Jake Paul has shocked the combat sports world before, but this time the mountain he’s chosen to climb looks more like Everest. On December 19, he’ll stand across from Anthony Joshua, a former two-time heavyweight champion, an Olympic gold medalist, and a man who has spent his entire career inside the true land of giants. Paul, who has danced between cruiserweight and celebrity-driven crossover fights, now steps into a sanctioned heavyweight bout with around 250 pounds of danger staring back at him.

The question practically asks itself: what exactly is he walking into? And if you ask Conor McGregor’s long-time coach John Kavanagh, the answer only takes five words. His prediction came during his recent appearance on The Ariel Helwani Show on YouTube, tucked between discussions about McGregor’s future and other MMA headlines.

When Helwani asked, “Who wins that one by the way?” Kavanagh didn’t hesitate. He didn’t build suspense. He didn’t offer qualifiers. He simply said in the interview, “It has to be Anthony.” Five words. No elaboration needed.

Why so confident? Because this matchup isn’t just unusual, it’s unprecedented. Jake Paul was originally set to fight Gervonta “Tank” Davis in a 195-pound exhibition. But that event collapsed when Davis faced a lawsuit over multiple serious allegations. Paul scrambled for a replacement, determined to squeeze one last fight into 2025.

Instead of another celebrity matchup, he ended up with Anthony Joshua, a man whose lowest pro weight is reportedly 229 lbs. The skill gap is massive. The size gap is bigger. Joshua has knocked out 25 opponents, fought on the biggest stages in boxing, and once unified the heavyweight division. Paul, despite improvements and a dominant win over Julio Cesar Chavez Jr. in June, has never faced someone who weighs 250 pounds and throws punches like bombs, just ask Francis Ngannou.

According to Most Valuable Promotions, Paul wanted to remain active before the year’s end. Talks swirled with several names, but once Anthony Joshua recovered from elbow surgery and expressed interest in a late-2025 return, the opportunity emerged. Paul had already placed Joshua on his “hit list,” expecting the matchup to happen in 2026.

Instead, timelines collapsed, negotiations clicked, and suddenly the YouTuber-turned-fighter was preparing for eight three-minute rounds under full heavyweight rules. But who were the other options that were laid out before him?

Terence Crawford and Ryan Garcia were being looked at as opponents for Jake Paul

Before Jake Paul landed Anthony Joshua, Netflix cast a wide net, and the process behind it was far more chaotic than fans first realized. When Gervonta “Tank” Davis was removed from the November card due to escalating legal troubles, the streaming giant scrambled. They needed a replacement, and not just any replacement, a legitimate challenger capable of headlining a global event.

So who did they put on the table? According to reporter Mike Coppinger, “Basically, what I am told is that Netflix came in and said, ‘Look Jake, we need a legitimate challenger for you now. Here are three names, Ryan Garcia, Terence Crawford, and Anthony Joshua.’ Ryan Garcia unavailable as he tries to close a deal with Mario Barrios. Terence Crawford, I am told, said no.”

Garcia, Coppinger revealed, was unavailable as he worked to finalize a deal with WBC welterweight champion Mario Barrios. Then came Terence Crawford, the pound-for-pound king who recently cemented his legacy by defeating Canelo Alvarez. His response? Just one word, no.

As per the report, Crawford wasn’t interested in a crossover spectacle, even with Netflix’s backing. With Garcia busy and Crawford unmoved, only Joshua remained, and suddenly the wildcard option became the front-runner. But what a gamble it is.

Anthony Joshua comes with enormous power, a heavyweight pedigree, and far more experience than anyone Jake Paul has ever faced. Even with the reported  245-pound weight cap, AJ has fought above that number multiple times. And while he may no longer be in his prime, especially after being knocked out by Daniel Dubois in his last fight, he is still the same man who flattened Francis Ngannou with a single shot. Do you agree with John Kavanagh’s prediction, or do you think ‘The Problem Child’ just might shock the world? Let us know your thoughts in the comments below!