CLEVELAND – Stephen Espinoza understands the skepticism many boxing fans have directed toward Jake Paul.

Espinoza was skeptical, too, before Showtime’s president of sports and event programming examined Paul’s potential as not only a fighter, but as an uncommon conduit who can broaden boxing’s fan base among younger people who don’t regularly watch the sport.

After analyzing the success of Paul’s previous pay-per-view event and Showtime’s positive experience with his older brother, Logan Paul, throughout the promotion of his exhibition against Floyd Mayweather on June 6, Espinoza determined that it would be a worthwhile risk to get into the Jake Paul business.

The announcement of Showtime’s multi-fight agreement with Jake Paul three months ago surprised plenty of people within the boxing industry. The younger Paul pounced on the chance because working with a premium cable network that has broadcast boxing for 35 years legitimized him in a way working with fledgling Triller Fight Club couldn’t do.

The 24-year-old Paul will make his Showtime Pay-Per-View debut Sunday night, when he’ll headline a five-fight show from Rocket Mortgage FieldHouse (8 p.m. EDT; $59.99). Paul is an approximate 2-1 favorite to defeat former UFC welterweight champ Tyron Woodley in their eight-round cruiserweight contest.

“We had a lot of questions, just like a lot of the traditional boxing people did, coming into it,” Espinoza explained to BoxingScene.com, which like Showtime, is owned by ViacomCBS. “But we were satisfied that it’s not gonna hurt the sport, it’s not gonna detract from the rest of what we’re doing and there’s a strong possibility that he could convert some new fans. I was skeptical at first, and particularly how he was marketed and how he was used.

“I think he can draw new fans to the sport and he can convert his fans if you serve those fans the right thing. You want action fights, and what’s not to like about a Daniel Dubois fight or an Amanda Serrano fight? So, I think if you’re new to boxing and it’s the first time you bought a pay-per-view, or you only buy Jake Paul pay-per-views, there’s enough on this card where you can say, ‘You know what? I’m a fan of boxing beyond just Jake Paul.’ And that’s by design.”

The 23-year-old Dubois (16-1, 15 KOs), a hard-hitting heavyweight from London, is scheduled to box Joe Cusumano (19-3, 17 KOs), of Danville, Virginia, in a 10-round bout Sunday night. Brooklyn’s Serrano (40-1-1, 30 KOs) is set to defend her WBC and WBO featherweight titles against Mexico’s Yamileth Mercado (18-2, 5 KOs) in the 10-round co-feature.

The televised portion of the card also will include an intriguing 10-round bout between former IBF junior welterweight champ Ivan Baranchyk (20-2, 13 KOs) and Cleveland’s Montana Love (15-0-1, 7 KOs). England’s Tommy Fury (6-0, 4 KOs), a younger brother of WBC heavyweight champ Tyson Fury, also will be showcased in a four-rounder against Anthony Taylor (0-1), an MMA fighter from Alameda, California.

Espinoza realizes, of course, that a significant faction of hardcore boxing fans simply never will take to Jake Paul or other outsiders that they perceive to have not earned his or her place on such a high-profile, expansive platform. Those same pessimists have little tolerance for the Jerry Springer-ish nature of the polarizing Paul’s approach to promoting his fights.

Nevertheless, as someone heavily invested in the financial health and future of this niche sport, the Stanford-educated Espinoza also recognizes that boxing undoubtedly needs new fans. As long as it didn’t impact the amount of money Showtime infuses into boxing through its exclusive rights deal with Al Haymon’s Premier Boxing Champions, Espinoza is willing to at times operate outside the box to try to develop consistent consumers out of younger Paul fans who don’t otherwise watch the sport.

“There are gonna be critics,” Espinoza said. “There were plenty of critics when we did the Mayweather deal, and that turned out to be a phenomenal thing for the network. And we satisfied ourselves. Not that there wouldn’t be negativity or criticism, but that it wouldn’t do damage to the sport. I think beyond that, it would be shortsighted and narrowminded to look at this opportunity and say, ‘We’ll only do exactly the types of events that we’ve been doing for the last 35 years.’ That is not good for the sport, it’s not good for the business and it’s not, personally, a good philosophy to me. Is it a bit of an experiment? Sure. And we do that occasionally. I think that is a positive thing. We should be trying to evolve and innovate within the sport.

“Time will tell how people look back on this – on this whole thing and Jake in particular. But I think based on what we’ve seen so far, it’s been a net positive for the sport. It’s not for everybody. Not everybody likes it, but not everybody likes women’s boxing. Not everyone likes heavyweights or the lighter weights. But is it hurting the sport? No, it’s not hurting the sport. And it’s not taking away from what we’re doing outside of Jake Paul. That’s probably the biggest key, that this is able to live side-by-side with ‘[Showtime] Championship Boxing,’ and simultaneously we’ve been able to have one of the strongest summer runs we’ve had in a while, while we’re also doing a Jake Paul event and a Logan Paul event. So, we’ve demonstrated that the two can co-exist without hurting each other. Look, people can choose if they’re interested or not. We have no problem with that.”

Paul promised Espinoza as part of their agreement that he would continue to incrementally increase his level of opposition. Woodley, though 39 and fresh off a fourth straight defeat in UFC, is typically considered much more dangerous than Woodley’s friend, former UFC welterweight Ben Askren.

Paul stopped an out-of-shape Askren with one right hand in the first round of their Triller Fight Club main event April 17 at Mercedes-Benz Stadium in Atlanta. The Westlake, Ohio, native stopped YouTube rival Ali Eson Gib in the first round of his pro debut in January 2020 and knocked former NBA point guard Nate Robinson unconscious in the second round last November 28.

If Paul gets past Woodley, he’ll likely fight an actual professional boxer, perhaps Tommy Fury, sooner rather than later.

“Boxing is the ultimate sort of truth-teller,” Espinoza said. “We can market and he can market and there can be all this social-media hoopla. But at the end of it, he’s gonna go as far as his talent takes him. If he turns out to be a good, quality boxer, he can go far with everything else. But if he doesn’t put in the work and he doesn’t perform, well, then those who are critics are gonna get their wish. He’ll fade away. I don’t think that’s gonna happen, but ultimately he’s gotta sink or swim based on his own talent.”

Keith Idec is a senior writer/columnist for BoxingScene.com. He can be reached on Twitter @Idecboxing.