The plight of the Latin emcee has been well-documented. For any mild fan of hip-hop, they know about Big Pun and Fat Joe. But those entrenched in the culture know about Kid Frost, Cypress Hill, Tony Touch and others whose contributions to the game have all hit at certain levels in the game. Pitbull has had a career that’s ran its rollercoaster ride in Hip Hop.

With his new album, The Boatlift, the Cuban-American rapper delves in to a varying array of topics even though it fails short on reaching the mainstream. Inside the offices of TVT, Pitbull is relaxed, even jovial while the weather outside remains frigid and cold. A warm smile and an innovative new project allows Pitbull to be seen and heard around the world. And as 2008, a tense political year, gets on the way, HipHopDX sits down with Mr. 305 as he discusses the ups and downs of the music business, his recent comments about Fidel Castro and why you cannot place Pitbull in a cage.

HipHopDX: Can you talk a little bit about growing up Cuban, the adversity you’ve felt and how they relate to your views on Castro?
Pitbull: You’re pretty much born into the world hating Fidel Castro. When you come from Miami and you’re Cuban-American, my views on Castro as a kid, you hear more and more stories and it really hurts your heart. You see people who manage to find a way into Miami and as a kid, it’s like little horror stories that you never really want to experience. That’s why I have my feelings about Castro. I’ve seen him destroy families. He’s destroyed my own family due to his idea of a better way of living [laughs]… which only works that way in a book or on television.

DX: There was a time where you were cited on another site talking about how you were offended by people wearing those Che Guevara t-shirts. Where did all of that stem from?
P: They’d always take what they want out of those interviews. I truly respect any and everyone’s opinion. I respect anything that anyone chooses to stand for in this life. My only thought is that if you’re going to make something as a symbol or as a hero – I’ll give you an example. Someone walks in here and wears a Hitler t-shirt in front of a Jewish person. Of course that person is going to feel offended and oftentimes he or she would be made that someone would disrespect their heritage given such a historic tragedy, right?

DX: Right…
P: Now, if you can justify why you’re wearing that Hitler shirt and it’s a valid reason behind it, then I can respect you for your opinion. You know Hitler; you know his background and all that. But because you have on a shirt that Jay-Z wore on MTV Unplugged and that’s your only reason behind rockin’ it, then that’s a problem. That’s the way I look at it. As far as how Cubans look at him back in the country, they don’t necessarily fuck with him like that because of how he was down with Castro back in the day. So, it’s sort of being guilty by association.

DX: Now, you went into the booth to make a song about Castro once he fell ill, right?
P: Right.

DX: So, why not push for more political content with your music?
P: I got plenty of political records. But at the end of the day, I’m in the music business. I love to make records. I love music. We got to survive to do what we want to do. As far as political records, there’ll be a right time and place for me to do that. I want to be able to have the power for people to listen to me when I do it. Do I have the ability to do it? Yes. But right now, I want to make sure that I’m doing what’s best to enhance my voice amongst the people.

DX: So, do you think with that limiting you that you’ll just hold on to them?
P: I got plenty of them in the safe. It’s all about timing. This is just the beginning of my career, I feel.

DX: Is this album your right time to shine?
P: This album is full of nothing but hits, man. It’s nothing but hits, man. At the end of the day, there’s nothing political about the album except the title. I hope to be able to put together that classic album. And when I do, I’ll definitely endorse it as such, real talk. Have I put together my classic or greatest work, yet? No. Even though I haven’t, it’s still there. It’s just locked safely away.

DX: What are your frustrations with the music business?
P: I don’t really have any frustrations. I just look at them like they’re lessons. Right now, the game doesn’t know how to categorize Pitbull. I’m too Latin for Hip Hop and too Hip Hop for Latin. Some say that I’m Reggaeton or that I’m crunk. But at the end of the day, my movement is my movement. I don’t give a fuck. It’s good music. With that said, everything in the game is how you get categorized and that’s very frustrating when you don’t think that you fit into one specific box. They can’t at the end of the day, do that. It’s also some bullshit to deal with the politics. Half of the people in the business don’t even know about music. But it’s gotten to the point to where I have my own team and if it feels right, then we go out and do it. I’ve built my own network which is good, so I’m able to navigate this business career-minded for our movement. Continued on page 2 »