Bill Underwood, Former Music Exec Granted Compassionate Release from Prison After 33 Years

The leader of a 1970s Harlem heroin trafficking gang — whose life sentence was touted by Sen. Cory Booker as an example of the unfair criminal justice system — has won release after more than three decades in prison.

William Underwood’s transformation from leader of the “extremely violent” Vigilantes gang to an upstanding inmate was chronicled by Manhattan Federal Judge Sidney Stein in a 10-page decision published Friday.

The judge noted the support of judges, prison staff, former inmates and Booker (D-NJ). The Senator said Underwood was the type of elderly prisoner suffering needlessly due to the draconian laws of the War on Drugs. Booker proposed a bill in 2019, the Second Look Act, and cited Underwood’s case.

Law enforcement says Underwood, 67, ran the Vigilantes beginning in the 1970s. The group allegedly imported heroin from Europe using a TWA flight attendant. According to the NY Daily News, in the early 1980s the organization sold as much as 5.5 kilos per week. Evidence at trial included five murders and one attempted murder committed at Underwood’s instructions.

Underwood was sentenced in 1990, as part of the first round of drug convictions made under the newly enacted federal Sentencing Guidelines of 1987 and the Anti-Drug Abuse Act of 1988. He received (3) mandatory minimum sentences of 20 years on drug conspiracy charges, plus a 4th charge — a life sentence without the possibility of parole. On the streets and in the music industry Underwood was known as a prominent music promoter from the late 70s up until his arrest in 1988. He promoted top acts such as Michael Jackson, Ray Charles, Earth, Wind & Fire, Kenny Loggins, Wham, New Edition and Guy. He managed the R&B funk band, Slave and lead singer Steve Arrington. He later went on to discover and manage R&B singer, Johnny Gill, ultimately aligning Johnny with the boy band, New Edition.