Last November, AT&T Stadium in Arlington, Texas, hosted a unique boxing event that brought together fans from different generations. The match between Jake Paul and Mike Tyson leveraged the curiosity surrounding both figures, drawing a diverse crowd.
Tyson, entering the ring with the familiar cutoff towel and intimidating scowl reminiscent of his `80s and `90s career, was cheered on primarily by fans in their 40s who grew up watching him. Paul, arriving in a lowrider alongside his brother Logan, garnered support mainly from Gen Zers familiar with their social media presence.
The visual contrast between Tyson and Paul was striking. Although the fight itself was largely one-sided, with Paul securing a decision victory over the 58-year-old Tyson, the event was notable.
“[I can fight] anyone I want next,” Paul declared in his post-fight interview after eight rounds against the aging Tyson. “Everyone is next on the list. I`m not going to call out specific names. I know [Canelo Alvarez] wants a payday; he knows where the money is at.”
Despite the significant 31-year age difference, the fight was a massive commercial success, attracting 108 million viewers on Netflix and generating a gate of $18.1 million, the largest for a combat sports event held outside of Las Vegas.
This event solidified Paul, 28, as a skilled promoter capable of creating huge cultural and financial spectacles. However, defeating an opponent who hadn`t won a meaningful fight in over two decades raised questions about how much closer this brought Paul to being considered a “real” boxer or someone worthy of challenging for a world title.
Paul continues his journey to transition from social media influencer to boxing champion as he prepares to face former middleweight champion Julio Cesar Chavez Jr. this Saturday in Anaheim, California. His ambitious boxing goals and unconventional path, perhaps inherently tied to his controversial presence in the sport, subject him to significant skepticism.
The announcement of this fight sparked widespread criticism regarding the choice of opponent. Chavez, 39, is over a decade past his prime during his 160-pound title reign. While he is closer to his peak than the 58-year-old Tyson was, critics still question the matchup.
“That`s not even boxing,” stated Top Rank CEO Bob Arum, Chavez`s former promoter. “Chavez Jr. should have hung up — I thought he had hung up the gloves a long time ago. Jake Paul is not a boxer. It`s a spectacle… I have absolutely no interest in a Jake Paul vs. Chavez Jr. fight because it`s not boxing.”
To some extent, this criticism is justified. In his 12 professional boxing bouts, Paul (11-1, 7 KOs) has faced a mix of opponents including five MMA fighters, a retired NBA player, a YouTuber, two boxing journeymen, a prospect, and a nearly 60-year-old former heavyweight champion. It`s clear that Paul`s boxing career trajectory is distinct from traditional fighters.
No boxer in history has commanded this level of attention heading into their 13th professional fight. Despite lacking a major title or amateur background, Paul boasts a social media following that dwarfs that of most boxing world champions.
Chavez, with a record of 54-6-1 (34 KOs), brings experience. However, his last name is arguably the most significant factor in this matchmaking decision.
“We know why he chose Chavez Jr.,” said Sean Gibbons, Chavez`s manager. “He`s the son of a legend [Julio Cesar Chavez] with name value. They look at his record and think they can take him but don`t know what`s behind his recent performances. I`m here to tell you that this is the best version of Chavez Jr. and there are levels to this. Julio, even at this stage of his career, is better than Jake Paul will be in his entire life.”
So, how challenging is it to find the ideal opponent for Paul – someone who offers a legitimate challenge while also helping to promote a major event and allow Paul to progress towards his ultimate goal of becoming a world champion? According to Paul, it`s a business in itself, one that he and his team at Most Valuable Promotions (MVP) take very seriously.
“There`s a two-sided approach for me where I have the big name to do big fights and we`ll entertain those,” Paul explained. “But at the same time, I`m in this to become world champion. That`s the only thing I haven`t done in the sport yet. But I do run a business at the end of the day, so Chavez is the perfect opponent because he`s experienced and he also has the drawing power with his Mexican fan base and legendary father.”
What began as a highly profitable side venture has now become Paul`s primary focus. As his boxing career develops, Paul and MVP, the company he co-founded in 2021, face the unique challenge of finding opponents who can both enhance Paul`s raw boxing skills and contribute to massive events expected from a social media superstar.
“It`s a bit of a balancing act for us,” commented Michael Leanardi, MVP`s head of boxing. “A big part of it is the spotlight Jake Paul has on him. People are expecting a certain level of opponent for a pay-per-view, but also expect the fight to be competitive. It`s a challenge for us to do both.”
Roberto Diaz, who served as a matchmaker for Golden Boy Promotions for 15 years, helping guide talents like Deontay Wilder and Canelo Alvarez, understands this delicate balance.
“Matchmaking is an art,” said Diaz, now president of Sheer Sports Management. “There is art in developing and progressing a fighter while identifying a good fight for fans. Every fighter is different with their goals. Do you want to win a world title, or do you just want to make the money? It`s not easy either way.”
Alongside the referee or judge, the matchmaker`s job is arguably the most thankless in boxing. When things go well, their contribution often goes unnoticed. However, when a fight doesn`t live up to expectations or a fighter loses unexpectedly, the conversation quickly turns to the matchmaking.
“If you talk to 10 matchmakers, nine out of 10 will tell you they don`t do it for the glory because there is no glory in matchmaking,” Diaz noted. “Anytime a fighter loses a fight, the fault goes to either the trainer or the matchmaker because they put them in too tough [a fight], too early. And the fans? The fans are the most difficult to please in boxing, more than in any other sport in the world.”
Diaz believes Paul`s matchmaking has been “brilliant” considering his limited experience.
“Jake Paul started his career late and has no background in boxing,” Diaz stated. “Say what you will about Chavez Jr.`s career today, but he`s a step forward for Paul as a former world champion with legitimate boxing experience. If Paul wants to get closer to the world title level in his 13th pro fight, with no previous amateur experience and limited opposition, this is the perfect opponent.”
Joe Quiambao, formerly a matchmaker for DiBella Promotions and now director of Split-T boxing, attributes the criticism Paul receives primarily to his fame rather than his matchmaking.
“Nobody would be complaining about who he has been fighting if his name wasn`t Jake Paul,” Quiambao suggested. “As a matter of fact, people would say he is overachieving considering that he has no amateur experience and he`s fighting a former world champion in his 13th fight.”
Another frequent criticism of Paul`s opponent selection is age. After Saturday`s fight, the average age of his opponents will be just under 37, with nine of his 12 opponents (he fought Tyron Woodley twice) being over 35. While critics argue Paul preys on older boxers, Leanardi counters by pointing to the ages of current top pound-for-pound fighters.
“There used to be this thought process that once fighters hit 30, they were washed up,” Leanardi said. “Fighters last a lot longer nowadays. There`s a lot more science and they take better care of their bodies. If you stop and look at pound-for-pound lists, almost all the fighters are in their 30s now.”
For instance, ESPN`s top pound-for-pound boxer, Oleksandr Usyk, is 38, and the No. 5 fighter, Artur Beterbiev, is 40. Terence Crawford (No. 3) and Canelo Alvarez (No. 7) are scheduled to meet in September at ages 37 and 34, respectively. Six of the top 10 pound-for-pound fighters are over 30. However, a closer look reveals that many of Paul`s opponents were well past their prime when they faced him. Chavez hasn`t won a significant bout in over a decade. Anderson Silva, Woodley, Ben Askren, and Nate Diaz were far removed from their best years and were not primarily boxers to begin with.
According to Bidarian, there is no shortage of potential future opponents for Paul. IBF heavyweight champion Daniel Dubois, former unified heavyweight champion Anthony Joshua, and lightweight champion Gervonta “Tank” Davis have all expressed interest in fighting Paul. A fight with Davis nearly happened but was put on hold after Tank`s draw against Lamont Roach Jr. in March.
The balancing act between pursuing a traditional path to a world title and engaging in mega-fights is expected to continue. Bidarian mentioned that Paul is targeting a fight with Joshua in 2026, alongside potential matchups with Alvarez and Davis. He is also still interested in a rematch with Tommy Fury, the only fighter to defeat him in 2023, but stated that Fury priced himself out of the opportunity.
“His ask was astronomical and I know he just fought on some club show,” Leanardi remarked about Fury`s May 9 decision win. “Jake`s career is fine without him.”
Paul claims his serious pursuit of a world championship began the day after his loss to Tommy Fury in 2023. That defeat forced him to confront the limitations he faced against a fighter who had dedicated his life to boxing. However, despite the loss, he didn`t lose his audience`s attention.
“Losing the Tommy Fury fight was the best thing to ever happen to me,” Paul asserted. “It showed that losing didn`t define me. I decided to double down and take my boxing career more seriously. I needed to change my coaching team, be more active and try to build my career like a traditional fighter would.”
Sustaining a strictly traditional path has proven challenging for Paul, as opportunities for high-profile fights continue to arise. After defeating journeymen Andre August and Ryan Bourland by first-round knockout, Paul deviated to face former UFC fighter Mike Perry in July 2024. Perry stepped in as a replacement after Tyson`s health issues postponed the original bout. Paul won by sixth-round TKO, and then the opportunity to fight Tyson finally materialized.
“The fights with Bourland and August were by design to start building his skill set against actual boxers,” Bidarian explained. “You can say that Tommy Fury is not a great boxer, but he has been trained purely as a boxer and knows what to do in the ring. After that loss, we wanted Jake to start getting experience against pure boxers.”
“But, from a Jake perspective — and I agree with this — when the opportunity presents itself to create another massive fight, you`re going to jump at that opportunity.”
Matching Paul with Chavez Jr. has been a consideration for several years, largely due to Chavez`s status as a former world champion.
“Two years ago, I met with [Julio] Chavez Sr. coming back from the WBC convention and I said his son should fight Jake Paul,” Diaz recalled. “His dad said `Who`s that?` and `Why would he fight him?` and I said it`s less risk for the most money. They wanted to set up a meeting in L.A., but a week later, Chavez Jr. gets checked into rehab for a year.”
Upon leaving rehab, Chavez Jr. was placed on the undercard of Paul`s fight with Perry, a deliberate move similar to how Fury fought on the undercard of the first Paul-Tyron Woodley bout in 2021. In both instances, the potential future fight materialized in a timeframe that made sense for both parties.
The Chavez fight was nearly derailed by a surprising development: Paul appeared close to securing another blockbuster against four-division champion Canelo Alvarez, potentially in May.
While the fight ultimately fell through, with Alvarez signing a deal with Turki Alalshikh, Paul and his team viewed the prospect positively.
“The way we looked at it was that it was going to be an economic juggernaut for everyone involved,” Bidarian stated. “But it`s a win-win for Jake if he can hang with Canelo because the expectation is that he would be thoroughly outclassed.”
Paul is less concerned with protecting an undefeated record and more focused on taking calculated risks for substantial rewards.
“It`s not a bad look for Jake to lose to Canelo,” Diaz commented. “If he loses to Canelo, it gives him more exposure and experience. You take those risks because the opportunity, if you pull off the upset, is huge. Boxing is all about opportunities.”
The path to a world title remains challenging, but Paul believes a win over Chavez Jr. will bring him closer.
“We are already talking to [WBC cruiserweight champion] Badou Jack,” Paul revealed. “The WBC may rank me depending on how the fight with Chavez goes, and that would be needed to get a fight with Jack approved. That`s what I`m focused on. But the biggest thing is that there is risk involved. Even if it is a 50-50 or 60-40 fight against Chavez [Paul is a -800 favorite], it`s a tougher fight than Canelo being a -3000 favorite for his decision win against William Scull in May.”
“I`m still taking a bigger risk than these other fighters are, who have been boxing their whole lives.”
WBC president Mauricio Sulaiman indicated via text that Paul could potentially be ranked after the fight if he secures a significant win on Saturday.
“The WBC ratings committee has been following Jake Paul`s career,” Sulaiman wrote. “If he defeats Chavez, and depending on how the fight plays out, the committee will make the decision. It`s very likely [Paul will be ranked] if he wins convincingly.”
There is no expectation that Paul`s fight with Chavez will match the financial scale of the Tyson bout. However, as long as the fight moves Paul closer to his goal of becoming a world champion, he plans to disregard the critics and continue on his chosen path.
“I have learned that no matter what you do in this sport, there are always going to be haters,” Paul concluded. “That`s just something I`ve accepted. I don`t care to make everyone like or respect me. A lot of this is for me and the next generation of fans. And I know some people are genuinely inspired and love me. I`m showing them what`s possible.”
Ellis Thorne 
Percy Harlow