Legendary Harlem hustler Kevin Chiles rose to prominence during the 1980s crack era. Busted at the height of the U.S. government’s “War on Drugs” in the early nineties, Chiles took the feds to trial twice. When the juries couldn’t reach decisions, mistrials were declared. But with federal prosecutors escalating their targeting of family and friends, Chiles eventually pleaded out to a ten-year sentence and was sent to prison to do his time.
It was during his incarceration years, in the belly of the beast, that Chiles founded Don Diva magazine, the outlaw’s bible.
Every issue features stories on infamous gangsters and street figures from the urban underworld. After getting locked up, Chiles could have rested on his street cred and let his legend reverberate through the chronicles of hip-hop lore. But he’s always been driven, and once he got his idea, he vowed to make Don Diva happen.
The magazine’s twist is that it interviews its subjects — many of them serving life sentences for their crimes — straight from the penitentiary. Its writers uncover stories you don’t see in mainstream news outlets, and Don Diva has an insider understanding of the world it chronicles. Chiles got out of prison in January 2004, and the magazine he founded from a cell block 20 years ago is still going strong.
Chiles and his wife Tiffany, who’s helped him run Don Diva since the start, have turned their enterprise into a thriving lifestyle brand complete with a highly trafficked website, a clothing line, DVDs, concert promotions, and books. The quarterly publication itself has been featured in the Washington Post, New York Times, VICE, and Huffington Post.
Penthouse sat down with Chiles to find out just how big he got during the eighties, who his contemporaries were, and what the Harlem drug-game was like back then. We also wanted to hear about his experience being thrown into the criminal justice machinery, his time in federal prison, and the tragic way his own mother got caught up in the chaos — subjects he’s retraced in a book he recently wrote about his life, called The Crack Era: The Rise, Fall & Redemption of Kevin Chiles.
What was it like growing up in the Bronx?
The Bronx is the birthplace of hip-hop. But prior to every urban kid having dreams of escaping the ’hood using two turntables and a microphone, most aspired to leave through hoop dreams or selling drugs. It didn’t feel like there were many other options available. In 1975, New York City was facing an economic crisis — it was nearly bankrupt. Basic city services like garbage pickup were suspended. You can only imagine how much less urgent it was for the city to address issues in predominantly black and Hispanic areas. Much of the Bronx was dilapidated, with burned-out, abandoned buildings. High crime rates made it feel like the concrete jungle was in irreversible decline. The hopelessness many New Yorkers felt was exponentially greater in forgotten areas like the Bronx,Harlem, and much of Brooklyn.