Sean ‘Diddy' Combs could lose his freedom – and his vast empire of mansions, art and cars

Yahoo

3 days ago

Sean 'Diddy' Combs' 1997 hit 'It's All About the Benjamins' sums up the rap mogul's voracious thirst for the good life and ostentatious trappings of wealth: 'Colossal-sized Picassos,' 5-carat diamond rings, Cristal Champagne and skiing in Aspen with 'chicks who win beauty pageants.'
By becoming a successful entrepreneur in the music, fashion, liquor and other realms, Combs became a mogul. He bought all that and more – private jets, exotic cars, mansions on both coasts.
Now, as Combs faces a jury trial that could send him to prison for life, he's also fighting a Justice Department forfeiture action that could cost him much – if not most – of an empire that prosecutors allege he used as part of a criminal racketeering enterprise from 2008 to the present.
Combs and his defense team have denied all allegations against him, characterizing some as baseless 'money grabs.' He has pleaded not guilty to federal charges of sex trafficking, racketeering and transportation to engage in prostitution.
But in a sign of how serious the disgraced entrepreneur is taking the asset forfeiture effort, his lawyers have hired as a consultant the former deputy chief of the Justice Department's Asset Forfeiture and Money Laundering Section, USA TODAY has learned.
Stefan Cassella, who serves as an expert witness and consultant to law enforcement agencies and wrote two books on the topic, has trained thousands of prosecutors and federal law enforcement agents across the United States and their counterparts overseas.
Cassella said he could not comment on the specifics of the case because of his involvement in it. Broadly speaking, though, he told USA TODAY that by charging Combs under the Racketeer Influenced and Corrupt Organizations Act, or RICO, the government is taking an aggressive approach to seizing as many of Combs' assets as possible.
'RICO forfeiture is intended to be very broad, and so it has significant consequences' for Combs, Cassella said in an exclusive interview. 'So, it's going to boil down to what they can prove was part of the enterprise.'
Prosecutors declined to comment, citing the ongoing case.
In many RICO cases, prosecutors include very specific allegations of what 'instrumentalities' were used as part of an alleged racketeering enterprise, legal speak for what people, cars, planes, houses and companies helped facilitate the criminal behavior, said James Trusty, the former longtime chief of DOJ's Organized Crime and Gang Section.
But in an ominous sign of prosecutors' intentions, Trusty said, the Combs indictment and related court documents essentially target all his business and personal assets.
'They've written a very broadly worded forfeiture allegation,' Trusty said. 'It's so vague and so broad that I would think the defense would push for a bill of particulars,' or a more specific explanation of what the feds are going after.
One thing for certain, Trusty said, is that the fancy cars, houses and planes that Combs has accumulated are in the prosecutors' crosshairs, as are any of his companies that could broadly be construed as being part of the racketeering enterprise in the slightest of ways.
For instance, if an assault took place at a record studio, it could implicate not only that studio but the record company Combs used to pay musical artists to record there, Trusty said.
If Combs is convicted, the jury must then decide how much of his empire is subject to forfeiture, according to Cassella, Trusty, Justice Department law and a breakdown of RICO and asset forfeiture statutes by Cornell Law School's Legal Information Institute.
So how much is Combs worth? What is the government explicitly seeking? And how accessible are his assets after years of Combs trying to protect himself from growing accusations of criminal misconduct?
In 2024, Forbes magazine estimated Combs' net worth at $400 million – a significant drop from its 2019 figure of $740 million. Both Combs and his team later claimed he was a billionaire, Forbes said, despite offering no documentation to back up the claim.
According to publicly available documents and news reports, Combs' most valuable personal possession is likely his 17,000-square-foot, 10-bedroom mansion, appraised at more than $61 million, in the tony Holmby Hills section of Los Angeles. It was raided as part of a criminal probe and listed for sale last September.
Combs also owns a 9,600-square-foot house in Toluca Lake just northwest of the Hollywood Sign. And he owns a $48 million mansion at 2 West Star Island in Miami and the adjacent property at 1 West Star Island. On Aug. 20, 2024, Combs paid off the $18.9 million mortgage so he could put up 2 West Star as collateral in his failed efforts to obtain bail and stay out of jail while awaiting trial, documents show.
Combs also owns a Gulfstream G550 jet valued at more than $25 million, known as LoveAir, which he rents out while also seeking a sale to help pay his enormous legal expenses.
Also, potentially open to forfeiture: Combs' Bad Boy Records, which still generates money from recordings and music publishing rights since he launched the company in 1993.
Combs is not known to own any 'Colossal-sized Picassos,' as he sings about in his hit song. But he is believed to have an extensive art collection, including works by Jean-Michel Basquiat and Keith Haring.
In 2018, he was revealed as the mystery buyer of the renowned painting 'Past Times' by Kerry James Marshall for $21.1 million.
At one time, his fleet of at least 20 luxury cars included a Rolls-Royce, Bentley, Ferrari, Lamborghini and an ultra-luxury Mercedes known as a Maybach.
In February 2023, Combs announced that 'after three decades of entrepreneurial success across his renowned brands,' he was 'rebranding' and changing the name of his parent company from Combs Enterprises to Combs Global.
That, Combs said, more accurately reflected his ambitious vision for the future, including his 'landmark acquisition of becoming the largest minority-owned, vertically integrated multi-state operator in the cannabis industry' for $185 million.
At its founding in 2013, Combs Enterprises included his New York City-based Bad Boy Entertainment, Combs Wines and Spirits, the AQUAhydrate water firm, Revolt Media, Sean John fashion and fragrances, Capital Preparatory Charter Schools and The Sean Combs Foundation.
Over the years, it expanded to include new business units and ventures such as Empower Global, Our Fair Share and Love Records, which focused on R&B.
"Combs Global represents the next chapter in my journey as a business leader and a bigger vision to build the largest portfolio of leading Black-owned brands in the world," Combs said. "I've enlisted world-class teams of top executives, specialists and strategic partners to bring this new dream to life and put us in the best position to keep making history while leading another 30 years of dominance across industries."
In November 2023, Combs' empire began to crumble following allegations of rape, beatings and abuse by his former girlfriend Cassie, also known as Casandra Ventura Fine.
His Bad Boy music catalog, once worth $125 million, plummeted in value because of bad publicity.
Combs had struck gold through his partnership with global distilled spirits conglomerate Diageo, which has said it paid him more than $1 billion for promoting its Ciroc vodka over the years. It also partnered with Combs to launch the DeLeón Tequila brand. But Combs sold his half of the tequila company in January 2024 for about $200 million.
His Sean John 'urban streetwear' clothing and fragrance line once sold more than $500 million annually but was reportedly dropped by Macy's department store in November 2023.
In June 2024, Combs sold his stake in Revolt Media, which he'd founded a decade earlier as a music industry-focused cable channel meant to boost Black representation on TV.
Combs' partnerships also ended with Love Records, Capital Preparatory Schools and the Empower Global online Black business marketplace. And the cannabis venture ultimately failed due to merger complications.
Prosecutors in the Southern District of New York, or Manhattan, have unsealed the indictment against Combs. Other alleged coconspirators are indicted under seal.
But the indictment also mentions Combs' business, 'headquartered at various times in Manhattan and Los Angeles,' under a variety of U.S.-based corporate entities, including Bad Boy Entertainment, Combs Enterprises and Combs Global.
Collectively, it refers to all of them as the "Combs Business.' And while it avoids specific entities, it says they include 'among other things, record labels, a recording studio, an apparel line, an alcoholic spirits business, a marketing agency, and a television network and media company.'
According to federal law, anything that's forfeited following a criminal conviction could conceivably be used to help some or all of those alleged to have been victimized by Combs.
Both Cassella and Trusty said, however, that the federal RICO statute is designed more to punish the convicted rather than compensate the victims. It does not, for instance, include the kind of headline-grabbing multimillion-dollar awards for the pain and suffering and reputational damage caused by the accused that is common in civil suits like the one brought by Ventura Fine.
Instead, victims in a criminal case would be eligible for using asset forfeiture money for repayment of medical expenses, funeral expenses if a death was involved, 'literal out of pocket reimbursement for victims' costs like that,' Trusty said.
'It's not a full picture of the restitution that they're actually owed under the law,' he said. 'The criminal law has just never been as expansive as civil law' when it comes to making whole victims of criminal acts.
Victims of alleged Combs criminal acts can, however, seek a share of forfeited assets through civil lawsuits and prosecutions, Trusty and Cassella said. To date, more than 70 lawsuits have been filed against Combs, many of them claiming sexual abuse.
In Combs' case, prosecutors and FBI investigators are likely looking for assets that the embattled music mogul may have hidden, especially in recent years as his legal problems mounted.
Combs himself might have alluded to a propensity to stash money away in the 1997 hit that helped launch his rapping career after years as a producer and impresario.
'And what you can't have now, leave in your will,' Combs sings in 'All About the Benjamins.' 'But don't knock me for tryin' to bury, seven zeros over in Rio de Janeiry.'
(This story was updated to meet our standards.)
Josh Meyer is a veteran correspondent focusing on domestic, national and global security issues, including transnational criminal organizations. Reach him at [e-mail]. Follow him on X at @JoshMeyerDC and Bluesky at @joshmeyerdc.bsky.social.
This article originally appeared on USA TODAY: Diddy net worth is huge. Prosecutors think 'Benjamins' up for grabs