Opinion | How a Coterie of Rappers Became Trump Evangelists

One oddity of Donald Trump’s Bronx rally last week was when the former president invited two rappers — Michael Williams, who performs as Sheff G, and Tegan Chambers, who performs as Sleepy Hallow — to the stage.

Both rappers are facing felony charges. And that fact actually makes their appearance at the rally make sense — it tracks with Trump’s seemingly transactional relationship with several hip-hop artists, a history of which I have no doubt Sheff G and Sleepy Hallow are aware.

For instance, just days before the 2020 election, the rapper Lil Wayne, who was weeks away from pleading guilty to a federal gun charge that could have resulted in significant prison time, met with Trump in Florida. Afterward, Wayne posted a picture of the two of them together flashing thumbs-ups and reading, “Besides what he’s done so far with criminal reform, the Platinum Plan is going to give the community real ownership.”

The Platinum Plan was Trump’s Black economic empowerment proposal that was announced toward the end of that year’s presidential race. In what certainly looked a lot like a quid pro quo, Trump pardoned Wayne as he was leaving office.

Trump has had an interesting relationship with hip-hop. For decades, particularly during the “get money” period of the genre, rappers would often name check Trump in their songs.

As the journalist and radio host Farai Chideya says in the new Hulu documentary “Hip-Hop and the White House”: “There are definitely aspects of Trump’s personality and actions that call to the baser nature of hip-hop.” She hypothesizes that at least in the past, the misogynistic cohort within hip-hop may have looked at Trump’s unrestrained sexism and saw it as aspirational.

But it was the hustler-cum-gangster vibe of Trump, particularly with his ostentatious displays of wealth, that endeared him to many in the rap community.

In the documentary, the rapper Waka Flocka Flame goes as far as saying that Trump was more like Tupac Shakur — a monumental figure in hip-hop — than Barack Obama was. That notion is, of course, highly offensive, since Shakur was the son of a Black Panther, grew up around the Panthers, and the organization’s ethos influenced his music and thinking.

But in the run-up to Trump’s first presidential race, in which he amplified birther conspiracy theories, questioning Obama’s citizenship and legitimacy, Black America was reminded of Trump’s history of racist words and deeds and his name became persona non grata in most of the hip-hop world.

Then Trump found a cheap and easy way to win favor with a few big names, (and not just in the hip-hop community): the apparent dangling of presidential pardons.

And the efficacy of this approach is almost undeniable.

In 2018, when Kanye West made a spectacle of himself in the Oval Office — wearing a MAGA hat and hugging Trump — he brought along an attorney representing Larry Hoover, a Chicago gang kingpin serving several life sentences. The meeting included discussions of prison reform and the effects of crime in Chicago, but West also argued for clemency for Hoover, saying at one point, “It’s very important for me to get Hoover out.”

Trump didn’t pardon Hoover, but he reaped the benefit of having the imprimatur of a Black superstar, at least until his relationship with West cooled a few years later.

After reportedly receiving encouragement from the rapper Snoop Dogg, Trump did commute the drug trafficking sentence of a Death Row Records co-founder, Michael Harris, known as Harry-O. And this year, Snoop Dogg — who was once a vocal Trump critic — said, “I have nothing but love and respect for Donald Trump.”

The rapper Kodak Black may have crystallized the link between Trump and clemency for figures in the rap industry when he was asked by the hosts of the “Drink Champs” podcast how his own commutation from Trump came about. Black joked, “I’m Mafioso, bruh,” illustrating the way that Trump has treated pardons and commutations: like gifts from a mob boss.

As the Harvard professor Brandon Terry, who has studied the aesthetics and sociology of hip-hop and Black youth cultures, told me, Trump’s grants of clemency “feed that kind of heroic, solidaristic picture of him as a strong man dispensing favor to people who stay in line.”

The way Trump uses the pardon power reduces our conception of justice to capricious acts of forgiveness, not so much bestowed as traded for loyalty, creating unwritten indentureship for the recipients.

Pretty clearly, Trump believes in an inherent and endemic link between Blackness and criminality. In a 2016 debate, he said that minorities in inner cities “are living in hell.” In 2020, he falsely implied that the 2020 election was stolen from him partly due to cheating in major cities with large Black populations. This year, he suggested that Black people identify with him because he has a mug shot.

The rot at the core of these beliefs is unmistakable, and yet a number of rappers have still allowed themselves to be used as Trump’s pawns.

Corey Miles, a Tulane University sociology professor who studies the relationship of trap music, a subgenre of hip-hop, to the carceral state, says that Trump is “double dipping,” routinely calling, on the front end, for the criminal justice system to get tough, but on the back end tying his selfish critique of the same criminal justice system now going after him to Black people’s legitimate critiques of that system.

He’s doing nothing to alter the predation of the system, only horse trading exemptions from it.

And the testimonials that Trump buys with his pardons matters, not because people take direct voting advice from musicians, but because these musicians quite literally have the mic, and what they say can soften the ground in the culture, making support of Trump for some feel less like treachery and more like rebellion.