50-o retired boxing legend Floyd Mayweather chose the moniker ‘Money’ for himself. At the time, it didn’t make a lot of sense to change his established ‘Pretty Boy’ gimmick, but Mayweather made it work. Much like how he turned being one of the most hated boxers in the world into a business opportunity.
WWE Chief Content Officer and the to-be Hall of Famer, Paul ‘Triple H’ Levesque, joined comedian Andrew Schulz on his podcast to promote Wrestlemania 41 yesterday.
As the two discussed everything from John Cena turning heel to the infamous ‘Internet Wrestling Community’, the conversation eventually steered towards character work- something that nobody in sports entertainment does better than WWE.
In fact, Triple H even revealed that Floyd’s ‘Money’ gimmick came from a place of being a WWE fan growing up, and it helped with the idea of becoming a heel and selling that persona to become a multi-millionaire.
“‘Look, I knew ‘Pretty Boy Floyd’ was only gonna get so far…what’s the greatest box office, how do you make that? I need to create a character, and I need an avenue in which to sell the character“, Lesvesque said of a conversation Mayweather had with him.
Schulz further elaborated on the subject and explained that Floyd’s defensive style of boxing meant that he really had to improvise to make the money he did.
“He becomes this ultimate heel, and people were paying $70 to watch him lose, and he would never f*cking lose“, he noted.
But it wasn’t just about becoming a heel either. According to Triple H, Floyd did quite a bit more to complement this character he had put on for the cameras.
Floyd made himself look worse than opponents to sell fights
Floyd would go on to sell his ‘Money’ character on HBO as a reality show based on behind-the-scenes preparations for fights, his family, and his entourage. It gave fans a glimpse into the life of a real boxer, or so they thought.
It also very subtly presented him as someone who was possibly losing his way amid all the glamor and the glitz. This would also allow fans to believe his opponents actually stood a chance against him.
As Triple H explains it, “the genius of what he did was not only make people hate him, but I will make you believe… this guy’s got an unorthodox style and Floyd’s starting to get older, like he’s showing you flaws in his buildup of 24/7. ”
The focus of the show was to ensure the popular notion that he wasn’t training right and eating well, to make him look beatable.
At the same time, every sports channel ate up the storylines Floyd was airing and would go on to cover what his opponents were doing and just how well they were prepared to defeat him.
Triple H joked that hyping up his opponents was Floyd’s idea of generating interest, all while he was walking through fighters like Canelo Alvarez.
The WBA, WBC, and WBO Super Middleweight champion took on Floyd in 2013 as a promising young prospect who was widely believed to possess the ability to destroy the American boxer.
Reminiscing about the fight, Triple H, who was present at the arena, chuckled and said, “Remember the part where Canelo threw a big wild punch and he just (moves out of the way in slow motion), seeing like ‘who are you trying to punch?’”
Needless to say, it has all worked out for Mayweather, who, as of 2025, is worth half a billion dollars! And why wouldn’t he? After all, he was gaming the system 10 years before anybody else thought it.
