LAS VEGAS - This time, he even took his closest friend and advisor by surprise.
Leonard Ellerbe, CEO of Mayweather Promotions, said during Wednesday's final press conference that when Floyd Mayweather mentioned in passing during a reporters' roundtable, and reiterated later that Saturday night's welterweight title fight against Marcos Maidana could be his last, even Ellerbe was taken aback.
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"I was shocked," Ellerbe said. "It was news to me. Obviously we have a long-term deal with Showtime. But we never know. Come Saturday night, this could be it."
This is the third fight of Mayweather's lucrative six-fight contract with Showtime, and he will make a guaranteed $32 million for the pay-per-view bout Saturday (Showtime, 9 p.m. ET).
"I'll be honest with you, I've been contemplating every day talking about getting out of the sport right now," he said during the reporters' roundtable, noting that he's really comfortable in every aspect of his life. He also mentioned his desire to buy the Los Angeles Clippers.
Mayweather, 37, talked retirement again Wednesday after the press conference, saying he was ready to settle down and get married.
"It's not really hard. If I choose to walk away, I'll walk away. It's just me being a human being," he said. "If an artist wants to stop painting, then he stops painting. It's like, 'I've reached my limit.'
"I'm thinking about wanting to settle down, get married and have a family."
Showtime Sports President Stephen Espinoza said it shouldn't come as a surprise that Mayweather is contemplating retirement.
"He is coming off a record-breaking year and he's been at this for nearly 20 years," Espinoza said. "He's achieved everything he's ever dreamed of.
"So it's not surprising that this issue of retirement has come up."
Espinoza noted that Mayweather got choked up during the press conference, which struck him as particularly poignant.
"There was a moment where he was talking about (co-trainer) Nate Jones, who he has had a relationship with for over 20 years," he said, "and we saw a moment when he looked at Nate and he realized how far he'd come in the last 20 years. ... We all saw it sink in right at that moment.
"That genuine emotion tells me it really is on his mind."
Asked what it would mean for his deal with Showtime, Espinoza said, "I wouldn't begrudge him that. He's never shortchanged the sport.
"Doesn't mean I wouldn't try to talk him out of it and make it really attractive for him to come back a couple more times. But certainly, if he decided to retire, he's earned it."
Richard Schaefer, CEO of Golden Boy, has helped orchestrate Mayweather's career the last several years and has helped him become incredibly wealthy.
His last fight against Canelo Alvarez in September was the highest-grossing fight of all time and made Mayweather a guaranteed $41.5 million, plus much more from the 2.2 million pay-per-view buys.
"Obviously, you have to listen to him, and it's his career and it's his thing. I haven't discussed it with him so I can't tell you how serious this is," Schaefer said.
"He also mentioned yesterday that he might even fight past his contract with Showtime. There's a lot going through his mind, and we'll have to see how he feels.
"I do hope as a fan and for the sport that this is not his last fight."