What’s Next for Jailed Sean “Diddy” Combs?

As Sean “Diddy” Combs awaits trial after being denied bail, he faces more than two dozen lawsuits and the impending release of the infamous Diddy List.

Combs was arrested by the FBI in a hotel in New York and charged with racketeering conspiracy, sex trafficking, and transportation for purposes of prostitution. Diddy pleaded not guilty to all charges but has since had at least two dozen lawsuits brought against him. He has been denied bail three times, most recently on the day before Thanksgiving.

The lead-up to Diddy’s arrest

The story of Diddy’s downfall begins with the November 2023 lawsuit filed by his ex-girlfriend Cassie Ventura. According to the Associated Press, Ventura accused Combs of physical and sexual abuse that began not long after they got together in 2007. The music mogul denied all charges brought against him by Ventura, but the public nature of the suit started the domino effect that would lead to additional accusations of sexual assault.

Ventura and Diddy eventually reached a settlement, the amount of which was never disclosed. Ben Brafman, one of Combs’ many lawyers, said the settlement was by no means an admission of guilt on Diddy’s part.

By the time the agents from Homeland Security raided Sean “Diddy” Combs’ properties in Miami and Los Angeles, he was already dealing with multiple sexual assault allegations. Diddy was in Florida when the raids happened, and, according to NBC News, authorities seized his phones before he was scheduled to go to the Bahamas.

In response to the raids, a lawyer for Ventura and another anonymous victim said in a statement to Good Morning America, “We will always support law enforcement when it seeks to prosecute those that have violated the law. Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct.”

Meanwhile, Combs’ lawyers called the raids “excessive” and said they were done to provide the media with content. On the same day, Combs’ lawyers released the statement regarding the raids, a video was released on CNN of Diddy assaulting Ventura in a hotel hallway in 2016.

The now infamous video shows Diddy in a towel grabbing Cassie Ventura by her hoodie, throwing her to the floor, and kicking her repeatedly before dragging her back into the elevator. She then tries to grab a phone before Diddy shoves her, and later in the video, he can be seen sitting in a chair and throwing an object.

A 2016 surveillance video obtained by CNN shows Sean “Diddy” Combs violently grab, shove, drag and kick his then-girlfriend Cassie Ventura during an altercation in a hotel in California. https://t.co/qgD40mRPtQ pic.twitter.com/1u7qJgn3mC

— CNN Breaking News (@cnnbrk) May 17, 2024

Sean “Diddy” Combs issued an apology video via Instagram, saying his actions towards Ventura were “inexcusable” and that he took responsibility for what he did.

“It’s so difficult to reflect on the darkest times in your life,” he said in the video. “Sometimes you got to do that. I was fucked up. I mean, I hit rock bottom. I make no excuses. My behavior on that video is inexcusable.”

He continued, “I went and I sought professional help. Going to therapy, going to rehab. I had to ask God for his mercy and grace. I’m so sorry, but I’m committed to be a better man each and every day. I’m not asking for forgiveness. I’m truly sorry.”

Sean “Diddy” Combs arrested

A couple of months later on September 16th, Sean “Diddy” Combs was arrested in a hotel in Manhattan following an indictment that was unsealed just a day after his arrest. The unsealed indictment revealed he was arrested on sex trafficking charges.

The indictment revealed what is now known as the Diddy “Freak Offs.” These were long-lasting sexual encounters with sex workers that the music mogul recorded. He kept the recordings to use as blackmail to keep victims from coming forward and for his own pleasure.

“This abuse was, at times, verbal, emotional, physical, and sexual,” says the indictment. “As part of his pattern of abuse, Combs manipulated women to participate in highly orchestrated performances of sexual activity with male commercial sex workers.”

The indictment goes on to explain how Diddy allegedly drugged and forced his victims to participate in the “Freak Offs” and how he would go to great lengths to keep them quiet.

“At times, Combs, and others acting at his direction, made arrangements for women and commercial sex workers to fly to Combs’ location,” says the indictment. “Combs ensured participation from the women by, among other things, obtaining and distributing narcotics to them, controlling their careers, leveraging his financial support and threatening to cut off the same, and using intimidation and violence.”

Since being thrown in a jail cell, Combs has been denied bail three times. This is despite proposals from his lawyers that he would obey the bail terms and stay in a New York apartment where he would have no access to phones and be surveilled by a security team.

The most recent bail hearing saw him being denied due to potential danger the music mogul poses to witnesses. While court documents have not yet been released, numerous reports say Diddy has broken the rules of the prison’s bureau by engaging in three-way calls and contacting people outside of his contact list.

On these grounds, Judge Arun Subramanian denied Diddy bail, citing the potential risk of harm and his prior inability to follow the rules.

He has also seen a massive wave of sexual assault accusations come his way since the time of his arrest, most of which talk about the “Freak Offs.” Furthermore, fashion designer Bryana “Bana” Bongolan is seeking $10 million in damages, claiming Combs sexually assaulted her and dangled her over the balcony of Cassie Ventura’s 17th-floor apartment.

Bail appeal, trial, and the Diddy List

Sean “Diddy” Combs is awaiting the decision from a panel of judges from the 2nd US Circuit Court of Appeals in Manhattan. However, experts say the decision from the panel of judges will most likely be the same as previous bail hearings.

Combs will be going on trial for racketeering conspiracy, sex trafficking, and transportation for purposes of prostitution on May 5, 2025.

Meanwhile, the world awaits the release of the infamous Diddy List. The list, which has garnered significant attention since the music mogul’s arrest, allegedly contains the names of several high-profile celebrities involved in Diddy’s parties and Freak Offs. The Diddy List could potentially lead to the arrest of many celebrities associated with Combs’ crimes.

It remains to be seen whether Kash Patel, Trump’s pick for FBI Director, will disclose the so-called ‘Diddy List’ once he assumes office.

“To me, what you mentioned is the most important part: restoring trust in our agencies and departments,” Patel said in an interview on the Benny Show Podcast. “And the way to do that isn’t to treat them like a piñata, hoping for something good to pop out. The way to do it is by giving the American people the truth. And that’s what they feared about Donald Trump. He’s going to come in there and might just give them the Epstein list, the ‘Diddy List,’ and everything else they’re terrified of being exposed.”