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Who wins Jake Paul vs Tyron Woodley? Predictions and preview

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Will Jake Paul make it 4-0, or does Tyron Woodley end the run Sunday?

Jake Paul v Tyron Woodley - Press Conference Photo by Jason Miller/Getty Images

The Jake Paul Circus is back in town on Sunday evening, as the YouTube celebrity-turned-semi-pro boxer returns to the ring to face former UFC champion Tyron Woodley in a Showtime pay-per-view main event from Cleveland.

Does Paul go to 4-0, or is Woodley the man to knock the kid off and make a lot of adults happy and a lot of kids mad, maybe, I actually don’t know how kids think or what they think of Jake Paul because I’m too old to know what children are into.

Anyway, our picks for the fight:

Scott Christ (45-14-3)

To keep it very simple, I think Jake Paul’s going to win because he’s got more ability and dedication to this than a lot of people still want to admit. Is he a world class boxer? No. That’s not the point. Here’s the point: Tyron Woodley isn’t, either, and Woodley is also smaller, older, and well past his peak days in his MMA career. I don’t think Woodley will ultimately have the desire to dig in and win this. Maybe he catches Paul cold with one shot, certainly possible. But if he doesn’t I don’t see him winning. I think Jake will have to go some rounds here, Tyron might be crafty enough to go a few, etc.

OK now that I did some kind of boxing analysis, here’s where I’m really at: Paul’s team would not have him in this fight if they weren’t sure he would win. This is all, on some level, a grift. I’m not saying the fights are fixed or fake, I am saying they are — like many, many, many other boxing careers — extremely carefully constructed and managed. I also don’t think it’ll go very long because Jake Paul is boxing mainly for kids who spend hours of their day on TikTok, attention span ain’t there for an eight-round fight. IS WHAT IT IS! Paul TKO-3


How to Watch Paul vs Woodley

Date: Sunday, August 29 | Start Time: 8:00 pm ET
Location: Rocket Mortgage FieldHouse, Cleveland, OH
Streaming: PPV (Click Here to Buy!) | TV: PPV
Online Coverage: BadLeftHook.com


Wil Esco (47-12-3)

I don’t know, I don’t know! Look, I’ve picked against Jake Paul last time out because he was actually facing a former professional fighter for the first time, but I don’t follow MMA and certainly didn’t know Ben Askren had a bum hip that left the man completely immobile and unable to defend himself. I’d very much like to think a former MMA world champion could beat a YouTuber in a fight — even if it’s a boxing match — but my expectations have been tempered. Paul and his team have been carefully constructing his boxing career and because I have no genuine insight on these two, I’m just going to assume with his backing that they’re not going to throw Paul into a fight they weren’t comfortable he could handle. Anyhow, anyway, I’ll just take Paul to win by decision. Paul UD-8

Patrick L. Stumberg (48-11-3)

Woodley’s raw power makes him far and away the most dangerous opponent of Paul’s brief career. There was a time when his right hand was to the UFC Welterweight division what Barry Bonds’ bat was to opposing pitchers. He could be as passive as he wanted, as nobody wanted to risk getting anywhere close to that thing.

Keep in mind, however, that I said most dangerous; I’m comparing him to Ben Askren and Nate Robinson here. As much as I’d love to see Woodley knock Paul’s scraggly-ass beard halfway to Dayton, he’s 39 years old, fighting 20 pounds above his ideal weight, and got thoroughly figured out several fights ago. The man simply does not function under pressure, meaning Paul can let Woodley back himself to the ropes and then ping away with his jab to his heart’s content. Woodley did show admirable urgency against Vicente Luque last time out, but that ended with him staggered and submitted by “The Silent Assassin,” so I’m not sure he’s in the headspace to push the issue again. Even if he does, Paul’s size should let him neutralize the attack in the clinch and then go back to patiently potshotting while avoiding the occasional overhand right coming back his way. Paul takes his time and outworks Woodley to his first decision Paul UD-8

And the staff winner is...

Jake Paul v Tyron Woodley - Press Conference Photo by Jason Miller/Getty Images

Jake Paul (3-0)!