5 most intriguing storylines to watch ahead of Jake Paul vs. Tyron Woodley

Jake Paul and Tyron Woodley face off during a press event
Jake Paul and Tyron Woodley face off during a press event

One of the biggest attractions in combat sport returns to action this weekend as YouTube sensation Jake Paul takes on former UFC welterweight champion Tyron Woodley. The mega-event will go down on Sunday, August 29, at the Rocket Mortgage FieldHouse in Paul's hometown of Cleveland, Ohio.

As always, an event featuring Paul offers a little bit of everything – celebrity appearances, a championship bout, a showcase of up-and-coming talents, and of course, a highly anticipated crossover match in the main event.

How is this different from previous Jake Paul events? Aside from the lack of musical performances (thank God!), 'The Problem Child' will face the toughest test of his career thus far. The 3-0 boxer will put his unbeaten streak on the line against a formidable former UFC champion in a bid to prove his legitimacy in the sport.

But beyond winning and losing, there are more variables at play when Paul collides with Woodley. Ahead of the biggest crossover bout of the summer, let's take a look at the five biggest storylines that will unfold come fight night.


#5. It's make or break for Jake Paul

YouTube sensation Jake Paul celebrates after knocking out Ben Askren
YouTube sensation Jake Paul celebrates after knocking out Ben Askren

Not only will Tyron Woodley be the toughest test of Jake Paul's burgeoning career as a pugilist, but he's also the opponent that Paul badly needs to beat. A win over Woodley could launch Paul's reputation to new heights, while a defeat would send his stock crashing down.

Paul is at the stage of his career where fans and his fellow fighters are starting to take him seriously. Gone are the days when Paul was overlooked and seen as merely an attraction who can only beat non-boxers.

Former UFC champion Daniel Cormier recently said it's time to stop thinking of Paul as an internet celebrity rather than a fighter. Meanwhile, MMA analyst Joe Rogan believes that Paul is a genuinely talented boxer.

Granted, that's exactly what his resume has to show for – a winning boxing record against unproven strikers. But that will all change if Paul can prove that he can perform at a high level against a fighter with championship pedigree.

Even though it's only his fourth professional fight, Sunday night's event is practically a must-win for Paul. Because if he loses...

#4. This could be the end of the Jake Paul experiment

Jake Paul at a media workout session
Jake Paul at a media workout session

What would Jake Paul have in common with NBA star Jeremy Lin, retired boxer James 'Buster' Douglas, and singers Gotye and Kimbra if Sunday night didn't go his way? He'd be a one-hit wonder just like the rest of them.

Paul received no respect from fans for his first two career wins, and rightfully so. He deserves no credit for dismantling fellow YouTuber AnEsonGib. He doesn't deserve brownie points for starching retired NBA player Nate Robinson – who was half his size – either.

As far as combat sports observers are concerned, the only victory Paul has that's worth talking about is his knockout of former Bellator and ONE Championship welterweight titleholder Ben Askren. Even then, many are hesitant to give Paul credit for that victory as Askren is not exactly known for being a respectable striker.

As it stands, there are already so many arguments to be made if the goal is to undermine Jake Paul's achievements. Losing to an undersized 39-year-old Woodley could be the final nail in Paul's coffin.


#3. Tommy Fury might be next for Jake Paul

Tommy Fury at a media workout session
Tommy Fury at a media workout session

The younger half-brother of undefeated boxing champion Tyson Fury will compete on the undercard of Jake Paul vs. Tyron Woodley. Tommy Fury has previously been one of the names floated as a potential opponent for 'The Problem Child'.

The only issue is Fury's unheralded status as a boxer and poor name recognition made him an unsuitable opponent for Paul, given what we know of the YouTube star's business model.

Like Paul, Fury is an undefeated up-and-coming boxer who's more famous for activities he has done outside the ring. The 22-year-old's claim to fame – besides being related to 'The Gypsy King' – was his appearance on the fifth season of UK reality television show Love Island.

Similar to Paul, he is also a promising fighter, but is far from a finished product. The Brit will take on MMA fighter Anthony Taylor, who competed under the Bellator banner as a lightweight.

Fury's inclusion on the fight card gives him the opportunity to introduce himself to Paul's fanbase. Should both Paul and Fury emerge victorious this weekend, it would be safe to assume they could meet one another in the near future.

#2. Would Tyron Woodley losing be a bad look for MMA?

Tyron Woodley at a UFC Fight Night weigh-in
Tyron Woodley at a UFC Fight Night weigh-in

Jake Paul's prominence is built upon his ability to make MMA fighters and the sport as a whole look bad. For that exact same reason, Paul has turned into the biggest heel among the MMA community.

It's no secret that most MMA fans tune into Paul's fights hoping to see him finally get his comeuppance. Of course, that hasn't happened yet as the only cage fighter Paul has faced thus far is one of the most unskilled strikers in MMA.

On paper, Paul defeating wrestling-based and post-prime fighters like Askren and Woodley shouldn't really reflect badly on the MMA community as a whole. After all, cage fighting and boxing are two entirely different sports even if they seem similar.

Nonetheless, it's almost inevitable that the MMA community will have to swallow a truckload of slander and trolling for the months to come should Paul walk away with the win. As unfortunate as it is, Anderson Silva's efforts to redeem the reputation of MMA could be all for naught if Woodley crashes and burns.


#1. Will Jake Paul and Tyron Woodley honor the tattoo bet?

Tyron Woodley and Jake Paul face off during a press event
Tyron Woodley and Jake Paul face off during a press event

Jake Paul's insistence on having a tattoo bet with Tyron Woodley adds another interesting wrinkle to what is already a fairly intriguing matchup. Basically, Paul challenged Woodley to a wager in which the loser of the fight will have to get an embarrassing tattoo.

'The Problem Child' is intent on making sure the bet pushes through that he even hired a tattoo artist to be present at the venue. In an interview with Haney on the 3 Things to Know podcast, Jake Paul discussed the terms of the bet.

“I have a tattoo artist, Tatu Baby, who’s one of the biggest tattoo artists in the world. She’s actually coming down to the fight. She’s going to be ringside for the fight. And after Tyron loses, I’m sending her into his locker room to make him get the tattoo."

The bizarre bet is very reminiscent of Vince McMahon and Donald Trump's hair vs. hair match at WrestleMania 23. And while the WWE chairman held up his end of the bargain and had his head shaved clean, it would be very interesting to see if Jake Paul or Tyron Woodley would do the same.

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