"He's doing it again. He's dropping hints. He's telling Freddie Roach, 'Get ready to train him,' because he knows Freddie will spread this news like it's fertiliser. And he knows, Floyd does, that he can now lead people to believe this fight is this close to happening," Bayless said.
"And when it gets that close, in the end Floyd will bow out and he will make the excuse that Conor McGregor is making 'outrageous, unrealistic demands.' He does it every time, because he wants no part of Conor McGregor."
Legendary boxing trainer Roach has coached the likes of Manny Pacquiao and Miguel Cotto in recent times and confirmed that Mayweather had attended his gym to ask him to help the UFC champion.
"Floyd actually came to my gym and told me 'Freddie, I heard that Conor had talked to you,' and I said, 'No, he never has,'" Roach said on the MMA Hour.
"But he said, 'If he reaches out to you and wants you to train him,' he says 'I would take that job, because I am going to fight him,' and he says 'we can all make a lot of money.'
"So according to Mayweather, yes, he told me he would fight him. Everything is pointing in that direction right now."
While Bayless may have his doubts over the bout ever happening, his co-host Sharpe doesn't agree. He feels the ridiculous amount of money the fight will generate is enough to convince Mayweather and McGregor to sign on the dotted line, and that the potential bout will shatter all existing records in the fight game.
"There's a simple creed in professional sports or any business: If it makes dollars, it makes sense," Sharpe said.
"This makes plenty of dollars, and it makes a lot of sense. Because let's just say when Floyd Mayweather fought Manny Pacquiao, it did 4.4 million buys. Over $400 million in pay-per-view dollars, and the gate was $72 million.
"A lot of people are going to watch (because) 'I want to see Floyd get his butt kicked.' A lot of people are going to watch (because), 'I want to see Conor get his butt kicked.' Now let's see what these styles are going to do stylistically, because they're totally different."
But Bayless feels no amount of money will be enough to tempt Mayweather into a fight with McGregor.
At almost 40 years of age, Mayweather will come up against a UFC champion in his prime, who despite having limited boxing experience has the knockout power to potentially hand Mayweather his first career defeat.
"He (Mayweather) cannot risk this. He cannot risk losing to some MMA fighter and going 49-1 and having his legacy tarnished and tainted, with the disgrace of losing to Conor McGregor," Bayless said. "Can you imagine what it would be to Floyd's career? He doesn't need this. Do you realise Floyd May-or-May-not-weather is about to turn 40 on Friday and Conor McGregor is still 28 years of age?
"Floyd May-or-May-not-weather is about to become a has-been. And what he is doing right now, he is using Conor McGregor to stay relevant. Because no one really cares about his Hermes bag or whatever it is ... That's about all he's got going right now.
"He is using Conor McGregor to keep Floyd's name in the news. He wants no part of this because he's too shrewd to want a part of this. Because he sees Conor McGregor, as Freddie Roach will be the first to tell you, has punching power. I think he has punching power that Floyd hasn't seen before.
"And I believe that Conor McGregor is the baddest man on the planet, and that Floyd sees it and knows he's just crazy enough to hang in with that little rat-a-tat, gnats on the windshield kind of punches, the pillow fight that is now Floyd Mayweather Jr."
In contrast, Sharpe believes the power struggle that exists between Mayweather and McGregor should firmly lay in the hands of the boxing star.
Mayweather is a noted pay-per-view draw and his career figures far outweigh what the UFC have been able to achieve. Floyd was a large part of the biggest fight in history and that confirms that he is the man fans hand over their hard-earned money to watch.
He feels his ploy to attach Roach to McGregor is Mayweather's way of making the matchup seem credible and a legitimate contest.
"What Freddie Roach said yesterday, it legitimatizes Conor McGregor, because there's only a few people he can go to and get legitimate boxing knowledge. Freddie Roach, John David Jackson, Naazim Richardson, etc," Sharpe said.
"So now, Floyd says, 'Hold on, Freddie. This gonna happen. I'm going to make me about 5, 600 million on this. Man you better train Conor McGregor and get yourself $5-10 million of this money because it's going to happen, and you need to be a part of this'.
"You noticed I said when Manny Pacquiao and Floyd Mayweather fought at the MGM, the gate was $72 million. Conor McGregor fought at Madison Square Garden, 20,000-seat arena. Made $17.7."
