Jake Paul vs. Anthony Joshua fight predictions: Tyson Fury, Oleksandr Usyk among fighters weighing in on bout

Jake Paul will be staring down the biggest risk of his pro careeron Friday nightwhen he clashes with two-time former heavyweight champion Anthony Joshua at Kaseya Center in Miami. Paul sits as a heavy +700 underdog days out from the fight, and many believe the social media influencer-turned-boxer has bitten off far more than he can chew this time.

Paul’s career has been a success in that he has made big money and drawn plenty of attention fight after fight, but his opponents have mostly been crossover athletes from the NBA and UFC, as well as former boxing champions well past their prime, such as Mike Tyson and Julio Cesar Chavez Jr. In Joshua, Paul is fighting a big, dangerous heavyweight who is not far removed from his prime.

Joshua is a former Olympic gold medalist who twice was unified heavyweight champion. While multiple recent defeats to Oleksandr Usyk and Daniel Dubois have shown that Joshua may no longer be among the top two or three heavyweights in boxing, he is still far more experienced and skilled than Paul, leading to many questions as to why Paul would agree to the fight.

As with any fight drawing this much attention, many professional fighters have weighed in with their prediction for how the fight will play out, and while the majority are picking Joshua (and expressing concerns for Paul’s health), there are a handful of fighters who believe Paul may be able to pull off a titanic upset.

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Let’s check out some of those predictions.

SPORTS UPDATE Pros picking Jake Paul

Tyson Fury, two-time former heavyweight champion:“Jake Paul chins AJ, yes. 100 percent. If they fight, I’m putting a million pounds on Jake Paul. I think that AJ is a spent force, and I think Jake Paul is on the rise. I like his new heavyweight look. He is a bit chubby, a bit bulky, he is getting there.”

Rolando Romero, former junior welterweight champion:“Let me ask you this right? Why would Jake Paul fight Anthony Joshua unless he truly believes he can win? Jake Paul has plot armor. When you have plot armor it’s like watching Harry Potter right? … When you just have plot armor you’re gonna win no matter what.” (via Fight Hub TV)

Demetrious Johnson, former UFC flyweight champion:“I think Jake can knock him out — Anthony Joshua’s been knocked out by some weird ass shots before. Andy Ruiz and [Daniel] Dubois knocked him out with a short overhand right — Jake Paul can land one of those shots, he can. If Anthony Joshua doesn’t get on his bicycle, start moving around, and fight Jake Paul, he can destroy Jake Paul, but I don’t see that happening.” (via MightyCast)

SPORTS UPDATE Pros picking Anthony Joshua

Oleksandr Usyk, former undisputed cruiserweight champion, two-time undisputed heavyweight champion:“If Anthony Joshua wants, he will kill this guy. … Anthony Joshua is an Olympic champion, first. Jake Paul, yeah, a sportsman, a YouTuber, a showman. [Joshua is a] Rolls Royce, [Paul is a] Fiat. Listen, it’s true. It’s just true.”

David Haye, former two-division champion:“I hope we’ve got a referee in there who’s quite compassionate because if Jake Paul is left up against the ropes with Anthony Joshua unloading on him, it could be the end for him. It could be [Paul’s] last day on earth. In reality, it shouldn’t go ahead.” (via TalkSport)

Conor Benn, middleweight boxer:“What chance do I give [Paul]? My head straight away just goes ‘have the ambulance ready.’ Then part of me goes, ‘but listen, we live in a world where anything can happen.’ So, I give it maybe ten per cent. He’s got gloves, he’s got a chin, he’s got hands.” (via IFL TV)

Roy Jones Jr., former four-division champion:“It’s a tough task because like even with Francis Ngannou, Francis did well with Tyson Fury, but Joshua’s a different animal. Keeping it real, keeping it 100 percent with you, if you had a hard time beating Tommy Fury, how do I believe that you beat Anthony Joshua? … Your only chance is to land that home run hit.” (via The Sun)

Lennox Lewis, former undisputed heavyweight champion:“Yeah…. Entertainment and money make strange bedfellows. This should be easy work for AJ tho. Shout out to Jake for stepping into a fight like this. I didn’t see that coming.” (via X)

Tommy Fury, former Paul opponent:“If I can beat Jake then — excuse my French — what the f— is Anthony Joshua going to do to Jake?” (via Stomping Ground)

Who wins Anthony Joshua vs. Jake Paul on Dec. 19, and which massive longshot prop should you target for a huge payday? Visit SportsLine now to see Josh Nagel’s best bets for the FridayDec. 19, heavyweight bout, all from the combat sports specialist who has covered the sport for more than 20 years, and find out.