Dipset's Parole Model

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

'Cause when music discouraged my pride/Zeke the only one with courage to rideCam'ron, "Dip-Set Forever"

Nothing could have looked quite so strange parked outside Durham Correctional Center's barbed-wire gates: a luxury Chrysler limo, pink morning sunlight gleaming off its polish, motor humming softly but still audibly to the 75 or so inmates huddled on the other side. For a few electric minutes, everyone waited. The tuxedoed driver. The stunning woman in a snug black dress. The prisoners breathing warmth into cupped hands.

Out bounded hip-hop magnate and entertainer Ezekiel "Freekey Zekey" Jiles, so delirious with joy he practically spoke in tongues. His manager, Rick Dalton, got a pound. The prisoners got a peace sign. Stephanie Awekey, the luscious fellow Harlemite, was received in eager handfuls. And with that, Jiles disappeared behind the limo's tinted windows and glided away from the squat brick complex. His three-year sentence for trafficking Ecstasy in North Carolina was finished. And back home, his prosperous rap family, the Diplomats, awaited him at LaGuardia Airport.

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

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That was November 20th. "I haven't fell asleep since my release date," Jiles says several weeks later. "Life is crazy-times-retarded with a little twist of 'Ohhh, shit!' "

Though his title is mostly symbolic, the 31-year-old is president of the platinum-selling Diplomats, a/k/a Dipset. The Harlem-based group—which includes Cam'ron, Juelz Santana, Jim Jones, and others—is known for its anthemic beats, garish fashion sense, and lyrical accounts of the drug trade. Fans thrive on their precise narratives about trafficking on Interstate 95, getting out of the saturated New York market to tap other states' drug-money potential. More devout followers might know that Freekey Zekey—who supplied the talky hook to the Cam'ron smash "Hey Ma"—went to prison for doing just that.

But few know the full story behind Jiles's underworld gamble gone wrong, or the violent twist that ultimately derailed the hip-hop millionaire. Over and over, he's heard these questions in the prison yard and now the street: "'Yo, Freekey, Cam and Jim got hit records!' " Jiles exclaims, mimicking his inquisitors. " 'Why was you selling any type of drugs? They wasn't giving you no money?' "

Not quite. Friends since childhood, Dipset's core members claim to be more blood brothers than business partners. Jiles, for instance, is Cam'ron's cousin, a friend of Jim Jones' since third grade, and a mentor to Juelz Santana since the crack-and-Uzis rapper was toddling in diapers. In the late 1990s, the Cam'ron-led crew signed to the Epic Records–affiliated Untertainment label, elevating them straight out of the projects. Cam'ron's 1998 album Confessions of Firewas Puff Daddy–era polished gangsta, best remembered for the single "Horse and Carriage," featuring Bad Boy Entertainment's Mase. The group gradually went more raw, starting with Cam'ron's 2000 release S.D.E., which marked Santana's big-market debut. The crew got marginally famous, but not rich. In fact, Jiles says the group once owed $1.4 million to the label. Moving narcotics, a skill the Diplomats learned growing up in Harlem, was the only way Jiles knew to shore up big money quick and clear that debt.

In contrast to the crew's triumphant and unapologetic rhymes, there's little bravado in Jiles's recollections of his real-life drug-pushing stints. He was actually pretty miserable. "I was up days upon days," he says. "You gotta look over your shoulder. You gotta worry about the stick-up kids, the police, your man getting you for money. I had to hit the highway, the I-95. But I wasn't doing it for the 28-inch rims. I never got fly. This was straight dedication to get back into a legal project."

In 1999, with the group's last $30,000, Jiles bought packs of Ecstasy and a bus ticket to North Carolina. He's still unsure why police knew to search him when he got off the bus in New Hanover County. "I don't know if they were tipped or what," he recalls. "But they snatched me up." Eager to return to New York, he made bail and fled his charge for Schedule I trafficking, a classification that includes heroin and opiates.

Fast-forward to 2003. Untertainment is defunct. Dipset has rebounded. Cam'ron is signed to Roc-A-Fella, then one of hip-hop's most successful labels. Authorities are oblivious to the fact that the Jiles lurking in their unserved-warrant stacks is the guy clowning in the champagne-drizzled, heavy-rotation "Hey Ma" video. "I was on the run that whole time," Jiles says. "The police probably figured I'd just get myself arrested again."

Instead, crime came looking for Jiles. That April, on a block near Greenwich Village, robbers shot Jiles in the chest over his diamond chain and murdered his childhood friend, Eric Mangrum. When Jiles regained consciousness, he was handcuffed to a St. Vincent's Manhattan Hospital bed. The NYPD mistakenly believed Jiles—who at one point overcame the gunman, handled his pistol, and thus left fingerprints—was Mangrum's killer. Jiles said he learned his friend died from his gunshot wounds while a detective was pushing him to confess. "I was like, 'Wait. Back up. He's dead?' Right there, I was just gone."

In an odd windfall for Jiles, street cameras posted in the wake of neighborhood gay-bashings captured the robbery and cleared him of murder. But during the investigation, police also discovered the North Carolina drug charge. They sent Jiles straight from the hospital to maximum-security prison. "I poked my chest out—I girded my mental up," Jiles says. "But it just ate at me."

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."

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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