When former President Donald Trump walked onto a Bronx stage in May 2024, he had some unexpected company. Alongside him were two rising stars of New York’s drill rap scene, Sheff G and Sleepy Hallow. Their presence drew cheers and headlines. With their help, Trump attempted to connect with young Black voters by showcasing rappers with massive followings.
But fast forward a year, and that moment looks very different. The Bronx stage lights have been replaced by the cold, unforgiving spotlight of a Brooklyn courtroom.
On Wednesday, Sheff G, real name Michael Williams, was sentenced to five years in prison. His crime: using his music money not to uplift, but to bankroll gang violence across Brooklyn.
At 27, Sheff G had already lived two extremes of fame. His songs had racked up millions of plays on YouTube and Spotify. His videos were part of the drill movement that brought Brooklyn rap global attention.
But prosecutors say behind the beats and streaming checks was a darker reality.
According to Brooklyn District Attorney Eric Gonzalez, Sheff G didn’t just rap about the streets. He funded them. “This defendant had talent and opportunity. But he chose to use them to fuel violence instead of building a better future,” Gonzalez said after sentencing.
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Investigators say the rapper showered money and jewelry on members of the 8 Trey Crips and their allies, the 9 Ways gang, encouraging their turf wars. They say he even played getaway driver during a 2021 shooting that left two innocent bystanders wounded.
In another case, prosecutors claim he treated fellow gang members to an expensive steakhouse dinner to celebrate a shooting that killed one rival and injured five others.
Facing a mountain of evidence from surveillance footage and text messages to lyrics that bragged about violence, Sheff G pleaded guilty earlier this year to attempted murder and conspiracy. Prosecutors pushed for a 20-year sentence. But in a deal with the court, the rapper and the judge agreed on five years in prison followed by five years of supervised release.
Sheff G is not alone. More than 30 alleged members of the same gangs have been indicted in recent years, with many pleading guilty.
Among them is fellow rapper Tegan Chambers, better known as Sleepy Hallow, who also stood next to Trump at that Bronx rally. Chambers was sentenced last week to one year in jail for conspiracy.