Diddy faces cash crisis: billionaire lifestyle, lawyer fees

Less money, mo problems?

Sean “Diddy” Combs appears to be facing a cash crisis as hefty legal bills mount and income from lucrative partnerships dries up, analysis of Diddy’s finances by The Post shows.

Diddy, 54, still lives the expensive lifestyle of a high-profile rap star despite the FBI raid — which he called a “witch hunt” — on his home in a sex-trafficking probe amid a series of civil suits.

He was about to board one private jet in Miami when SWAT teams stormed into his homes in Miami and Beverly Hills last month — while the Gulfstream he owns was last spotted in Antigua.

The Post’s analysis puts Diddy’s total annual bills conservatively at $35m per year — without the impact of his secret settlement with Cassie. His reps declined to comment

And in 2023 the core of his income, a lucrative deal with drinks giant Diageo for his vodka and tequila brands, hit the rocks.

His family is also likely to be an increasing financial drain on him. Diddy is a father of seven, four under 18, and while he currently has no long-term partner, is believed to pay for the upkeep of several exes.

And in another financial threat, his son Christian “King” Combs was sued in Los Angeles Thursday by a woman who claims that he sexually assaulted her in 2022, when he was 24. He denies what he calls a “lewd and meritless” claim.

The booze deal that went flat

The biggest single source of Diddy’s wealth for almost two decades was his partnership with drinks giant Diageo.

It brought in cash first, from 2007, through being a 50-50 partner in the Cîroc vodka brand and then from 2013, by jointly buying DeLeón tequila.

As part of his 2007 deal Diageo gave him 50% of Cîroc’s profits and he was also given a marketing budget to promote the alcohol of as much as $15m a year, according to Bloomberg — which he used for lavish parties on yachts, at his homes and around the country.

In May, 2023 Diddy sued the company British-based alcohol giant alleging that he was being treated as a second-class partner to other celebrity booze pitchmen like George Clooney, because of his race, setting up a bitter battle — in which Diageo revealed he had been paid $1 billion since 2007.

He enlisted Rev. Al Sharpton to paint his fight as one that would help the entire black community, “It’s like a slave master beating a slave” Sharpton said of Diageo’s relationship with Combs.

But after getting slapped with a series of lawsuits starting last November which alleged he assaulted, raped, and trafficked women last November, Diageo had clear legal momentum.

Among the claims in the lawsuits were that women were assaulted at the private parties funded by Diageo — and which had “gift bags” sex toys, body chocolate and strippers.

Diddy dropped his suit in January of this year with the drinks firm taking complete control of the brands, suggesting they effectively scored a complete legal victory — leaving him with no future income.

While the marketing budget funded Diddy’s social life, the revenue stream from Cîroc “floated all his other companies,” Bloomberg reported.

The fallen media empire

The highest-profile of those other companies in recent years was Revolt TV, a cable channel which Diddy and other, undisclosed, investors set up in 2013.

Cable channels can be lucrative cash cows when managed well because their owners receive a “cable carriage fee,” a share of people’s cable payments, which is a steady and predictable income, on top of which they sell advertising.

In 2013, Forbes reported his stake to be above 50% and suggested that he could be seeing as much as $12.5m a year in income from Revolt. It later also spawned a website.

But when Diddy’s ex Cassie accused him of rape and sex trafficking last November, Diddy stepped down as chairman.

Last month TMZ reported that he offloaded his stake in Revolt to an anonymous buyer for an undisclosed sum.

The fall of Revolt was not his only media disaster. At the same time as he was sued, a reality show which was due to be produced for Hulu about Diddy’s life was canned.

Businesses also quickly cut ties with his marketplace for black business Empower Global.

But perhaps the more bitter personal blow for Diddy now will be that Bad Boy records, which powered his rise through the 1990s with hits both from him and its top-rank artists, most famously the Notorious B.I.G., is a shadow of itself.

Diddy sold a 50% stake to Warner Brothers Music in 2005 for an undisclosed sum — a 2001 valuation suggested it was worth $100m — but in recent years it has failed to retain or sign major names. Aside from Diddy, whose last releases were flops, its biggest artist is Machine Gun Kelly.

The failing clothing line

Diddy was trying to revive Sean John — a once successful clothing brand that he sold for $70m in 2016 — and bought out of bankruptcy for just $7.5m in 2021.

While the company website proclaims “I got my name back” Diddy had yet to introduce new collections or post any of the existing clothes on the Sean John website or Instagram. While the clothes can still be purchased on Amazon, Walmart and Lyst, Macy’s has halted sales.

Sean John, like Diddy’s other ventures are all private which allows him to obscure the financials. Likewise, his complex network of LLCs makes it difficult to determine his assets. But his conspicuous lifestyle and the bills it comes with are far more easy to put a price on.

The A-list moneypits

Diddy’s Gulfstream 550 — a jet that can fly 6,500 miles or farther than the distance between Los Angeles and London without refueling — costs $60m up front and then an additional $3.5m each year to maintain, according to jet research firm Conklin & de Decker.

While Diddy has long been widely reported to have his own yacht, he appears to be a regular user of charters.

The yachts on which he has been seen as a host on can cost up to $300,000 a week to charter, suggesting that his annual yacht bill is north of $1m.

Diddy’s two homes — a $35m, waterfront compound in Miami and a $40m LA mansion with an underwater tunnel — could cost him an extra $5m in taxes, repairs, and staffing, a source who works with luxury home owners said.

Diddy is also on the hook for two hefty mortgages totaling nearly $100m which expire in 2029 and 2036 respectively — costing him nearly $8.5m a year.

In 2018, Diddy shelled out $21.1m on a painting of a Chicago Park scene entitled “Past Times” by Kerry James Marshall — it was the most expensive painting ever sold by a living black artist.

Diddy also has a multi-million dollar jewelry collection including a $300,000 Richard Mille watch, a 30 carat diamond pinky ring — which could be worth millions according to jewelers — and a $500,000 diamond chain necklace.

The family he supports

It’s unclear how much Diddy spends on child support in total but a court filing from 2005 shows he was ordered to pay monthly child support of $21,782 on just one of his seven children. That comes out to $261,420 per year.

If he still paid that exact amount, without adjusting for inflation, it could add an extra $1.8m just for his kids. It’s unclear if Diddy still supports all his children, one of whom is 32 but reports suggest he supports several girlfriends.

The biggest new bill: lawyers

Mark Geragos, who previously represented Diddy — as well as Usher, Chris Brown, Michael Jackson, and Nicole Ritchie — estimated Diddy’s current legal bills will be the annual equivalent of a “high seven figure commitment.”

“Generally cases like this are handled on an hourly basis and Diddy has always availed himself of a top shelf legal team which can cost up to $1750 an hour.”

On top of that he settled with Cassie for an undisclosed sum and now faces mushrooming legal claims and a federal investigation which, if it resulted in charges, would be costly to defend.

But does he have a secret stash?

Of course, given Diddy has been making millions since the 1990s its very possible he has put plenty of cash in investments, can live off his assets, and has a war chest for his legal bills, his former lawyer contends.

While Geragos says he has no inside knowledge of Diddy’s finances he notes, “He’s been in challenging situations before and generally lands on his feet… he’s extremely smart and savvy.”