The Fyre Fest Fraudster Is Connecting Trump With Rappers

On June 14, entrepreneur and infamous Fyre Fest organizer Billy McFarland uploaded a photo of himself alongside former president and presumptive 2024 Republican nominee Donald Trump to Instagram. His caption read, “Pres’ birthday featuring your new cabinet.” While that’s not likely to happen, McFarland has played a role in connecting Trump with rappers throughout his campaign — as the Republican seeks to court Black voters.

A source close to Detroit rapper Icewear Vezzo tells Rolling Stone that McFarland reached out to the rapper’s camp and connected him with Trump ahead of the presidential hopeful’s visit to the Motor City. McFarland previously told media personality Angela Yee that he helped link Brooklyn rappers Sheff G and Sleepy Hallow to Trump, which resulted in their appearance at a May campaign rally in The Bronx.

McFarland didn’t respond to multiple interview requests from Rolling Stone. Three sources on or close to the Trump campaign insist he has no formal role with the former president’s 2024 campaign. McFarland is, however, one of the contacts that Team Trump has reached out to when the campaign or Trump has sought to connect with certain celebrities, rappers, and other musical artists, two of those sources say.

In Trump’s campaign and within his close social circle, there is a broader effort to arrange meetings and public events with the former and perhaps future president and an array of hip-hop artists, the sources add. Several Republicans in Trump’s orbit have been working behind the scenes since last year to recruit different rappers or hip-hop producers to meet him or even campaign for him, with varying degrees of success so far. One GOP operative shared with Rolling Stone a list of rappers — some have been publicly Trump-curious, others have not — that this operative had discussed with Trump months ago, telling the ex-president that they were working on getting all of them to endorse Trump 2024 and perform campaign events for him. At this time, none of them have.

Further, sources close to Trump tell Rolling Stone that these meetings are a reflection of the 2024 presidential candidate’s continued desire to be in proximity to hip-hop artists — particularly ones willing to ask their followers to defect from the Democratic Party for the MAGA movement.

To this day, the former president grows visibly elated when discussing the rappers, such as Lil Wayne, who have endorsed him, two Republicans close to Trump say. At times, he compares it to when certain actors in Hollywood endorse his White House bids. Trump has also made clear that he’d like to see more of these 2024 hip-hop-related appearances — even if the artist doesn’t explicitly endorse him.

Since January, one of the sources adds, Trump has privately lamented at least a couple times that Snoop Dogg probably won’t endorse his 2024 campaign, speculating that the famous rapper does not want to lose business or endorsement deals. (Early this year, Snoop Dogg made headlines for saying he now has “nothing but love and respect for Donald Trump,” just years after backing Hillary Clinton in 2016 and telling Trump to go “fuck” himself during his term in office.)

Throughout his political career, Trump has sought to appeal to Black voters through meetings with Black celebrities, including rappers. A month after the 2016 election, Trump had a meeting with Kanye West, who was a staunch advocate for Trump throughout his presidential term — and may have run a sham campaign in 2020 to siphon votes from Joe Biden, who won. In 2018, Philadelphia rapper Meek Mill was scheduled to appear at a White House summit on prison reform, but eventually turned the offer down. In the months leading up to the 2020 election, Trump pardoned rappers Lil Wayne and Kodak Black from federal charges. And he also had rapper Lil Pump at a November 2020 rally — calling him “Lil Pimp.”

Since then, Trump has won favor with rappers like 50 Cent and Waka Flocka, who’ve expressed interest in voting for Trump. During election season 2024, Trump is seeking to capitalize on public appearances with rappers to help sway Black voters, who are a key demographic that will help swing the 2024 election.

Biden has been losing favor with some Black voters, who historically vote Democrat. A May Pew Research survey showed that on a nationwide basis, Black voters preferred Biden to Trump 78 percent to 18 percent. But there’s a perception among Democrats that Biden is abnormally vulnerable among Black voters in several key states he needs in order to win the election. New York Times and Sienna polls of six battleground states show that 71 percent of Black voters would vote for Biden, while Trump’s tally is 22 percent; the latter accrued just 8 percent of Black votes in the 2020 election. Some believe Trump is attempting to sway those voters with his anti-immigration rhetoric, as well as public encounters with hip-hop artists.

So far, McFarland has helped connect rappers with Trump at least twice.

It’s a fascinating turn of events: Fyre Festival was such an infamous, unmitigated disaster — full of chaos and unfulfilled hype — that the term “Fyre Fest” quickly entered the pop-cultural lexicon as being synonymous with mayhem and catastrophe. Trump’s Justice Department prosecuted McFarland, and in October 2018, he was sentenced to six years in federal prison on two counts of wire fraud. McFarland allegedly used fake documents to deceive investors into putting over $27 million into his Fyre Media Inc. company.

While on bail in that case, he started a company that sold tickets to events that didn’t exist or weren’t publicly accessible, such as the Met Gala. McFarland was released from prison in 2022, and has begun working on a “virtual immersive decentralized reality” festival, called PYRT. He’s also apparently become a liaison of sorts between rappers and Team Trump.

McFarland has said that he connected Brooklyn rappers Sheff G and Sleepy Hallow with Trump, telling media personality Angela Yee: “I just love bringing different people together.” On May 23, the Winners Circle rappers took the stage during a Trump campaign rally in The Bronx. “One thing I wanna say…they always gonna whisper your accomplishments, and shout your failures,” Sheff said, before proclaiming, “Trump gonna shout the wins for all of us.“ Sleepy Hallow followed up by bellowing, “Make America Great Again.”

Afterward, spectators and reporters like Joy Reid noted that both men are currently on bail on a slew of charges, including murder conspiracy. For some, their appearance evoked Trump’s prior comments that “the Black people” like him because he’s been “discriminated against” by the legal system, and his claim that “the Black population” had “embraced” his mugshot “more than anyone else.” Days later, 50 Cent told Capitol Hill reporters that he felt Black men were “identifying with” Trump because “they got RICO charges.”

McFarland told Yee that because Trump’s rally “was the first time a president’s done a rally in the Bronx since Ronald Reagan,” he thought he should “capitalize” on the moment by bringing “New York rap to the Bronx.” He also claimed that “over 35 artists” asked him to attend the rally.

A source close to Vezzo tells Rolling Stone that McFarland also helped set up the June 15 meeting between Trump, Icewear Vezzo, and another Detroit rapper, Peezy. McFarland connected the MCs with a Trump campaign worker who works at Wayne State University, the source says. Vezzo told Rolling Stone in February that he would vote for Trump over Biden (though he prefers independent candidate Robert F. Kennedy Jr., who he’s also met).

He later responded to online backlash to the Trump meeting, surmising in a clip posted to social media that prior generations of Black people “voted blindly” for Democrats, but adding that he “decided to ask questions” of both Trump and Kennedy. The source says that Vezzo and Trump met in the back of Detroit’s 180 Church for an “undisclosed time,” where Vezzo got to tell the presidential candidate about the issues that matter to him.

Weeks later, Trump met with Philadelphia rapper OT7 Quanny. His managers Kim Simpson and Tav C. tell Rolling Stone that they can’t recall if McFarland reached out to them, but say that someone DMed them on Instagram and linked them with Trump’s 2024 deputy campaign manager for operations, Justin Caporale, who arranged for Quanny to spend time with Trump while he campaigned in his home city.

“[Caporale] said, ‘Look, we’re coming to Philly tomorrow. We’d love to have you guys riding the motorcade,’” Tav C. recalls. “We want to bring you on the jet to hang out with [Trump]. Then he’s going to get some cheesesteaks. We want you guys to ride with him.” Tav C. says that Quanny was initially reticent about the optic of being used “as a pawn,” but became receptive once he secured private time to speak with Trump.

Tav C. says that they first met while Trump’s jet was on the tarmac. He recalls that they initially watched UFC and talked about the combat sport, but then began talking about local issues in Philadelphia, including the influx of people seeking asylum in the city.

“I feel like right now people do feel safe, but I also feel like [other] people don’t feel safe, especially in places like Philadelphia [and] New York City,” Tav C. says. “I don’t know if that’s something that the migrants have brought or it’s something that happened post-pandemic, but it’s just something that I feel like we need to do better at. I feel like we were able to express that to the ex-president, and [were] able to bend his ear on that.” Tav C. says he feels like Caporale reached out to Quanny “because Quanny has the eyes and the ears of the young inner city kids and also the young suburban kids.”

Viral clips showed the two at local restaurant Tony & Nick’s Steaks, and they later took a photo together on the candidate’s private jet. Trump shouted out Quanny during his rally speech, noting, “We have a Philly rapper, he’s going places … he’s got so much cash he doesn’t know what to do with it,” before commending Quanny for how his MAGA hat fit him. Tav C. says that their time together wasn’t intended to be a Trump endorsement, and says he personally had no qualms about meeting with the former president.

“I feel like anytime there’s an opportunity to have a sit-down and have a conversation with somebody of that stature, it’s less about reservations, [less] about my political beliefs, and more about [realizing we] we have to have these open conversations and be open-minded about educating each other,” he says. “Donald Trump, he’s not from our world, we’re not from his world, but we’re all grown men who are successful in business and can sit down and have a conversation with each other.”

“We got it done, but I don’t know if we were the easiest to work with,” Tav C. says, adding, “I think that went a long way with their team because [Quanny] wasn’t trying to go viral. They could tell that he was genuine in wanting to actually sit and speak with the ex-president.”

Asked about this reporting, Trump’s spokesman Steven Cheung simply emailed: “Americans of all backgrounds are coalescing around President Trump because they have seen what a disastrous Biden presidency represents — skyrocketing inflation, an out-of-control border, and spiraling crime across our communities.” Apparently, they believe that bloc includes fans of artists like Quanny.

In March, the up-and-coming rapper had only officially released 11 songs over three years, a sparse output compared to his generational peers. Still, he was able to sell out New York’s Gramercy Theatre; it’s that influence that Trump was looking to tap into.

Quanny’s other co-manager Kim Simpson says that she was initially reticent about how hip-hop fans would interpret Quanny meeting with Trump. But she says that she views the meeting as a positive in hindsight. “It did go viral, so it was good,” she says. “I would say it boosted him as an artist. I’m pretty sure a lot of people were googling him.”

While only Sheff G and Sleepy Hallow have appeared to advocate for Trump, the recent photos of Trump with Vezzo and Quanny have sparked controversy with potential voters who view Trump as a dangerous candidate. But Vezzo says that his meeting wasn’t an endorsement, as does Tav C., who says that he and Quanny are also open to meeting with President Biden.

“[The Trump meeting] was literally getting in front of him and having that conversation and letting him know what Philly is about,” he says. “There are certain things about the city and about the kids that people forget in the bigger picture. And if President Biden wants to sit down, we’ll be open to that. It’s more about just having the conversations and opening up these dialogues than anything else.”

More from Rolling Stone

Best of Rolling Stone