Sean ‘Diddy' Combs Could End Up Broke Amid Lawsuits, Legal Fees and Tarnished Business Deals
The 'All About the Benjamins' rapper, 55, was recently acquitted of sex trafficking and racketeering charges — but found guilty on two counts of transportation to engage in prostitution, which could earn him up to 20 years in prison.
A judge denied a bail request from his attorney and ordered Combs to remain in custody ahead of his hearing.
Prosecutors had accused the Bad Boys Records cofounder of masterminding a criminal conspiracy that used intimidation, brute force and cash to arrange drug-fueled parties dubbed 'freak offs.'
Combs has long maintained that he's innocent — but he's been held in a New York City jail since his arrest in September 2024. Even if he's sprung with time served, experts tell The ENQUIRER that the former billionaire could see his estimated $400 million fortune siphoned off by legal bills and potential payouts.
According to The New York Times, Combs has been clobbered with more than 50 civil lawsuits from men and women accusing him of sex abuse. His team has denied the charges and suggested that the flood of lawsuits is a money grab.
Renowned New York City lawyer Pete Gleason believes that Combs has already coughed up 'millions' for his defense and tells The ENQUIRER, 'These lawsuits have the potential to bankrupt Diddy.'
Combs promptly settled an explosive 2023 suit lodged by his singer ex-girlfriend Cassie Ventura, who was a star witness for the prosecution.
The BBC reports Cassie testified that Combs was an abusive bully, who stifled her career and forced her into 'humiliating' drug-fueled hookups with male escorts during their 10-year relationship — and told the court that he paid her a $20 million settlement.
Devin White, a celebrity financial advisor for rappers, tells the Enquirer that he believes Combs, who started the fashion and lifestyle brand Sean John, may also lose major revenue from dashed opportunities.
White explains, 'He's going to be radioactive, so his Sean John business deals with Macy's and other stores are going to be finished.'
Combs has also put his Los Angeles megamansion on the market for $61.5 million, raising concerns that a total real estate sell-off could possibly leave the scandal-scarred star without a home to hang his hat.
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Atlantic
a day ago
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A Requiem for Puff Daddy
Black cool is one of America's great innovations, right up there with basketball, blue jeans, and the internet. It blends several forms—music, sports, fashion, speech, ways of cutting through space—into a wholly distinctive, globally influential aesthetic. There are French fashion houses in thrall to silhouettes first spotted in Harlem, Japanese men who have devoted their lives to spinning jazz records in Shibuya, and lavish murals of Tupac Shakur as far apart as Sydney and Sierra Leone. Sean Combs, the disgraced record mogul, certainly did not invent Black cool. But like Miles Davis, Muhammad Ali, and Michael Jordan before him—and like Jay-Z, Kanye West, and many others who followed—for a flicker of time he was its most formidable ambassador. That moment coincided with my adolescence, which is why the revelation of Combs's extravagant cruelties —the depravity with which he used all that he'd gained—has left my childhood friends and me feeling so betrayed. We had looked up to Diddy, whom I will always think of as Puff Daddy or Puffy. When we were at our most impressionable, he taught us what to want and gave us a model for how to behave and succeed. Seeing him fall apart in our middle age feels like a kind of heartbreak. The verve and swagger he injected into our childhood dreams have curdled into something rancid. Certain photographs of Puffy are permanently etched into my memory. In 1995, dipped in a flowing black-and-gold Versace Barocco silk chemise, liberally unbuttoned to flex a thick Cuban link anchored by a diamond-encrusted Jesus piece—the definitive signifier of inner-city affluence. September '96, on the cover of Vibe magazine: head peering from behind his greatest protégé, the Notorious B.I.G.; signature blackout shades; a perfect S-curl relaxing the weft of his fade. The cool he exuded in these moments was inspirational, even masterful. My friends and I had never seen anything like it so fully pervade the culture, certainly not from someone we felt we could relate to. I have not admired Combs for decades now, since well before his trial this year. But I will always be partial to the Puff Daddy of the '90s: from 1993, when he founded his record label, Bad Boy Entertainment, through the spectacular rise and death of the Notorious B.I.G., and peaking around 1998 during hip-hop's 'shiny-suit era,' which he pioneered with Ma$e and the Lox. By the time I got to college, Puffy was even wealthier, and my cultural references had begun to change. I vaguely remember the preposterous images of him strolling beneath a blazing Mediterranean sun while his valet spread a parasol over his head. He was mainly in the news because of a shooting at Club New York, which resulted in bribery and gun-possession charges against him and a highly publicized trial (he was acquitted). For my friends and me, his shocking newness had begun to fade. Back in his prime, though, Puffy conveyed a sense of youthful ambition that we revered. He was able to transition from sidekick and hype man to dealmaker and multiplatinum performer. Before turning 25, he had founded his own culture-defining business—soon-to-be empire—and knew precisely how to leverage his growing fortune into social capital. More than his success, we were struck by two qualities that seemed novel to us. The first was the amount of effort he openly displayed, which counterintuitively amplified his cool. Puffy made no pretense of obscuring the maniacal work required to achieve his goals. When he closed a million-dollar deal, he slammed the phone down and screamed. (Years later, he would become one of the original hustle-culture influencers on Twitter.) He showed us that flourishing was not a condition one had to be born into—that luxury and labor were connected. The second quality was his ability to make Black people and Black culture—even its less compromising, more street-inflected iteration—feel at home in places, such as the Hamptons, that had not previously welcomed them. Puffy's motto 'I'ma make you love me' felt innocent and aspirational to us, not least because he actually achieved it. We were still many years away from realizing just what he would do with all the love he was given. Helen Lewis: The non-exoneration of Diddy Puff Daddy seemed to us then like a Black man utterly free in a moment of expanding opportunity. Before the age of social media, before we'd ever stepped on a plane, Puffy represented our first intimation of an unrestricted way of being-for-self in the world. On the one hand, he was the antidote to the soul-crushing squareness of upwardly mobile middle-class life that we so feared—degrees, office jobs, bills. On the other hand, he was perfectly assimilated into the good life of the American mainstream, to which we desperately craved access. This made him dramatically unlike his peers. Tupac and Biggie were confrontational, and look where it got them. Rap entrepreneurs such as Master P and Brian 'Baby' Williams were rich but ghettoized; any number of establishments wouldn't seat them. Puffy, by contrast, looked like a marvelous solution to the problem of success and authenticity that my friends and I had been struggling to solve. Yet we were suffering from a kind of myopia. And it wasn't unique to us. The generation after us put their faith in Kanye West, whose most recent contribution to the culture is a single titled 'Heil Hitler.' Role models are like seasons. One passes irretrievably into the next, but for a moment they might reveal possibilities that outlast and surpass them.
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Country Superstar Is ‘Back in the Saddle' With NASCAR Legends on New Project
Country Superstar Is 'Back in the Saddle' With NASCAR Legends on New Project originally appeared on Parade. is back with a new single and music video with a little help from some friends. The video for 'Back in the Saddle,' which debuted on Friday, July 25, features NASCAR legends and Richard Petty. 🎬 SIGN UP for Parade's Daily newsletter to get the latest pop culture news & celebrity interviews delivered right to your inbox 🎬 'So much work goes into making these songs—so much time we spend making them, from the studio writing them to the videos. I got to make the video with Dale Jr. and Richard Petty, which is a total dream come true. My grandpa would be rolling over in his grave in a good way if he knew that I got to hang out with Richard Petty and Dale Jr,' Combs said in the statement about the song, which is not a cover of the Aerosmith hard rock classic, but a new tune he wrote with Dan Isbell and Jonathan Singleton. The release of the new song and video comes as Combs is having a banner year. He recently performed at Bonnaroo and the New Orleans JazzFest, has dates at the Newport Folk Festival (July 26), Lollapalooza (July 31) and Austin City Limits (Oct. 3) coming up, and is making some history along the way. He's the first country artist ever to top the bill at Bonnaroo and the video for 'Back in the Saddle,' the two retired NASCAR legends return to the track at Daytona as Combs belts out his new song. After racing around the track in his iconic number 8 car, Earnhardt Jr. offers Combs the opportunity to take his vehicle for a spin, until Petty makes a surprise appearance, saying, 'Hey guys, let me show you how it's done.' Fans are already reacting favorably to the video in the comments on YouTube. 'this song is so Lightning McQueen coded, I swear 😮💨🤘🏻🔥⚡️Ka-Chow!!!!' wrote one. 'This track is 🔥,' added another. 'I think Luke is one of the best country musicians in my time😊❤,' added another. Country Superstar Is 'Back in the Saddle' With NASCAR Legends on New Project first appeared on Parade on Jul 25, 2025 This story was originally reported by Parade on Jul 25, 2025, where it first appeared. Solve the daily Crossword
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