• Undefeated Star Wanted To Lose To The Big Show
Floyd Mayweather’s clash with The Big Show at WrestleMania 24 remains one of WWE’s biggest celebrity matches. The undefeated 50-0 boxing legend earned $20 million for going one-on-one with The World’s Largest Athlete, a match he ultimately won.
According to WWE Chief Content Officer Triple H, Mayweather actually wanted to lose that match, at a time when he was at the peak of his career.
This was revealed by country star and four-time Grammy nominee Jelly Roll during an appearance on INSIGHT with Chris Van Vliet.
Jelly Roll, who teamed up with Randy Orton to face Logan Paul and Drew McIntyre at SummerSlam 2025 in his debut match, shared that WWE originally planned for him and The Viper to win, but he personally requested to lose.
This led to Triple H comparing Jelly Roll’s mindset to that of Mayweather.
“It was originally, babyfaces up. So the day of, I’d been dropping it in on Shane (Helms) the whole time. Shane, I want to lose this match. And he was like, ‘Brother, you got to take that up with them.’
So I came down and me and Triple H talked about it right there at the ring that day. I said, ‘You know what I’m coming to talk about?’ He said, ‘I want to hear it.’ And I gave it to him. And he was like, All right, all right.
It was an easy pitch. It took three things. One, it’s the right thing to do, let’s just start at core values here. No celebrity has any business coming in and pinning a wrestler on their first run without some extreme circumstance.
Two, I can always come back, I don’t think any other celebrity ever really cared enough to think full angle through. Drew, too. If I really owe one of them, it’s Drew. So that was part two of it.
I was also smart enough to be like, Yo, I want to angle in. I don’t want to be remembered as a celebrity who did the thing, and then Triple H stopped me.
This will probably be on Unreal because it was so gangster. He said, ‘I will tell you this though.’ He said Floyd wanted to lose to The Big Show. I don’t know if I should be sharing that, but he told me that, and I thought that was cool.”
• Celebrity Wants To Have A 6 To 9 Month Full-Time Run In WWE
Country star Jelly Roll kicked off SummerSlam 2024 and helped Awesome Truth take out A-Town Down Under later in the show. He made his in-ring debut at SummerSlam 2025 and teamed up with Randy Orton to take on Logan Paul and Drew McIntyre.
During an interview on INSIGHT with Chris Van Vliet, the four-time Grammy-nominated artist said that he wants to return to the ring after suffering a loss in his first wrestling match and have a six to nine-month run as a pro wrestler.
“I wanna run it back; I wanna do one more; I know why Bad Bunny had to do Backlash now, because I know he walked out that ring that night knowing how much more he could give; I don’t really know what I want, I just know that I need to, and I promise y’all I’m not going to keep darkening y’all’s door.
But, one dream scenario is I want to get involved for a while. I’d like to wrestle every Friday. I’d like to get involved for a six to nine-month run.
I’ve definitely got to do one more, though, man. Just because… it’s like anything else in life. You do it once in life, and you think you were prepared, but you wasn’t. And, you leave there, and all I can think about is everything I know I could have done a little better.
I just started getting really comfortable bumping the week we went out. I’m so much more comfortable taking full-blown clotheslines now.”
Jelly Roll was also in attendance for Clash In Paris back in August.
