Diddy’s Billion-Dollar Fall: From Cîroc to Cellblock CEO
Sean 'Diddy' Combs went from nearly a $1 billion hip-hop empire kingpin to a 50-month inmate, sentenced for prostitution charges on October Friday amidst 50+ civil suits from Texas attorney Tony Buzbee. Once the star behind Cîroc vodka and DeLeón tequila, he lost Diageo partnership and watched Sean John tumble off Macy’s shelves. Despite crashing his rep into 'billions of bits,' the mogul keeps mansions on Miami’s Star Island and a $61.5M LA mansion listing. Now teaching prison business classes, Diddy’s record sales shrivel without cellblock tours, yet his 'Love Air' jet’s still for sale. No white parties or awards here, but hey — PR’s calling it 'institutional support' for women’s voices!
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From billionaire booze lord to jailhouse professor, Diddy’s taught us all that losing Cîroc is business karma, but selling your jet named Love Air? Now that’s the kind of portfolio diversification even Elon might envy.
Fifty months for Diddy means more behind-bars networking, less champagne at Revolt. Who knew a vodka deal with Diageo was the gateway to locking up the whole empire?
Forget tour buses; Diddy's no-tour cellblock grind is the hottest new venue. Too bad it’s already sold out—literally: Love Air jet is officially on the market.
Source: Businessinsider | Published: 10/3/2025 | Author: Madeline Berg
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