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Whether genuine or contrived, President Donald Trump has been trying to endear himself to the rap community for years. From aligning himself with rappers like Ye, Lil Pump, Fivio Foreign, Sheff G and others, to getting cosigns from the likes of Wacka Flocka Flame, Chief Keef and more, the polarizing POTUS’ ties to hip-hop have been surprisingly ever-present. In some cases, he even used his presidential power to help rappers with their legal issues.
In the summer of 2019, Trump tried to throw his weight around concerning A$AP Rocky’s assault case in Sweden and demanded the Harlem rapper’s freedom, drawing side eyes from the Swedish government. Rocky was found guilty but allowed to return to the States. The rapper was labeled ungrateful by members of Trump’s camp after he didn’t thank the president.
As Trump was leaving office following his first term in January of 2021, he commuted the sentence of Kodak Black, who was serving a nearly four-year bid on a federal firearms charge stemming from his May 2019 arrest prior to the Rolling Loud Miami Festival. The same day, Trump pardoned Lil Wayne, who was awaiting sentencing for federal gun charges.
Most recently, on May 28, 2025, Trump pardoned YoungBoy Never Broke Again, who was on five years of probation for federal gun charges. He also commuted the sentence of Death Row Records cofounder Michael “Harry O” Harris and the federal sentence of former Gangsta Disciples gang leader Larry Hoover.
On May 29, 2025, Trump was asked about the possibility of pardoning Diddy if he is convicted of sex crimes. “I’d look at what’s happening,” Trump told the assembled press. “And I haven’t been watching it too closely. Though it is certainly getting a lot of coverage. I haven’t spoken to him in years. He used to really like me a lot. I think when I ran for politics, that relationship busted up.”
“I would certainly look at the facts,” Trump continued. “If I think somebody was mistreated, whether they like me or don’t like me, it wouldn’t have any impact.”
Check out a list of rappers who have received pardons or commuted sentences from President Trump below.
Written by: jarvis
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