MIKE TYSON SAT on the canvas with his back against the ropes, exhausted and defeated.

That was the final image of the once seemingly invincible heavyweight champion in the ring for a sanctioned fight, TKO'd in embarrassing fashion by journeyman Kevin McBride.

Tyson was weeks shy of his 39th birthday for his boxing swan song on June 5, 2005, in Washington, D.C.

"I do not have the guts to be in this sport anymore," Tyson said after that fight. "I don't want to disrespect the sport that I love. My heart is not into this anymore. I'm sorry for the fans who paid for this."

Nearly 20 years later at the age of 58, Tyson will once again lace up the gloves for a sanctioned bout Friday at AT&T Stadium in Arlington, Texas (Netflix, 8 p.m. ET). His opponent is social media star Jake Paul, who has carved an in-ring career out of novelty fights but has gained respect from top-level boxers such as former heavyweight champion Tyson Fury and former two-division champion Devin Haney.

Though Paul possessed no boxing background before he turned pro in January 2020, the 27-year-old has developed into a competent boxer, feasting on former UFC fighters with some spectacular KOs. He's competed 11 times over the past four years and has never been stopped or even knocked down. His only loss was a split decision to Tommy Fury in 2023. Paul is a -235 favorite, per ESPN BET, to defeat Tyson, one of the most recognizable people in the world.

Now, Paul will fight on his biggest stage yet, even if this latest novelty boxing match features him in a headliner against a man 31 years older with a history of health issues.

This event, which was organized by Paul's Most Valuable Promotions, features two world title fights on the undercard including a rematch between two-division undisputed champion Katie Taylor and seven-division champ Amanda Serrano. It was originally set for July 20 but was postponed in late May after Tyson suffered an ulcer flareup while on a flight from Miami to Los Angeles.

Ulcers occur when stomach acid damages the lining of the digestive tract and results in abdominal pain. Perhaps more worrisome, Tyson revealed on Netflix's prefight documentary, "Countdown: Paul vs Tyson," that he threw up blood during that same flight.

"I had a big ulcer, two-and-a-half inches, and it was bleeding," Tyson said. "All my friends were calling me like I was dying. I asked the doctor if I was going to die, and she didn't say 'No.' ... You wouldn't believe what I endured from my ulcer. I lost 26 pounds."

Tyson and Paul were unavailable for comment to ESPN.

"That was the moment they [MVP] should have realized that this was actually a bad idea," said Matchroom Boxing CEO Eddie Hearn, one of the sport's top promoters.

While the fight is sanctioned by the Texas Department of Licensing and Regulation, there are three major caveats. Tyson and Paul will wear 14-ounce gloves rather than the standard 10-ounce gloves for heavyweight fights; the rounds will be two minutes rather than three minutes; and the fight will be contested over eight rounds rather than 10 or 12.

"It was [Tyson's] choice, not that Jake didn't want to do it [as a sanctioned fight]," Nakisa Bidarian, the co-founder of Most Valuable Promotions alongside Paul, told ESPN last week. "We were bringing Mike Tyson back into the sport, and I believe that it was more meaningful as a pro fight."

Hearn will be ringside to support his champion, Taylor, in the co-main event. However, Hearn told BBC Sport last month he will leave his seat before the main event because he doesn't want to support a bout with a fighter Tyson's age.

"The reality is that 20 years ago when Mike Tyson retired from the sport he was shot, completely finished," said Hearn, who sued Paul for defamation in 2022 after the fighter accused him of bribing a boxing judge. "It was actually sad to watch then, 20 years ago.

"...You only need to speak to him and look at him to know this guy should not be in a ring again. ... If I was Jake Paul, I'd just feel a little bit embarrassed to be honest with you. ... This is dangerous, irresponsible and, in my opinion, disrespectful to the sport of boxing."

WHILE OPINIONS ON this event are split, there's one matter everyone can agree on: It's going to generate a lot of interest.

The event has been heavily promoted, from social media, where Tyson and Paul both boast 10s of millions of followers, to larger-than-life, 40-foot floats of the fighters at the State Fair of Texas and on TV spots during nationally televised college football games. The promotion is expecting over 60,000 fans in attendance with a gate that exceeds $15 million, which would be the largest U.S. boxing gate in history outside of Las Vegas. Already, Tyson-Paul is 60% above the previous Texas gate record for a boxing/MMA event, which was $9 million for Canelo Alvarez-Billy Joe Saunders in May 2021, also at AT&T Stadium.

Given the popularity of Tyson and Paul, there's little doubt this will easily become the most-watched boxing match in years, particularly since Netflix reported 282.7 million worldwide subscribers at the end of the year's third quarter.

It was Paul who closed a deal with Netflix in November 2023 to stream its first boxing match -- and first live professional sporting event -- before Tyson was even in the mix.

"Many names were being floated around, but once you hear the name Mike Tyson, it's hard to unhear it," Gabe Spitzer, Netflix's vice president of sports, told ESPN. "Mike is a global superstar, someone who would potentially bring in casual boxing fans or even non-boxing fans, and we are always looking for big, global events that add value for our members.

"... The event is sanctioned by the Texas Athletic Commission and we'll be following all their guidelines and protocols and feel very comfortable working with the commission and MVP on this."

In the promotional social media videos leading up to the fight, Tyson has looked explosive in training clips, but they are edited in such a way that he's shown training in spurts rather than in extended footage of more than a few seconds. When a sparring session was mentioned during the countdown documentary series, the camera panned to his trainer, Rafael Cordeiro, rather than Tyson in the ring.

Just two years ago, Tyson was photographed in a wheelchair and holding a walking stick at the Miami International Airport. Tyson later confirmed in an interview with Newsmax that he has "sciatica every now and then" and when it flares up, he "can't even talk."

Sciatica is pain that travels along the path of the sciatic nerve, from the glutes down each leg. Usually, it's caused by a herniated disk, according to the Mayo Clinic.

Tyson's back issues are well-documented, none more so than his famous "my back is broken" comment after his first-round KO of Clifford Etienne in 2003. That was the final win of Tyson's Hall of Fame career.

Tela Mange, a spokesperson for the Texas commission, told ESPN that officials evaluated Tyson's fitness to compete during a sparring session. She said MVP first proposed the bout as an exhibition, and the commission responded that it would require two-minute rounds and 14-ounce gloves.

"Women fight under two minutes most times," Bidarian said. "So there's no reason that the men can't fight two-minute rounds for a championship fight or a pro fight. There's zero difference. If you actually think about equality, there should be zero difference. ... And so for someone to say, 'This is only two-minute rounds' is like saying, 'Ooh, then women's fights aren't pro fights because they're two-minute rounds.'"

Most women aren't competing in two-minute-round fights by choice, though; just the opposite. Last year, more than two dozen women fighters petitioned boxing's commissions and four sanctioning bodies to allow 12 three-minute rounds rather than the standard 10 two-minute rounds. Serrano and her promoter, MVP, helped organize the statement ahead of her fight in October 2023 that became the first women's title unification contested over 12 three-minute rounds.

Once it was shifted to a fully sanctioned fight, the promotion asked if the commission would allow the fight to maintain those same gloves and round requirements, which is highly uncommon for a professional boxing match.

"Our combative sports staff evaluate numerous factors to determine if an event can be held in a manner that is both safe for both contestants and in compliance with Department laws and rules," Mange said. When asked what additional testing or medical clearance the commission required due to Tyson's age and inactivity level, she responded that it "will conduct the usual prefight physicals the day before the fight."

Per the TDLR website, "contestants who are age 36 or older, must submit a report of favorable physical testing including, but not limited to, an EEG (electroencephalography), and an EKG (electrocardiogram)."

MVP failed to comment when ESPN reached out Monday regarding what happens if Tyson were to fail the prefight physical.

"We went through extensive medicals, whether it's scans, whether it's physicals, to ensure that we were comfortable first and then two, that the commission was comfortable," Bidarian said. "There was a reason that when he had an ulcer, we ... pushed it back four months from the actual fight date to ensure that [Tyson] was 100 percent healed.

"We could have done this fight [at the] end of September, and still it would've been good based on his healing timeline, but we wanted to be absolutely comfortable that the ulcer was fully healed before he got back into training. So we've done everything we can to create a safe environment for both athletes. Paul's never been hit by someone like Mike Tyson. So people can say about the danger for Mike Tyson, he's older. What about the danger for Jake Paul, who's never fought at this weight? He's never been in there with a true heavyweight in his career. You could say it to both sides."

Still, not everyone is convinced the fight will be safe for Tyson, given his advanced age and lack of activity. Tyson's last time in the ring was his November 2020 exhibition with fellow boxing legend Roy Jones Jr., during which both fighters mostly threw body punches.

Dr. John Neidecker, a member of the Association of Ringside Physicians, explained that "as people age, changes occur in the brain and its vascular system, increasing the risk of intracranial hemorrhage." However, Neidecker noted that while he clearly doesn't have access to Tyson's medical record to make a full assessment, "he appears to be in far better shape than an average sedentary person of the same age."

Even so, Paul is 31 years younger and far more active, bringing inherent risk to Tyson though the vaunted power puncher has shown off an impressive physique in the lead-up.

"Jake Paul's been relatively active, and he's not a bad boxer either," an acting state athletic commissioner who's sanctioned several world title fights told ESPN. "We need to get away from this stuff that he's a YouTuber or something. He's a good boxer. And I've been impressed with him every time I saw him."

Paul has enjoyed top-level sparring and training at his compound in Dorado, Puerto Rico. And while the MMA fighters he's knocked out aren't experienced boxers, he's displayed solid skills and an ability to deliver a sharp, powerful right hand.

"My concern about this one is Tyson's an iconic figure," the commissioner said. "He's world-renowned and he's one of the most well-known figures on the planet. And I just don't think that it would be good for boxing if he were to get hurt."

PERHAPS THIS IS all much ado about nothing. Maybe neither fighter is in any danger of getting hurt, and this truly is just about entertainment in the vein of WWE, which would be fine normally.

There have been scores of exhibitions in recent years, from Floyd Mayweather-Logan Paul to the aforementioned Tyson-Jones event and even Vitor Belfort-Evander Holyfield, where Belfort did KO the 58-year-old legend in the first round. Holyfield replaced De La Hoya on short notice and when that happened, California refused to sanction the fight, leading to the event's relocation from Los Angeles to South Florida.

In the other two exhibitions, it was clear neither fighter was throwing punches with bad intentions. However, Tyson-Paul is a sanctioned event, meaning the fight will count on their records, there will be three judges ringside and an official winner.

Tyson isn't the only former heavyweight champion who will compete in a sanctioned boxing match over the next week. Oliver McCall, who last competed 5 years ago, is 59. He'll fight 54-year-old Stacy Frazier (a journeyman with a 16-22 record) in a four-round bout on Nov. 19 in Nashville, Tennessee. McCall's last title fight was a TKO loss to Lennox Lewis in a 1997 rematch.

Ike Ibeabuchi, a heavyweight puncher, was on the cusp of a title shot in 1999 when he was imprisoned for attempted sexual assault. Now 51, Ibeabuchi will fight for the first time in 25 years with a Dec. 7 fight against 47-year-old Ayman Farouk Abbas (4-10-1).

One other outcome from a sanctioned fight is that Tyson-Paul allows for betting action, as sports wagering is currently legalized in 38 states and has exploded in popularity. Not all 38 states are on board with taking bets on the fight, however.

New York, Pennsylvania and Colorado are among the seven states that decided not to offer betting action on the fight. A spokesperson for the New York State Gaming Commission told ESPN that the bout wasn't eligible for wagering due to the fight's "non-traditional rules" (two-minute rounds and 14-ounce gloves).

Spokespeople for gaming in Colorado and Pennsylvania echoed that sentiment; Colorado added "that not all fighters are professionally ranked" as another reason, while Pennsylvania added that the number of rounds was also a consideration.

"Given the totality of factors, the decision was made in the best interest of the betting public not to permit wagering in Pennsylvania," a spokesperson for the Pennsylvania Gaming Control Board told ESPN.

And for the 31 states that are offering action, if this isn't a fight where both contestants are trying their best, it's an issue. One of those states is Nevada. A spokesperson for the Nevada Gaming Control Board told ESPN that the fight passed the state's "three-prong test we give to casinos as guidance when they ask if they can take wagers on a sporting event." That includes whether the results of the event will be published and if there's oversight from a governing body.

"Forget about lying; there's no reason for us to create a federal fraud, a federal crime," Bidarian said. "... These are pro fights that consumers are making legal bets on. I don't think the critic who says these are not real fights, thinks about there would be jail time if we actually did this type of stuff.

"... We have never, and we'll never do anything that's other than above board and 100 percent a pro fight unless we come out clearly and say, 'Hey, this is an exhibition fight that is a show.'"

There's no dispute that Paul has made an impact on boxing with events that have garnered younger fans in droves. He'll also deliver key exposure for the undercard that includes the Taylor-Serrano rematch, the Mario Barrios-Abel Ramos WBC welterweight title fight and featherweight contender Bruce "Shu Shu" Carrington. (Barrios and Ramos are with PBC, while Carrington is promoted by Top Rank). But those other events all pale in comparison to his fight Friday with Tyson, where no one really knows what to expect.

"I don't see how that serves the sport's interest. ... It's clearly for entertainment, which is fine," the commissioner said. "But there's all these mitigating circumstances with the inactivity, the age, all these things that make this match more problematic in my view."