your flight gets in, a car picks you up and brings you to the hotel. A guy from his camp meets you at the check-in, and he's got all your stuff and the layout for you. He takes you up to your room and sees if you need anything.

"The next day, somebody comes and gets you in your room to take you down to the press conference. All the little things that make your life easier. You never have to worry, 'I wonder where I'm supposed to go for this? I wonder what happens when I get there?' He just makes it all easy for you."

Triple H first got to know Mayweather in 2008, when the budding star was in the midst of reinventing himself as "Money," shedding his identity as a generic technical boxer and embracing the dark side. Wins over De La Hoya and Ricky Hatton had established him as a star worth watching. More importantly, the documentary series 24/7 had revealed a personality that lit up the small screen.

"His success as a boxer comes from knowing what really sells tickets is entertainment. You can be a great boxer and win a lot of fights and still have nobody really care about you that much. I think he gets that," Triple H said.

"We've even talked about it a little bit. He's not afraid to play the bad guy and push the buttons of the people who are going to pay to see him fight. He's a smart guy. He's created this persona that has driven people crazy. They can't wait to see him get beat.

Credit: WWE.com

"When you think about how smart Floyd is, think about HBO's 24/7 and Showtime's All Access. Those were his concepts. His gigs. He created a character and creates environments that make you fascinated by him as a personality. That's what sells fights."

The attention to detail and presence that catapulted Mayweather to the top in his sport bled over to wrestling as well. Celebrities have dallied with wrestling since Gorgeous George played in front of the Hollywood set at the Olympic Auditorium in the 1950s. Success has been mixed.

But Floyd Mayweather doesn't believe in failure.

"When I was working out with Floyd to get him ready for WrestleMania, his whole crew would be there," Triple H remembered. "He always has 4,000 people around him. He's got a huge entourage, and he would be laughing and everybody carrying on.

"And there would be that moment when we'd say, 'OK, let's get started,' and he'd say, 'Everybody out,' and everyone who didn't need to be there would leave, and no one made a peep. He was laser-focused. Mentally he was like a trap. We'd work on something, I wouldn't see him for two weeks and he'd remember exactly what I had said. To be honest, it was super easy to get him ready."

The relationship continued into the next year. After a brief retirement, Mayweather returned to the ring against Juan Manuel Marquez on September 19, 2009. Once again, WWE helped launch his fight, making Mayweather part of the family for millions of loyal wrestling fans.

"We were in Vegas for one of our shows, and Floyd texted that he was going to come by," Triple H said. Soon enough, instead of just "coming by," Mayweather had agreed to guest-host the show. "I remember he came to the arena with this birthday cake for [WWE owner] Vince [McMahon]. Somehow, he knew it was his birthday. It was really cool."

Soon after, the offer came for Triple H to be a part of Mayweather's entourage on fight week. Welcoming a rare respite from the brutal wrestling road schedule, he jumped at the chance to see athletic greatness up close. He made a speech at the weigh-ins, sat with Mayweather as he worked the press and then helped the champ while away the long hours before the fight.

"Walking him to the ring, it was a trip," he said. "To sit there with Floyd, the greatest boxer of his generation, to be around him while he was in his dressing room warming up, it's amazing to be around somebody at that high a level and see what they go through.

"To me, one of the coolest things was to sit and listen to his Uncle Roger talking game plan with him, while he was warming up, and then watching him execute exactly what they discussed."

As he heads out to Mayweather's fight with Manny Pacquiao next week, Triple H is well aware that anything can happen. Who knows? If Mayweather catches wind that he's there, he might even find himself in the ring for the biggest fight in boxing history.

Jonathan Snowden covers combat sports for Bleacher Report.