This week, VladTV asked Big Daddy Kane, in the multi-part interview, if he’d battle longtime rival, contender as one of the greatest MCs of all-time, Rakim. Specifically, DJ Vlad  proposed the notion of the Brooklyn, New York Juice Crew legend taking on his Long Island, New York contemporary for a $500,000 purse. “Sure I would do it,” said Kane, at the notion of winning half-a-mil.

“I was supposed to battle Rakim back in ’89,” Big Daddy Kane revealed in this week’s interview with VladTV. “What happened was there was this PayPerView event called ‘Rap Mania.’ And they televised it in ’88 and it made a lot of money. They made great numbers. So, the guy Van Silk was financed again to do it the following year. So, that year he chose to do Rap battles instead. So, he had Sparky D versus Roxanne Shante confirmed, [The] Furious Five versus Cold Crush [Brothers]. And LL [Cool J] told him that he would be willing to battle Kool Moe Dee if he could confirm the [Big Daddy] Kane and Rakim battle. To my understanding, we were gonna do it. And then Van Silk asked me can I talk to Eric [B] and Ra because he said they were having a problem.”

Kane reached out to longtime friend Eric B, who was Rakim’s band-mate as Eric & Rakim. “I talked to Eric, he said it’s going down. And then a few days later Van Silk called me back and was like ‘I don’t think it’s Eric. Is it any possibility you could call Rakim?’ And I was like ‘I don’t know dude like that. I don’t have his number and I don’t know dude. You gotta work that out on your own.’ And then they upped the ante. ‘Cause it was like for $50,000 apiece. And then they upped it to like 75. But it never happened…They ended up cancelling the whole thing.”

Back in the late 1980s, Kane and Rakim both worked extensively with producer/DJ Marley Marl. Legend has it that Rakim had multiple songs with lines directed at B.D.K, including unreleased tracks “Hypnotic,” “Break The Wrath In Half,” and a demo version of “Let The Rhythm Hit ‘Em.” In 2009, asked about a purported battle, Rakim told BET.com, “As far as I’m concerned, I would have put a new hole in my dude’s…nah mean?” With a laugh, he added, “I love you, my dude.”

Kane has long maintained that he never addressed Rakim in a song.

In the 2010s, the pair has performed together, most notably at Harlem’s Apollo Theater last month.

Think with this story, the $500,000 battle could ever, finally, happen? If so, who’s winning?

Related: Big Daddy Kane Says He Asked Kool Moe Dee For A Battle When He Was 14 (Video)