Can Cassie testify? Do viral videos hurt defense? Legal experts weigh in.

Sean “Diddy” Combs remains jailed ahead of his criminal trial, and according to legal experts, he’ll likely be there for a while, having lost an appeal to be released on bail.

The embattled music mogul was charged on Sept. 17 with three felony counts of racketeering, sex trafficking and transportation to engage in prostitution. Diddy pleaded not guilty and has denied wrongdoing amid multiple lawsuits over the past 10 months alleging sexual abuse.

The latest lawsuit, filed on Sept. 24, is from a woman who alleges she was drugged, raped and bound by the Bad Boy Entertainment founder and his former bodyguard in 2001. She claims she found out in November 2023 the alleged rape was recorded and sold as pornography. She’s the 11th person to accuse Diddy of sexual assault.

While the world has yet to hear directly from Diddy about his alleged “freak offs,” the internet has resurfaced old videos of him talking about his infamous parties.

How damaging are these resurfaced clips to Diddy’s case? Could a plea deal be on the table? And what happens next? Yahoo Entertainment has spoken to legal experts about those burning questions.

Do any of these old viral Diddy videos matter?

In the court of public opinion: yes. At trial: no.

Multiple resurfaced clips of Diddy have gone viral since his arrest — including a 2002 interview on Late Night With Conan O’Brien where he talked about how locking “beautiful women” in rooms makes for a “killer party.” Ashton Kutcher’s quotes about partying with Diddy have made headlines as have various videos of Diddy with a young Justin Bieber. Unless one of these people comes forward with an allegation against Diddy to support the government’s case, it likely doesn’t mean much.

“Out-of-court statements made by other people cannot come into evidence because they are hearsay statements,” criminal defense lawyer Lauren Johnson-Norris tells Yahoo Entertainment. “However, if witnesses actually observed [alleged crimes related to the indictment], those witnesses could be brought to court to testify against Combs as to what they actually saw.”

There are lots of unverified rumors flying on X, formerly Twitter, “but rumors are not evidence.”

“The government is going to be focusing on proving the charges they have alleged and putting the pieces of the puzzle together,” Johnson-Norris explains.

Where is Diddy right now?

Diddy is still being held at the Metropolitan Detention Center in Brooklyn, N.Y., but NBC News reports that Diddy has been moved from suicide watch to an area reserved for detainees who require special protection. Sam Bankman-Fried, the cryptocurrency entrepreneur who was convicted of fraud, is among the 18-20 inmates in the same section.

Diddy has been denied bail twice, and Johnson-Norris doesn’t see him getting out: “Unless there are some significant changes in circumstances, which I don’t see happening here, it appears that Combs is likely to remain behind bars until his trial.”

The rapper has reportedly spoken briefly with his “shock[ed]” children.

Will others be charged?

Diddy is accused of operating a criminal organization, but former federal prosecutor Jennie Wang VonCannon, tells Yahoo Entertainment she doesn’t believe others will be charged at this time.

“Combs is alleged to be ‘the leader of the Combs Enterprise,'” she says, referring to wording in the indictment. “Based on the allegations, it appears that the government already has the evidence it needs to charge those whom Combs allegedly directed as the leader of the Combs Enterprise; the fact that it charged only Combs indicates that there will likely be no additional lower-level persons charged for conduct described in the indictment.”

Does the government have any reason to offer a plea deal?

“The short answer is yes,” VonCannon, partner at Crowell law firm, says.

“There are real victims who have suffered [alleged sexual] abuse and who would be exposed to a years-long process,” she says, calling Diddy “a heavily resourced defendant.”

“If a defendant pleads guilty, that would be a quicker resolution that would not require victims and witnesses to testify at trial,” she adds. A plea deal also “severely curtails” Diddy’s right to appeal, which could also be helpful to prosecutors.

However, Diddy would have to plead guilty in order to make that happen. Aside from publicly apologizing when surveillance footage leaked of him assaulting ex-girlfriend Cassie Ventura, he’s maintained his innocence.

Can Ventura testify?

Diddy was sued by Ventura, his longtime ex-girlfriend, in November 2023 for sex trafficking, rape and physical abuse. It was quickly settled out of court and terms were not disclosed, but a nondisclosure agreement (NDA) was likely involved, legal experts agree.

However, an NDA “does not override a court subpoena or order for a witness to testify in a criminal case,” Johnson-Norris says, opening the door for Ventura to testify.

“NDAs usually include exception language in them, or if they don’t, the court will find it would be otherwise against public policy to preclude a witness from testifying,” she says. “A court order will always take precedence over contracted language about who can and can’t make statements. That means we should hear Cassie testify in this criminal case.”

Ventura seems very connected to the federal case against Diddy as the wording in her 35-page civil suit matches some of the allegations against him in the government’s indictment.

Sexual abuse cases can be difficult to prosecute as the defense typically claims that acts were consensual; however, VonCannon says this isn’t a typical “he-said, she-said” case.

“While the consent defense is common in cases where the alleged acts happen between two people and behind closed doors, this case is much broader than that, with racketeering allegations involving non-sex acts such as kidnapping, arson, bribery, witness tampering, forced labor and distribution of narcotics and controlled substances,” she explains. “All of the predicate acts of the RICO conspiracy, taken together, make it very difficult to Combs to mount a successful ‘consent defense.'”

What happens next?

Johnson-Norris says that in these types of federal cases, it typically takes “two years between the filing of an indictment until sentencing.”

“I expect there will be periods where we hear about the case due to motions filed by the defense, and then there will be periods of time that we hear nothing at all,” she explains.

The next status conference in the case is on Wednesday, Oct. 9 at 2 p.m. ET.

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