In 1989, the FBI sent a letter accusing the rap group N.W.A of encouraging “violence against and disrespect” for law enforcement with its song, “F--- Tha Police.” The lead verse on that song — a righteous, venomous indictment of how police officers deal with young Black men — was written by Ice Cube, a 20-year-old artist who had become a gangsta rap revolutionary, channeling the anger of young, Black, inner-city men who felt America’s systems of authority were holding them back.

Flash forward another three decades, and Ice Cube was advising President Trump, who has backed police violence and railed against the Black Lives Matter movement, on how to connect with young Black men who felt left behind economically. Specifically, Cube advised the Trump campaign on its “Platinum Plan,” which promised support for Black churches and businesses as well the “highest policing standards” for urban neighborhoods.

It’s easy to doubt Trump’s sincerity when it comes to raising policing standards. Early in his presidency, he told officers it was okay to be rough with handcuffed suspects. Later, he called the slogan “Black Lives Matter” a “symbol of hate” and told governors they should “dominate” protesters who took to the streets in solidarity with victims of police violence. He has defended Confederate monuments and downplayed the effects of racism in America. People celebrated his reelection defeat by dancing in the streets to the anti-Trump rap anthem “FDT” (it’s an acronym, you can probably guess what it stands for) as if a dictatorial regime had been overthrown.

So it was puzzling when Ice Cube, who titled his 1990 debut album “AmeriKKKa’s Most Wanted,” decided to lend his credibility to a president who embodies White grievance politics. But before Election Day, Ice Cube wouldn’t be the only rapper to hop aboard the Trump train.

Londell McMillan, the owner of legendary rap magazine the Source, called Ice Cube’s relationship with the Trump campaign “preposterous.” He said it was absurd for rappers to try to represent Black America in a negotiation with the president. “They don’t even negotiate their own contracts for themselves,” McMillan said. “How are they negotiating for an entire ethnic group of people who are very diverse and have different interests?”

Five days before Election Day, Lil Wayne also endorsed the Platinum Plan and tweeted out a photo of himself and Trump. Clever, since he helped popularize the term “bling bling,” shorthand for fancy jewelry and other flashy markers of wealth.

Wayne isn’t very political, although he has distanced himself from Black Lives Matter and claimed racism wasn’t a big deal — which might have flagged him as a possible recruit for Trump’s campaign as it attempted to court Black male voters with a pitch about economic opportunity.

“I’ll admit, I was personally disappointed,” said Cameron Trimble, co-host of the podcast “Hip-Politics.” “Lil Wayne is literally one of my two favorite rappers, next to Jay-Z. I can quote Lil Wayne albums, mix tape, features. I’ve seen Lil Wayne in concert at least five or six times over the last decade,” said Trimble, who said he advised the Biden campaign’s ads to reach young Black voters.

“I felt like he was being used as a last-minute ploy and prop by Donald Trump’s campaign,” he said.

There’s another wrinkle to this. On Tuesday, federal prosecutors charged Lil Wayne, born Dwayne Carter Jr., with one count of possession of a firearm and ammunition by a felon. The charge, brought by the U.S. attorney for the Southern District of Florida, stems from a December 2019 incident in which federal agents searched Wayne’s plane after receiving a tip from Miami-Dade police that guns and drugs were on the plane, according to the Miami Herald. If convicted, Carter could face up to 10 years in prison.

Fellow rapper 50 Cent suggested that Lil Wayne might want to cash in a favor with the president who is known to hand out pardons to those who’ve been nice to him. “Wait a minute Trump still got 63 days left, call him wayne. get that fool on the phone. they gonna try to put you in jail for supporting trump,” he tweeted Tuesday.

Whether the support of a few famous rappers helped Trump is hard to know. Among Black voters, Trump once again got trounced by his Democratic opponent, winning only 13 percent, according to preliminary data from Edison Research. While more detailed data about raw vote totals is yet to come, there is some evidence that Trump improved his standing among Black men by six percentage points from 2016.

In the rap world, Trump has long been an avatar for ostentatious wealth. He was seen as a boss and a self-promotional hustler — basically, most rappers’ idea of a rich person. “There’s some real odd commonalities in Donald Trump and the characters that are portrayed by these hip-hop artists,” McMillan said. “They have big egos. Many of them promote making money, whether it’s real or not.” Born rich in Queens, the real estate scion nonetheless projected qualities of a “hood billionaire,” said Trimble — someone who was “a representation of what we thought it meant to be wealthy.” Over the years, Trump’s been name-checked in more than 300 rap songs.

The relationship between rap and Trump began to sour after Trump launched his political career by using the racist birther conspiracy theory to attack President Barack Obama, a man who by then had surpassed Trump as a hip-hop icon. (That isn’t to say Obama enjoyed universal support among rappers. Lupe Fiasco once critiqued Obama’s foreign policy by calling him a terrorist.)

Reflecting on Trump’s modest electoral gains with Black men, Obama has acknowledged a (somewhat simplistic) kinship between his successor and some rappers. “I have to remind myself that if you listen to rap music, it’s all about the bling, the women, the money,” Obama told the Atlantic. “A lot of rap videos are using the same measures of what it means to be successful as Donald Trump is. Everything is gold-plated. That insinuates itself and seeps into the culture.”

Hip-hop, like Black culture, is not monolithic. It has diverse thinkers with their own internal contradictions. In rap lyrics, you’re likely to hear about Black capitalism, social consciousness, veganism, communist revolutionaries like Che Guevara, Black Panthers like Mumia Abu-Jamal and financial titans like Warren Buffett — and that’s just in Jay-Z’s music. (Jay-Z also sported a Colin Kaepernick jersey during a “Saturday Night Live” performance before cutting a deal with the NFL to advise on live music and social justice projects, and declaring to be “past kneeling.”)

Rap has been around for almost 50 years now. While younger artists such as Kendrick Lamar and Cardi B tend to focus on issues like social justice and immigration, the genre’s biggest stars have grown older and richer, with the priorities of some wealthier veterans of mainstream rap shifting as they age. Take 50 Cent, who reacted angrily to a CNBC graphic showing New York’s top combined tax rate would be 62 percent under Joe Biden’s plan.

“I don’t care Trump doesn’t like black people 62% are you out of ya f---ing mind,” he posted on Instagram in October.

And then there’s Lil Pump, whose name Trump couldn’t be bothered to actually learn, introducing him as “Lil Pimp” during his Grand Rapids, Mich., rally. The 20-year-old rapper is such an enthusiastic MAGA supporter he changed his Instagram name to “Lil Pimp MAGA 202020” after Trump’s gaffe.

The Washington Post sent messages seeking comment to representatives for Ice Cube, Lil Wayne and Lil Pump and received no responses.

In any case, endorsements from a handful of famous rappers weren’t enough to put Trump over the top. No matter to him; the president had nothing to lose in the deal. But what about Ice Cube, Lil Wayne and Lil Pump? Could throwing in for Trump cost them with fans?

“It depends on the artist,” said Chuck Creekmur, who runs the website AllHipHop.com. Different musical styles help to cultivate different musical fanbases. Lil Pump, for instance, has no political leanings whatsoever, Creekmur said, and therefore his fans probably won’t care.

“We can’t assume that all hip-hop fans are Black, right or even supported by Black people,” he said. “In fact, I think that someone like Lil Pump could have made a new fan base — like, say Kid Rock — and completely dissociate with the Black community completely.”

As for Lil Wayne, “It made me not want to stream his music for a few days,” said Trimble, but it wasn’t enough to make him swear off Weezy’s records permanently.

Aaron Miller, a 46-year-old who grew up in Texas listening to rap, felt betrayed by Ice Cube.

The first time Miller heard Cube’s voice it was “borderline earth shattering,” he said. As a teenager searching for his political voice, he was primed by groups like Boogie Down Productions and Public Enemy, who were far less profane. But Ice Cube was something completely different. He was raw and angry, reflecting the rage at injustice Black people had been feeling on the streets of Los Angeles. Miller, a Black supporter of Sen. Bernie Sanders (I-Vt.) who describes his politics “as far left as they can go,” listened to N.W.A. without irony. It hurt him now, years later, to see Ice Cube helping Trump out with his reelection pitch.

“I’m wondering what made him think that he could be transactional, in good faith with these people that have shown such blatant fraud and manipulation and racism?” Miller said. “I think there’s maybe such a thing as reaching too far across the aisle. I don’t participate in the shallower parts of ‘cancel culture’ or whatever, but I’m mad enough that it changes my perspective.”

The president did, in fact, lose. So, what to make of it all — Trump’s modest gains among Black male voters, Biden’s overwhelming margin with Black voters and the awkward relationship between rap artists and mainstream electoral politics?

“What I saw, was the beginning of a potential serious crack in the Democratic Party if not managed carefully,” McMillan said. “And an opportunity for the Republican Party to engage this audience and this group of people.”

Democrats, he added, need to learn how to have a better conversation with Black men.

Public Enemy frontman Chuck D once called rap the Black CNN, channeling the realities and anxieties of the Black underclass. That may have been an overstatement, but it did reflect what some mainstream rappers saw as their responsibility to be spokespeople for Black culture. Lil Wayne and Ice Cube may or may not have affected Trump’s 2020 margins. Their beats and rhymes have moved more hearts and minds than their political endorsements ever could.

Correction: A previous version of this article said President Trump introduced Lil Pump at a rally in Detroit. The rally took place in Grand Rapids, Mich.