'His boxing career is on the line': Inside the high-stakes Paul vs. Diaz matchup (2024)

"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."