The April 17 passing of early 2000s hip hop artist Black Rob came while rap fans were still mourning the loss of rap icon DMX.

While the internet questioned how a man once signed to arguably the most popular record label in hip-hop history could wind up ill with no health insurance, the conversation inevitably turned to Bad Boy label founder Sean “Diddy” Combs’ business practices and storied relationship with his signees.

With a renewed focus on Black business and ownership in the wake of the surge of the Black Lives Matter movement, one is left to wonder when we’re going to have an honest conversation about Diddy and other Black capitalists. 

Success and money has long been a barometer for praise especially among Black folk. After all, one of the song’s from Bad Boy’s former act is centered on none other than money, power and respect. More on them, later. However, Bad Boy’s alleged exploitation of its artists goes back decades in Bad Boy patient zero, Craig Mac.

Mac put Bad Boy on the map with his infectious 1994 hit “Flava in Ya Ear” and despite his success and Grammy nomination, a second album with Bad Boy failed to materialize. That year, in an interview with Yo! MTV Raps, a visibly confused Mack can be seen with a screwface following Diddy’s claims they were working on a second album. In what was either a cruel or ill-advised bit of marketing, Mac’s debut was overshadowed when Biggie’s Ready to Die album was released exactly seven days before Mack’s “Project Funk da World.”

Mack died in 2018 following health problems. Reports came out that he had begun living a secluded life in a controversial religious commune, as Blavity previously reported. That same year, for the first time since Forbes began calculating rappers’ wealth, Diddy was ranked only second to a blossoming Jay-Z, having amassed a humble net worth of over $825 million.

Though Biggie solidified Diddy’s status in history, it didn’t allegedly come without its price. In 1997, Lil Cease called in during an explosive interview with The Lox to claim that Diddy purchased the slain star’s publishing for $200,000 before the rapper’s death. Lil Cease claimed Biggie was broke despite his smash hit “Juicy,” as OkayPlayer reported.

More than two decades later, Biggie’s daughter, Tyanna Wallace, said her father’s former collaborator “does nothing” for their family. She later said the two had a heart to heart. While those claims have not been substantiated, what is for certain is that despite Biggie’s death, Diddy continuously released material featuring the artist and profited off of his imagery with two posthumous albums. 

In a 2005 sit down with NYC’s Hot 97, The Lox threatened to drop a refrigerator on Diddy like something out of the Looney Toons if he didn’t return their publishing, as Billboard previously reported.

It worked. Diddy relinquished publishing to the trio shortly after the confrontation, according to Styles P in an interview he did with DJ Vlad. Blasting the entrepreneur has historically been an effective way to get his attention, as shiny-suited wingman Mason “Mase” Betha had to employ the same tactics in his 2009 bid to be released from his contract.

Though he may have gotten released from his contract, just as early as last year, Mase still called for Diddy to be accountable to Black creators and the Black community.

At the 2020 Clive Davis pre-Grammys gala, Diddy admonished the awards show for its mistreatment of Black creators and art.

“So I say this with love to the Grammys, because you really need to know this, every year y’all be killing us man. Man, I’m talking about the pain. I’m speaking for all these artists here, the producers, the executives,” the “It’s All About The Benjamins” artist said. “The amount of time it takes to make these records, to pour your heart into it, and you just want an even playing field.”

“Truth be told, hip-hop has never been respected by the Grammys,” he added. “Black music has never been respected by the Grammys to the point that it should be.”

Mase took to Instagram with a call to action for the music mogul following his viral speech. 

“I heard u loud and clear when u said that u are now for the artist and to that my response is if u want to see change you can make a change today by starting with yourself,” read a caption in a January 2020 post by the “Harlem World” artist.

“For example, u still got my publishing from 24 years ago in which u gave me $20k. Which makes me never want to work w/ u as any artist wouldn’t after u know someone is robbing you & tarnishing your name when u don’t want to comply w/ his horrendous business model,” it continued.”

Total front woman Pam Long has yet to do a major radio interview dissing the label head, but she did speak out that she went back to work at fast chain White Castle, Rolling Stone reported. In fact, in recent years Diddy has been on a campaign that takes aim at the exploitation of Black entrepreneurs and artists. This April, Diddy released a scathing letter directed at General Motors and other white owned business. He was immediately dragged on Twitter for the perceived hypocrisy, considering his track record with his own Black artists. 

But despite Diddy’s criticisms, he still has a loyal and grateful fan base such as what was displayed when the businessman was extolled at Black Rob’s funeral. And to be fair, it’s not like Diddy invented the questionable record deal, nor is he the only Black music entrepreneur to come under scrutiny.

“Milkshake” singer Kelis blasted Neptunes founder Pharrell Williams as recently as last year, saying he kept the proceeds from her initial two albums. Motown, the original Black music powerhouse, was known to have its artists signed to several in-house arms of the company, ensuring profits were considerably eaten up before the artist saw a cent. Marvin Gaye once commented on Berry Gordy’s “money making schemes” and Tammi Terrell’s mother infamously barred everyone from Motown, except Gaye, from Terrell’s funeral stemming from the mistreatment she felt her daughter had endured.

More recently, Lil’ Wayne’s complicated feud with surrogate father and Cash Money executive Birdman has played out for years. In 2015, Wayne sued Cash Money for $51 million. The parties eventually settled out of court for a unspecified amount over $10 million, as Billboard reported. 

Black artistic spaces created by community members have long come with the expectation that they’ll be safer and fairer than the alternatives. Little Richard essentially received no money or royalties from his classic rock hit “Tutti Frutti,” because abuse of Black people was the norm.

While we praise Black business tycoons for being “self-made,” we rarely question at whose at expense that wealth was built on. As the Black wealth gap widens and hip hop’s early stars grow older, coupled with calls of action for restorative justice for Black artists, we may need to begin looking a little closer to home if we’re thinking about cleaning house.