‘His boxing career is on the line’: Inside the high-stakes Paul vs. Diaz matchup

LOS ANGELES — Nate Diaz came out of one of the six bedrooms of a preposterously large villa overlooking the posh Bel-Air Country Club and walked down a spiral staircase.

Diaz, wearing a Mike Tyson T-shirt, faded jeans and black Travis Scott Nike Air Jordan sneakers, slipped on a black baseball cap with a white “R” on the front, for his sponsor Represent, and then took it off. He did the same for a pair of black Ray-Ban sunglasses.

“Hat or no hat?” Diaz asked a few members of his team, including his president of Real Fight Inc., Zach Rosenfield, and cinematographer Elijah Gutierrez. “Shades or no shades?”

Both gave a thumbs-up, but Diaz wasn’t feeling the hat, so he cast it aside. He then walked onto the stone balcony of the rental home in the hills and settled into a white chair for a video interview. Below him was a pool area with a small waterfall and hot tub. Below that, a lush, 18-hole golf course.

Diaz’s first fight outside of the UFC in 17 years was less than three weeks away, a boxing match against popular YouTuber-turned-prizefighter Jake Paul. The two men are 50-50 partners in the pay-per-view event. Paul had expressed disappointment in the media with how Diaz was promoting the fight, with little to no trash talk.

This interview was Diaz’s chance to turn up the heat, to start slinging some insults Paul’s way. To sell more pay-per-views.

He balked.

“I think my fighting from over the years promotes my fights,” Diaz told ESPN. “I’m not gonna get in a little-kid argument with the guy and act like [it’s] any realer than it is. Don’t get no realer than this anyway.

“If we’re going to argue, we’re gonna fight.”

Diaz, one of the biggest MMA stars of his generation, does things on his terms. He won’t be prompted or swayed by outside forces — otherwise, he might still be in the UFC. Paul isn’t so different in that regard. For the past three years, he’s been disrupting boxing, putting on major events outside the traditional promotion formula. In each other, Diaz, the street tough from Stockton, and Paul, the former Disney Channel kid, have found the perfect dance partner for this pivotal moment in their respective careers.

It took a little time for them and their teams to realize that. Diaz had potential fights with Floyd Mayweather and Paul’s brother, Logan, on the table. Paul had options including Mayweather, fellow YouTuber-turned-prizefighter KSI and a rematch with Tommy Fury. Ultimately, several factors, including the real-life heated history between them, led Diaz and Paul to decide on each other.

In the genre of crossover boxing — one that Paul has pioneered — this 10-round match on Aug. 5 in Dallas will be the highest-stakes one yet.

In ways big and small, the result of this matchup will tremendously impact the future of both fight careers and what could be next for this current trend of influencers in combat sports. Nakisa Bidarian, the co-founder of Paul’s Most Valuable Promotions, believes this could be Paul’s final boxing match.

“He may retire if he loses to Nate Diaz,” Bidarian told ESPN.

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Rosenfield and Bidarian had a video call just hours after Paul lost via split decision to Fury on Feb. 26. Bidarian was still in Saudi Arabia, the site of the bout. He and Rosenfield had been discussing a potential fight between Diaz and Paul since Diaz became free of his UFC contract in late 2022.

Bidarian said Paul fighting Diaz after Fury was “always” their team’s plan. But Rosenfield knew Diaz wouldn’t be interested anymore because Paul lost, which he told Bidarian on their call after congratulating him on a successful promotion and asking about Paul’s health.

“Well, it would have been fun,” Rosenfield said to Bidarian on the phone in February. “Good luck chasing your rematch. … Maybe we’ll see you down the road.”

The two sides then moved in different directions. Paul said he wanted to fight Fury again, a natural reaction after the first defeat of his young boxing career. There were also talks with Mayweather, which included a face-to-face confrontation in Miami, and social media banter with KSI, who, along with Jake and Logan Paul, helped launch the influencer boxing craze.

Diaz, meanwhile, had several irons in the fire, too. His team was also in discussions with Mayweather. A fight between Diaz and Logan got very close — so close that Logan told his younger brother that Diaz was his next fight.

Rosenfield said there was a “very interesting and attractive offer” on the table for Diaz to fight Logan. But WWE got involved, and Diaz soured on the idea. Logan has become a top attraction for the pro wrestling company, and former WWE co-CEO Stephanie McMahon said at a summit last year that the promotion was interested in getting into boxing.

“The WWE came in and then they wanted to take over the whole thing,” Diaz told ESPN. “And I’m like, ‘I just got out of the UFC, why am I going to sign with WWE?’ I fight for real. I’m not gonna be doing a real fight on a WWE card or no funny s— like that.”

Logan said he heard that was one of Diaz’s reasons for not being interested any longer, calling it a “weak cop-out.”

“You can still be a real fighter with the biggest sports organization in the world promoting your fight,” Logan told ESPN. “It’s a little lame to me, and I can definitely sell more tickets. I see what he’s doing. I’m the harder fight. I’m the bigger brother, I’m the stronger brother, I’m the faster brother.”

WWE did not respond to a request for comment on the matter.

Paul started to change his tune about a Fury rematch, too, when he realized that the loss really didn’t hurt his stock in the eyes of fans or media. KSI, Bidarian said, was an opponent Paul put on the back burner for later this year or beyond. Bidarian felt it only made sense for Paul to fight a “legitimate opponent” again, which led to Paul’s team making a proposal to Mayweather.

While Diaz’s team was in talks with Logan (and Mayweather) and Paul’s team was talking to Mayweather, Rosenfield got to his Los Angeles home on the night of March 8 and popped on an interview with actor and comedian Michael Rapaport from “The MMA Hour” with Ariel Helwani. The topics of Diaz and Paul came up.

“Nate Diaz versus Jake Paul?” Rapaport said. “You want smoke? F— with Nate Diaz. I’d pay $199.99.”

Rosenfield said it all became clear to him after watching that. The brash Paul had been someone whom fans, especially from MMA, wanted to see get his comeuppance. He had beaten former UFC champions Tyron Woodley and Anderson Silva in boxing, the former via one-punch knockout. Diaz himself felt like Paul has talked disrespectfully about MMA fighters. Diaz slapped a member of Paul’s team backstage in October before Paul’s fight with Silva. Paul then called out Diaz in his postfight interview, telling Diaz to “stop being a b—- and fight me.”

Based on the interview with Rapaport, Rosenfield realized that Paul had lost none of that “heel heat,” to borrow a pro wrestling term, in his loss to Fury. There was still a story between Paul and Diaz that had been left unexplored.

“So, from the outsider’s point of view, you’re wondering how Jake is really received,” Rosenfield said. “And what Michael was able to show is there’s still very much this desire for the right guy to come in and end this for him. We started thinking, ‘Well, maybe this makes sense.’ Maybe it’s our opportunity, from a business standpoint, to put an end to Jake Paul boxing, while he can feel the same way and get what he’s been chasing for years, which was the opportunity to fight Nate.”

Rosenfield called Bidarian and told him as much. Then the two of them called their respective business partners, who were on board. And the negotiations began. There were plenty of things to discuss, from finances to pay-per-view distribution to weight to number of rounds. The vital agreement from the beginning was that Paul’s Most Valuable Promotions and Diaz’s Real Fight Inc. would be 50-50 partners on everything. Things were set in motion once Paul and Diaz gave their sign-off. The fight was announced on April 12.

“Jake has had that [drawing] power on his own, but he’s never had a true peer, side by side, that can carry an event himself,” Bidarian said. “Now there’s two ‘A’ sides fighting for the first time in Jake’s career.”

While Diaz has said he wants to fight only people coming off a win, Rosenfield said Diaz saw similarities to his own UFC defeats in Paul’s loss to Fury. Paul was the only one who scored a knockdown in that fight, in the final round — not unlike when Diaz fought current UFC welterweight champion Leon Edwards in 2021 and rocked him with a punch in the fifth round, arguably the most damaging single blow of the bout.

“Jake’s the one doing the biggest things,” Diaz said. “I believe he’s the tougher brother. He’s the one who’s been boxing more people and at a higher level. He’s motivated and hungry and moving forward. And I’m on the same page as that.”

Paul knocked out ex-NBA veteran Nate Robinson in November 2020 on the undercard of an exhibition match between legends Mike Tyson and Roy Jones Jr. Then, he knocked out former MMA champion and Olympic wrestler Ben Askren in April 2021.

All the while, Paul created a ton of attention for himself on social media and in interviews. Logan, who had two popular boxing matches with KSI, then fought Mayweather in an exhibition in June 2021. Influencers and celebrities were getting in the ring and boxing became big business, seemingly overnight. MMA fighters, including former UFC champions, were also getting in on the action. Some promotions that just put on that genre of fights started to sprout up in multiple countries.

Paul felt responsible for the boom and the potential bubble bursting on this newly developed commodity, for better or worse.

“For the longest time, I was carrying the influencer boxing wave and my worst fear was losing, because I didn’t know what would happen on the other side of that,” Paul said.

Experiencing his first loss, against Fury, has changed that. Paul isn’t any less of a star now than he was before, and influencer boxing keeps on trucking.

“I think the loss actually made me more relatable, because for some reason people think of celebrities as not humans,” Paul said. “If anything, it’s grown my fan base and given me the opportunity to come back, and people see now how serious I am about it, doubling down now after a loss.”

Some would say he’s even put himself into a corner. Paul, 26, is more than a 3-1 betting favorite over the 38-year-old Diaz, so people expect him to win and win big. That’s a dangerous position to be in against Diaz, who has made a career out of being the durable underdog with otherworldly cardio. Just ask Conor McGregor, whom Diaz handed his first UFC loss in 2016 after weathering a huge storm of haymakers.

A loss to Diaz could change the course of Paul’s career.

“His boxing career is on the line, in terms of being one of the top three or four guys in the entire sport globally,” Bidarian said, referring to Paul’s drawing power. “I think if he was to lose, he’d just go to being another prospect that’s coming up in the ring.”

If Paul beats Diaz, he’s hoping to lure him into doing an MMA fight in PFL, which Paul has signed with as an equity partner and for a future run in MMA. Paul and PFL have offered Diaz $10 million for that possible fight, which Rosenfield confirmed is legitimate.

Diaz said he could be open to that, but he’s facing his own major stakes. One of the biggest fights in combat sports history, a trilogy with McGregor, is still out there, and Diaz has made it known he’s willing to return to the UFC for big fights that he finds interesting. If he beats Paul, finishing the story with McGregor — as well as several other fights like the aforementioned bouts with Mayweather and Logan — becomes even bigger. With a loss, it’s hard to say. Depending on what the fight with Paul looks like, Diaz’s leverage could be diminished.

“Everything changes with every fight,” Diaz said.

Diaz is already a legend in combat sports, and a win or loss here won’t necessarily affect that. But an ugly defeat could impact his future negotiating power and the cachet of a third fight with McGregor.

“I don’t think his place in the sport is at stake,” Bidarian said of Diaz. “I just think it’s about what’s next for him and how much leverage does he have in dictating what’s next versus having to accept what’s next.”

Plus, if Paul wins, he’s made no secret that he wants to fight McGregor in boxing and he is willing to work with the UFC and parent company Endeavor to make it happen.

“I see a roadmap where I knock out Nate and then go to Conor McGregor,” Paul told ESPN in May. “[I can] do what Conor couldn’t do — knock out Nate. And then that’ll be the biggest fight in combat sports that could possibly be made, is me versus Conor.”

Win or lose, Saturday will be a lucrative night for both men. Paul and Diaz will each make “well into the eight figures,” per Rosenfield, who added that each fighter will make seven figures just from the event’s sponsors on the ring alone. Paul and Diaz will get cuts of pay-per-view buys, ticket sales and merchandise, and the money from their own sponsors.

That’s new territory for Diaz, who complained before the final fight on his UFC contract last September that he had to wear Under Armour shoes from Dwayne “The Rock” Johnson’s line and he wasn’t getting paid for that. The UFC also takes around 80% of its revenue annually, per revelations from an ongoing lawsuit, with the fighters getting the rest. By comparison, the major team sports leagues in the United States split revenue evenly between owners and players. In this bout, Paul and Diaz will get the vast majority of the revenue.

“Forget about how much he’s making,” Rosenfield said. “It’s where he’s making it. And when you start to take a look back at Nate Diaz interviews where he might be complaining about not being paid his worth, his worth goes far beyond just what he’s doing as a profession. People and companies are paying to see him fight, and now he is going to be paid [directly] by those people to fight.”

With Paul and Diaz splitting that pay-per-view money evenly, Paul said Diaz is “shooting himself in the foot” by not talking more trash and drumming up further interest in the fight. But Diaz refuses to play Paul’s game. Rosenfield said that Paul had done a good job in past fights making his opponents “subordinate” to him, and Diaz will not fall into that trap.

Whether it’s deciding on a hat or sunglasses or whether to flip Paul a double bird, Diaz is going to do what Diaz does. Especially now, after being in the UFC for nearly two decades, he controls his own destiny, as well as the destiny of others. Paul, oddly enough, finds himself in a similar position. They’re the perfect pairing for each other at the perfect time.

“I’m talking about real boss s—,” Diaz said. “And that was my plan the whole time. And that’s part of being the best fighter in the world. No one’s going to tell me what to do.”