It wasn’t long after Tyron Woodley finished his UFC contract that the former welterweight champion was already entertaining a potential offer for a boxing match against YouTube superstar Jake Paul.
According to Woodley’s longtime manager, First Round Management CEO Malki Kawa, the seeds for the fight were first planted back in April when Ben Askren was preparing for his own showdown with Paul on a Triller pay-per-view.
On that night, Kawa had a chance to speak with Paul’s advisor, who also happens to be a former UFC executive, and that laid the foundation for the start of negotiations.
“Jake Paul’s manager and I go way back from his days in the UFC,” Kawa explained when speaking to MMA Fighting. “When Jake Paul beat Ben Askren, I had Frank Mir on that card at Triller, and when Jake beat Ben the way he did, a lot of people thought Ben threw the fight and there was a lot of hype around it. A lot of people actually gave Ben a chance, which I knew for a fact he didn’t have. I started talking to Nikisa [Bidarian] and started telling him ‘listen bro, you need to give him a legit opponent at some point.’ Kind of giving him my wisdom of how to manage somebody and all that.
“Usually a guy who’s 3-0 should take his time and get opponents at his level but when you’re making the type of money he’s making getting the type of attention he’s getting, you can mess that up. Because if he keeps fighting the Ben Askren types — like say he would have fought Dillon Danis, which makes no sense — I feel like people would have continued to just think he was a joke and it would have just stopped.”
While Kawa conceded that the boxing formula to pad a fighter’s record with wins over less than stellar competition is not uncommon, Paul finds himself in a unique situation because he’s already commanding a huge audience just three fights into his career.
That’s when Kawa suggested that perhaps Woodley would serve as a perfect next opponent for the 24-year-old social influencer as he seeks to face tougher competition while not exactly jumping into the deep end of the boxing pool without a safety net in place yet.
“Tyron Woodley is the perfect opponent,” Kawa said. “He’s 0-0 as a boxer, he’s a former UFC champion, he’s a little older but the guy’s got dynamite in his hands. He’s boxed his whole life. Training in boxing his whole life. I think there was a time when Tyron was in L.A. training with Freddie Roach so it’s not like you’re talking about somebody that doesn’t know how to box.
“I talked to Nakisa and I said now is the time to make a match where it’s an even playing field with somebody who knows how to box. He may not be a pro boxer but it didn’t matter. To me it was just the perfect opportunity.”
Kawa says Paul’s advisor was hesitant at first but it didn’t take long for the entire team to come on board with the idea, especially considering the long term objective to make a career out of boxing.
“I think Jake Paul realizes himself he needs a good opponent to take that next step,” Kawa said. “If he can beat Tyron, people really got to start paying attention to this guy. I know we’re already paying attention but I’m talking about taking him serious.”
Once talks officially started, Kawa battled to get Woodley what he wanted in order to book the fight against Paul, but like any deal where millions of dollars are involved, nothing was settled without an intense negotiation.
In the end, Kawa was happy with the terms of the deal that will see Woodley make a seven-figure paycheck before he ever steps into the ring.
“He’s getting paid really well,” Kawa said about Woodley’s contract. “It’s one of the best deals I’ve ever done. For a guy in his situation, it was a tremendous deal. He’s getting a large base number. He’s getting a cut of the pay-per-view globally. He’s participating in a lot of different things. He should walk away with a multi-million dollar payday. His base guarantee is in the millions already. Add on all the extra stuff, it’s a really nice payday.
“In this case, I worked with Nakisa, I worked with Stephen Espinoza, I gave them what I was looking for. We worked back and forth for a good amount of time. Sh*t got ugly sometimes, other times it was pleasant. We just got to a point where we felt comfortable with it and Jake is probably making the lion’s share of the money, which he is, but nonetheless Tyron, this is a real good day for him.”
When the fight got announced on Tuesday, Woodley revealed that he was making a bigger payday for his fight against Paul than any other bout during his career and that includes a long stint as UFC welterweight champion.
Kawa backed up that claim while adding that when it’s all said and done, Woodley will be walking away with a very hefty paycheck.
“He definitely got paid in his base guarantee more than he ever did in the UFC, whether as a champion or non-champion, that’s a fact yes,” Kawa said.
Despite Woodley’s vast experience advantage over Paul in combat sports, the former UFC welterweight king still opened as a slight underdog for the boxing match scheduled for Aug. 28 on Showtime pay-per-view.
Woodley will face Paul after dropping the last four fights of his UFC career but that doesn’t negate the kind of threat he represents in this matchup.
In fact, Kawa knows Paul respects the inherent danger that comes along with a fight like this because his team negotiated an additional clause in the contract in the case that Woodley is successful.
“Jake Paul’s team negotiated an automatic rematch clause,” Kawa revealed. “That’s how much this is a scary fight to them. If we win this fight, if Jake Paul wants it, then we have to run it back with him.”
Of course, Kawa fully acknowledges that win, lose or draw, Woodley’s accomplishments in the UFC will far exceed anything that happens in a boxing match against Paul but that doesn’t discount the magnitude of this fight when it comes to his overall resume.
Getting the chance to bounce back from the recent losing streak while receiving the kind of worldwide attention that will follow this event gives Woodley every motivation possible to put on his best performance in years.
“This is a major, legacy fight,” Kawa said. “Could you imagine if Tyron Woodley has lost his last four fights, comes in, demolishes this guy or say it’s a really good fight, Tyron pulls it out, goes and does another rematch, gets paid even more for the rematch. Let’s say beat him twice in a row and then decided to hang the gloves up forever.
“His legacy, although it’s already cemented, that takes it to another level and that’s why we got paid what we got paid and for Tyron it also fires him up because it’s something completely different, it’s something new to train for and I think it’s an opportunity to erase the last four fights. That’s what we set out to do with this deal.”