Pitbull: Get Rich or Die Shilling

Photograph by Christopher Leaman

Pitbull, born Armando Pérez, self-titled Mr. Worldwide, and often known simply as Pit, slides into his seat at a hotel restaurant about 25 minutes inland from South Beach. The place is well outside the Miami party scene and its paparazzi, and is either purposefully retro—deco chairs, white tablecloths, a waitress who must be 80 wearing bright coral lipstick—or hasn’t been updated in 50 years. It’s empty save for one of the biggest pop stars in the world and a group of his associates, all wearing suits, and clustered at two tables. Pitbull taps his water glass, and the waitress hurries over to fill it. His lawyer, Leslie Zigel, hands him an agenda, which offers topics like “Endorsement Deal Matters,” “Investments,” and, in capital letters, “DISRUPTION.”

Zigel and Pitbull started working together in 2010, after Pitbull closed his first major sponsorship deal, with Dr Pepper (DPS), which Zigel was representing at the time. “He told me he appreciated my approach to dealmaking and asked if I would consider joining his team,” says Zigel. “I’m a jazz bass player, and he liked that I thought like a musician, not a typical lawyer.” Zigel looks like Stanley Tucci and speaks to Pitbull encouragingly, like a cheerful high school gym teacher.

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  Courtesy Youtube

  Cars: In a series of Spanish and English ads for the Dodge Dart. En Español: “Cómo hacer un auto.” Beer: Stars in two Bud Light ads as part of a multicultural campaign. Both spots take place in a club and feature his song Bon Bon (“Don’t stop the paaaarty!”). Soda: Appears in a Dr Pepper TV ad titled “Dream,” about making it as an immigrant. “I’m Pitbull, and I’m one of a kind.”
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  Alcohol: A partner in Voli, billed as the first low-calorie vodka. Flavors include Raspberry Cocoa and Espresso Vanilla. Fragrances: Launches men’s and women’s scents in 2013. Cologne has notes of “warm spices of cardamom and sage.”
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  Courtesy Playboy

  Hot Girls: Strikes up a “strategic partnership” with Playboy Enterprises, features the mansion in his Wild Wild Love video.
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  Food: Has a “significant” equity stake in the Miami Subs Grill sandwich chain, which offers items such as the Big Havana Burger. Water Filters: Investor in EcoloBlue, a startup that manufactures a filtration system that claims to “create water from air.”

Zigel slides over a stack of articles about Bitcoin and mentions a possible sitdown with Merlin Kauffman, who runs a $7.5 million Bitcoin investment fund focused on the hardware that runs the currency. Pitbull flips through the pages quickly, not displaying much interest. In public, Pitbull is rarely seen without an enormous pair of aviator-style sunglasses, but he’s left them off for this meeting. His exposed eyes are ocean-colored, surrounded by little-girl lashes. Freckles dot his nose. There’s a Twitter (TWTR) joke that compares a picture of Pitbull to Lord Voldemort, and while uncharitable, there’s something to it, with that crowded, leonine smile and menacing cannonball-like head.

“I still want to know, what exactly is Bitcoin?” Pitbull says. “How real is it? Is it going to be adopted and be disruptive?”

“The people who are going to adopt it are young,” Zigel replies. “If it’s something they decide they want to do, it’s going to be a force to be reckoned with.”

“What makes this real money?”

Zigel, looking unsure, glances quickly at the articles Pitbull has shoved back toward him. “It’s very speculative right now,” he says. “There’s nothing that’s holding it together.”

Pitbull is dubious. “No gold, no nothing?”

“No banks behind it, no.”

“Are they having problems with the streets?”

Zigel’s eyebrows rise. Pitbull may be referring to the financial markets, or he may be referring to streets of a grittier variety. Pitbull, 33, spent much of his life navigating them, as he’s quick to mention. He’s a first-generation American whose parents came to Miami from Cuba, his mother in the 1960s as part of Operation Pedro Pan—Miami’s effort to get children out of the communist country—and his father in 1980. Armando Sr. was a low-level criminal and drug dealer; he met Pitbull’s mother while she was what Pitbull calls a “burlesque dancer.” By the time Pitbull was a teenager and trying to make it as a musician, he’d dropped out of school and was dealing drugs. In 2001 he hooked up with successful rapper Lil Jon and producer Luther Campbell, the frontman for 2 Live Crew, and in 2004 released his first album, M.I.A.M.I. It featured the single Culo, which peaked at No. 32 on the Billboard Hot 100. Culo, which translates, roughly, to “ass,” is what’s referred to as reggaeton—an upbeat sound that combines hip-hop, Jamaican dancehall, and more traditional Latino music such as salsa. In it, Pitbull raps in English and Spanish, and his style is hypnotizingly monotone, making it an ideal counterpart for a great hook.
In the decade since, Pitbull has become ubiquitous and is moving into the territory of empire builder, along the lines of 50 Cent or Jay Z. His publicist, Tom Muzquiz, a peppy man with spiky hair who’s lingering at the next table, promised to figure out the perfect day for us to spend together to help me understand his boss’s reach and ambition. And it didn’t involve a yacht or a crazy night out in South Beach or anything to do with his outsize lifestyle. Exciting for Pitbull, now, is thinking about things other than partying, studio time, and ladies. (He has six children with an undisclosed number of women.)