DJ Envy is a poster child for hip-hop’s crossover into the mainstream. Over the past three decades, the 46-year-old Queens native went from hustling rap mixtapes to anchoring the Good Morning America of urban radio – The Breakfast Club, where he plays the role of schoolmarm on “the world’s most dangerous morning show”. The role of failed real estate tycoon, however, might well prove to be his swan song now that Envy’s own listeners accuse him of perpetrating a fraud scheme they say bilked them out of millions.
In October, federal agents in New Jersey arrested a 45-year-old influencer friend of Envy’s and repeat Breakfast Club guest named Cesar Pina for his suspected role in a “Ponzi-like investment fraud scheme”, charging him with wire fraud. Prosecutors say Pina took money from dozens of individual backers to flip houses in New Jersey, promised up to 45% returns in five months, and skimmed those funds for himself and early initial investors.
At least 20 lawsuits filed around the same time as the federal indictment characterize Pina as a conman and a slumlord: they claim he solicited funds for properties he didn’t own or even bother to fix up and suckered multiple people into investing in the same pieces of properties, and all while pocketing cash for his personal use or to make whole with old investors. Alleged victims even accuse him of attempting to pay them back in bling, including branded pieces made by his brother. Half of the lawsuits against Pina also named Envy (real name: Raashaun Casey), blaming the DJ for platforming Pina on The Breakfast Club and social media. Just last month, Pina and Envy were named in a $2m lawsuit accusing them of using the string of real-estate seminars they hosted together as “funnels to draw in victims”, and alleging violations of organized crime law and the New Jersey Consumer Fraud Act.
The conservative estimate for Pina’s alleged fraud stops at $25m, but that barely covers the growing headcount of victims or Pina’s alleged side hustles: $200 for seminar tickets, private consultations for $2,500. The final figure could be in the hundreds of millions, says Alexander Schachtel, a New Jersey attorney who represents many of the victims suing Pina and Envy.
“Envy and Pina said in recorded videos that they own 2,000 properties together worth over $100m,” Schachtel says. “If that’s true, why are they raising money from Joe Schmo the mechanic? It just doesn’t make sense.”
Pina, who’s out on a $1m bond and faces a maximum 20-year sentence plus a $250,000 fine if convicted, asserts his innocence. Envy has not been charged with a crime and even claims he lost $500,000 in a real estate deal with Pina. That the feds nonetheless noted Pina had partnered with “a celebrity disc jockey and radio personality to conduct real estate seminars around the country” should worry Envy and his employers. At the very least, Envy is guilty of having Pina, an ex-con who supposedly mastered the real estate game while serving time for credit card fraud, on The Breakfast Club multiple times over the past five or six years. “I created Cesar,” Envy boasted in a recently resurfaced audio clip. “Cesar wouldn’t have the lifeline or the life he has without a DJ Envy.”
“I thought they had some vetting process in place to make sure that this guy was legit,” says Stanley Acosta, a 31-year-old retail banker from Queens who invested $150,000 in Pina’s real estate venture after hearing him on The Breakfast Club, which Acosta listened to on his commute into work. “They promote other people on there constantly – doctors, lawyers, other businesses – and they’re all legit.”
Typically, a scandal of this scale would send heads rolling, if only to reinforce public trust in the show. After all, in a year that saw the digital audio industry rocked by an advertising swindle that has depressed the podcasting market, it was this alleged fraud blasted out on radio waves that really grabbed listeners. But iHeartRadio hasn’t issued a statement, and New York’s Power 105.1 FM hasn’t yanked anyone from The Breakfast Club lineup. (Neither the parent company nor the station responded to the Guardian’s multiple attempts to reach them for comment.) Apart from the DJ taking the mic in October to distance himself from Pina in a glib, two-minute digression – and all traces of Pina getting scrubbed from the show’s official YouTube page and social media account – the beat goes on as if the show doesn’t have a celebrity endorsement crisis on its hands.
It’s enough to raise the question: how did The Breakfast Club let things get this out of hand?
‘The last guard of what hip-hop journalism used to be’
To even begin answering that, you’ve got to go back to the early years of The Breakfast Club (only related to the John Hughes film by name).
“It exists in this very long tradition of Black radio as a place where folks get information on news, pop culture, even dating and relationships,” says AD Carson, professor of hip-hop and the global south at the University of Virginia. “But they’re also gatekeepers. They have a really important place in the culture, in that last guard of what hip-hop journalism used to be.”
The Breakfast Club was forged in the fires of New York City’s urban radio scene, soon carving out a niche nationally in a crowd dominated by the Family Feud host Steve Harvey and urban radio titan Tom Joyner. The insurgent production launched in 2010 as a junior varsity team: DJ Envy was an apprentice to the New York mixtape king DJ Clue, Angela Yee was a deputy to the DJ-comedian Cipha Sounds, and Charlamagne Tha God had been Wendy Williams’s sidekick. Any show anchored by those three was going to be an experiment – let alone a show trying to get rowdy first thing in the morning. But The Breakfast Club caught lightning in a bottle, quite explicitly redefining what it means to make “good radio” and pushing Power 105.1 out of the long shadow of Hot 97, the Big Apple stalwart with a Midas touch for minting future legends in the recording booth (Jay-Z) and in the radio booth (Williams).
The Breakfast Club copied the simulcasting model that Howard Stern and Rush Limbaugh used to dominate the airwaves. But without its own TV deal, the show dumped clips on to YouTube that allowed audiences to watch back whatever interviews got cut off during their morning commute. “It goes back to JFK versus Nixon, radio versus visual. It’s to the point where now you can’t imagine The Breakfast Club without the visual element,” says Adrien Sebro, a media studies professor at the University of Texas. YouTube turned what would otherwise be terrible radio – Charlamagne insulting a female emcee’s looks to her face, the New Orleans rapper Birdman demanding “respek on my name”, Envy storming out of a Desus & Mero interview – into hugely viral moments. Nowadays, the show boasts more than 5.4 million YouTube subscribers (plus millions more who tune in via radio).
With sprawling influence came the power to elevate eggheads like Michael Eric Dyson and advance social causes like the Black Lives Matter movement, to pivot from mixing it up with Migos to grilling Joe Biden. The Breakfast Club became the place for politicians to make their pitches to the Black community (and see their pandering efforts turned into memes). When it wasn’t Hillary Clinton bragging about the hot sauce bottle she carries in her purse, it was Biden telling The Breakfast Club crowd “you ain’t Black” if they didn’t vote for him.
The Breakfast Club was also early to engage followers directly on social media and even invites listeners to rail against the show in a segment called Slander the Breakfast Club. When it comes to policing itself, however, The Breakfast Club isn’t as quick to engage. And its buccaneering attitude can make it sound especially tone-deaf when wading into matters that run counter to “accepted” hip-hop culture, amplifying anti-trans rhetoric when its hosts – including Charlamagne, who’s been accused of sexual assault (he denies wrongdoing) – aren’t laughing at rape jokes. “The beauty of it is … no one is censoring any of this,” says Carson. “Like, nobody who’s really listening cares, and nobody who cares is really listening.”
By 2019, Envy’s tight association with Pina had become something of a running gag with Breakfast Club guests and listeners, who likewise couldn’t make heads or tails of this real estate venture. “Joe Budden told me it was a Ponzi scheme, and I was gonna go to jail,” Envy deadpanned in 2021, referencing his former labelmate turned hip-hop tastemaker, while telling an anecdote about calling up friends for advice about Pina’s real-estate pitch. Charlamagne and Yee were in the room for Pina’s Breakfast Club appearances and registered their skepticism, albeit jokingly – but the show still wasn’t checking itself.
Even before the Pina controversy, the production showed obvious signs of decline. Hot 97 has reclaimed its lead on New York’s Nielsen charts, and the online following for its rival show Ebro in the Morning is nearly as strong as The Breakfast Club’s. The Breakfast Club also has softened its confrontational approach to political guests, making it easier for Eric Adams, Vivek Ramaswamy et al to exploit appearances for clout. Perhaps worse: this isn’t the first time Envy’s off-air dirt has tarnished the show. Long before the Ponzi scheme allegations, the self-styled family man was outed for his extramarital affair with a leading lady from the reality TV series Love & Hip Hop. Envy and his wife went on a PR charm offensive just to make the tawdry headlines disappear. Breakfast Club followers still remember.
But by far the biggest blow was Yee signing off at the end of 2022 to helm her own midday program at Power 105.1. Yee was the adult in the room, the host you could most count on to ask pointed interview questions and otherwise take her role (relatively) seriously. Above all, she had a squeaky clean personal record; if she brought scandals to the show, it was via the Rumor Report segment. (The Breakfast Club is trying out celeb guests to fill her role, Daily Show-style, and they’ve advertised her job to plebes on LinkedIn.)
The departure of a major talent would be a blow to any hit show, particularly one in danger of losing its edge, and its audience too. “It’s like, not only was that person the lynchpin of it all,” says Carson, “but now that she’s gone, we realize how far over the line we are.”
‘He has to be legitimate’
“I started with no money,” Pina bragged in one of his Breakfast Club appearances, “and here I am, $50m later, in real estate.” Really, his main qualification for appearing on the show seems to be that he had Envy to vouch for him.
In general, Envy comes off on mic as a moral authority who defaults to respectability politics – about on par for the son of a New York City cop. He wags his finger at single fathers, brags about his Hampton University education, and supports stop-and-frisk (he has said he was shot at three times in 2016 carjacking). In his brief on-air apology following Pina’s federal indictment, Envy said, by way of explanation: “I’ve never stole anything from anybody.” But Acosta, the scammed Breakfast Club listener, calls bullshit.
He points to a clip from a podcast Envy co-hosts with his wife, in which the DJ harks back to college days spent shoplifting from Sam’s Club in his Sunday best. (“It worked,” Envy said. “I did this about three, four times.”) Acosta also harbors suspicions about the wealth displayed on Envy’s social media accounts – the cars, the chains, the glow-up. “There’s all this wealth that’s unaccounted for,” Acosta says, “and he’s saying he had no benefit from that whole situation? Nobody with two eyes would believe that, right?” (Envy’s social media accounts suggest his apparent wealth predates Pina’s appearances on The Breakfast Club.)
His skepticism was hard-earned. Acosta was listening to The Breakfast Club when Envy swore by this buddy of his, building him into a Trump-like mogul with thousands of properties and the keys to generational wealth. He was watching when, in one promotional video shot with Pina, Envy held a fan of envelopes that he said contained rent checks from his investment. Also in the shot was DJ Prostyle, another Power 105.1 personality, who held up rent envelopes while touting the fourth real estate deal he was about to close with Pina. “This guy’s tryna get more houses than me! He’s gonna start speaking at the seminars!” Envy joked before turning serious: . “That’s what it’s about, teaching and learning how to do it.”
“This was my first real estate deal ever in life,” Acosta says. “I’m thinking to that point Cesar [Pina] is legitimate. He has to be legitimate. Envy has been backing him for at least two to three years. I saw over 20 videos of him promoting this business. It just didn’t strike me at all in any possible way that this could have been a scam. The Breakfast Club is too big of an organization. iHeartRadio was too big of an organization for that to go down, right?”
When Acosta met Pina in March 2022 at his New Jersey office to close his $150,000 real estate deal, he found Pina charismatic and authoritative. It helped him ignore his concerns about the way Pina conducted business – that he didn’t follow the proper steps for notarizing documents (“but the stamp looked legitimate,” Acosta says), that he demanded the $150,000 in cash and didn’t bother to count it (“he made a joke like, ‘If it’s not there, I’ll let you know’”), that he was pitching Acosta on crypto and NFTs before the ink was dry on their real estate deal. “He started telling me that he was going to become a private money lender himself, so that he wouldn’t need to come to people like us for loans – that he would be the one that actually providing the loans in the future,” says Acosta.
Pina kept asking Acosta if he had more money to invest besides the $150,000 – a nest egg Acosta had built from years of savings, cash gifts from his wedding and a side hustle reselling sneakers. “I told him, ‘I’m broke,’” Acosta says.
But after that meeting, Acosta had a hard time reaching Pina. He’d call or text to ask when he could expect to collect the promised return (30-45% in six months, he says). After a stretch of non-responses, Acosta returned to Pina’s office hoping to catch him. “I would see notes from FedEx or UPS that would be on the door for like a week and a half, like no one was here,” he says. “That’s when I got fed up with everything and filed my lawsuit.”
The doomed investment with Pina cost Acosta his marriage and complicated the future for his four-year-old daughter and two-year-old son. He is suing Envy, Pina, Pina’s wife, Jennifer, and their related businesses in New Jersey state court for damages and losses totalling $329,500 (Schachtel is his lawyer).
Acosta has considered calling in to Slander the Breakfast Club “maybe once or twice”, he says. “But I never had luck in the past. I did think about trying to go on as a fan and then hit them with the hard question.” Ultimately, he went for a more diplomatic approach and slid into the Instagram DMs of Tom Poleman, iHeart’s chief programing director, calmly outlining his situation, Acosta says. He got silence in return.
Tamara Holder-DeMaio is a Chicago-based attorney who has represented former iHeart employees in workplace harassment lawsuits against the company. “There are rules about advertising your own business interests on air [without disclosure]. FCC rules. You literally can’t do that,” says Holder-DeMaio, raising the possibility that Pina’s relationship with Envy relative to the Breakfast Club could be construed as (at least) an indirect form of payola. For context, she cites Dave Ramsey, a Christian radio host who promoted a timeshare exit company that allegedly fleeced his listeners; he was recently hit with a $150m class-action lawsuit. (Ramsey, who has not responded to the allegations, has attempted to have the class action dismissed on grounds that it’s too broad.)
The rumblings about Pina’s Breakfast Club appearances reached a fever pitch in May of this year, when the real estate influencer Tony “the Closer” Robinson, an ex-NFL player with a reputation for uncovering scams, began posting interviews with upset Pina investors. “I’ve been working with the victims who have given me a laundry list of receipts, text messages, phone conversations, email exchanges,” Robinson said on his YouTube show. “I passed an entire file to the federal government … Yes, I’m a proud rat for anybody that thinks they can come and steal hard-earning people’s money.”
Envy confronted Robinson directly with a full-fledged denial: “[Pina] does not owe me money,” he snarled in a tense Instagram Live exchange in May. “We don’t have any dealings with each other.” He also sued Robinson for defamation. (Robinson denies defaming Envy and plans to vigorously fight the motion.) Pina brushed the accusations off but made a point of distancing Envy from the allegations.
In mid-October, the feds arrested Pina and reportedly visited Envy at the iHeart studios in New York to inform him of Pina’s arrest. A month later, Pina filed his own $10m defamation lawsuit against Robinson. (Robinson stands by his statements.)
Schachtel, the victims’ attorney, reckons it shouldn’t be much longer before iHeart, which brags about reaching “90% of Americans each month”, finds itself the subject of a class-action litigation brought on behalf of the victims. “I think what we want to see at this point is a little bit more of that direct evidence of exactly what was being aired on the radio [about the alleged fraud] before we pull the trigger,” he says. “That’s really the missing piece.”
Sticking to the script
Suffice to say, if it weren’t their co-host in the middle of this messy drama, The Breakfast Club would be snickering about it louder than anyone. Instead, disinclined to address the elephant in the room, The Breakfast Club sticks faithfully to the script. One recent episode led off with the hosts discussing a story out of Jackson, Mississippi, about police burying Black homicide victims without notifying their families. Another episode featured an interview with Busta Rhymes. Throughout, there were the usual digressions into mating habits, celebrity foolishness and trending topics – with Envy steering the conversation, as ever.
That’s not to say the idea of a Breakfast Club without Envy hasn’t occurred internally. “I think the Breakfast Club is bigger than any of us as individuals,” Charlamagne said in a recent Rap Radar interview. “What I’ve always wanted for The Breakfast Club was new talent constantly comes in and is a part of this, is under this umbrella of the Club. So whether Angela Yee is there or I’m there or Envy’s there, the platform can still continue.”
Either way, Acosta’s too angry to listen any more. He trusted The Breakfast Club, and he feels the show betrayed him.
Meanwhile, alternatives abound. Ebro in the Morning is a more grounded, thoughtful rival. Just as star athletes dived into the content creation game to bypass the sporting press, hip-hop needle-movers who might have relied on The Breakfast Club for relevance or record sales now have platforms of their own – like NORE’s Drink Champs podcast, which is broadcast on the P Diddy-founded Revolt TV network. ESPN’s Shannon Sharpe is one of a handful of upstarts with buzzier long-form interviews than The Breakfast Club. Roland S Martin, on YouTube too, is more robust on Black news. Budden is a sharper music critic. Tasha K, the internet gossip who lost a $4m defamation lawsuit to Cardi B, is more outrageous.
“The Breakfast Club created ripples that folks might not even trace back to that original plop in the water,” Carson says. If indeed the Breakfast Club loses listeners from a scandal brought home by Envy, its weakest link all along, it’s because the show itself became such an easy mark.
