After promising to make New York City’s streets safe again at a campaign rally in the Bronx on Thursday night, former President Donald Trump enthusiastically invited some special guests onto the stage: Rep. Byron Donald (R-Fla.), former New York City Council Member Ruben Diaz Sr., and Brooklyn rappers Sheff G and Sleepy Hollow.
While endorsements from local celebrities are common political ritual, some of the former president’s guests were rather unusual. Sheff G (real name Michael Williams) was charged with attempted murder by the Brooklyn district attorney last year as part of a major gang crackdown, but the rapper was serving time in prison on a separate weapons charge, and Sleepy Hallow (real name Teagan Chambers) is charged with conspiracy in the same gang case; he previously served eight months in prison for weapons possession.
Prosecutors allege that members of the rapper’s gang were involved in 24 violent incidents, including one in which a man opened fire on a Brooklyn sidewalk, hitting two passersby.
“Do you guys know Chef G? Where’s Chef G?” Trump asked the audience at the end of his speech on Thursday, before introducing Sleepy Hallow.
“President Trump, my man,” Chef G responded warmly.
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“I have one thing to say: They’ll always whisper your accomplishments and shout your failures. Trump will shout the victory of all of us,” the rapper told the crowd. Sleepy Hollow then performed Trump’s slogan, “Make America Great Again.”
The two musicians are part of a group of pro-Trump rappers that includes Chief Keef, Azealia Banks and Kodak Black, who was serving a four-year prison sentence for a federal firearms offense but had his sentence commuted by Trump.
“Sheff G was there to support President Trump’s election victory at the campaign trail, and like all Americans, he has the right to make his feelings known,” Sheff G’s attorney, Arthur Aidala, told USA Today. “At this time, he is presumed innocent. We are in active litigation with the Brooklyn District Attorney’s Office and am cautiously optimistic that a satisfactory outcome will be achieved for my client.”
Asked about the accusations, Trump campaign spokesman Steven Chang wrote in an email, “As Chef G said, ‘They will always whisper your accomplishments and shout your failures.'”
An attorney for Sleepy Hollow did not immediately respond to a request for comment.
Trump’s rhetoric and his organizations
President Trump has taken a tough stance on crime during recent campaign stops in New York, including a stop at a Harlem liquor store that was the scene of a deadly stabbing.
Speaking in the Bronx, the former president claimed the city was home to “squalid encampments of drug-addicted homeless” and “madmen who push innocent pedestrians onto train tracks and kill them.”
“We’re going to bring safety back to the city,” he promised.
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All four of the men Trump called to the stage have had run-ins with the law: Rep. Donald, who grew up in Brooklyn, was indicted on marijuana charges in 1997 but had them dismissed as part of a pretrial diversion program and had a bribery charge dismissed in 2000. Diaz was indicted on felony charges of possession with intent to distribute heroin and marijuana in 1965 and pleaded guilty to a misdemeanor drug possession charge.
Sheff G and Sleepy Hollow are two of the leading figures in drill rap, a subgenre of hip hop that has come under fire from local elected officials, including New York City Mayor Eric Adams, for its extremely violent lyrics and videos, which often feature rappers brandishing guns and threatening rivals.
“We’ve had several shootings in Brooklyn recently that are directly tied to drill rap,” Brooklyn District Attorney Eric Gonzalez told Fox News in 2022. “Rappers are taunting rivals in rival gang turf, saying, ‘We’re here. Come get us. If we see you, we’re going to shoot you.'”
Trump has had connections to people who have been convicted of crimes in the past. Notable examples include:
- Steve Bannon, a former Trump campaign official and White House strategist, was convicted of contempt of Congress in 2022 for failing to comply with a subpoena from the committee investigating the Jan. 6 attack on the U.S. Capitol. Bannon also faces money laundering and conspiracy charges in New York state for allegedly defrauding supporters of President Trump while soliciting donations for a wall on the U.S.-Mexico border.
- Allen Weisselberg, the Trump Organization’s former chief financial officer, served more than three months in prison for tax evasion and was sentenced last month to five months for perjury.
- In 2018, President Trump’s former campaign chairman, Paul Manafort, was convicted of federal tax evasion and bank fraud and also pleaded guilty to federal conspiracy and witness tampering charges. He was sentenced to seven and a half years in prison but was pardoned by President Trump.
- President Trump’s former national security adviser, Michael Flynn, pleaded guilty to lying to the FBI about his interactions with Russia’s ambassador before he took office. President Trump pardoned Flynn.
Facing their own legal problems
Trump is currently visiting New York regularly as he awaits trial on 34 counts of falsifying business records to cover up the crime of paying hush money to porn star Stormy Daniels. While the hush money itself was not illegal, prosecutors argue that it was made to silence an affair allegation just before the election and therefore constituted an illegal contribution to Trump’s 2016 campaign.
Closing arguments in Trump’s hush money trial are scheduled for Tuesday. A conviction could bring prison time.
“Trump himself is on trial and they are on the same side,” said Aidala, Shehu G.’s lawyer. “Just as Trump is presumed innocent, Michael Williams is presumed innocent.”
Meanwhile, Trump was indicted in federal court in Florida on 40 counts for hiding classified documents at his Mar-a-Lago estate after leaving the White House, and in Washington, DC, on four counts of conspiring to steal the 2020 election. Trump also faces 10 counts of fraudulent conspiracy in Georgia to steal the 2020 election by recruiting additional presidential electors and pressuring state officials to recognize their legitimacy.
In Arizona, Trump is accused of being a co-conspirator in a separate election fraud scheme in which his lawyer, Rudy Giuliani, and 17 others were recently indicted.
Reaching out to new constituencies
Trump has made it a priority to appeal to black and Latino voters during this election, partly by embracing streetwear and hip-hop culture, and in February he touted a pair of branded, $399 gold high-tops at a sneaker convention in Philadelphia.
But Trump’s efforts go beyond apparel: In February, he told a mostly black audience in South Carolina that his 91 criminal indictments were helping him win over black voters.
“A lot of people have said that black people like me because they’ve been so hurt and discriminated against, and they actually see me as the one being discriminated against,” he said of his criminal case at an event hosted by the Black Conservative League.
His comments sparked immediate and widespread backlash.
“Though I find it disgusting, I am not at all surprised that Donald Trump would equate the suffering and injustice of Black people in America with the consequences they currently face because of his own actions,” former Rep. Cedric Richmond, a Louisiana Democrat and co-chair of the Biden-Harris 2024 campaign, responded in a statement. “For Donald Trump to claim that Black Americans support him because of criminal charges is insulting, stupid and just plain racist.”
Black voters have overwhelmingly supported Democrats in recent elections, including the 2020 election, in which President Biden received the support of 87% of Black voters.
Controversy over audience size
The Trump campaign claimed that 25,000 people gathered to see him at Crotona Park in the Bronx.
Reports and police estimates were much lower and roughly in line with the 3,400 tickets the campaign had distributed for the rally.
The New York Daily News reported that “several hundred” people attended, while The Daily Beast estimated it to be “over 1,000, if not exactly thousands.”
An NYPD officer patrolling the park told Raw Story that there were 3,500 people on the air team monitoring the event from a helicopter.
According to The New Republic, aerial photos showed about 800 people inside the rally’s fence, and “several hundred” outside it.
“The aerial photo was taken just hours before the speech and has been debunked,” Trump campaign spokesman Chung told USA Today.
The New Republic reported that the aerial photo was taken during Trump’s speech. It shows a white man wearing Trump’s trademark navy blue suit onstage. The Daily Mail also published a larger version of the photo, which clearly shows Trump onstage.
“More than 25,000 people gathered, as confirmed by journalists and media personnel,” Chan added.
When asked which journalists corroborated that figure, Chang cited a Voz Media article, which did not say the outlet independently verified the 25,000 attendees. The article linked the figure to a Fox News article that credited the Trump campaign. Fox News also quoted an anonymous law enforcement official as telling the New York Post that between 8,000 and 10,000 people attended.
