Grayson Gregory is not exactly a Floyd Mayweather Jr. fan, but he will be linked — and inked — to the fighter for the rest of his life. That’s because the 31-year-old on Monday got a tattoo on his leg of Mayweather’s face to pay off a lost bet.
Gregory, who runs operations for a social media marketing company, bet a co-worker last month that Conor McGregor would beat Mayweather during their boxing match in Las Vegas on Saturday. The terms of the bet dictated that the loser had to get a tattoo of the victorious fighter.
Here’s the result for Gregory:
For those of you that didn't know.. I made a tattoo bet that @TheNotoriousMMA would defeat @FloydMayweather.. Today I honored that bet. pic.twitter.com/Ap1eKPoYSz
— Grayson Gregory (@Grayson_Gregory) August 28, 2017
That tattoo appears on Gregory’s left shin nearby his other leg tattoo. He now has 7-8 tattoos total, he estimates, including nearly a sleeve on his arm.
So how did the tattoo bet come about?
Gregory says he was sitting around in his office with his business partner 5-6 weeks ago talking about the fight. Gregory is a big MMA fan and was so confident “in Conor’s belief that he could win,” that he was convinced to make the tattoo wager, he told Larry Brown Sports over the phone Monday.
Gregory bought into McGregor’s confidence so much that he took a straight-up wager even though McGregor was viewed as a heavy underdog entering what was his first professional boxing fight.
He doesn’t regret making a straight up bet, though he now cheerfully acknowledges that he was full of “pure bravado” and “just being an idiot with it” when he made the wager.
Gregory admits he was “nervous” before the fight began, knowing what was at stake.
Even as the fight was progressing and McGregor was showing signs of losing, Gregory still opted not to back out. The man with whom he made his wager offered him the chance to buy his way out of the bet for $250, but Gregory declined. By that point, he figured he would “ride or die” with his choice.
McGregor put on a respectable showing but lost via 10th-round TKO to Mayweather.
Less than 48 hours later, Gregory didn’t want to “chicken out” in his words, so he made the call to set up his tattoo appointment. He got the work done by Kenny Herring at Heritage Tattoo in Temecula, Calif. on Monday, with the cost of the tattoo being split evenly by Gregory and the winner of the bet.
Does he regret the bet and going through with the tattoo?
“Not at all,” Gregory told LBS. “I’ve been giggling ever since I did it.”
And even though he says he wears shorts a lot — exposing his Mayweather tattoo and the funny story behind it — Gregory says he will not cover up the ink. He also says he wouldn’t be afraid to put a tattoo on the line in a future bet, acknowledging that this “kind of opened up the floodgates.”
Gregory, who hosts the Prove Me Wrong Podcast, says he felt McGregor did well despite the loss.
“I thought he held himself very well. As a UFC fan, I felt we had a lot riding on in it,” Gregory said. “Granted we wanted him to win, but he wasn’t knocked out. All sides kind of won on it.”
Gregory hopes that McGregor will choose to fight Nate Diaz next in what would be the third fight between the men. For his sake, let’s hope Gregory doesn’t end up with a portrait of Diaz tattooed on his other leg after that one.
