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 ride—Cam'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 Fire was 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."

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