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Jake Paul vs. Tyron Woodley fight: Five biggest storylines to watch from an interesting card in Cleveland


The last big fight of the summer for combat sports presents a little of everything on Sunday night when YouTube sensation Jake Paul continues his turn into professional boxing when he faces former UFC welterweight champion Tyron Woodley.  

The Showtime PPV event will take place at Rocket Mortgage FieldHouse in Cleveland, Ohio, the hometown of the 24-year-old Paul (3-0, 3 KOs), who has predicted a knockout of his 39-year-old foe in Woodley (0-0 in boxing; 19-7-1 in MMA).  

As we draw closer to the crossover event, let’s take a look at the biggest storylines entering fight night.  

1. Paul-Woodley is the best example yet of this celebrity, crossover experiment 

How much longer will the bubble last as everyone from entertainers to MMA stars and retired boxers continue to throw their hat into the ring amid boxing’s latest trend? Probably as long as the fights are still action-packed and competitive. This matchup has the opportunity to be the best example yet of what this genre of the fight game can be when it’s done right. Boxing experts still don’t quite know what they have yet in Paul nor do they have much footage to gauge how Woodley, fresh off four defeats to close out his UFC run, might do in his attempt to moonlight into a new combat sport. But given the credentials of both, you can pretty much bank on two things: First, it’s a very well-matched bout, which should produce an equal amount of predictions going to either side. Secondly, someone is getting knocked out. The fighters also don’t seem to like each other much, which surely doesn’t hurt. For all the hype and buildup entering Showtime’s last endeavor into the carnival side of boxing in June, when Jake’s older brother, Logan Paul, took on retired pound-for-pound king Floyd Mayweather, the fight turned out to be a dud from the standpoint of entertainment. Unlike that matchup (which was an exhibition), Paul-Woodley is a real professional bout featuring two fighters who will likely try to win at all costs, even if it means risking a highlight-reel defeat. Star power alone can get people to the gate or hit “buy” on their remote control but to keep them there, promoters need to deliver what is promised. This matchup appears to offer everything that is right with this genre.  

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2. Woodley is the right opponent to find out more about whether Jake Paul is for real 

The difficult thing about Paul’s short professional resume up to this point is that we still don’t know whether Paul is just very good at cosplaying as a legitimate boxer or whether he might just be well on his way to becoming the real thing. A trio of knockouts over brutally unprepared foes showed us Paul has big power, but it’s hard to gauge much more. Social media influencer AnEsonGib, retired NBA guard Nate Robinson and retired MMA fighter Ben Askren ended up splattered across the canvas before Paul’s chin or gas tank, for example, could have a shot at accurately being challenged (or exposed). Woodley has long possessed big power in his right hand and remains explosive despite both his age and a puzzling series of lifeless defeats that led to his exit from MMA. Unlike Askren, who possessed a striking prowess that was almost remedial compared to his fellow elites in stops at Bellator MMA, ONE Championship and the UFC, Woodley has made a living excelling at his chosen sport by using his hands. Unlike Logan Paul, who seemed to take pleasure in the idea of trolling the traditional boxing guard by moonlighting as one for big paydays, Jake Paul is hoping to be taken seriously by said group and defeating Woodley would take him a lot closer than any of his previous wins have teased.

3. The bubble might burst if Paul loses badly 

This might sound like too much pressure to put on one person in a single fight, but it’s hard to argue against the idea of Paul being the face of the current celebrity boxing movement. He reportedly drew over 1 million buys in his Triller PPV main event against Askren and has seemingly even surpassed his brother as the true lightning rod of the boxing sub-genre. The whole “gotcha hat” fiasco at the Mayweather-Paul press conference caused by Jake stealing Mayweather’s hat to start a near riot is proof alone. If Paul keeps winning while creating entertaining events, the potential pool of big-name opponents vying to test him should only get bigger and more lucrative. In many ways, Paul has the potential to be a sensation similar to that of what Kimbo Slice meant to MMA more than a decade ago. Like Slice, Paul can fight a little bit and that hint of legitimacy pairs perfectly with his eccentric and disruptive persona to create a polarizing market of those who cheer for him because they can relate to his rebel ways and pray for his demise so they can prove he’s anything but legit. Either way, both sides will watch and will happily pay to do so. Paul has called out everyone from Conor McGregor to Canelo Alvarez. For him to get there, he will need to keep winning. And for the genre to have a shot at staying around a while, a bad loss to its biggest name could be disastrous to the momentum being built.  

4. Like Paul, Woodley is working with all the right people to prepare  

Like the Paul brothers, who deserve credit for creating an atmosphere that gives them the best chance to succeed by hiring experienced trainers and sparring partners to build a reputable camp in Puerto Rico, Woodley has taken strong steps to ease his transition. He has largely worked in Miami at the gym of Cuban boxing trainer Pedro Diaz, a defensive and technical specialist, who has previously had huge success in the corners of star fighters like Miguel Cotto and Guillermo Rigondeaux. But Woodley made even bigger headlines during training camp when he accepted Mayweather’s public offer to work with him in Las Vegas. Although it’s hard to expect an overnight transformation, Woodley could do much worse in terms of the type of instructors he sought out. And for what it’s worth, the video footage of his training time with both has given off the feel that Woodley will look like anything but a novice entering his pro debut.  

5. Tommy Fury’s undercard bout could be a tryout for a future opportunity 

Among the four support bouts below the main event on Sunday’s PPV main card is the 22-year-old half brother of unbeaten heavyweight champion Tyson Fury. Known as “TNT,” Tommy Fury is a sometimes professional boxer who is 6-0 with four knockouts as a light heavyweight. But he’s far more known as a reality television star in his native Great Britain thanks to his 2019 run as the runner up on Season 5 of “Love Island.” Like Paul, Fury has proven that he can fight a little but is far from a finished product. He’ll be matched with Anthony Taylor, an MMA fighter who has competed under the Bellator banner and trains with Paul in Puerto Rico. Fury’s placement on the card should bring a good deal of attention, especially from those overseas. Should both win this weekend, it wouldn’t be rocket science to assume they could meet one another in the near future.  

Who wins Paul vs. Woodley? And what prop should you back for a huge return? Visit SportsLine now to see Brandon Wise’s best bets for Sunday, all from the CBS combat sports specialist who was all over Jamel Herring’s win, and find out.



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