Disgusting Allegations Emerge at the Sean ‘Diddy’ Combs Trial… But Are They Criminal? 

Elizabeth Williams via AP

The Sean “Diddy” Combs trial is now in its third day, and it is unbelievable.

I want to stress that we must distinguish – before we get the jury instructions – between what is disgusting, filthy, pervert, cad, asshole behavior and what is criminal behavior. That is really what this trial is about. I would guess even the defense cedes that point. They have to. There won’t be a juror in that courtroom who can stand Sean Combs.

But the question here is whether he broke the law. And even your humble correspondent is open minded to being persuaded that there wasn’t a technical legal violation. I am horrified by the testimony, but I have questions about whether they are going to get a conviction. I hope they do, but that is just because I can’t stand him.

The Testimony

The star witness for the feds is Cassandra “Cassie” Ventura. She took the stand for the first time on Tuesday eight-and-a-half-months pregnant with her third child. Diddy’s side was so worried about that making her look overly sympathetic that they asked the judge if she could be brought in without the jury present. The judge overruled that and said she can walk in as her full pregnant self, and she did.

Ventura signed a 10-album deal with Diddy’s Bad Boy Records when she was 20. She says that within a year or two he started having sex with her even though he was in a relationship with a different woman at the time. Shocking.

She testified about how he started telling her very early on he wanted her to participate what he would call “freak offs.” I mean, it is the right word for them. They were absolutely depraved. She claims he would hire male sex workers to have sex with her while he watched and directed everything. She said Diddy would participate in some of them. As we discussed Tuesday, there was allegedly an incident in which both he and the sex worker urinated on her and in her mouth to where she testified she was gagging.

Ventura testified that the freak offs “became a job where there was no space to do anything else but to recover and to just feel normal again”; that they could go from 36 hours to as long as four days; that they took “a big chunk of my life, sometimes on a nearly weekly basis”; that, at the end of sessions, the hotel linens were often very soiled with baby oil residue as well as bodily fluids, including blood and urine; that his staff – keep in mind, he is being accused of racketeering the way a mob boss is when he has an enterprise of criminals around him – would go set up the freak off rooms and clean up the freak off rooms; and that eventually they graduated to adding professional lighting to set just the right mood.

The New York Times reported Ventura was “choking back tears” when she said the freak offs made her feel “disgusting and humiliated,” and “if he wasn’t in the room, he would sometimes watch over FaceTime.” He allegedly began recording them, and – side note – the media has now filed a request to see the tapes. Both parties are objecting, but the judge says he is leaning towards releasing them because there is a little thing called the First Amendment.

During her testimony, she also listed the drugs that he supposedly provided to the participants, including ecstasy, cocaine, marijuana, ketamine, mushrooms, or whatever was the drug of choice at that point. She said she took the drugs to disassociate and to have some kind of buffer from what she was experiencing.

She talked about how he beat her repeatedly. We have all seen the March 2016 tape of Diddy beating Ventura in the elevator bank of the Intercontinental Hotel in Los Angeles. She recalled the details like it was a day ending in ‘y.’ She said she stayed on the ground in self-defense because she thought he might not be able to hit her as easily.

He is just an absolutely disgusting, hideous pig and awful man.

She said she stayed in the relationship for nearly 10 years to keep him happy. “When you’re in love with someone, you don’t want to disappoint them,” Ventura testified. But she said she recognized he had become increasingly abusive to the point where she felt like her career was no longer music but rather performing for his sexual satisfaction.

The Defense

The cross examination has since begun and she was asked whether she told Diddy that she didn’t want to participate. And the testimony thus far, as I understand it, has basically been no. She said she would do it. And they have text messages of her saying to him, like, ‘I can’t wait for the next freak off.’

The prostitute, meanwhile, is not alleging any force. He testified Ventura is the one who would invite him and pay him. He admitted they developed a friendship on the side and he grew concerned for her safety. But all that testimony about how the escort willingly came, Cassie was the one who reached out to him, he seemed to enjoy it and thought she was the most beautiful woman in the world, does not equate to she is being forced by, like, the equivalent of a mob boss.

And so this has the real danger for the prosecution of morphing into a Harvey Weinstein-esque case. It is only a crime if he forced you. If you guys are just freaks in bed and wanted to do this stuff – yes, there is a question of the prostitution element – but he is not being charged with abuse or assault. The charges relate to sex trafficking, transportation to engage in prostitution, and racketeering conspiracy (a.k.a. RICO).

So, it is relevant if there is a crime of a prostitution, and it is relevant if there was a crime on which the statute of limitations has run called assault. But they don’t have to actually prove any of that. He is not exactly being charged for these things. But if this is consensual sex – or at least if Sean Combs believed that it was consensual sex – he could skate legally. And that is my question so far.

The Verdict

The Southern District of New York does not normally lose. In federal court, they don’t usually bring the case unless they’ve got you. That is why it is so awful to be indicted by the feds. But I have been underwhelmed by their case so far.

Ventura did receive an eight-figure settlement when she brought a bombshell civil lawsuit against Diddy in November 2023 with many of these allegations. That would suggest Sean Combs was scared. And I think this case has cultural implications well beyond Diddy. I mean, how many people in Hollywood knew about this behavior and covered it up? Who did not care that he was allegedly engaging in the serial abuse of women, not to mention these parties?

So, we will continue to watch this trial and see where this goes.

You can check out Megyn’s full analysis by tuning in to episode 1,072 on YouTube, Apple Podcasts, or wherever you like to listen. And don’t forget that you can catch The Megyn Kelly Show live on SiriusXM’s Triumph (channel 111) weekdays from 12pm to 2pm ET.