When Jake Paul announced his intention to become a boxer, most didn’t take him seriously. Remember his first fight? The Disney star went against Deji Olatunji. Cut to seven years later, and YouTube star-turned-boxer Jake Paul is currently on a collision course with former WBC middleweight champion Julio Cesar Chavez Jr. However, his dream was to fight someone else entirely. Who? If you haven’t been living under a rock, you must know by now that ‘The Problem Child’ initially intended to fight two-time undisputed super middleweight champion Canelo Alvarez. Contracts were signed, and the hype was there. Unfortunately for him, the fight never happened.

‘Cinnamon’ instead chose to sign a four-fight deal with GEA Chairman Turki Alalshikh, which has set him on a path to produce the biggest fight of 2025 against two-division undisputed champion Terence Crawford in September. Paul’s initial reaction was to attack Canelo, and he continues to do so every opportunity he gets. However, besides the mega purse Paul would have made from the fight, now it appears ‘El Gallo’ missed out on making a whopping $20 million from the Canelo fight. 

“I can bet on myself,” Paul told ‘The Iced Coffee Hour’ when the hosts of the podcast grew curious about whether fighters can bet on themselves. “I was going to bet against Canelo, I was going to bet like 2 million on myself.” This prompted one of the hosts to question Paul whether he had placed a bet on himself to win the Mike Tyson fight. “No,” Paul replied, explaining that betting on himself in the Tyson fight, which unfolded last November in Texas, would have been fruitless. Why?

Well, in the Tyson fight, Paul was the betting favorite to defeat 58-year-old Mike Tyson. However, that would not have been the case if he had fought Canelo Alvarez. “But with Canelo, I would have been probably like a plus 1,000 underdog,” Paul continued. “If I [had] bet $2 mil, I probably would have made like $20 [million],” he concluded, regretting his $20 million loss. It’s worth noting that though a boxer is allowed to bet on themselves to win, they can’t bet on their own loss. 

There are strict regulations set in place to avoid match-fixing by sanctioning bodies, and violating one can result in severe consequences. Even when boxers place bets on themselves, they have to disclose those bets to the sanctioning bodies to avoid suspicion of malpractice. Regardless, Paul has now received a serious warning from a potential opponent. 

World champion asks Jake Paul to start planning his funeral

Even though Chavez Jr. is the one Paul will fight next, jabs are being exchanged between Paul and his potential next opponent. WBO cruiserweight champion Gilberto Ramirez recently delivered a chilling warning to ‘The Problem Child’ after Paul had expressed interest in a fight against him for his WBO strap. 

While acknowledging Paul’s success and hard work, Ramirez told World Boxing News, “He’s a YouTuber at the end of the day. There are levels to this game.” Ramirez is set to fight Yuniel Dorticos on the Paul-Chavez Jr. undercard, but claimed he’d be open to facing Paul next. And in case Paul is ready, Ramirez had a haunting message for Paul.

“He knows best for himself to stay away from a real fighter like myself,” Ramirez added. “All talk is cheap. But Jake Paul knows he should plan a funeral if he commits to a fight against me.”

That said, Jake Paul not only lost out on making $20 million, but he also seems to be getting serious threats from fighters he intends to square off against. However, do you really think Paul would have won the Canelo fight to make that money?