Skip Bayless has never been Floyd Mayweather’s biggest fan - with the American sports reporter frequently siding against the boxer.
He notably predicted Manny Pacquiao would defeat Mayweather, and after the Filipino lost via decision in May 2015 Bayless sided with Pac Man's excuse that he had an injured shoulder, and cited ‘Money’ would lose a rematch.
Two years later when Mayweather took on UFC star Conor McGregor, who had never boxed before, Bayless told FOX Sports colleague Shannon Sharpe that The Notorious would be too big and win the fight, despite being a debutant to the sport.
Many believed Bayless siding with McGregor was one step too far in terms of trolling - but Mayweather is again the topic of discussion after making his own questionable decision with the shock announcement he will fight a Japanese kickboxer on December 1, in Tokyo, Japan.
Mayweather is set to meet Japanese kickboxer Tenshin Nasukawa on December 31, in Tokyo, Japan with MMA promotion RIZIN Fight Federation promoting the event - and Bayless and Sharpe discussed the news on their show: Skip and Shannon: UNDISPUTED.
Bayless has his say on Mayweather's announcement
Bayless, for once, seemed honest in his evaluation of possibly Mayweather’s most surprising move, and claimed the McGregor bout has more credibility.
“So I’m just guessing that somebody in Tokyo pretty much guaranteed Floyd Mayweather Junior dare I say $100 dollars to take on their MMA star, and box him,” Bayless said.
“I’m pretty sure Floyd’s not going to be doing an MMA fighting, I don’t think so. So the kid is going to box Floyd, the 20-year-old - and it’s going to be a farce and Floyd will toy with him, and play around with him.
“At least I gave Conor McGregor some chance, and I thought Conor acquitted himself pretty well. He hung in there and at least it was fun to watch and I paid my money for it because it deserved my money.”
Mayweather has made an estimated $1.3 billion dollars in his career with almost $500m of that being generated in his last three contest, leaving Bayless to question what the motivation was for this bizarre fight.
“So if (Mayweather) is going to make 100-plus-million dollars what price is your credibility? Seriously, would you sell you your competitive soul for that?
“It’s not worth it because at some point we’re going to remember Floyd for this - like at the end of his career, he’s 41-years of age.
“Is it possible he needs the money? It just can’t be. I just don’t get what’s the win in it for your legacy?”
It’s hard not to agree with Bayless’ comments, as it seems clear this fight cannot do anything to boost the already unblemished legacy Mayweather looked set to leave behind him.