The hip-hop community is buzzing with heated debates after Brooklyn rapper Sheff G made a surprising appearance at Donald Trump‘s presidential campaign rally in the Bronx on May 24, 2025.
The rally, held at the iconic Yankee Stadium, was intended to be a triumphant homecoming for Trump as he seeks to reclaim the White House in 2024. However, the spotlight quickly shifted when Sheff G and Sleepy Hallow took the stage, embracing Trump and voicing their support for his candidacy. Considering the former President’s divisive and harmful rhetoric, the unexpected endorsement sent shockwaves through the music industry.
Hip-hop has long been a platform for social commentary and political expression, so Sheff G publicly supporting a politician is not a problem per se. However, the musical movement has its roots in marginalized communities, with hip-hop often being used as a tool to denounce the world’s injustices and expose the cruelty of privileged people. Sheff G should have the right to express his political views, regardless of the controversy. However, it’s always disappointing to see a hip-hop artist stand with a man so determined to attack minorities of every kind.
Do we know what motivated Sheff G to support Donald Trump?
In their short appearance on the Trump rally stage, Sheff G only grabbed the microphone to say, “They always gonna whisper your accomplishments and shout your failures. Trump gonna shout the wins for all of us.” Sleepy Hollow was even more succinct, repeating Trump’s empty sling, “Make America great again.” The vague statement doesn’t allow fans to understand the reasoning behind the rappers’ unexpected Trump support. Still, it has brought renewed attention to the recent legal battles Sheff G and Sleepy Hollow have faced.
In May 2023, Sheff G and Sleepy Hollow were indicted on serious charges, including two counts of conspiracy to commit murder and criminal possession of a weapon. Prosecutors allege that Sheff G, whose real name is Michael Williams, used proceeds from his music career to fund gang violence in Brooklyn. He is accused of offering money and expensive jewelry to members of the 8 Trey Crips and affiliated 9 Ways gangs in exchange for committing acts of violence, including murder.
One of the most shocking allegations is that Sheff G hosted a lavish dinner at a Manhattan steakhouse to celebrate the killing of a rival gang member in 2020. Prosecutors claim to have video evidence of the rapper confirming the “score” against rivals and sending pictures of the victims to his sister. He is also accused of acting as the getaway driver for a 2021 shooting in Brooklyn that injured two innocent bystanders. Authorities say this incident was captured on surveillance footage.
Both rappers have pleaded not guilty. Sheff G was initially denied bail but was released in April 2024 on a $1.5 million bond after a judge deemed the evidence against him to be “open to interpretation.” His next court appearance is scheduled for Aug. 9, 2024. So, while there seems to be no ideological overlap between the rappers and Trump, perhaps what connects them is their eagerness to avoid justice.
