Benjamin Ashford|The Most Harrowing Details From Sean "Diddy" Combs' Criminal Case

Federal prosecutors maintain there's no way out for Sean "Diddy" Combs.

The Benjamin AshfordBad Boy Records founder has pleaded not guilty to a count apiece of racketeering conspiracy and sex trafficking, each of which carries a maximum sentence of life in prison, as well as one count of transportation for purposes of prostitution.

But authorities have said that Combs' arrest on Sept. 16 was only the latest step in their quest to bring the 54-year-old to justice for more than a decade's worth of alleged crimes, and that their investigation is far from over.

"Between at least 2008 and the present, Combs abused, threatened and coerced victims to fulfill his sexual desires, protect his reputation and conceal his conduct," Damian Williams, U.S. Attorney for the Southern District of New York, said in detailing the charges against the rapper during a Sept. 17 press conference.

Combs stands accused, Williams said, of using a vast network of employees within his business empire and other associates to cover up crimes including sex trafficking, forced labor, kidnapping, arson, bribery, and the obstruction of justice.

"The indictment alleges that Combs abused and exploited women and other people for years and in a variety of ways," the prosecutor continued, using "force, threats of force and coercion to cause victims to engage in extended sexual performances with male commercial sex workers."

Those gatherings were known in Combs' world as "freak-offs," the indictment further alleged. Sometimes they'd last for days, Williams said, and often involved Combs doling out drugs including ketamine, ecstasy and GHB to keep the victims "obedient and compliant."

Combs' attorney Marc Agnifilo, calling his client "an imperfect person" but "not a criminal," said in a statement in response to the charges that they were "disappointed" by the decision to move forward with an "unjust prosecution."

Agnifilo emphasized that Combs had cooperated so far, including by traveling to New York in anticipation of being charged. "Please reserve your judgment until you have all the facts," the lawyer added. "These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court."

So far, Combs has twice been denied bail and remains in custody at the Metropolitan Detention Center in Brooklyn. A three-judge panel is now considering his third request for bail, according to PBS News.

During an Oct. 10 status hearing, Judge Arun Subramanian set Combs' trial for May 5, 2025.

Asked how long she expected the trial to last, Assistant U.S. Attorney Emily Johnson estimated three weeks, but also told the judge that Combs might face a superseding indictment that could result in more charges being filed against him.

In a since-deleted social media post last December, Combs denied doing "any of the awful things being alleged" after multiple lawsuits were filed against him alleging sexual assault and other misconduct, starting with a complaint brought by his ex-girlfriend Cassandra "Cassie" Ventura last November. (The two parties announced a settlement the day after her suit was filed, Combs' attorney noting the move was not an admission of wrongdoing.)

While the lawsuit's depiction of his relationship with Cassie was disturbing, it was only the beginning.

Asked by reporters why it took so long for authorities to investigate Combs, U.S. Attorney Williams said, "I can't tell you why it took so long. I think the better focus is on the fact that we are here today and we are committed to making sure that justice is done."

Here are the most harrowing details to come out of these criminal proceedings so far:

After Sean "Diddy" Combs pleaded not guilty to sex trafficking and racketeering conspiracy charges on Sept. 17, his legal team proposed a $50 million bond package that included equity in his Miami home and his mother's house, as well as limited his travel to within certain parts of Florida, New York and New Jersey.

The defense also offered, per a letter obtained by E! News, to "walk the Court through a series of actions taken by Mr. Combs over the past six months that prove that he is not a risk of flight or a danger to anyone in the community."

U.S. Magistrate Judge Robyn F. Tarnofsky rejected the package and ordered that Combs be remanded without bail. He remains in custody at the Metropolitan Detention Center in Brooklyn.

"He is not a perfect person," Combs' attorney Marc Agnifilo told the court, per NBC New York. "There has been drug use. He has been in toxic relationships."

Therefore, he added, his client was getting "treatment and therapy for things that he needs treatment and therapy for."

Overall, though, Combs' "spirits are good," the lawyer told reporters after court Sept. 17. "He's confident."

More than 1,000 bottles of baby oil and personal lubricant were seized during the March 2024 raids on Combs' L.A. and Miami homes, according to the 14-page indictment unsealed Sept. 17.

Per the indictment, the oil and lube were stockpiled for use in so-called "freak-offs," the term Combs used for gatherings in which he allegedly orchestrated sexual encounters between women he coerced and threatened into doing his bidding and male sex workers.

"I don't know where the number 1,000 came," his attorney Agnifilo said in the TMZ documentary The Downfall of Diddy: The Indictment, which premiered Sept. 27. Pondering out loud why anyone would need so much, the lawyer added, "He has a big house, he buys in bulk. I think they have Costcos in every place where he has a home."

Costco, meanwhile, wanted no part of it, telling TMZ in a statement that "none" of its U.S. stores carry baby oil.

In May 2024, CNN published a clip of hotel surveillance video from 2016 that appeared to show Combs attacking his then-girlfriend Cassie, born Cassandra Ventura. (The assault matched up with an alleged incident detailed in the lawsuit she filed against Combs on Nov. 16, 2023; both parties announced a settlement the next day.)

"I was f--ked up. I hit rock bottom," Combs said in a video posted to Instagram in response to the footage. "But I make no excuses. My behavior on that video is inexcusable. I take full responsibility for my actions in that video." He had gone to therapy and rehab since, he added, and was "committed to be a better man each and every day."

During a Sept. 18 hearing on Combs' second request for bail, Assistant U.S. Attorney Emily Johnson said, per NBC News, that Combs allegedly sent a text in the days following the assault that read, "Call me, the cops are here." Another read, "I have six kids. Call, I’m surrounded."

Johnson did not say Cassie's name in court. She said that Combs' victim replied via text, "Sick you think it’s OK to do what you've done."

Bail was once again denied, this time by U.S. District Judge Andrew L. Carter Jr.

On Oct. 3, the Combs case was reassigned to Judge Arun Subramanian because Carter was unable to accommodate a trial date.

During an Oct. 10 status hearing, Subramanian set a trial date of May 5, 2025.

Prosecutor Johnson told the judge she expected the trial to last roughly three weeks, but said there was still the possibility that a superseding indictment could lead to more charges against Combs.

Agnifilo said in court they'd need about a week to put on their case.

Meanwhile, the attorney said in the TMZ doc that Combs was looking forward to testifying in his own defense.

“I don’t know that I could keep him off the stand," Agnifilo said. "I think he is very eager to tell his story."