Ahead of Sean “Diddy” Combs’ arrest in September 2024, the mogul was already dealing with a few legal situations. The now-56-year-old rapper did, however, still seemed to be living his life as he was accustomed to. As part of that, he apparently made at least one public appearance. It’s been reported that Combs actually made a paid appearance at a club months before facing various lawsuits from Cassie and others. And it would seem that he requested quite a bit of cash before he agreed to participate.
What Reportedly Happened With The Club Appearance?
Diddy was reportedly hired to show up at the M2 nightclub in Miami back in May 2023 as part of the “kickoff party” for Race Week. That event specifically revolved around the Miami portion of the Formula 1 racing championship, which was to take place on May 4th. Page Six reports that a few days before the event, organizers were ironing out the details with Diddy’s camp and received a specific request. A contract they received specified that $100,000 be paid and that “all payments shall be made via cash pursuant to . . . written directions.”
Per the aforementioned news outlet, the deal also stipulated that the payment should be split up into two installments. What’s also notable about this transaction is that it was made with a company called Janice Combs Music Holdings Inc., which is named after Sean’s now-84-year-old mother.
The “Bad Boy for Life” performer did ultimately appear at the gig, which would seemingly suggest that the money went through as requested. Page Six’s report doesn’t provide specific information regarding why cash was specifically requested or give additional information on the company that bears Janice Combs’ name.
What Happened With Diddy In The Months That Followed His Club Appearance?
Sean Combs’ club appearance came only months before his former girlfriend, Cassie Ventura, filed suit against him in November 2023. At the time, Ventura – known mononymously as Cassie – sued her ex for alleged sex trafficking, sexual assault and domestic abuse. The suit was settled less than 24 hours after it was filed, though Combs denied any wrongdoing. Shortly after that, others began to file suit against the rapper, accusing him of sexual violence, verbal abuse and other purported offenses.
By 2024, Diddy’s homes in the U.S. were being raided as part of a federal investigation into sex trafficking, and he would be arrested later in the year. The “I’ll Be Missing You” star was eventually charged with several offenses, including some related to sex trafficking and racketeering (or RICO). Diddy’s trial began in May 2025 and ended in July of that same year, with the rapper being convicted on two counts of transportation to engage in prostitution. During the court proceedings, Cassie also testified along with a number of others.
Combs has since been sentenced to four years (or roughly 50 months) in prison and is now serving that time at FCI Fort Dix in New Jersey. All the while, he and his legal team are seeking to appeal the sentence, and that process is moving forward, with a hearing for oral arguments even having been set for April. The New York native is currently set to be released in June 2028, and Cassie expressed concerns about Combs seeking “retribution” against her and others when he’s released.
On that note, there have been questions regarding what Diddy’s post-prison life might look like. What’s known right with certainty right now is that he will be subject to some conditions following his release. So it’s hard to say if club appearances will still be feasible for him and, if they do happen, it can only be speculated as to whether Diddy could still fetch $100k for showing up.
