P. Diddy, Cassie and The Curse of Bad Boy.

Lee Pinkerton
11 min readNov 20, 2023

Sean ‘P. Diddy’ Combs — the A&R man who shaped the early careers of Jodeci and Mary J. Blige; the label mogul behind the legendary Bad Boy Records; the man who brought us The Notorious B.I.G; music producer; entrepreneur; the face of Sean Jean clothing and Ciroc vodka. Now sadly, we must add ‘rapist’ to that list of credits.

In case you missed the news at the tail end of last week, in a lawsuit filed on Thursday November 16th 2023, Casandra Elizabeth Ventura — better known as R&B singer Cassie — detailed horrifying claims about how Combs allegedly treated her during their relationship, citing multiple years of sexual and physical abuse.

Cassie, now 37, had a successful solo career in the 2000s, and is best known for her 2006 hit Me & You. In the lawsuit, Ventura alleged Combs lured her “into an ostentatious, fast-paced, and drug-fuelled lifestyle, and into a romantic relationship with him” within a few years of their meeting in 2005 or 2006. Combs signed her to his Bad Boy Records record label shortly after.

Cassie and Diddy — in happier times?

Combs and Ventura dated for six years publicly, but the allegations of abuse span nearly the entire time they knew each other. She claims that her career was controlled by Combs, who paid for her car, housing and clothing and exercised his control over her abusively.

She accused Combs of regular abusive behaviour, including coercing her into taking drugs, forcing her to have sex with male prostitutes, and hitting her on numerous occasions. She also claims that one on occasion in 2019, he forced his way into her home and raped her as she “repeatedly said ‘no’ and tried to push him away.”

Ventura further claimed in the suit that she struggled with addictions to drugs and alcohol “that were established and fuelled by Mr. Combs” throughout the course of their relationship.

In response to Ventura’s suit, Combs’ lawyer Ben Brafman said: “Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail. Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday.”

But despite his lawyer’s vehement protestations of innocence, in a shock move the two parties reached a financial settlement the very next day. No repeated denials and going to trial as Harvey Weinstein, Bill Cosby and R. Kelly had done before him. Just a straight payout within 24 hours.

“We have decided to resolve this matter amicably. I wish Cassie and her family all the best. Love,” Combs said in a Friday statement.

“I have decided to resolve this matter amicably on terms that I have some level of control. I want to thank my family, fans and lawyers for their unwavering support,” Ventura said in a statement.

In his classic song Bad Boy for Life, Diddy famously rapped “Don’t worry if I write rhymes, I write cheques.” But we know from the complaints of previous signings to his record label, that Combs doesn’t part with his money easily. We don’t know the exact terms of the agreement, but nothing screams ‘guilty as charged’ like a quick pay-off.

Though these accusations of sexual abuse may come as a shock to casual observers, the fact that most people who do business with Sean Combs, leave with a bitter taste in their mouths, has been well documented over the years. It’s almost as if signing to Bad Boy is like selling your soul to the devil, and a high price must be paid in return for the fame and success. The tragic ends of so many former Bad Boy artists has given birth to the legend of ‘The Curse of Bad Boy.’

Most labels will have disgruntled artists who claim to have been ripped off and cheated out of royalties — that is the nature of the music business. But Bad Boy is on another level. Their former artists are not just disgruntled — many after parting company with Combs have dramatic religious conversions, wind up serving long jail sentences, or suffer early deaths.

The most famous of these is the 1997 shooting of his most successful signing The Notorious B.I.G, but there are many other tragic stories.

Craig Mack

Craig Mack and B.I.G were the two first signings to the Bad Boy label.

Although he was the first to release an album on the label, he was quickly overshadowed by Biggie, who became the label’s talisman. Disillusioned with being the ugly step-child of Bad Boy and overlooked in favour of Biggie, he left the label and found God.

After disappearing from the spotlight, he re-emerged some years later, apparently a member of religious cult. In 2012 he appeared on a YouTube video for Overcomer Ministries in South Carolina, going as far as purchasing property and living on their commune. In 2016 the Overcomer Ministries You Tube channel released a video showing Mack rapping about his new life. Mack had suffered from a heart condition for some years and eventually succumbed to it, dying of heart failure in 2018. But despite his religious conversion, Mack held animosity towards Combs until his dying day. He refused to take part in the 2015 Bad Boy reunion concerts and requested that Combs and Bad Boy have no part in his funeral service.

The Lox

Rapping trio Styles P, Sheek Louch and Jadakiss — ‘Free The Lox’!

The LOX were a central part of Bad Boy’s early success, contributing to Puffy’s first solo album and appearing on the hit All About the Benjamins. But when he started to take the label into a more mainstream direction, their brand of hard-core hip-hop fell out of favour. They weren’t happy having to wear shiny suits like Mase, and do collaborations with Mariah Carey. They wanted off Bad Boy, but Combs wouldn’t let them go. Instead of back-room threats and intimidation they employed public campaigning. They started a ‘Free the Lox’ campaign, trying to embarrass Puff into letting them go. When he finally relented, it was at a cost of 3 million dollars. They quickly signed with Ruff Ryders, but still had to give him an advance of $300, 000. And even after they left, he still kept half of their publishing. But unusually they were able to continue their careers after their departure. Once on Ruff Ryders they released another album — We Are The Streets in 2000 which contained the classic — Ryde Or Die Bitch. It also contained a skit entitled Rape’n U Records, which was a thinly disguised swipe at Puffy and their experience on Bad Boy.

Shyne

Shyne with his former mentor — his promising rap career ended when it had barely begun.

Shyne was being sold as the next Biggie, due to similarities in their voice. But his promising career was cut short when he when on 27 December 1999 he and Puffy were involved in an incident in a New York nightclub. There was an altercation in the VIP lounge of the club between Puffy and some other patrons. Shyne fired shots into the air and three people were injured in the ensuing fracas. This pales in comparison to the shooting incidents involving 2 Pac, Biggie and 50 Cent — but how Puffy dealt with it added to his legend of shystiness.
Puffy himself, his driver Wardel Fenderson, his bodyguard Anthony Jones and Shyne were all facing charges, but Puff chose for he and his driver to have a separate legal team to his artist. Diddy was facing 15 years for gun possession and bribery for allegedly trying to bribe his driver Fenderson to say that the gun belonged to him. One of the witnesses for Puffy’s defence, incriminated Shyne and critics accused Puffy of throwing Shyne under the bus to save his own skin.
In 2001 Puff and his driver were acquitted of all charges while Shyne was convicted of assault and possession of weapons and sentenced to 10 years. His contract with Bad Boy was terminated.
In 2009 Shyne was deported back to Belize after serving 8 years in jail and then began the process of re-inventing himself. He converted to Judaism in 2010 and then pursued a career in politics. He is now the leader of the opposition party In Belize.

Anthony “Wolf” Jones.
Combs’ former bodyguard Anthony Jones was also with him during the nightclub incident in December 1999. After the seven-week trial and 22 hours of jury deliberation, Combs and Jones, who was Combs’ best friend from childhood, were acquitted.
After the trail, Jones relocated to Atlanta working in the music and entertainment industry. But just two years later in November 2003, “Wolf” Jones was gunned down along with another man, apparently after an argument over a woman.

Loon
Loon stepped into the spotlight on the Puffy tracks I Need A Girl Parts 1 & 2. He released his own solo album in 2003. He left Bad Boy and released another album on a diferent label without much success. Loon changed his name and converted to Islam in 2008 after travelling to Mecca, later relocating to Egypt. But Islam couldn’t save him from his fate. In 2011 he was arrested while on a trip to Brussels, extradited to the US and in July 2013 sentenced to 14 years for conspiracy to traffic heroin.

G Dep
In 2000 G Dep signed a five-album deal with a $350,000 advance and released Child of The Ghetto in 2001, which spawned the Bad Boy classic Special Delivery. But by 2002 he was broke. After he was dropped from the label, he descended into drug abuse. Between 2003 -2007 he was arrested 17 times for petty drug related offences, but he was haunted by a shooting he had committed in 1993, years before he was even signed. For a number of years he balanced a dependency on PCP with an intermittent rap career, releasing albums in 2007 and 2010. But he couldn’t fight the ghosts of his past. In 2010 he turned himself into the police admitting to the murder and, at the age of 38, was sentenced to 15 years. He will be eligible for parole in 2025 at the age of 51.

Black Rob
Black Rob’s breakout hit was 2000’s Whooah. He released another album on Bad Boy (The Black Rob) report in 2005 which didn’t hit as hard. But he was plagued with ill health. In 2014 he suffered his first stroke of four and was suffering from a kidney condition. In his final years he was homeless and couldn’t afford medical expenses. On the day DMX died, a video was released of sickly-looking Black Rob from his hospital bed. A Go Fund Me campaign was started to pay for his care but it was too late. He died in 2021 aged 52.

Mase

Mase was one of the biggest sellers on Bad Boy, but received little in the way of royalties

Mase was one of Bad Boy’s most successful signings and yet seems to hold the most animosity towards Combs. Upon signing to Bad Boy in 1996, Mase was writing for Puff Daddy’s debut album. He had already enjoyed the spotlight when he appeared on the Biggie track Mo’ Money, Mo’ Problems, but after Biggie’s death Mase was immediately thrust into the void. His own debut album, Harlem World, released in 1997, would go quadruple platinum. But his follow up album Double Up only managed Gold status, due partly to the fact that he found God shortly before the album’s release and refused to do any promotion. In 1999 he quit Bad Boy and announced the formation of SANE Ministries. But after five years of preaching the gospel, he returned to the music business with the album Welcome Back released in 2004, again on Bad Boy Records. The album portrayed Mase’s new Christian lifestyle and “cleaner” image and eventually went gold, but again he wanted to leave the label.
He attempted to join 50 Cent’s G-Unit, but Combs blocked the deal by requesting 2 million dollars to release him from his contract. He eventually got out of the deal and relations between him and Diddy were good enough for him to rejoin the old gang for the Bad Boy reunion tour in 2016. But when Combs made a speech at the 2020 Grammy awards complaining about the discrimination that Black artists suffer at the hands of the industry, Mase flipped out. He wrote a long Instagram post calling out Combs’ hypocrisy, saying that HE was the one exploiting artists. Mase went onto claim that he offered Combs two million dollars to buy back his publishing but was refused. He also claimed that he only received $20,000 over 16 years despite selling 8 million units worldwide during his time on Bad Boy.

But in September 2023 it seemed that the hard-nosed mogul had had a change of heart, when he offered to give all of his artists their publishing. But now we discover that his motives were not entirely altruistic.

Danity Kane

With MTV’s Making the Band, Combs went into the arena of reality TV and manufactured pop groups.

Bringing Bad Boy into the 21st century, Diddy formed girl-group Danity Kane on MTV’s Making the Band in 2005.

Aubrey O’Day, was removed from the group in 2008, though she later returned in 2013. She previously alleged in a December 2022 episode of the Call Her Daddy podcast that Diddy fired her because she wasn’t willing to do what was “expected” of her. “Not talent-wise, but in other areas,” she said.

O’Day also claimed in an interview this year that Diddy had offered to return rights to Danity Kane’s music … if she signed a nondisclosure agreement agreeing to never publicly “disparage” the rapper or his Bad Boy label. O’Day, who said she personally encouraged every member not to take the deal, reposted an Instagram Story suggesting that the NDAs were meant to keep Diddy’s artists quiet.

Legacy

So, how will Sean Combs be remembered? His legal problems do not just involve former girlfriends and label signings. 27 years after the shooting of rapper Tupac Shakur, last month the LAPD finally made an arrest, and there are rumours that Combs will also be implicated.

In the light of Ventura’s suit, numerous previous girlfriends and employees are coming forward with claims of physical and psychological abuse. Sadly, despite his massive contribution to Black music and entertainment, I think it is more likely he will be categorised alongside other abusers like Ike Turner, R. Kelly and Bill Cosby, rather than other music moguls like Berry Gordy and Quincy Jones, as he would’ve wished.

ENDS

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Lee Pinkerton

I’ve been writing for over 20 years and am the author of two books — Amazon page — https://amzn.to/3ivwW0L Blog site = https://theblakwatch.wordpress.com