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Sean “Diddy” Combs seems to be keeping things close to home, especially when it comes to business decisions involving his family.
Sources reveal that the renowned rap icon, Diddy, navigated his affairs with an air of caution months prior to his arrest. In a notable instance, during 2023, he made a club appearance in Miami and opted for a rather old-school payment method. Instead of a digital transaction, the club paid a $100,000 fee in cash to an entity named after his mother, Janice Combs, who was 84 years old at the time.
This appearance took place at the M2 nightclub, serving as a “kickoff party” for Race Week, coinciding with the Miami leg of the Formula 1 racing championship on May 4, 2023. The event was part of the vibrant festivities surrounding the prestigious car racing series.
According to a contract dated May 1, the agreed-upon $100,000 appearance fee was to be divided into two installments. The document specified that these payments were to be made in cash, adhering strictly to written instructions provided by the involved parties.
On May 1, organizers got a contract stipulating that the “one hundred thousand US dollars” appearance fee should be made in two installments and that “all payments shall be made via cash pursuant to . . . written directions.”
Meanwhile, the contract was made with “Janice Combs Music Holdings Inc.”
The “I’ll Be Missing You” singer’s home was raided by the FBI less than a year later in March 2024, and at the time, he was facing a number of civil suits seeking hefty damages.
Needless to say, he was soon on the stand in one of the most heavily covered celebrity trials of all time.
In September 2024, Diddy was indicted in federal court on charges including racketeering conspiracy, sex trafficking and transportation to engage in prostitution.
In July 2025, a jury found him not guilty of those first two charges but guilty on two counts of transportation for the purposes of prostitution.
He was sentenced to four years and two months in prison, and he was given a $500,000 fine and five years of supervised release.
Diddy is now serving his sentence in Fort Dix, NJ, and he settled several of the civil suits against him, including one filed by ex Cassie Ventura for a reported $20 million.
A rep for Diddy didn’t respond to our request for comment.