Sean ‘Diddy’ Combs may have known his fate early on when he started being careful about receiving payments. According to Page Six, the disgraced rapper received his payment of $100K in full cash from a Miami club in 2023. He made an appearance at the club months before his arrest and asked the club to pay him in cash.
The payment was not directly made to him, but to a company named after his 84-year-old mother, Janice Combs. Diddy attended the race week party for Formula 1’s Miami Grand Prix at the M2 nightclub on May 4.
Sean ‘Diddy’ Combs had Miami club pay $100K in cash ahead of appearance months before his arrest https://t.co/RDhJJ2ffeT pic.twitter.com/xqFbrzxYOJ
— Page Six (@PageSix) February 10, 2026
He asked the club to pay cash to “Janice Combs Music Holdings Inc.” in two instalments using a contract. The directions were mentioned in the contract in advance, notifying the organizers about his demands. More such transactions may get revealed considering how crafty the rapper got when it came to moving funds and using his assets for liquify cash.
Just a few months after Diddy’s appearance at the club, his home was raided, followed by civil lawsuits against him. After a long public trial, he was sentenced on two counts of transportation for the purposes of prostitution.
He also had charges such as s– trafficking and racketeering conspiracy. But they did not add up to his prison time. He got over four years in prison, along with a $500,000 fine and supervised release for five years.
Diddy Sells Iconic Private Jet Following Federal Prison Sentence
Sean “Diddy” Combs has officially parted ways with his custom matte black Gulfstream, six months after a federal conviction that landed him a 50-month sentence.#Diddy #fyp #explorepage #CelebrityNews #PopCulture pic.twitter.com/EOjFl2K8GY
— MEAWW (@meawwofficial) January 13, 2026
Diddy was also reported to be totally broke after his sentence. Getting convicted impacted his career and business altogether. He had to sell his 14-passenger Gulfstream G550 black jet in a hush deal.
Just after six months of imprisonment, he transferred the jet’s ownership for $15-30 million. Despite being in jail, he has legal fees and a series of civil lawsuits to pay off, so he needs money, so selling assets has been working for him.
Diddy has also attempted to sell his Holmby Hills home. The house was listed on the market in Sept. 2024 a few days before his arrest. But it was taken off the market after the property was labelled “unsellable.” The home was removed from the market on Dec. 24 after it was raided by Homeland Security officials to find evidence related to Diddy’s crimes.
