Huh? Nate Diaz drops massive wager on Jake Paul to defeat Anthony Joshua

Nate Diaz learned firsthand about Jake Paul’s boxing talents.

The UFC fan favorite squared off versus “The Problem Child” in August 2023 for 10 rounds of boxing. Unfortunately, Paul largely dominated the contest, including a nasty knockdown in the fifth round (watch here). In typical Diaz style, he’s made some excuses about a suboptimal training camp and accepted a possible rematch as recently as a few weeks ago, but Paul instead opted to fight former world Heavyweight champion Anthony Joshua.

Joshua is quite literally a giant step up from Paul’s original opponent, the embattled Gervonta Davis. 6’6” and 36 years of age, Joshua is not only bigger than Paul, he’s closer to his prime than most previous Paul opponents. As a result, he’s widely expected to mop the floor with “The Problem Child.” Diaz, however, sees opportunity in his former foe, and he’s backing Paul to the tune of $20,000.

“I’m betting on this b—ch,” Diaz wrote on Instagram, while his X post stated, “I’ll takem both out same nite MMA fight.”

On the whole, it’s been a quiet year for Diaz overall. Since exiting the UFC in 2022, he’s competed as a boxer just twice, losing to Paul and then winning a controversial majority decision over Jorge Masvidal in July 2024. Both Diaz and Masvidal had difficulty getting paid for their boxing match, so perhaps tracking down his purse in the court of law has kept Diaz busy in 2025.

As for whether Paul can pull off a Miami miracle and septuple Diaz’s investment? We find out on December 19.