One of the odd things about Donald Trump's Bronx rally last week was that the former president invited two rappers, Michael Williams, who goes by Sheff G, and Teagan Chambers, who goes by Sleepy Hollow, onto the stage.
Both rappers face felony charges, a fact that makes their appearance at the rally significant. It coincides with Trump appearing to have business relationships with several hip-hop artists, a history that Sheff G and Sleepy Hollow surely know about.
For example, just days before the 2020 election, rapper Lil Wayne met with Trump in Florida, despite weeks later pleading guilty to federal firearms charges and facing a lengthy prison sentence. After the meeting, Wayne posted a photo of the two of them giving a thumbs up, writing, “Building on past criminal reform gains, the Platinum Plan will give communities true ownership.”
The Platinum Plan was Trump's black economic empowerment plan, unveiled in the closing days of that year's presidential election. In an apparent return, Trump pardoned Wayne when he left office.
Trump has had an interesting relationship with hip-hop: For decades, especially during hip-hop's “money making” days, rappers would often name-drop him in their songs.
“There are certainly aspects of Trump's personality and behavior that evoke the vulgar nature of hip-hop,” journalist and radio host Farai Chideya writes in the new Hulu documentary “Hip Hop & the White House.” She speculates that, at least in the past, hip-hop's misogynist contingents may have looked to Trump's unrestrained sexism and idolized it.
But it was Trump's hustler-gangster vibe, especially his ostentatious displays of wealth, that endeared him to many in the rap world.
In the documentary, rapper Waka Flocka Flame goes so far as to say that Trump resembles hip-hop landmark Tupac Shakur more than he does Barack Obama, a notion that is deeply jarring, of course, because Shakur is the son of a Black Panther, grew up around the Panthers, and the ethos of the organization has influenced his music and his thinking.
But in the run up to his first presidential run, Trump promoted birthright conspiracy theories questioning Obama's citizenship and legitimacy, reminding black Americans of his history of racist rhetoric and making his name unwelcome in much of the hip-hop world.
And Trump found an easy way to garner the support of a few big names (and not just in hip-hop): dangle the threat of a presidential pardon.
And the effectiveness of this approach is almost undeniable.
In 2018, when Kanye West donned a MAGA hat and hugged President Trump in the Oval Office, he was accompanied by the lawyer for Chicago mob boss Larry Huber, who was serving a life sentence. The meeting discussed prison reform and the impact of crime in Chicago, but West also advocated for a pardon for Huber, saying, “It's very important to me that Huber be released.”
Trump did not pardon Hoover, but he did benefit from the endorsement of a black superstar, at least until his relationship with West cooled a few years later.
After reportedly receiving encouragement from rapper Snoop Dogg, Trump commuted the drug trafficking sentence of Death Row Records co-founder Michael Harris, known as Harry O. And earlier this year, Snoop Dogg, once a vocal critic of Trump, said he had “nothing but love and respect for Donald Trump.”
Rapper Kodak Black may have made Trump's connection to pardons of rap figures clear when he was asked by the hosts of the podcast Drink Champs how Trump came to commute his sentence. “I'm the mob,” Black joked, illustrating how Trump treats pardons and commutations like gifts from a mob boss.
As Brandon Terry, a Harvard professor who studies the aesthetics and sociology of hip hop and black youth culture, told me, Trump's pardons “further his heroic, solidary image as a strong man doling out favors to a submissive public.”
Trump's use of the pardon power has degraded our concept of justice to a capricious act of forgiveness; pardons are not given but are offered in exchange for loyalty, creating an implicit contractual relationship for those who receive them.
Trump clearly believes there's an inherent and deep-rooted link between blackness and crime. In a 2016 debate, he said minorities in inner-city neighborhoods “live like hell.” In 2020, he falsely suggested that fraud in large black cities cost him the 2020 election. This year, he suggested black people identify with him because of photos of his face.
The corruption underlying these beliefs is clear, yet many rappers continue to be used as pawns by Trump.
Corey Miles, a sociology professor at Tulane University who studies the relationship between the hip-hop subgenre trap music and the carceral state, said Trump is “double-dealing”: On the front lines, he constantly calls for stronger criminal justice, but behind closed doors, he's combining his own self-serving criticism of the same criminal justice system that's now attacking him with legitimate criticism of that system by black people.
He has done nothing to change the predatory nature of the system, he has simply traded on its exemptions.
And the testimony Trump buys with his pardons matters, not just because people will receive voting advice directly from musicians, but because these musicians will literally take the microphone, and their voices will soften the cultural soil so that, for some, support for Trump will feel more like treason than betrayal.
