NEW YORK – Rapper-turned-boxing promoter Curtis “50 Cent” Jackson is skeptical about whether his former business partner Floyd Mayweather Jr. will fight six times over the next 30 months, as is reportedly planned in the new deal that brought the pound-for-pound king to Showtime pay-per-view from HBO.

“I doubt it strongly,” said Jackson at a press conference Wednesday afternoon to announce his client Billy Dib’s IBF featherweight title defense this Friday at the Foxwoods Resort in Mashantucket, Conn. Jackson’s SMS Promotions will promote the event, which will be televised by ESPN2’s Friday Night Fights, alongside DiBella Entertainment and Top Rank.

Jackson’s skepticism is well-founded; Mayweather (43-0, 26 knockouts) has fought just once a year since 2009 after taking off 2008 due to “retirement.” Fighting six times in 30 months would mean Mayweather would have to fight once every five months, something he hasn’t done since 2005.

Still Jackson, who was a fixture of many of the 36-year-old veteran’s promotions leading up to fights, says the deal, which begins on May 4 when Mayweather faces Robert Guerrero at the MGM Grand in Las Vegas, was a savvy one.

“I think it’s a good deal for him. I think if they can keep exciting enough opponents in front of him to continue sustaining a million views, it’ll make sense. If he starts to fight guys that don’t…,” said Jackson trailing off.

A Forbes.comarticle last week reported that Mayweather could stand to make between $200 and $250 million, with more revenue coming from rights as the events’ lead promoter.

Jackson’s passion for boxing was cultivated as a young man growing up in the Jamaica section of Queens, N.Y., where he competed as an amateur boxer before hitting it big as a hip-hop artist.

Now as a promoter, Jackson handles the careers of Dib, WBA super featherweight interim titleholder Yuriorkis Gamboa, super middleweight contender Andre Dirrell and Donte Strayhorn, a Cincinnati-based amateur standout who makes his professional debut on Friday’s card.

“It started with me wanting to collaborate with Floyd because I don’t see anything else that he’s passionate about,” said Jackson. “If you don’t have income away from boxing when you’re not boxing, what can you expect? I was trying to help develop what happens for him following fighting. I hear him think out loud and say ‘I think I got two or three more left in me.'”

He says his friendship with Mayweather, which resulted in a short-lived partnership as “TMT Promotions,” or The Money Team, remains intact despite their business rift and public feuding on Twitter.

“He’s like my brother,” said Jackson. “You ever have an argument with your brother? Then you know what I go through.”

Jackson left the press conference with one parting shot against Mayweather, after a reporter praised Mayweather’s choice of competition.

“You must be down with the ducking and dodging then,” said Jackson, before leaving the dais.

Photo / Isaac Brekken-Getty Images

Ryan Songalia is a member of the Boxing Writers Association of America (BWAA) and contributes to The Ring magazine and GMA News. He can be reached at [email protected]. An archive of his work can be found at www.ryansongalia.com. Follow him on Twitter: @RyanSongalia.