A Baltimore drug lord who sent teenagers to Brooklyn to rob jewelry stores hoped a recent Supreme Court ruling would mean an early release from prison — but a federal judge found a way to keep him behind bars for a few more years.
David Gregory, 60, got a shot at freedom after a U.S. Supreme Court decision in a Virginia robbery case nullified one of his criminal charges, offering the prospect of shaving 20 years off his nearly 47-year sentence.
With that decision, and a plea that he was a changed man devoted to his family, he was hoping Brooklyn Federal Court Judge Edward Korman would sentence him to the time served in prison since his arrest in 1997 — resulting in his immediate freedom.
Instead, Korman — who expressed concern Gregory did not appreciate the enormity of his crimes — resentenced him to 405 months, or nearly 34 years.
That means that Gregory will stay in prison for at least a few more years, depending on how much good behavior credit he has.
Gregory was the leader of the murderous “Double Seal” gang in the 1990s, so named for the way it packaged its heroin. He used teenage girls as drug mules who hid drugs in tampon-shaped packages, according to court documents.
Federal prosecutors contend in court filings that Gregory orchestrated the 1992 murder of a rival, was linked to the killings of two women in Baltimore, had sex with some of the underage girls in his employ, and used a cigarette lighter to burn the genitals of young boys who stole from him.
Prosecutors compared him to Fagin, the “Oliver Twist” villain who taught children how to pick pockets, according to press coverage at the time of his 1997 arrest and conviction in Brooklyn Federal Court.
But that plot to rob Brooklyn jewelry stores to fund his drug operation brought Gregory’s criminal reign to an end when one of his teenage proteges left behind a gun during a $200,000 heist in Park Slope in 2005 in which a jewelry store owner was shot in the neck.
After Gregory’s trial, Judge Korman imposed the 40-plus-year sentence.
Gregory has been trying to get released for more than a decade, describing himself as fully reformed by his experience in prison.
In July, the U.S. Supreme Court made a decision in a similar case that gave him his best chance.
One of Gregory’s charges involved the use of a gun during a violent crime. But in a 7-2 ruling, the Supreme Court ruled that type of offense can’t be considered a violent crime under the law, because prosecutors don’t need to prove force was used.
That decision’s application in Gregory’s case brought him back before Korman for new sentencing proceedings.
In a 2020 hearing in the case, Korman was put off by Gregory’s argument that he took no part in his teen robbery squad’s violence. Last week, the jurist pointed to language in one of the gang leader’s recent court filings that suggested he still had not taken full responsibility for his crimes.
“He struck me as essentially a sociopath …. Even at this late date, he’s still not essentially accepting any kind of responsibility for the violence that he was involved with,” Korman said.
Gregory tried to explain in court that his words didn’t come out the way he intended. “I had a twisted understanding of my innocence in this whole thing,” he said.
He added that his family tried to set him straight about the severity of his crimes. “They all got on me, helping me see how wrong I was holding on to this notion of being innocent,” Gregory said. “I’m not.”
Korman was not swayed. Gregory’s hopes for freedom now hinge on an appeal of the new 34-year sentence.