Ambassadors of the Harlem streets, the Diplomats have always repped the criminal lifestyle to the fullest in their music and, as recent events would indicate, in real life as well. With the incarcerations of Hell Rell, Freekey Zekey, and now affiliate Max B, the crew that once boasted “diplomatic immunity” from the authorities seems to be anything but above the mercy of the law. Legal woes have never stopped the Diplomat collective’s loyalty: constant shoutouts to locked up members (“Freakey Zeekey hold ya head up, you already know what it is!”), and even acapellas delivered from jacks (see Hell Rell’s freestyle on Diplomatic Immunity), keep their memory alive and poppin’. And listening to Freekey Zekeyy talk from his North Carolina correctional facility, it doesn’t sound like he has lost any of his Dipset swag.

In addition to being the Set’s prized hypeman and skit creator, Freakey also played an important role as President of Diplomat Records, and was behind the business plan that enabled the Set to emerge as a force in their own right. We all know the history — back when Cam was signed to the Roc and enjoyed platinum success with 2002’s Come Home With Me, he wanted to put his whole crew on. Feeling limited by Roc-A-Fella’s distribution, the Harlem group went on their own marketing campaign, saturating the streets with mixtapes before it was widespread practice. The result was the successful launch of Juelz Santana’s solo career and the release of a group album that introduced the world to Jim Jones the Capo and Freekey Zekey, the 7:30 Dip.

Just as the crew was enjoying the success of Diplomatic Immunity in 2003, Freakey was the victim of an attempted robbery that led to him being nailed for an old drug trafficking charge from North Carolina that he had skipped bail on. Sentenced to three years in prison, Zekey was forced to watch from behind bars as the Diplomat movement moved on. Now that he’s about to be out, the “Lennox Avenue Sosa,” who once declared “I’m real, jailbird free!” sounds off on life from the inside, the roots of the Dipset hustle, and why people should be shook when he touches down at the tail-end of November. How many days you got left until you’re out?

Freekey Zekey: Right now, the countdown is popping. It would’ve been November 1st, but a little altercation came through where I had to get at this dude and that pushed my time back 20 more days. So now. it’s the 21st or the 20th or something. Did you get into any scuffles before this last one?

Freekey Zekey: That’s part of the reason I’m going home later now. I had to slap somebody, but other than that, yeah, I had about two other fights. Nothing major, I knocked them out, slammed a couple of ’em and then homie jumped on him did him dirty. But within the three years, nah, I can honestly say I only had about three fights, so I was proud of myself. What’s a day in the life?

Freekey Zekey: A day in the life in this joint is real, real, real, hectic. It’s like ongoing traffic, but with people. Always keep your eyes open, look in back of you, in front of you, left, right, everything. A day in the life is basically staying on your p’s and q’s and building with your peoples to keep them focused on the bigger thing at hand, because when you in jail, you with the kind of people who don’t want to do nothing, but beat people up, stab people and kill people. Like honestly, this is really what’s on they mind. So, I changed two people. I honestly can say I changed their direction, somewhat. They still got that raw fire if you look at them wrong. They ready to slit your throat, but I calmed them down and put a bigger perspective in their mind. It’s bigger than this jail, it’s about getting out and getting that money when you get out and being successful and holding your family down. Now you’ve always been known as the wildest member of the Set, but now you’re saying you’ve been calming people down. Would you say you have matured somewhat?

Freekey Zekey: I was always wild, but I always thought first. So, the things that I did was wild, but I thought and made sure Imm’a be aight once I do it. I wasn’t just a hothead with no thought. That’s a fool if you just react without thinking of you actions and how it might hinder or just destroy you. I’m the President of Diplomat Records, you can’t be the president running around like your head chopped off. But yes, I can agree to me maturing because there was a lot of things that I would just say you know what I’mma do what the hell I’mma do. Now, I really put a lot more thought and focus on what I’m about to do before I’m about to do it. So, I stepped my game up, which made it more dangerous for these people out here ’cause when I touch now, I got a whole new mind frame then what I had going in at the end of 2003. Cam once referred to jail as vacation time, what do you think about that statement?

Freekey Zekey: Yeah well, you can make it vacation time. You can make jail whatever you want. People come to jail and they were ex-crackheads and they were ex-dope fiends and all they was looking for was the high they stole for the high. But, when they get to jail, they was big time drug dealers, they had keys upon keys and they knew the Columbian people. So for some people, it’s not vacation for them. It’s just a new place and a rebirth, something they never had. But for someone who understands that this was a mistake for them and they need to really reevaluate they life and change it and move it into a different direction because what they did obviously brought them in there, I’d say their years is vacation time ’cause its time to lay back on your bed and focus on your mistakes and how you did it, why you did it, and now what you’re going to do to reinvent yourself. So for me, I would say, “Yeah, I was on vacation time.” So is it very different from a lifer’s perspective, as opposed to people on short bids?

Freekey Zekey: Oh yeah, yeah ’cause when I was in jail before — this is my first major bid where I was doing years — years opposed to months is totally different because a couple months, you’re not missing so much. The thought about you coming home is still on the tip of your tongue, no homo. You still smell like a pu*** if you a dude, you still smell like d*** if you a girl, you from the world. But, you start to get years and it takes a major toll on your mind that you actually come find like one day — some people it may take them four years, some people it may take them two years and some people it may take them ten years — but one day, you gonna be in jail on the yard and it’s going to hit you like 50 Mack trucks, like “oh sh**, I’m locked up.” Because once that judge hits that mallet that sentences you to 110 months, 70 months, 50 months, 42 months or whatever, where you know you gonna be gone a couple years, that’s a shock within itself. Your brain goes through a shock and it’s a subconscious shock where you like, “Aight, you don’t know.” If you a real G, you prepared yourself already for the time, so its nothing. Once he hear it, its’ already been reiterated in his mind. He already made it a redundancy to repeat himself, “I’m gonna do years.” I’m gonna do years is in his mind, so when the judge hits that, it doesn’t affect him. But once he starts doing his time, once he associates himself with the jail prison system and understanding the movement and the life of being locked up, it’s gonna hit him — POP, like a mean backslap from your grandma if you touch something you not supposed to. So, it’s a major difference from a little kid doing a skid bid running around, he doing a DWI sentence as opposed to a dude who got them keys or he bodied somebody. So you posted bail for a drug charge in ’01 right? And then you went back to New York?

Freekey Zekey: The situation was — I think it was 2000, I forgot it was a couple years ago — they gave me bail and I ran. I got low, not because I was afraid of doing the jail time, it was more that I did what I had to do to keep my company on the up rise. I had to put in more hustling time. I had to keep it moving on the streets and get my paper organized, so my peoples could stay straight. Because in 2000, we was living, but it was a lot of things going on where we wasn’t at the apex of our career. So being a hustler, still had to be in my resume. So I had to run, I got locked up at the time and I couldn’t stay in jail, so I ran on them n****s, gingerbread man style and kept it moving, kept the money flowing. And then what happened is I got shot in a robbery attempt that didn’t go well for nobody. The dudes didn’t get the chain, my man died and the motherf***in’ dudes I was running from found me. That’s actually how I got caught, after I got shot, the warrant popped. It wouldn’t have popped up if I hadn’t beat one of the dudes up that pulled a gun out on me and what happened is I stole his gun. I got shot in the process and once I went to the hospital and woke up, I woke up with handcuffs on me because I had the gun that was used to body my man. So, I was accused of murdering my own friend, so the warrant popped up and it’s been history since. With that incident and an older one that resulted in that infamous scar you have on your stomach, you’ve had a lot of severe battle wounds. Do you ever regret any of your actions or question if is it worth it?

Freekey Zekey: Yes and No. No to the fact that there is a chance that I would have been gone from this existence and my sons, they wouldn’t have known their father at all. But on the other hand, I was fighting for a cause each time. It wasn’t like I was just out causing trouble. Well, I was a major force in Harlem, so a lot of dudes wanted to get at me, but in these situations here, I was actually defending somebody. That time before I was defending a friend who got slapped — I thought he was gangsta, his name was Benjamin — but he didn’t keep it gangsta, so I intervened and I ended up beating the dude down and that situation went sour. Then on the other situation, when they found out I was a fugitive, they was trying to rob me, so I had to do me. I had to snatch dude up — it was four dudes with guns, so I had to find a shield. So one of the guys that had the gun, I made him my human shield and I got shot in the process, so it’s not like I’m just walking around. I was really fighting for a cause in the two times I got shot. That’s probably why the soldier strength stayed in me and I’m still here to talk about it. Cam had a similar, although not as serious situation this year, Hell Rell has been locked up… what do you think of people who say that Dipset isn’t real?

Freekey Zekey: People say actions speak louder than words. Our actions speak so much louder — well, I’ll say its neck in neck ’cause we talking about our actions. So, if you think that it’s phony, you honestly in a fantasy world. No one wants to get shot, no one wants to go to jail, and these are the things that are happening to us. We on the streets, we moving, not because it’s the things we want to do, but because it’s the things we had to do. The type of living that we wanted and that we needed to obtain, wouldn’t come from working 9 to 5 for $8, waiting 2 years to get another dollar. And honestly, I don’t care what race you are, I don’t care who you are, every legal organization was backed by something illegal, dating way back to the United States. The British people used to come down and turned on Britain. Tell them n****s, f*** you, we staying down here and you can’t have no more money. How we obtained our States was through battle, violence, murder, so everything from day one, that’s just the U.S.A way, and that’s the Dipset way. Now, we went legalized and everything is cool. So to say that we’re phony, that’s phony. And you gonna have haters, no matter what you do. You got people hating on gospel music like, “he doesn’t really like God as much as he say.” Look at Jesus — they hated on Jesus, they hated on Mohammed, every religion always had battles. Back in the day, it was religion that ran the world. Everybody hates, it doesn’t matter what you do, it’s when you become successful that the problems come. What do you think of Max B’s situation right now; it seems like he’s kind of in deep…

Freekey Zekey: Being that I’m incarcerated, I don’t get a chance to speak on my jacks like that. All I can say is Max B, you my dude, love you to death man. Hold your head, it gets greater later. We got the money, so we’ll get out of the situation. Stay focused, stay strong, you know what it is man, Dipset in the building, that’s all I can really speak on right then and there. I can’t really touch on that subject ’cause I’m not too familiar with it, but what they’re allegedly saying is I guess kind of serious, but like I said, hold your head Max B, you be out in a minute. Ok, let’s talk about Dipset and go back a bit. You grew up with Cam and Jimmy, how close were you to Bloodshed and Big L?

Freekey Zekey: Bloodshed and Big L, that’s family. That’s blood orientated, we considered ourselves family. You can’t get no closer than that. Cam, I knew him since he was — I don’t even know, there wasn’t no number. Jim, I met him in third grade; we found a token on the floor and we split it up and bought a soda and since then, we been tight. I knew Juelz from when he used to snatch the pampers off and run around the house, we just been close. R.I.P. to both Big L and Bloodshed, it’s a major, major, major loss. Those two dudes were going to have a major impact on the world as far as anything is concerned. They had a big, big, big focus ahead; I wish they was here everyday and I always send a shout out or shot up to the dudes.

But you know, that’s why I love Diplomats Records, because of the fact that we stay family orientated and we got a tight knit family because we don’t hold our tongue. If I’m arguing with Cam, I’mma let him know why I’m mad, he gonna let me know why he’s mad at me. But at the end of the day, we know our future goal, we know what we should be striving for — me and Cam, Jim Juelz, JR Writer, Hell Rell, Jha Jha. The whole set could be in a royal rumble fighting among ourselves and the phone rings and we gotta do an interview or show — we gonna stop, do the show, we party, rock like it’s nothing and then we gonna go back from stage and start killing each other again. We know the level of command, it’s Killa, Jim and me and Juelz and everybody respects that. It’s just what it is, it’s just like breathing. You don’t think how many times you breathe, you just do. That’s why I love our people, because it’s just like clockwork. When did you first get involved as President?

Freekey Zekey: Like I said, before we knew each other since 0 years old, before mustaches and beards was involved in our life. The click, back in the day, used to be BBO back in the 70s, it was Best Bombers Out. As we started to grow up in late 80s, early 90s, we changed it to “Bending Bitches Over,” so we already had a little crew and we branched off and the branch off was Big L had NFL and COC. We had the Children of the Corn, which considered of Big L, Bloodshed, Ma$e, McGruff, Cam, a whole lot of people and that broke up. Ma$e got a deal with Bad Boy, running around crazy, so he introduced us to Big. When he introduced Cam to BIG, [BIG] cut Cam off in mid sentence and said, “Listen, spit” and Cam spit and Biggie did the James Brown spin around spilt and jumped back up and he said, “Oh, I’mma sign you now,” but unfortunately — rest in peace — B.I.G. died and we had to run around for years trying to get on. So finally, Ma$e touched the world with Bad Boy and then we had our opportunity, but the guy who was going to give us our opportunity was killed. Un came through though…

Freekey Zekey: Exactly, he kept it all the way real and that’s what’s up. I was feeling that. Where’s Un at now?

Freekey Zekey: I dunno, he’s somewhere. Un is a business man; he’s a schemer he’s a dude who knows how to get and flip a dollar. But knowing him, he’s somewhere probably flipping a dollar or two, I know. You were one of first crews to go hard with the mixtape grind, what was the strategy?

Freekey Zekey: Approaching the mixtape was due to the fact that they wasn’t giving us our recognition. We came out with Confessions Of Fire; we wanted to put a song that would take us over the top, Un didn’t let us do that. So, we still went well over gold. We was trying to push platinum and it would’ve happened. We learned that mistake there; S.D.E. We learned the fact that people kept pushing our album back. We wasn’t trying listen to A&Rs. We was in tune with our own work, but the situation got hectic. Un was spending a lot of our money and put us in debt $1.4 million and we learned the fact that we needed to stay more in tune with our situation. So, it was a learning process and Dame bought us out and took us to Roc-A-Fella and we went platinum that first time on “Oh Boy” and Come Home With Me, and asked to put Juelz on. Juelz is major kid, his impact on wax is just ridiculous. Like every time I hear him, it touches my soul. We went platinum on Come Home With Me and ever since Confessions Of Fire, we’ve all been on Cam’s albums no matter what.

We always was hosting, guest songs, hooks and everything. So when we decided to branch off to let Juelz get his solo deal, they was like, “Nah, we don’t think he can do it by himself. We can’t take a risk.” So, we was like, “Oh sh**!” First of all, we sold the most. Besides Jay Z, there was no other artist on Roc-A-Fella that sold more than Cam. Plus, there was no artist that had more spins on the radio as far as Roc-A-Fella, so we broke Roc-A-Fella history — as far as spins and selling more that 999,000. But now, when we asked to put one of our dudes on, Juelz, they was like “nah,” so that’s what started the mixtape thing. That’s why I was running back and forth, setting up while I’m on the run. We put out our mixtapes, everybody loved Juelz and they signed him. After that Juelz gets on, now we like, “We need to do a Diplomat Records.” They like, “Oh no, we don’t think Diplomats needs to be signed,” so we let the mixtapes drop. Now, everybody love the Diplomats. Now, they signed them, so that’s really how the situation started. Cam had some tension with Jay from the beginning of the Roc-A-Fella days, and the story goes that he wasn’t really acknowledging you guys fully. From your perspective, what was going on between the two of them? Were they both too big headed to get along?

Freekey Zekey: They are big headed, both of them (no homo). But, it’s confidence. Their confidence level is 100,000. But the real reason, I honestly don’t know why the dude, Jay, was really f***ing with us like that because of the fact that we was ready when we signed to Roc-A-Fella. We was doing cartwheels. Roc-A-Fella was at the top of their game, like “You on Roc-a-Fella, What?! You gonna blow! (no homo)” So, once we signed to the Roc, we had Jay behind us, we had Dame behind us, we had Beanie Sigel behind us and we was unstoppable. Plus, Diplomats was a major force, so we was doing cartwheels, doing backspins. We were the happiest in world.

So then, Jay wasn’t trying to come around when Killa was finishing his album. Cause he threw a couple Roc-A-Fella artists on the album — he had Bleek on the album, Beans on the album and we needed Jay to do a song with us and Jay wouldn’t respond. We calling him on the office, telling people to call him, Cam is leaving messages and he’s not responding. He’s not coming through. It’s like, “What’s going on?” So one day, we at Baseline and we ran into him and Cam said, “You going to get on that album or not, man. I’m already pushing my album back a month.” So, he went in there, bobbed his head (no homo) 8 or 9 times and said he ready. He didn’t write nothing down and what happened was “Welcome To New York City.” Juelz was on the hook and Cam and Jay, and it was one of the biggest songs in New York when it touched the airwaves. After we seen how successful it was, we said we need to make that the single and we gonna do a video and he said, “Nah.” So, we was like, “Dude, you was bullsh**ting with us. We gonna let you know, we get it popping. We not going to use none of your sh**.”

It was just to show the dude how we could prosper without the help, so imagine with the help. We was trying to get a point across. So Cam goes platinum, and I guess he took offense to that. I dunno, there was so much bullsh**, but what really set of the major beef was, Cam left it alone, but once he chilled on this dude, once Jay took Roc-A-Fella and didn’t give Dame anything, that’s when Cam couldn’t hold it anymore. He lost all control and that’s when he came out with that dis record and it was over from that day. They tried to stop him, but it was over. So it sounds like on the one hand, Cam is trying to look out for Dame, but Dame wouldn’t have wanted the dis record to go down?

Freekey Zekey: Dame never was. Dame don’t get down like that. He’s a business minded man and at the end of the day, it hurt Dame to his heart. Him and Jay been together for 20 or some odd years. They built an empire, they started something from scratch. Dame wanted to sign Cam for $2,500. He said, “We got this Roc-A-Fella thing, we gonna do it. I’m telling you, I’m going to give you $2,500 and just grind with us,” as opposed to the $250,000 for the signing bonus we was getting from Sony, plus the $500,000 we was going to get off that. So, we said, “Nah, Dame. We gonna roll with this $750,000.” But for him, at the end of the day, Dame is not that type of dude. He is going to fight for a reason and he felt he was somewhere where he could probably mend the situation. His focus isn’t on violence, it’s about money. He’s a cakeaholic, but it was too late.