Actor and rap-music legend L.L. Cool J portrayed notorious Boston drug lord Darryl (God) Whiting in the 1999 film In Too Deep. In the movie, Whiting’s character’s name was changed to Dwayne Giddens.

On top of the Beantown narcotics game from the late 1980s into the early 1990s, the New York-born Whiting became the first person in Massachusetts history to be sentenced to life in prison without the possibility of parole for a drug crime in 1992. Recently-enacted legislation provided the 62-year old Whiting a chance to go in front of a federal judge in 2016 to get his sentence reviewed and possibly altered (potentially allowing him to gain his freedom after almost three decades behind bars), but his plea for mercy was rejected, largely because of a self-published book where he threatened to harm at least two specific people who had testified against him at his trial if ever released.

Fleeing trouble in his hometown of Queens, New York, “God” Whiting arrived in Boston in 1986 and quickly took control of the crack trade in the Orchard Park Housing Projects, located in the hardscrabble urban center of Roxbury, by force. Importing a crew of over 100 loyal foot soldiers from the Empire State, he fought and won wars for territory against both the Intervale Street Posse (ISP) and the so-called OPT (Orchard Park Trailblazers) and then firmly established an intricate network of distribution routes, communication codes and money washing methods that were, at least for a short time, difficult for the feds to combat. His gang was called the “New York Boys.”

At their peak, Whiting and his New York Boys gang were pumping out millions of dollars per year in cash profits and flooding Roxbury and its surrounding area with cheap rock cocaine at epic rates. In November 1987, Whiting opened up the Crown Social Hall in the heart of the Orchard Park projects. For all intents and purposes, the “Crown” became a drug emporium masquerading as a community center, and Whiting made it his headquarters. His second-in-charge was Edwin (Freedom) Carmichael and his main enforcer was Kenny (Cheyenne) Bartlett who went on to become one of the most feared hit men in Boston gangland history. They got 20-year and 30-year sentences, respectively.

Per court documents and testimony by federal agents at his sentencing hearing, Whiting ordered at least two murders in his reign in Orchard Park – a 1990 killing of a rival drug dealer and a 1988 slaying of a one-time close friend and lieutenant in his organization in what was described by the government as an “internal housecleaning measure.”

The real Darryl “God” Whiting circa 1990

The New York Boys’ Boston crack kingdom came crumbling down to the ground in December 1990 with the dropping of a titanic federal racketeering and drug indictment that ensnared the entire organization. The case was mainly made by the undercover work of a pair of DEA agents, Jeff Coy and Maurice Hawkins, and became so encompassing it had to be broken up into three separate trials. The onslaught of forthcoming convictions, tipping off at Whiting’s July 1991 trial, hinged on the testimony of Coy and Hawkins.

Coy infiltrated Whiting’s inner-circle through one of his lieutenants, Raymond (L.A. Ray) Ward, who ran a video rental store owned by Whiting and used as one of his fronts. Hawkins got in tight with Whiting gang crew leader Steve (Mad Muhammad) Wadlington. Coy began buying and selling guns with Ward and soon gained an introduction to Whiting. With the DEA watching and snapping photos, Coy purchased 2 ounces of pure Colombian cocaine from Whiting and Whiting’s bodyguard David (Divine D) Waight. Days later, a wired-for-sound Coy recorded Whiting making a deal to purchase eight automatic weapons in a meeting in Whiting’s office located in the back of a barber shop he owned.

Sadly, Coy struggled to acclimate to life after “lifting out” of his undercover persona, reportedly battling drug addiction and post-traumatic stress disorder, finally committing suicide in 1994. The week following his work on the God Whiting case concluded, he was hospitalized in a mental institution for more than a month. Prior to his death, Coy taped an emotional confessional for the DEA to show to all undercover-officer trainees and warn them of the unique side effects of the heavily stressful and extremely dangerous job of going “deep cover.”

After Coy’s suicide, the video-taped confessional made its way into the hands of a Hollywood producer and became the basis for the movie In Too Deep. Actor Omar Epps played Coy (switched to Jeff Cole in the script), with the setting changed from Boston to Cincinnati, Ohio. Jeff Cole was Coy’s alias in his undercover work.

Epps’ Cole, who went by the alias “J-Reid,” tells L.L. Cool J’s God character in the film that he was from Akron, Ohio, while in real-life Coy’s “J-Cole” told Whiting he was from nearby Providence, Rhode Island. Like shown in the film, early on in the covert op, Coy is jumped by a pair of Whiting gang thugs in an attempted robbery he was forced to shoot his way out of.

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