Dana White has built a reputation not just as a fight promoter, but also as a prolific gambler who puts serious money on the line just for the fun of it. Known for his high-stakes gambling habits, White often backs his instincts without hesitation. But ahead of the boxing debut of a former NFL star, the UFC boss has now placed a huge but equally unusual $10,000 wager on him.

Uploading a clip on his social media platforms, Dana White announced that former NFL quarterback Johnny Manziel, who made history in 2012 by becoming the first freshman to ever win the Heisman Trophy, will face comedian and former Nelk Boys member Bob Menery in a celebrity boxing match under streamer Adin Ross’ Brand Risk Promotions on May 16. Both celebrities will be making their boxing debut at the event. Ahead of the event, the UFC head honcho placed a $10,000 bet on Bob Menery not even showing up for his fight with Manziel.

“So, you guys have seen all the stuff that’s going on with me and Nelk and Bob Menery over the years,” White stated in a recent clip on X. “Menery is back and he has supposedly signed a deal at Adin Ross’ fight showdown in Miami to fight Johnny Manziel, okay! So Menery hits me up and says, ‘Who are you betting on? I’m betting on you don’t even show up, that’s my bet.’ Menery never does anything that he says he’s gonna do.

“Adin Ross’s fight show in Miami: Menery vs. Manziel… I’m betting $10,000 Menery doesn’t show up. And Bob, if you do the night before it looks like you’re gonna fight, I’m flying to Miami to watch this one.”

Despite White’s confidence in the ex-NFL star, the former Cleveland Browns QB isn’t without controversies himself. During his NFL career, Manziel grabbed headlines due to his persistent off-field behavioral issues and legal challenges. In March 2016, the Browns released him after his lifestyle hindered his ability to fully commit to the team. The same year, Manziel was also involved in a domestic violence case, with charges later dropped in 2017. Following his release from the Browns, Manziel also played in other leagues, like the CFL. However, there is no history of his boxing before this one.

Even with that history attached, the UFC CEO decided to bet on Menery for not showing up at the event. What’s the reason? Well, Dana White and Bob Menery have a complex past. The comedian and social media personality claimed that he introduced the UFC boss to Nelk Boys’ Kyle Forgeard, sparking their business relationship. In 2022, Menery got into a payment dispute with the Nelk Boys and ended up splitting from them. According to the podcaster, the Nelk Boys owed him $1.2 million, while Forgeard claimed that the comedian was paid fairly.

Amid the developing beef, Menery started uploading clips to social media, bragging that he introduced Dana White to the Nelk Boys, which turned into a successful partnership. The UFC CEO accepted it, yet he sided with the Nelk Boys during the dispute and lambasted Menery on Instagram, calling him a “crybaby p—s” for splitting from Kyle Forgeard and company.

This has prompted Dana White to bet $10,000 against Bob Menery not actually showing up for the event. Still, the ex-Nelk Boys member remains excited to perform in his first-ever boxing match.

Bob Menery promises a ‘good old scrap’ at Adin Ross’s boxing event   

Adin Ross’s boxing promotion, Brand Risk, has already featured multiple events with a somewhat unique ruleset. Unlike traditional boxing, it leans more toward amateur-style fighting with gloves, giving the event a chaotic, Dirty Boxing-like vibe. Previously, former UFC light heavyweight champion Quinton ‘Rampage’ Jackson appeared on the stream alongside other creators like NEON and commented on the unpredictable nature of the fights.

So, keeping that chaotic atmosphere alive, Bob Menery shared his thoughts on the upcoming bout with Johnny Manziel. He also claimed he is putting his entire paycheck on the winner of the fight.

“We both agreed even tho a boxing event, no boxing, just a good old school scrap,” the comedian posted on Instagram. “One and done. Bucket list. Had to do it before I die. I put my entire paycheck on the winner. I will not be receiving a dollar unless I win. @kyle and @steiny too big of p—s.

“Good on Johnny to step up. Just another million+ in ur pocket for your boy. I love you. But I will try to kill you on that day. This s—t gonna be fun. Main event too 👀 💪 I alwyas love being an underdog @adinross @brandriskpromotions.”

With Dana White’s high-profile bet adding fuel to the fire, the celebrity bout is now positioned to draw a much larger audience than initially expected.