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The chief suspect in the 1999 murder of rapper Big L was gunned down in Harlem almost 20 years after his arrest in the case, sources said.

According to the NYPD, Gerard Woodley, 46, was in front of his apartment building on West 139th street Thursday night when someone shot him in the head. Woodley was later pronounced dead at Harlem Hospital.

Woodly, a childhood friend of Big L (real name Lamont Coleman) was arrested for the up-and-coming rapper’s murder back in 1999. Prosecutors later dropped the charges due to a lack of witnesses and a failure to turn up reliable surveillance footage. Although he got off the hook in the Big L case, Woodly’s criminal history lengthened.

Woodley has been arrested six times for a number of weapons and additional murder charges in the early 90’s and into the 2000’s. Though the murder cases didn’t stick, he did serve time on gun charges and was released on parole in September 2015. While investigators don’t believe Woodley’s murder was tied to Big L, it is certain that he made a lot of enemies over the years and someone was clearly out for revenge. Woodley leaves behind a 28-year-old daughter.

Big L’s untimely death was a blow that hip-hop never quite recovered from. The Harlem MC’s life was taken just as his buzz in the underground hip-hop scene was flourishing. Many thought he would be a household name alongside legends Notorious B.I.G and Tupac Shakur had he lived to see his success through.

SOURCE: DNA-info | Images: Getty, Instagram