As Trump eyes Diddy pardon, a look back at hip-hop's complicated past with the president

Since President Donald Trump's rise as a businessman and political figure, he has been a subject of fascination in hip-hop culture.
Rap music, with its braggadocious fixation on financial success, has named-dropped the billionaire CEO on dozens of occasions. He has been highly revered as a symbol of success, going as far back as Wu-Tang Clan's Raekwon in his 1995 record "Incarcerated Scarfaces," in which he calls himself the "Black Trump."
But after the 2016 election, the messaging about Trump − from gangsta rap artists like YG to lyricists like Kendrick Lamar − has largely turned from heralding to scorn. That's not to say all of hip-hop has turned its back on the president, especially when a pardon for disgraced music mogul Sean "Diddy" Combs is on the table.
Trump has publicly discussed the possibility of issuing a presidential pardon to Combs, who was found guilty in July on two counts of transportation to engage in prostitution following a landmark sex-trafficking trial in Manhattan court. Despite repeated attempts at bail, the Grammy-winning rapper has been incarcerated at Brooklyn's Metropolitan Detention Center since his arrest on Sept. 16, 2024.
During an Aug. 1 interview on Newsmax, the president spoke about potential pardons for Combs, convicted sex trafficker Ghislaine Maxwell and former Rep. George Santos. When asked directly about pardoning Combs by host Rob Finnerty, Trump kept mum on confirming his release but said that negative comments that Combs previously made about him would make it "more difficult."
Here's a look at the biggest rap songs that have mentioned Trump.
Mac Miller's 'Donald Trump' and Rae Sremmurd's 'Up Like Trump'
One of Mac Miller's first hit records, the 2011 platinum-selling track "Donald Trump," found the Pittsburgh native rapping about wanting global dominance, like the real estate mogul: "Take over the world when I'm on my Donald Trump ..."
But five years later, Miller distanced himself from Trump. In one notable appearance on "Nightly With Larry Wilmore," Miller said he hated the then-presidential candidate.
"I think for a while, I was like, 'Donald Trump is gonna end up being the president. Ha ha ha!' And the more I say that, the closer he gets, so I think it's really important for everyone to not take this as a joke," the late rapper told Billboard in September 2016. "This (man) could possibly be the president of the United States, and that's terrifying, that's horrible. Especially at a time like this when our country needs to move forward."
Another Trump-centric record asserting financial dominance, hip-hop duo Rae Sremmurd released "Up Like Trump" in 2015. At the time, one half of the group, Swae Lee, told Complex that Trump was "cool" and "rich."
YG's 'FDT'
Eight months before Trump's 2016 election victory, YG released one of the biggest records in admonition against the Republican candidate, "FDT" featuring fellow California rapper Nipsey Hussle (the DT for Trump's initials, the F for the pejorative exclamation).
A rhythmic take-down, YG gets straight into it. "Just when I thought it wouldn't get no sicker, woke up one morning and heard this weird ... talkin' out the side of his neck," the Compton native starts in the intro.
"Me and all my peoples, we always thought he was straight influential ... when it came to the business. But now, since we know how you really feel, this how we feel," he adds before getting into the chorus, which simply repeats the song's title over and over.
He later raps that he hates Trump and that if he wins the election, he's going to "crash us," while Hussle raps that Trump "spent his trust fund money on the vote."
Kendrick Lamar's 'Determined,' 'Lust' and 'The Heart Part 4'
An early career record from Lamar, 2009's "Determined," mentions Trump in a positive light: "I don't wanna be a dealer, I wanna be a Trump / Donald, that is."
However, since the president's political rise, Lamar has mentioned Trump explicitly in much of his music.
Two months after Trump's 2017 inauguration, Lamar released "The Heart Part 4," rapping: "Donald Trump is a chump / Know how we feel, punk – tell him that God comin' / And Russia need a replay button, y'all up to somethin'."
And in "Lust," from his 2017 Pulitzer Prize-winning album "Damn," Lamar again references the election.
"We all woke up, tryna tune to the daily news / Looking for confirmation, hoping election wasn't true / All of us worried, all of us buried, in our feelings deep / None of us married to his proposal, make us feel cheap / Stale and sad, distraught and mad, tell the neighbor 'bout it / Bet they agree, parade the streets with your voice proudly."
Contributing: Edward Segarra, Jay Stahl and Kinsey Crowley, Paste BN