Toward the end of a rally in the Bronx on Thursday that his campaign staged to try to bolster and highlight his support among Black and Hispanic voters, former President Donald J. Trump called upon two hip-hop artists who have been accused of participating in violent gang warfare fueled in part by their music.
The rappers, Sheff G and Sleepy Hallow, were among several guests invited to voice their support for Mr. Trump, the presumptive Republican presidential nominee. After they did so, Mr. Trump expressed his gratitude, and then complimented Sheff G’s glittering jewel-encrusted grill. “I like those teeth. I want to find out where you did — I got to get my teeth like that,” he said. “I want that to happen to me.”
But Mr. Trump — who earlier in his speech had vowed to restore the rule of law in New York City, denounced urban crime and touted his allegiance to the police — did not address the charges the two men are facing: counts of conspiracy to commit murder and weapons possession.
Presidential candidates typically try to distance themselves from people accused of violent crimes. But the joint appearance, which was clipped and shared on social media by the Trump campaign and many in the hip-hop media ecosystem, was not a one-off event but rather one in a series of Mr. Trump’s blunt and sometimes clumsy overtures to court Black voters, and particularly Black men.
In appealing to Black voters to break with President Biden and the Democrats, Mr. Trump insists that Mr. Biden’s handling of issues like immigration and the economy is disproportionately harming them.
But he has also repeatedly trafficked in stereotypes about Black Americans. Indicted four times and standing trial on felony charges in Manhattan, the former president earlier this year told a group of Black Republicans that the criminal charges he faces were a key reason that Black people liked him. He has also suggested that his popularity among Black people rose when his Atlanta mug shot was published because they could relate to it.
Earlier this year, Mr. Trump went to a sneaker-focused convention in Philadelphia hawking gold-colored, Trump-branded sneakers to a younger and more diverse crowd than is typical of his usual rallies.
Stefanie Brown James, a co-founder of the Collective PAC, an organization that aims to elect Black officials, said that Mr. Trump was engaging in antiquated stereotypes, promoting the idea that a vast majority of Black people, particularly Black men, have some sort of criminal record.
“We don’t hold it up in our community as a badge of honor to have gone through the court system,” she said. “And I think that he uplifts it as if it’s a badge of honor.”
But all in all, Mr. Trump is having some success in his efforts to reach more diverse communities: Polls show him trending better with Black voters than any Republican presidential candidate has in decades.
Democrats have also been working hard to shore up Black support. On Thursday, the Biden campaign released a new ad portraying Mr. Trump as a racist, in particular singling out how he fueled anger over the Central Park Five case decades ago.
In a statement, Jasmine Harris, the Biden campaign’s director of Black media, accused Mr. Trump of being “the poster boy for modern racism.” She criticized his attempts to curry favor with Black voters as offensive and hollow, saying that “he thinks janky rap concerts, free chicken and his own mug shot are the key to winning our votes.”
“President Biden knows he has to earn — not ask — for every American’s support,” she added.
But attendees at the Bronx rally, who included Black and Hispanic voters, suggested Mr. Biden had much work to do.
Jamaal Kennedy, 35, a Bronx rap artist, echoed Mr. Trump’s message that he had done more to help boost the economic prospects of Black people than Mr. Biden or Barack Obama, the nation’s first Black president.
He added that Mr. Trump’s brashness was part of his appeal. “He’s got no filter,” Mr. Kennedy said, though he noted: “I think that’s a reason why a lot of people don’t like him.”
Mr. Trump did not explain why he called to the stage Sheff G and Sleepy Hallow, whose real names are Michael Williams and Tegan Chambers. Their appearance came during a moment typical of his rallies, when he recognizes key figures in attendance.
Both men are pioneers of Brooklyn’s drill rap scene, a hyperlocal, pugnacious style of modern gangster rap with a tough sound and subject matter that often centers gun violence.
Though drill music, as it’s known, has moved toward the mainstream, its rise has not always been celebrated: In 2019, Mr. Williams was removed from the lineup of a rap festival after the New York Police Department said he and other artists had “been affiliated with recent acts of violence citywide” and posed a safety risk.
Last year, Mr. Williams and Mr. Chambers were among 32 people charged in a 140-count indictment accusing the men of using profits from their music to bankroll two Brooklyn gangs, the 8 Trey Crips and 9 Ways. Both men had previously served time in prison for weapons possession.
Prosecutors in the case, which is ongoing, said that Mr. Williams awarded cash, contracts and cameos in his videos to those who committed acts of violence on his behalf.
Sleepy Hallow was released on bail last year. In April, after 14 months awaiting trial, Sheff G was also released on bail. “They counted me out,” he wrote in capital letters on Instagram. “They thought I was done.”
Asked whether Mr. Trump was aware of the charges against both rappers and how he viewed them in light of his tough-on-crime stance, a spokesman, Steven Cheung, pointed to the comments Mr. Williams made from the stage.
“They’re always going to whisper your accomplishments and shout your failures,” Mr. Williams said. “Trump will shout the wins for all of us.” Representatives for both rappers declined to comment.
Mr. Trump’s association with hip-hop stars dates back to the 1990s, when he was frequently seen at New York clubs with rap impresarios and his name was used frequently in lyrics as shorthand for financial success.
As president, Mr. Trump deepened those relationships, appearing alongside Kanye West and including hip-hop figures among his final batch of pardons and commutations, including for the rappers Lil Wayne and Kodak Black, who faced charges related to guns.
Still, Mr. Trump’s appearance with two men accused of ordering gang murders exemplified a fundamental tension that has characterized his campaign. Even as he faces criminal charges, Mr. Trump frequently calls for tougher policing that he says could crack down on murders and assault.
On Thursday, he again vowed to protect police officers from lawsuits so they could be more aggressive in tackling crime. Mr. Trump has framed that protection — which already largely exists — as a boon to communities of color. “Remember, Black, Hispanic, Asian people need this protection and safety more than anyone else,” he said.
But while the optics and the message may have seemed incongruous, the appearance of the rappers was not that unusual for Mr. Trump, who has shown no qualms about appearing alongside others accused of crimes, including many political allies. He has embraced those being prosecuted for their roles in storming the Capitol on Jan. 6, 2021.
And earlier this week, those joining him in court in Manhattan included Chuck Zito, a former leader of the New York chapter of the Hells Angels motorcycle gang, who spent years in prison on drug charges.
Hurubie Meko and Chris Cameron contributed reporting.
