Queens, New York veteran MC Akinyele has not released an album of new material in more than 15 years. However, the raspy-voice rapper remains very much tied to the Hip-Hop culture he came up through. DJ Khaled and Drake’s current hit “For Free” is an homage to a 1997 single by Ak’ of a similar title. Not far from Khaled’s home, the onetime Interscope Records artist now devotes his time to an ownership stake in Miami, Florida gentlemen’s club, King Of Diamonds. In an effort to expand his business and change legislation in South Florida, Akinyele has now begun campaigning to become the mayor of South Beach.

In the latest episode of the Drink Champs podcast, Akinyele speaks with fellow Lefrak City native (and friend) N.O.R.E. and DJ EFN about his political aspirations, his foray into strip clubs, and why he charged Khaled nothing for the rights to sample “Fuck Me For Free.” To Hip-Hop fans, the discussion about Akinyele’s early 1990s days may be most interesting. Alongside Nas and Joe Fatal, Akinyele would make his music debut on Main Source’s “Live At The Barbeque.” Notably, when MC Serch made another similar posse cut one year later in “Back To The Grill,” he tapped Chubb Rock, Red Hot Lover Tone, O.C. as well as Nas and Akinyele. Ak’s verse would not make the release—though he still has the tapes.

Relive The First Time Main Source, Nas, Akinyele & Fatal Performed Live At The BBQ (Video)

However, in revisiting those early ’90s days under the tutelage of Large Professor, Akinyele provided some interesting context surrounding the eventual 2000s battle between Nas and Jay Z. In 1991, Main Source and Jaz-O (a/k/a The Jaz) would co-headline a tour, promoting Breaking Atoms and Ya Don’t Stop, respectively. This was where the famed Jay Z takeover line “I showed you your first Tec, on tour with Large Professor / Then I heard your album about your Tec on your dresser” allegedly came to be—and Ak’ says it’s 100% true.

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After discussing his early days roaming New York City with Nas and cyphering with The Notorious B.I.G. and 8-Off Agallah, Akinyele talks his role between Jay and Nas. (34:50) “I would see Jay Z at skating rinks. We’d sit there and just rhyme to each other, for a minute. Time after time, we’d just go at it—[back and forth rhyming]. After that, we became friends. It was funny, ’cause I met Jay Z when he was with Jaz-O.” Here, Ak’ recalls that important set of concert dates. “Me and Nas was [down] with Large Professor and [Main Source, who was signed to] Wild Pitch Records. We was on tour together.” He continues, “Jay Z was with Jaz; me and Nas was with Large Professor. They were singin’ ‘Hawaiian Sophie;’ we were singin’ ‘Live At The Barbeque’ every night. We got good. Me and Nas, our per diem was like $10 a day. We got $10, and we had to split it.” The hopeful understudy rappers Akinyele, Nas, and Jay Z grew closer through the tour. “At that point, we all bonded. When we bonded, we was like, whoever makes it first gotta drag the [others]. Eventually, Nas was the one who broke out first. So me and Jay felt like, ‘Yo, this dude [made it. So] who’s AZ? Who’s Foxy [Brown]? Who are these people [in] The Firm? [Laughs] The Firm, they’re movin’!”

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Akinyele’s timeline is interesting. Of the three artists, he would be the first to release an album, care of 1993’s Vagina Diner. Released through Interscope, the album’s title, artwork, and subject matter caused it to be pulled from many shelves. Produced by Large Professor, the LP remains an out-of-print collectors item—that did not allow commercial success. He reveals that Interscope signed him for $500,000 in the early 1990s. It would be the only album he released with the label. Nas, although he signed (according to Akinyele) “a bad deal” with MC Serch’s Serchlight Publishing, would release 1994’s Illmatic to phenomenal acclaim, and a #12 chart spot. While Large Professor handled much of the production, the only vocal guest was a then-unknown MC named AZ. AZ was promptly signed by EMI Records following the appearance. As Nas would take AZ and build out a late ’90s team known as The Firm (with Foxy Brown, and eventually Nature), Akinyele alludes to the feeling that he and Jay Z may have been passed over.

“So then me and Jay Z got real cool. When we got cool, every night we’d go out on the road together. He’d sing ‘Ain’t No Nigga;’ I’d sing ‘Put It In Your Mouth.’” Notably, 1996’s “Ain’t No Nigga” (produced by Jaz-O) would feature Foxy, who was also working closely with Jay. “We’d practice shows together. Me, him, Dame Dash [would] hit the stage every night.” By 1995 and 1996, success continues to shuffle the deck for the friends. “Nas is [famous]. Then Jay Z starts taking off. So when Jay Z starts takin’ off, it gets weird now. Me and Jay, we’re in a different place [comparatively]. It was ‘a.k.a.fella’ and ‘Roc-A-Fella Records.'” On Akinyele’s most successful single, ’96’s “Put It In Your Mouth,” he re-introduced himself as “a.k.a.fella.”  He continues, “It got to a point where Jay Z got real big. Me and Nas was always best friends, from [the days] with Large Professor. So with Jay Z, Jay was so big that it got to the point where when you’d put a record out, you’d have to go to Jay and be like, ‘Yo Jay, I’m gonna put a record out in October. Is it cool?’ He’d be like, ‘Alright.’ It got to the point where I went to Jay like, ‘You got this #1 spot. This isn’t right, man.’ [Laughs] I felt a way. You’re here—we’re over here. Even when I see him [these days], I’m like, [jokingly] ‘Sup! Let me hold something.’ [Laughs]

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Due to this weird middle relationship between the two New York Rap giants, Akinyele says he was later pitted as a go-between. “If you listen to Dame Dash, Dame will say, ‘Akinyele started the whole beef.'” In the conversation, N.O.R.E. recalls hearing the same accusation from Dame. Explaining why, Ak’ says, “Because me, Jay, and Dame would sit in a room, and I’d be like, ‘Jay, this isn’t right.’ He’d say, ‘What’s not right?’ I’d be like, ‘That [you’re so successful, and Nas and I are not in the same league]. Now, Jay was moving! Remember, we was all friends [since we were eating] bologna sandwiches. I’m talkin’ to him at a different angle. ‘This isn’t right.’ He was like, ‘Whatever.’ We got real cool. Then they went at each other. And when they went at each other, me and Nas was always cool…I think Dame kind of blamed me because me and the both of them was always cool. Me and Nas came in [the industry] together. Me and Jay kinda hitched up because when Nas started blowin’ [up, Jay Z and I were left behind]. When Jay was blowin’—when they caught their deal with Def Jam, I’m thinkin’ a.k.a.fella, Roc-A-Fella [why shouldn’t we be in business together?] It got kinda different.” Jay Z’s 1996 debut album Reasonable Doubt became a Top 25 debut. His 1997 Def Jam follow-up, In My Lifetime, Vol. 1 debuted at #3.

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By the early 2000s—when the feud escalated, Akinyele said that he was only hearing from both parties when they heard bad news surrounding him. He praises all three (including Dash) throughout the interview though. Besides a 2004 compilation of rare unreleased, demo, and live material, Ak’s last album release was 2001’s Anakonda.

In 2005, Jay Z would sign Nas to Def Jam Records in a public peace offering. Nas, who co-owns Mass Appeal Records today, reportedly has one album remaining on his Def Jam contract.

Elsewhere in the lengthy conversation, he discusses owning his publishing, his Manhattan strip clubs in the 1990s, and saving Nas’ from retiring from Rap as a teenager.