How Canelo Alvarez navigates the complex world of boxing and delivers the best matches possible

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ZAPOPAN, MEXICO - MAY 06: Canelo Alvarez of Mexico punches John Ryder of Great Britain during the fight for the Super Middleweight Championship at Akron Stadium on May 06, 2023 in Zapopan, Mexico. (Photo by Hector Vivas/Getty Images)

Canelo Alvarez has become a master at navigating the boxing business world, as well as being a master inside the ring. (Photo by Hector Vivas/Getty Images) (Hector Vivas via Getty Images)

LAS VEGAS — One of the things about Floyd Mayweather that has never been fully appreciated was how deeply he understood the business of boxing. He also knew what the public wanted. And he used that knowledge to make himself into the dominant force in the sport for a decade.

His greatness in the ring was obvious to anyone who watched him. He was good enough that he could at least have contended for a world title in his first professional fight. But once he gathered a full understanding of the business — and he can primarily thank Al Haymon for that — there was no one bigger. And even though he has been retired for more than six years, he still carries huge sway over the sport.

We’re sitting a bit of a replay of that now with Canelo Alvarez, the undisputed super middleweight champion who is one of the few fighters in the sport who can sell tickets and pay-per-views.

It’s going to be tough sledding by Alvarez’s lofty standards Saturday, when he defends his titles against undisputed super welterweight champion Jermell Charlo at T-Mobile Arena.

Alvarez is the successor to Mayweather and Manny Pacquiao as the biggest pay-per-view draw in boxing. They were the successors to Oscar De La Hoya and Mike Tyson. Those four men, in particular, along with others like Lennox Lewis and Evander Holyfield, were so good at selling pay-per-views that anything under a million seemed like a terrible night.

The business has changed dramatically now, and there aren’t going to be many million-buy fights any more. Alvarez’s bout with Charlo is one of those. Not long ago, just putting Alvarez’s name on the marquee meant a $20 million paid gate and a pay-per-view sale in the million range.

If they do 450,000 to 500,000 Saturday, they should be grateful. It’s an exorbitantly high $85 to buy the show, and so the PPV pirates will be out in full force. As always, the thievery of the pay-per-view signal will be extraordinarily high.

There are strong indications that Showtime isn’t long for the boxing world. Stephen Espinoza, its president of sports, is on an expiring contract. Many employees have wondered aloud how much longer they’ll have jobs. Showtime’s boxing schedule is light for the rest of the year.

The successful fighters like Alvarez demand huge purses, and the ability to make that up by selling pay-per-views has diminished greatly.

Alvarez, though, has navigated the system like a champion. He was with Matchroom and seemed to develop a close relationship with Eddie Hearn. But when he couldn’t get a rematch with Dmitry Bivol, the light heavyweight champion who defeated Alvarez 16 months ago, Alvarez surveyed the scene.

He realized that Premier Boxing Champions had the best roster of potential opponents and so earlier this year, signed a three-fight deal with it. The first of those is Saturday against Charlo. After that, it could be David Benavidez, or David Morrell or Charlo’s twin, Jermall Charlo, among others.

But pay-per-view fights sell when the fighters are known commodities, the bout is compelling and it has a narrative to go along with it. None of the options out there are going to be slam dunk PPV hits like Canelo-Gennadiy Golovkin 1 and 2 were, but they were the best for him.

NEW YORK, NEW YORK - AUGUST 15: Canelo Alvarez speaks to media during a press conference to preview their September 30 super middleweight undisputed championship fight against Jermell Charlo at Palladium Times Square on August 15, 2023 in New York City. (Photo by Sarah Stier/Getty Images)

Canelo Alvarez is a 4-1 favorite to defeat Jermell Charlo on Saturday at T-Mobile Arena in Las Vegas in their bout for Alvarez’s undisputed middleweight title. (Sarah Stier/Getty Images) (Sarah Stier via Getty Images)

And Alvarez recognized how to work the system brilliantly.

“We understand business and I have a good team,” Alvarez told Yahoo Sports. “We always try to have good relationships with the people [we work with] and leave all of our doors open. We’re good and loyal and open, and we do what we say we’ll do. So when you have those relationships, you can go with anybody, like we’ve done.”

Alvarez signed a deal with DAZN in 2018 that was for 11 fights at a total price of $365 million. It seemed he would be tied to the hip with DAZN for the rest of his career.

DAZN started promisingly enough, but it’s suffered an extraordinary amount of issues. It has raised its subscription fee by 2.5 times in the five years it’s done business in the U.S. and while it repudiated pay-per-view at its inception, of course it’s embraced it now. Not only are subscribers forced to pay $240 a year, but they have a lot of pay-per-view bouts.

A common problem in boxing is there are far too many pay-per-view bouts, and DAZN provided an example of that Tuesday when it announced a super lightweight title bout on Dec. 9 in San Francisco, California, between undisputed lightweight champion Devin Haney and Regis Prograis. Neither of those fighters are a draw and — mark my words when I tell you — that PPV will do abysmally.

Yet, even if you have paid for a DAZN subscription, you’ll have to fork over more money to see that.

Three bouts into the DAZN deal, Alvarez sued to get out of it and was granted his free agency. And while walking away from a guaranteed $35 million a fight for his next eight fights had to be tough, he said there was never a doubt about what he needed to do.

“I had no doubts,” he said of the decision to seek to get out of the DAZN contract. “When you do the correct things, and you do your job, and you do everything right, you don’t have to fear anything. … I just wanted to get out of that contract because [I was having] a lot of troubles making the fights.”

He’s gone back to work with DAZN, but he’s learned never to burn bridges and to always put himself in the best position. There’s not a lot of reason to stay with the same promoter and same network long-term if you can advance your career more quickly by flowing with the current.

If he loses Saturday — and he’s a -400 favorite to win — he’ll likely have a rematch with Charlo that will be significantly more lucrative. If he wins, he’ll go on to face whichever PBC star is the most attractive at the moment.

Boxing is a fight, inside and outside of the ring. In both areas, Alvarez has had his hand raised consistently.

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