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DIDDY DOLLARS
Inside Diddy’s ‘economic armageddon’ as he sells $60m private jet & LA mansion…and sick reason his royalties could go UP
An insider reveals he could continue to rake in the dollars even with his reputation in tatters
HE was one of the most powerful moguls in hip-hop history, linked to businesses worth millions and with a fortune of over a billion dollars.
But, after being accused of rape and sexual abuse by his ex-girlfriend in November last year, Diddy's reputation lies in tatters and his multi-million dollar empire is crumbling.
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Since then, even more sordid accusations have emerged, culminating in the rapper’s arrest in September of this year on charges of sex-trafficking, racketeering and transportation to engage in prostitution.
He currently sat in jail after being denied bail at $50million (£38m) and is set to go to trial in May, where he could receive a sentence of 15 years to life.
More than a hundred civil suits are also expected to be filed against the disgraced mogul in the coming weeks over allegations of sexual assault, covering a period from 1991 to 2004, with claims running into the millions of dollars.
As lawyers’ fees mount, Diddy has already started to flog assets to cover costs - including his private jet, a Gulfstream G550, which he reportedly selling for $25million (£19m) after a judge threw out his bail plea on the grounds he is a "serious flight risk."
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The move spells the end of the extravagant and flashy lifestyle the rapper enjoyed for decades, thanks to a lucrative network of business built up over the years, that covered everything from alcohol to fashion.
Speaking exclusively to The Sun, music industry insiders have given their view on the rapid collapse of Diddy’s fortune - and revealed he and all the brands associated with him, face "economic armageddon."
Private jets and luxury mansions
In a 1999 interview with Forbes, Diddy told the magazine he “wanted to be very, very, rich” - a dream the rapper set about achieving from the moment he founded his label Bad Boy Records in 1993.
With signings such as the Notorious B.I.G. and Mase, the label quickly became the go-to place for East Coast hip hop talent in the 90s.
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In its heyday, Bad Boy Records was bringing in more than $130million (£100m) dollars annually, with Diddy personally earning a huge cut thanks to the success of the label’s catalogue.
His own debut album, 1997’s No Way Out, was a massive hit and was certified platinum seven times over.
In the decades since, Diddy looked beyond the music industry and built up a business empire that ranked him among the richest men in hip-hop - earning him billionaire status by 2022.
As his wealth soared, so did his spending on an eye-catching and extravagant lifestyle.
Among his biggest purchases was a $60million (£46m) private jet he dubbed “Combs Air”, a revolving fleet of 20 sportscars, and a record-breaking art collection including a $21million (£16m) painting by Kerry James Marshall, and works by Andy Warhol, Keith Haring and Jean-Michel Basquiat.
He even rocked up to the 2022 Oscars flashing a 30-carat diamond ring.
In 2003, the rapper dropped $14.5million (£11m) on a Miami mansion now worth more than $30million (£23m)and in 2014 bought a sprawling mansion in LA for $39million (£30m). Both properties were raided by federal authorities in the run up to his arrest.
But he soon started diversifying his business interests, building up an empire that covered fashion, alcohol, and Cable TV.
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One high level East Coast recording-business veteran, who has personally crossed paths with the now-disgraced rapper, spoke exclusively to The Sun and praised the mogul’s business success.
“Sean Combs' unusual business acumen was on full display from the second he broke into the hip-hop world in the mid-nineties, he was diversifying his business," he says.
“The guy practically invented the side-hustle, and turning that into your main hustle by leveraging your popularity with audiences as a marketing tool."
His clothing brand, Sean John, was sold in Macy’s and at its peak brought in over $400million (£310m) annually.
While the brand’s value declined, it still proved a substantial money earner for the rapper.
He founded a cable TV network - Revolt - in 2013, and also invested in numerous other ventures including andidyd Alkaline water brand and cannabis companies.
Is anybody going to want to buy clothes with this man's name on them ever again? Of course not
Unnamed industry insider
But by far his biggest money earner came from his role as brand ambassador for Ciroc Vodka, thanks to a deal that saw him take a cut of every case sold.
Although the partnership came to an end in 2023 after a bitter legal battle, court documents revealed Diddy had earned nearly a billion dollars throughout their 15 years working together.
Reputation collapses
But in November 2023, everything changed when Cassie Ventura, Diddy’s ex filed a shocking lawsuit against him alleging rape, abuse, and sex trafficking.
With the floodgates opened, numerous other people came forward with allegations of serious wrongdoing.
By the time his LA and Miami mansions were raided in March, his business empire was in free fall.
Macy’s wasted no time in dropping his Sean John label, and numerous other organisations have cut ties with the rapper.
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“Is anybody going to want to buy clothes with this man's name on them ever again? Of course not,” the music industry insider told The Sun.
The source added: “At the moment Sean is out of the Ciroc business, but the charges and lawsuits against Sean come across like a mortal blow to the Ciroc brand because everybody still knows it as 'Diddy's vodka' and he is the person who made it famous in the US.
“The details that will be potentially uncovered at trial will mean economic armageddon not just for Ciroc's current owners, but for the beverages in which Sean's company Combs Enterprises still has an interest."
Even before his actual arrest in September, estimated his wealth had collapsed to $400million (£300m) with his brands becoming “increasingly worthless” in the face of mounting allegations.
And with further fees to pay, as well as the threat of paying out lawsuits, the rapper has begun a firesale of some of his most expensive assets to cover the costs.
This included putting his 17,000 sq ft LA mansion on the market for $60million (£47m) as well as selling his custom private jet.
Who is suing Diddy?
- November 17, 2023: Cassie, Combs' longtime girlfriend, sued him, claiming she endured “a cycle of abuse, violence, and sex trafficking” until their relationship ended in 2018. Combs and Cassie settled the suit the day after it was filed.
- Combs was hit with two more lawsuits a week after he settled with Cassie.
- November 23, 2023: Joi Dickerson accused Combs of drugging and raping her and filming the attack when she was a 19-year-old college student in January 1991.
- November 24, 2023: A second unidentified accuser in a separate lawsuit claimed that Combs and another man sexually assaulted her and a friend in 1990 or 1991, then showed up at her apartment and beat her several days later.
- December 6, 2023: Combs was sued again by an unidentified woman who claimed he and two men gang-raped her in 2003 when she was 17 years old.
- February 26, 2024: Rodney 'Lil Rod' Jones, who helped produce Combs' most recent album, claimed that the mogul sexually harassed, drugged, and threatened him from September 2022 to November 2023 as they worked together.
- May 21, 2024: Model Crystal McKinney accused Combs of sexually assaulting her after meeting at a Men's Fashion Week event in New York City in 2003. McKinney claims she was drinking alcohol and smoking weed with Combs and several of his colleagues when she took a hit off a joint that she claims was laced with another drug. McKinney claims she felt woozy, and Combs ordered her to the bathroom, where he allegedly forced her to perform oral sex on him.
- May 23, 2024: April Lampros, 51, claimed in her lawsuit that she met Sean Combs in New York City in 1994 while attending the Fashion Institute of Technology. Combs is accused of drugging and raping Lampros in a hotel after promising to help mentor her in the fashion industry.
- July 3, 2024: Adria English, an ex-porn star who went by Omunique, accused Combs of grooming her into sex trafficking in the early 2000s, according to .
- September 24, 2024: Thalia Graves sued Combs, alleging he and his former bodyguard, Joseph Sherman, violently raped her at the Bad Boy Records studio in New York City in 2001. Graves, who was 25 at the time, said Combs offered her a glass of wine, which made her feel "lightheaded, dizzy, and physically weak" before losing consciousness. Graves alleged when she awoke, she found herself tied up and restrained while Combs and Sherman raped her.
He even put his Miami home up as collateral in a proposed $50million (£38m) bond deal that also featured a plan to let him stay at home under the watch of his own private security, and deal that - unsurprisingly - was rejected.
Ultimately, the future of Diddy’s business empire lies in the outcome of the trial, lawsuits, and exactly what details emerge as part of the legal process.
Surprisingly, streams of his music are up 36 per cent since his arrest in September, boosting the rapper’s income at least in the short term.
However, the unnamed insider to whom we spoke suggested this was a trend that was unlikely to last.
“People are only streaming Diddy's music more because he has been so prominent in the headlines and people are talking about him all over social media - but this kind of bump, 90 per cent of the time, goes away,” they said.
“As a case like Sean's grinds on and more sad details come out, radio and satellite DJ's start playing the music less and less because it just puts a bad taste in your mouth. When was the last time you heard R Kelly on the radio?”
“If Sean gets a long sentence, his time in the music business is done forever and revenue from his recording business will eventually shrink down to a trickle."
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Future profit
In September 2023, three months before the first allegations emerged, Diddy took the unusual step of handing back publishing rights to artists under the Bad Boy label.
At the time, the rapper simply claimed he wanted to “do the right thing". However, the subsequent accusations suggest the move was far more cynical than it first seemed.
This is a view shared by Jamie Collinson, a music industry professional with over twenty years in the business.
Speaking to The Sun, he said: “It’s speculation - but it’s my strong view that it was a totally preemptive move.
“He knew that his reputation was just about to go into freefall, and he wanted to get something out there to re-emphasize the idea of him being some sort of benevolent figure - but it’s a totally cynical thing to do in many ways, because those publishing rights have seen their best years.
“He probably also thought that those artists would be less inclined to attack him when the allegations from Cassie came out."
Some people will think it's all just being whipped up to drag someone down and that it won't be as bad as everyone says it is
Jamie Collinson
While he has relinquished the publishing rights, it is unclear if Diddy has also let go of the rights to the master recordings, which provide another valuable stream of royalties.
If Diddy does still own these masters, then they could provide him with a financial lifeline regardless of how deeply scarred his reputation ends up.
“It seems to me that he’s selling off the things that are easy to sell - the jets and the houses,” said Jamie.
“But I would have thought the last thing he’ll want to sell is those masters and if he’s thinking about estate planning, then those copyrights are gold dust.”
As the trial gets underway, increased media attention around the 90s artists who were part of Bad Boy Records will likely boost their streaming numbers.
But ownership of the masters would see this interest directly profit Diddy himself, even if people shun the disgraced mogul.
“I'd be amazed if anyone licenses a Diddy song to anything for the foreseeable future - it would just be suicide,” explained Jamie.
"And artists associated with him, if they are found to have been involved in what was going on, will have their reputation trashed.
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“But at the same time, this is where, in a way, he wins on both sides, because there’ll probably be an outpouring of sympathy for a lot of the artists that he worked with and got signed into these draconian deals.
"So there may be an upturn in people listening to Mase or Notorious B.I.G.
“Ironically, that will be boosting his income because he still owns those masters.”
While his image is almost entirely damaged beyond repair, Diddy may still be able to draw on his most die-hard supporters.
“He was able to become so successful because he's a massively beloved, inspirational figure in black American music,” explained Jamie.
“He has a very strong fan base - and not all those people are going to turn their backs on him.
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"Some people will think it's all just being whipped up to drag someone down and that it won't be as bad as everyone says it is.
“It might be that his reputation can be rehabilitated at some stage, but I think it will all depend on what exactly comes out in the trial.”
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