THE MANAGER AND coaches of UFC featherweight Max Holloway trickled into the conference room, where walls were covered with screens showing the stats of NBA players. At the front of the room, leading the discussion, was Toronto Raptors general manager Bobby Webster.
Webster brought in the Raptors’ department heads in health, nutrition, operations and media to speak and answer questions. Then, Holloway’s associates were given a tour of the team’s facility. The group was there for about six hours.
“It was a crash course in franchise management,” said Holloway’s manager, Christopher Daggett, who set up the meeting.
Daggett & Co. took what they learned from the Raptors on that day in January 2019 and brought it back to Holloway in his home state of Hawaii. The plan, they told him, was to reshape nearly every aspect of the inner workings of his career — to structure the then-featherweight champion as if he were a pro sports franchise.
Holloway’s medical and nutrition plans were overhauled. His financial planning was streamlined. A corporation was set up, and Holloway, the fighter, was put on salary to promote savings and investments. The idea was to take the distractions out of Holloway’s day-to-day life and have him concentrate solely on training and fighting. Daggett would be the general manager, and Holloway could lean into being the star player.
As Holloway heads into UFC 251 on Saturday in Abu Dhabi, United Arab Emirates, where he’ll try to regain the featherweight title from Alexander Volkanovski, Holloway’s life outside the Octagon is drastically different than it was 18 months ago. Daggett, a behavioral scientist and former innovation fellow who served in the White House under former President Barack Obama, has spearheaded one of the most unique fighter-team infrastructures in all of mixed martial arts.
“Before, I was the CEO, the CFO, the broker,” the 28-year-old Holloway said. “Whatever you want to name it as a role in the franchise, I was it. And the player. Now, I’m just the player. They’re not taking anything away from me. They didn’t demote me in any way. I just get to focus on fighting now.
“[Daggett is] really running this like a sports franchise. Holloway, Inc. is in business, and it’s booming right now, even in this pandemic.”
IT WAS AN incident on July 4, 2018 — three days before Holloway was scheduled to defend his featherweight title against Brian Ortega — that made Holloway reexamine his career. He and his team, including then-manager Brian Butler, and Daggett, who was an adviser, were sitting in a Park MGM hotel room in Las Vegas, having just finished open workouts. Holloway was moments away from a satellite interview with Michael Bisping and the other hosts of “UFC Tonight” on FS1.
But something wasn’t right, and his team knew it. Two days earlier, Holloway had checked himself into the emergency room. His speech was off; his facial features were almost droopy. Concussion-like symptoms was the best description the team could come up with, even though doctors had ruled that out.
Holloway’s team was unanimous: They wanted him to pull out of the fight with Ortega. Holloway pushed back — hard. Things got heated and emotional as Holloway prepared for the interview.
“He had said, ‘I expect you guys to ride with me until the wheels fall off,'” Daggett said of Holloway. “Our response really was like, ‘No, our responsibility is not to ride with you until the wheels fall off; it’s to make sure they never do.'”
Holloway did the interview with “UFC Tonight,” and the MMA world saw what his team saw. Bisping even called it out in the interview, asking Holloway if he had just gotten out of bed and if he was sleepy.
The clip went viral. Fans, friends and UFC peers expressed concern, and Holloway finally relented. He checked himself back into the ER, and the title fight was pulled from UFC 226.
The team meeting urging Holloway to drop out of the fight was a turning point. The fighter felt something had to change, especially from a medical and nutrition perspective.
“I remember every single word from every single coach,” Holloway said. “I remember everyone that was in the room. I think I even remember the shorts I was wearing. That’s how in-depth my memory is.
“It’s something that just stuck with me. I had this idea of loyalty. … These motherf—ers were being more loyal to me than I was being to myself. They were actually being super loyal in what they said.”
Holloway’s Brazilian jiu-jitsu coach Rylan Lizares said he did research that day into what happens when UFC athletes pull out of high-profile fights during fight week. His best example was when Amanda Nunes pulled out of UFC 213 in 2017 after not feeling right on the day of the fight. UFC president Dana White said she wouldn’t get another main event, and fans ravaged her.
“She got killed for it,” Lizares said. “That’s the only type of example that we had. So we were just in this nightmare. You can’t just pull out of fights like that.”
The worst part was Holloway and the team still didn’t know what was wrong. Doctors had concluded it wasn’t a concussion or a weight-cutting issue. The team said they didn’t find out until weeks later what the issue was. They believe it was something Holloway ingested that is “available commercially off the shelf,” Daggett said, though he wouldn’t provide additional details.
“Let’s just say he went into the fight under those circumstances and won,” Daggett said. “That doesn’t mean anything. He could have collapsed after the fight and died. That was really the risk for us, because we didn’t know what was wrong with him.”
Heading into 2019, Daggett was Holloway’s friend and adviser. He was known as “cupcake man,” because he delivered Holloway’s favorite desserts after fights. And in early 2019, Daggett became Holloway’s manager. Holloway’s team wouldn’t specify the reasons for the switch.
DAGGETT, 38, WAS reluctant when Holloway first approached him about becoming his manager. He had no experience in MMA and was making more money with his behavioral science consulting business, Paid Lunch.
Daggett, who was a friend of Lizares’ wife, Tiffany, met Holloway in 2013. As the friendship grew closer, Daggett would take Holloway to meet some of his clients. That list included Google and a billionaire from Hawaii — “one of the most powerful people in Hawaii,” said Holloway, though he wouldn’t divulge the name.
“I saw the way he was moving and things he was doing,” Holloway said of Daggett. “I was like, man, I could really benefit from this.”
Daggett was new to MMA, but he knew what a successful sports operation looked like. So he reached out to Webster, who also is from Hawaii and had met Holloway and Daggett in December 2016 during fight-week preparations before Holloway beat Anthony Pettis at Toronto’s Scotiabank Arena.
Daggett wanted to see if he could apply best practices from a successful pro sports team — the Raptors were on their way to their first NBA title — to the career of a high-level UFC fighter.
“How do you build the proper management team, performance team, business team around Max?” Webster said. “To me, I think it makes sense. We have 15 players on a team. Max is one player. But everything we do is to support and push and motivate and create the best 15-man team. … How do you set things up so that your athlete can excel and perform at the highest level? I think if you take a step back from that point of view, it’s very similar.
“Daggett didn’t want me to be another statistic, one of these guys going [hard] and then becoming broke. We want to be on an ESPN 30 for 30 sometime, but not for the wrong reason.”
Max Holloway, on his manager, Christopher Daggett
“[The players are] elite at what they do, so no different than for us with Kyle Lowry or somebody like that. Let’s put them in a position so that they don’t have any distractions. They have nothing else to worry about other than playing basketball, leading their team, getting better recovery, taking care of themselves.”
Daggett attended the January 2019 meeting in Toronto with Lizares; Holloway’s striking coach, Ivan Flores; strength and conditioning coach Darin Yap; and primary training partner Michael Nakagawa. They brought back the ideas they gleaned from the Raptors, wanting to incorporate some of them into Holloway’s career and life.
But Holloway was reluctant.
“At first, I had my doubts, just like anybody else,” Holloway said. “Nobody else [in MMA] is doing it. I can tell you that right now. … I’m a hothead. I’m a fighter. I was like, ‘Man, we don’t need this.'”
The most difficult thing for Holloway to accept, he said, was becoming his own corporation and drawing a salary. Holloway now gets a direct deposit every two weeks into his checking account. The money comes from his fight purses, endorsements and investments. The rest of his income goes into savings, retirement and investment accounts.
Once he got over the feeling that he wasn’t controlling his own money, Holloway saw the big picture.
“Daggett didn’t want me to be another statistic, one of these guys going [hard] and then becoming broke,” Holloway said. “We want to be on an ESPN 30 for 30 sometime, but not for the wrong reason.”
One of the first things Daggett did was have Holloway’s financials audited to make sure there were no “landmines.” Holloway said just a few months later the state of Hawaii made an inquiry into his finances, and he already had the information readily at hand.
“I was like, what perfect timing, huh? This guy stepped in at the right time,” Holloway said. “We got everything right; we got everything fixed. It’s so good, man.
“It doesn’t feel great paying the taxes. But at the end of the day, it is so much easier not having to worry about them.”
Daggett, who once worked for the Internal Revenue Service, said all the accounts are in Holloway’s name, and Holloway has veto power over everything. Daggett set up Holloway with the ability to see Holloway, Inc.’s profit and loss statement on his phone in real time.
There were some changes on the branding side too. Holloway is no longer with Monster Energy and Anheuser-Busch Hawaii. While the team won’t comment specifically on other current or future endorsement deals, Holloway has a unique deal with the men’s grooming company Manscaped, wherein Holloway and his team provide creative ideas for campaigns. Manscaped is tentatively scheduled to shoot a commercial with Holloway later this summer, Daggett said.
Daggett also has reshaped Holloway’s health and nutrition team. Holloway got a new primary care physician. And a digital group was set up so that Holloway’s doctor, all of the fighter’s specialists and his sports therapist can communicate with each other as well as Holloway’s martial arts coaches and his strength and conditioning coach. Holloway’s nutrition coach is now Jennifer Sygo, who works for the Raptors and the Cleveland Clinic.
Lizares said the biggest thing he took away from the Raptors meeting was how the team was proactive and not reactive with players. Holloway’s team has implemented some of those aspects, with the coaches, doctors, nutritionist and meal-prep partner all having input after seeing data and lab reports and getting information from Holloway himself.
“[The Raptors] can almost predict when their athletes are going to get injured,” Lizares said. “Just using data and certain wearable technologies, they know if their athlete is at a green light or at a yellow light. Sometimes they’re at a red light, and they’re like, ‘OK, you need to rest this week,’ even before anything dramatic happens.
“Seeing that in practice makes you look at MMA and how many injuries there are and makes you see if there’s a better way to do it.”
Holloway started training with Lizares in 2011 and made his UFC debut after four pro fights at just 20 years old. Eight years later, Holloway is considered one of the best featherweight fighters of all time. Being open to change even when he is at the highest level of the UFC shows growth, Lizares said.
And Holloway wants even more.
There’s a Kobe Bryant quote about not wanting to be remembered for just basketball that Holloway has taken to heart. He isn’t sure what he’ll do when his fighting career is over — working on his YouTube streaming has been a recent hobby — but he won’t settle for just being a great MMA fighter. Holloway wants to bring his “Blessed” moniker to other mediums with the ultimate goal being “leaving the world a better place than when you got here.”
“It’s cool and all being called the GOAT, whatever,” Holloway said. “Being known as one of the best fighters in the world. But that’s not it. That was never my plan. I always wanted to be the best fighter in the world, don’t get me wrong. But my plan was always greater than that.”
WEBSTER ATTENDED HOLLOWAY’S third-round TKO win over Pettis in December 2016, and the two have kept in touch. They text each other regularly, and Webster flies to Holloway’s fights whenever possible, including UFC 245 in December, when Holloway lost the belt to Volkanovski. Holloway has become a major Raptors supporter and vice versa.
“I’ve been on the ‘Blessed Express’ ever since,” Webster said. “If you’re from Hawaii, it’s almost like instantaneous credibility and respect. So from that point of view, if this kid is where he is and he’s from Waianae, he’s from Hawaii, it’s automatically an immense amount of respect for who he is and what he’s done.”
Before being hired by the Raptors in 2013, Webster, who has an economics degree, worked for the NBA in roles having to do with collective bargaining, salary cap and luxury tax planning. He was a numbers guy — not a basketball guy. In that way, Webster sees a bit of himself in Daggett.
“I’m an outsider,” Webster said. “I have a ton of respect for that.
“At [Daggett’s] age, to be able to have the vision to see that that’s where the best future for Max and for the team was, obviously it says a lot about who he is and how he pushes himself and how he’s willing to take risks.”
When Daggett agreed to be Holloway’s manager, both knew there would be some learning on the job and tangible change wouldn’t happen right away. Holloway trusted Daggett. Lizares said the team has “the ultimate level of trust” for each other.
Holloway’s fighting career did not slow down, though the results in the Octagon have been mixed since the switch. He moved up to lightweight and fell to Dustin Poirier in an interim title fight at UFC 236 on April 13, 2019, then turned around and retained his featherweight title against Edgar at UFC 240 on July 27, 2019. A notable year ended with Holloway losing the belt to Volkanovski on Dec. 14.
Including a win over Ortega at UFC 231 on Dec. 8, 2018, Holloway fought in title fights four times in 12 months.
“I feel good,” Holloway said. “Sometimes you’ve gotta trust the process. You don’t see these changes overnight.
“Of course, we had our ups and downs. We had to do a bunch of hard things. At the end of the day, things will turn around. I’m one of those guys, like no worries. It’s gonna turn. I’m a cup-half-full kind of guy.”
Next up is Abu Dhabi and the Volkanovski rematch at Fight Island — a chance to regain the featherweight gold Holloway has held as either interim or unified champ since 2016.
Webster said he and his friends have joked that it would be fun to travel to the Middle East for Holloway’s fight in person. But of course, he and the Raptors will be in Orlando, Florida, preparing for the restart of the shortened NBA season. That does not mean they won’t be watching.
“On July 11, we’ll all be stuck in Disney,” Webster said. “But I’ll make sure we have a big ballroom and everybody is watching and cheering for him. … Obviously, we’ll all be there huddled around a TV, probably physically distanced and wearing masks, but we’ll all be there.”
Webster and the Raptors won’t be with Holloway in person, but their influence, administered by Daggett, will be present.
“We’re not quite at that NBA level of money,” Holloway said. “I understand that. But we make it work. And that’s one thing that I respect. We took what we needed [from the Raptors], we took a lot of information and we’ve gotten pretty dang close to it.
“It’s exciting times.”