Dipset's Parole Model

The Harlem crew's president and cred-enhancer is once again free to fly high

The occasional scrape aside, prison was mostly a dull waiting game for Jiles. He dodged the hangers-on, committed himself to inmate jobs—trash duty was his favorite—and whittled his sentence down with good behavior. Superintendent David Cates of Durham Correctional cited Jiles as a no-trouble inmate who didn't get special treatment. "If they gave me a 'pick-up doo-doo' job, then I'd have my gloves on," Jiles says. "I had a trash job, but my treasure was freedom."

While Jiles lugged garbage bags, Dipset grew more influential than ever, rising to prominence (alongside other practioners like Kanye West) thanks largely to beats driven by sped-up, high-pitched soul samples. Mimicking the group, young black men nationwide started wearing pastel pink. And this year, the absurdly popular phrase "Ballin!" rose to power thanks to Jim Jones's smash hit "We Fly High."

Meanwhile, Dipset did their part, keeping the Freekey Zekey name alive in lyrics, interviews, and mix-tape interludes. On a staticky phone call recorded for Jones's Hustler's P.O.M.E.—for weeks Billboard's No. 1 independent album—Jiles solicits Jones to send a plane flapping a "Free Zeekey" banner over his prison yard. But for the most part, the best Jiles could do behind bars was lend legitimacy to his blood brothers' drug-hustle verses. "Through me, definitely, fans can be like, 'Wow, Zeke was really that guy in the streets,' " he reasons. "It glorifies their fantasies."

"Life is crazy-times-retarded": Ezekiel "Freekey Zekey" Jiles
Mark Hartman
"Life is crazy-times-retarded": Ezekiel "Freekey Zekey" Jiles

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Prison also gave Jiles time to carefully craft a comeback vision. In an echo of his ill-fated Ecstasy road trip eight years ago, he's hoping to capitalize on North Carolina's less crowded market. Jiles, pushing music instead of drugs this time, is starting an arm of Diplomat Records called Dipset South in Greensboro. "People don't understand how big North Carolina's going to be," he says. "It's going to rise. Honestly, I do want to conquer this spot, because this is where I got locked up. I'm committed to this state."

Dipset South's first artist? Freekey Zekey, of course. When he walked out of prison that November morning, Jiles was already sitting on roughly 50 tracks—while locked up, he'd bought a Durham studio with a friend and started quietly building up songs during six-hour day releases, another perk of good behavior. Just two weeks after Jiles's release, Asylum Records, parent to Diplomat Records, offered him a multimillion-dollar album deal. The largely autobiographical Book of Ezekiel, his solo debut, is slated for a spring release. With freedom, Dipset's dark horse can now do more than merely reinforce his crew's criminal credibility. He can sell it direct.

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