Brooklyn Rapper Sleepy Hallow Released After Serving 8 Months

Brooklyn drill rapper Sleepy Hallow, whose real name is Tegan Chambers, has been released from prison after serving approximately eight months of a one-year sentence imposed in connection with a sprawling New York gang conspiracy case.

The rapper announced his release Thursday in an Instagram post featuring photographs of himself posing alongside luxury vehicles and music plaques.

“I’m back, now go pick a side n’ stay there,” Chambers wrote.

Chambers was among 32 defendants named in a 140-count indictment unsealed by New York prosecutors in May 2023. Authorities alleged that members and associates of a Brooklyn street gang participated in a range of criminal activities, leading to charges that included conspiracy and violent offenses against multiple defendants.

In October 2025, Chambers pleaded guilty to fourth-degree conspiracy and was sentenced to one year in prison. Court records show the plea resolved his role in the prosecution’s broader gang conspiracy case.

Brooklyn Rap Star Sleepy Hallow Released After 8 Months, Prepares “First Day Out” Track

The case also ensnared fellow Brooklyn drill artist Michael Williams, known as Sheff G. Williams pleaded guilty to second-degree attempted murder and second- and fourth-degree conspiracy charges. He received a five-year prison sentence in October 2025.

Chambers’ release marks the latest development in a prosecution that drew significant attention because of the involvement of prominent figures in New York’s drill music scene.

The rapper indicated he intends to quickly return to his music career. In addition to announcing his release, Sleepy Hallow said he’s filming the “First Day Out” music video.

He invited fans to the video shoot in New York City. “First Day Out” tracks are commonly associated with songs released by artists following incarceration.

The planned release suggests Sleepy Hallow is seeking to capitalize on renewed public attention following his prison term. Sleep Hallow is set to perform at Hot 97’s Summer Jam on July 24.

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