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Howard had no way of knowing at the time, but the FBI was listening in on Howard’s conversation with an acquaintance through a wiretap. In a joint investigation with D.C. police, federal agents were following more than a dozen suspected members of a violent drug-trafficking and murder-for-hire organization in Washington. Authorities said one of its leaders was Kevin Gray.

Howard and Gray had been friends since childhood. Gray even helped raise money for Howard to post bail after he was arrested in the Keontaye Smith case, according to court records.

The two men grew up a few apartment buildings apart on Southern Avenue in Southeast Washington in a neighborhood ravaged by drugs and killing. Their teenage years marked a time of unprecedented violence in the nation’s capital.

From 1985 to 1991, the number of homicides in Washington more than tripled from 157 to 509, according to the District’s medical examiner. The killing, most of it by gunfire, coincided with the influx of crack cocaine into the city.

Gray and Howard and their associates, many of them childhood friends, made up to $50,000 a week selling cocaine on Robinson Place, a small dead-end street in Southeast Washington known as “the dungeon” among drug dealers, according to testimony.

“We protected ourselves. We had guns. We had guns everywhere around there, and we didn’t let nobody else come in there,” one-time Gray associate Maurice Andrews testified. Like Howard, Andrews pleaded guilty to conspiracy in the Murder Inc. case and entered the witness protection program, according to court records.

“We was making so much money … so many cars, so many clothes, jewelry and stuff like that, so people knew we was getting a lot of money, and they’d get jealous and they’d come around and try to rob us or kidnap us or stick us up, stuff like that,” Andrews said.

Howard was “part of our family,” according to Andrews, adding that Gray and Howard were like cousins.

Gray aligned with another drug dealer, Rodney Moore, a one-time associate of Rayful Edmond III, one of the first major crack dealers in the District, according to prosecutors. Moore was convicted in 10 murders. Like Gray, Moore’s conviction is under appeal.

In contrast to the flamboyant Edmond — who reportedly wore a Rolex, drove a Porsche and handed out $100 bills to neighborhood children — Gray and Moore operated more discreetly in the decade after Edmond’s 1989 conviction, according to court records.

If Moore was the businessman, Gray was the enforcer, killing to settle old drug debts, to keep people from talking to police or just to make money, according to prosecutors.

“He gets suspicious and thinks you’re asking him questions for a reason, and he ends up killing you,” Andrews testified.

By 1999, investigators had enough evidence to arrest Gray, Moore and other suspected drug associates. Gray was arrested at the Club 55 strip club in Washington on a tip from an FBI informant. Weeks later, the informant was paralyzed in a retaliatory shooting for which Howard said he supplied the gun and getaway car.

Despite the high-profile arrests, announced in a press conference by then-U.S. Attorney for the District Wilma A. Lewis, investigators still couldn’t find at least one high-ranking member of the organization: Frank Howard.

Howard talked by telephone to a detective in the Gray case, promising to turn himself in. But he instead fled to California. Months later, an undercover federal agent showed up at the home of a relative of Howard’s in Los Angeles. Dressed as a delivery man, the agent knocked at the door and said he had a package for Frank Howard.

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