LAST NOVEMBER, PAST and present generations packed AT&T Stadium in Arlington, Texas, for a one-of-a-kind boxing match. Jake Paul vs. Mike Tyson was a unique event that leveraged the curiosity of fans from different eras and brought them under one roof.

Tyson, who walked to the ring alone with his trademark cutoff towel and scowl that intimidated boxers in the ’80s and ’90s, was urged on mostly by fans in their 40s who grew up watching “Iron Mike” on cable television. Paul, who rode to the ring in a lowrider with his brother, Logan, was cheered on mostly by Gen Zers who consume the brothers’ social media content.

The visual of Tyson versus Paul was epic, even though the fight underwhelmed as Paul cruised to a decision victory over the elder Tyson.

“[I can fight] anyone I want next,” Paul said during his postfight interview after beating the 58-year-old Tyson for eight one-sided rounds. “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.”

Although there was a 31-year age gap between the influencer-turned-boxer and the former world heavyweight champion, the fight was a massive success, with 108 million viewers on Netflix. It also generated a gate of $18.1 million, the biggest for any boxing or MMA event outside of Las Vegas.

It proved that Paul, 28, is a masterful promoter who can stage huge cultural events that make millions. But did beating an opponent who hadn’t won a meaningful boxing match in over two decades get Paul any closer to proving to the world that he’s a “real” boxer and worthy of challenging for a world title?

Paul continues his quest to transform himself from social media star to boxing world champion when he faces former middleweight champion Julio Cesar Chavez Jr. on Saturday in Anaheim, California (DAZN PPV). Between his lofty boxing goals and nontraditional path, or maybe because of his mere presence in the sport, Paul faces many skeptics.

The announcement of this fight led to widespread criticism of the matchmaking. Chavez, 39, is 13 years removed from his 160-pound title run. Although Chavez is closer to his prime than Tyson was at 58, it hasn’t prevented Paul’s naysayers from criticizing the choice of opponent.

“That’s not even boxing,” Top Rank CEO Bob Arum, Chavez’s former promoter, told Fight Hub TV. “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.”

The criticism is warranted to a degree. In his 12-fight boxing career, Paul (11-1, 7 KOs) has fought five MMA fighters, a retired NBA player, a YouTuber, two boxing journeymen, a prospect and a nearly 60-year-old former heavyweight champion. But it’s obvious that Paul’s boxing career operates differently from other fighters’.

No boxer in the long history of the sport has ever commanded this amount of attention heading into their 13th professional fight. Despite not winning a major title or having any amateur experience, Paul has a bigger social media following than the vast majority of boxing world champions.

Chavez, with a record of 54-6-1 (34 KOs), brings experience, but perhaps the most important factor in this matchmaking equation is his last name.

“We know why he chose Chavez Jr.,” Sean Gibbons, Chavez’s manager, told ESPN. “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 difficult is it to find the right opponent for Paul? One who can provide a challenge but also help to promote a big event and allow Paul the opportunity to keep taking steps toward his ultimate goal of becoming a world champion? According to Paul, it is a business in itself, one that he and his team at Most Valuable Promotions don’t take lightly.

“There’s a two-sided approach for me where I have the big name to do big fights and we’ll entertain those,” Paul told ESPN. “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 STARTED AS a lucrative side quest for Paul has now become his primary gig. But as his boxing career evolves, Paul and MVP, the company he founded alongside Nakisa Bidarian in 2021, have the unique task of finding opponents who can develop Paul’s raw boxing ability while also helping deliver massive events befitting a social media superstar.

“It’s a bit of a balancing act for us,” MVP’s head of boxing, Michael Leanardi, told ESPN. “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.”

One person who understands the delicate balance of matchmaking is Roberto Diaz. While serving as a matchmaker for Golden Boy Promotions for 15 years, he helped guide the careers of future world champions such as Deontay Wilder and Alvarez.

“Matchmaking is an art,” Diaz, now president of Sheer Sports Management, told ESPN. “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.”

Next to being a referee or a judge, matchmaker is arguably boxing’s most thankless job. When things are going right, their jobs are hardly noticed or discussed. But when things go wrong, the conversation 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 said. “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 feels Paul’s matchmaking has been “brilliant” for a fighter with so little experience.

“Jake Paul started his career late and has no background in boxing,” Diaz said. “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.”

Ex-DiBella Promotions matchmaker Joe Quiambao believes the criticism Paul receives is due to his notoriety and has little to do with his matchmaking.

“Nobody would be complaining about who he has been fighting if his name wasn’t Jake Paul,” Quiambao, now director of Split-T boxing, told ESPN. “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 criticism of the way Paul is being matched is his opponents’ age. After Saturday, the average age of Paul’s opposition will be just a shade under 37 years old, with nine of his 12 opponents (he fought Tyron Woodley twice) over the age of 35. While critics will say that Paul is preying on veteran boxers, Leanardi asks people to look at the current crop of pound-for-pound fighters and their ages.

“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.”

ESPN’s No. 1 pound-for-pound boxer, Oleksandr Usyk, is 38, and the No. 5 fighter, Artur Beterbiev, is 40. Terence Crawford (No. 3) and Alvarez (No. 7) will meet Sept. 13 at ages 37 and 34, respectively. Six of the top 10 pound-for-pound fighters are older than 30. However, a keen eye will look at where Paul’s opponents were in their careers before they faced him. Chavez hasn’t won a meaningful fight in over a decade. Anderson Silva, Woodley, Ben Askren and Nate Diaz were far removed from their best years and weren’t boxers to begin with.

Bidarian said there is no shortage of opponents for Paul to choose from for his next fight. IBF heavyweight champion Daniel Dubois, former unified heavyweight champ Anthony Joshua and lightweight champion Gervonta “Tank” Davis have called for a fight with Paul. The latter nearly came to fruition but was put on ice when “Tank” fought to a majority draw with Lamont Roach Jr. in March.

The balancing act between going the traditional route to a world title and competing in megafights isn’t expected to end anytime soon. Paul is targeting a fight with Joshua in 2026, Bidarian said, along with potential fights with Alvarez and Davis. And he’s still after a rematch with Tommy Fury but said that the only man who defeated him, back in 2023, priced himself out of the opportunity.

“His ask was astronomical and I know he just fought on some club show,” Leanardi said about Fury’s May 9 decision win over Kenan Hanjalic. “Jake’s career is fine without him.”

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What to know ahead of Jake Paul’s bout vs. Julio Cesar Chavez Jr.

Take a look at the facts and figures to know ahead of Jake Paul’s next fight.

ACCORDING TO PAUL, his journey to become world champion began the day after his loss to Fury in 2023. Paul was forced to face the harsh reality of his limitations against an opponent who had spent much of his life training to be a boxer. But even though Paul lost the fight, he didn’t lose the attention of his followers.

“Losing the Tommy Fury fight was the best thing to ever happen to me,” Paul said. “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.”

The latter part has proved difficult to sustain, as Paul had other opportunities that were too good to pass on. After beating journeymen Andre August and Ryan Bourland, both by first-round knockout, Paul veered from that path to face former UFC fighter Mike Perry in July 2024. Perry was a replacement opponent for Paul after Tyson was sidelined from the original fight date due to health issues. Paul won by sixth-round TKO, and then the chance to fight Tyson once again materialized.

“The fights with Bourland and August were by design to start building his skill set against actual boxers,” Bidarian told ESPN. “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.”

The idea to match Paul with Chavez has been in the plans for several years 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 said. “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 was placed on the undercard of Paul’s fight with Perry by design, similar to how Fury fought on the undercard of the first Paul-Tyron Woodley fight in 2021. In both cases, the next fight materialized in a timeline that made sense for both parties.

But the Chavez fight was almost disrupted by a stunning turn of events when Paul appeared to be closing in on yet another blockbuster: a fight with Alvarez — a four-division boxing champion — that would have happened in May.

Although the fight fell apart at the 11th hour, with Alvarez opting to sign a four-fight deal with Turki Alalshikh, chairman of Saudi Arabia’s General Entertainment Authority, Paul and his team saw the positives.

“The way we looked at it was that it was going to be an economic juggernaut for everyone involved,” Bidarian said. “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 isn’t protecting an undefeated record. He’s all about taking a risk if he’s going to be rewarded handsomely for it.

“It’s not a bad look for Jake to lose to Canelo,” Diaz said. “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 task at hand remains challenging for a world title, something that Paul believes he will come closer to accomplishing with a win over Chavez.

“We are already talking to [WBC cruiserweight champion] Badou Jack,” Paul said. “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 per ESPN BET], 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 told ESPN via text that Paul could be ranked after the fight if he scores a big win on Saturday.

“The WBC ratings committee has been following Jake Paul’s career,” Sulaiman wrote to ESPN. “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 illusion that Paul’s fight with Chavez will be remotely close to the financial success of the Tyson bout. But as long as the fight takes Paul closer to his goal of becoming a world champion, he’ll turn a deaf ear to the naysayers and continue down his path.

“I have learned that no matter what you do in this sport, there are always going to be haters,” Paul said. “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.”