Jake Paul may point to a couple of early rounds and claim small victories. But for those whose wallets grew lighter, that offers little consolation. Even if Paul’s assertions hold some truth, they do little for bettors who backed him with hard-earned money. The YouTuber-turned-fighter closed out the year with a highly anticipated and heavily debated clash against former heavyweight champion Anthony Joshua. The bout ultimately ended with Paul suffering the first knockout loss of his career.

The noise of the setback, however, echoed well beyond the ring at Miami’s Kaseya Center. Probably trusting Jake Paul‘s star power and promise of a Buster Douglas-style upset, several bettors placed wagers on him to topple Joshua. Among them was Adin Ross. The Kick streamer, who posted viral videos from Paul’s training camps, reportedly wagered $25,000 on Paul. The bet nonetheless backfired. It had made him the butt of jokes. Even Terence Crawford, who joined Ross during a studio appearance, couldn’t hold back once he learned of his ill-fated wager.

Terence Crawford mocks Adin Ross’ risky Jake Paul gamble

The interview took a humorous turn when Ross asked whether Paul’s team had reached out to Crawford ahead of the Joshua fight. After the scheduled exhibition with Gervonta Davis fell apart, Paul’s camp had reportedly explored multiple options. It included names such as Francis Ngannou and Ryan Garcia. Crawford was among those contacted. “Yeah, they reached out to the team,” the Nebraskan switch-hitter confirmed.

Switching gears, Ross then asked Crawford for his take on the fight itself. “Well, we all knew what was going to happen,” Crawford replied, echoing the sentiment of most boxing diehards. Ross, however, admitted he believed Paul had a chance. When he added, “Dude, Jake won the first two rounds,” Crawford was visibly stunned. How could Ross put his money on Jake?

“Everybody in the world that knows boxing knows if it wasn’t scripted that he was getting knocked out,” Crawford asserted, and dismissed Ross’s boxing knowledge entirely. When pressed, Ross confirmed he had indeed wagered $25,000 on Paul.

To Crawford, it was money poorly spent. He remarked that the sum could have been put to far better use, including charitable causes.

The night fans and celebrities chased a Jake Paul upset

While it is easy to take shots at Ross and others who believed Paul could pull off a historic upset against a bona fide heavyweight puncher, even one past his prime, the narrative reflects a broader trend. It’s about the behavior of casual fans entering the betting market.

Ahead of the match, Paul stepped in as a massive underdog. Yet, as a report from Morning Star reveals, his popularity as a YouTuber-turned-boxer seemingly drew casual bettors in droves. Many chased a life-changing payday by backing a heavy underdog.

And Ross was not alone. Rapper Drake reportedly lost $200,000 betting on Paul. So even high-profile bettors found themselves on the wrong side of public sentiment.

From a business perspective, however, the Paul-Joshua fight appears a resounding success. The Netflix broadcast reportedly drew more than 33 million viewers worldwide. While bettors may have backed a losing underdog, the episode once again highlights Jake Paul’s impact on boxing, sportsbooks, and the streaming platforms.