Dateline: True Crime Weekly
Sean Combs: A personal assistant and The Punisher take the stand.
Wed, 21 May 2025
For two years, David James ran errands for the head of Bad Boy Entertainment, bought his snacks and packed his prescriptions. And once, he says, he was the driver when Combs went looking for his longtime rival Suge Knight -- with three handguns in his lap. Also on Tuesday, a male stripper whose performs under the name The Punisher testified that during his paid sexual encounters with Combs and Cassie Ventura, he felt like he and Cassie were actors, and Combs was the director. If you want to read NBC's coverage of the trial, check out our newsletter, “Diddy On Trial”: NBCNews.com/Diddy
Chapter 1: What is the focus of the Sean Combs trial?
This is On Trial, a special series from Dateline True Crime Weekly, bringing you daily coverage from the Sean Combs racketeering trial. He has pleaded not guilty to all the charges against him. I'm Andrea Canning, and it's Tuesday, May 20th. Just a heads up, in this episode, we're going to be talking about some graphic details and harrowing subject matter.
The cast of characters at the Sean Combs trial gets bigger every day as the prosecution makes its case that he conspired with other people to commit illegal acts. In the indictment, the way they phrase it is the defendant abused, threatened and coerced the people around him to protect his reputation and conceal his conduct, even if it meant breaking the law.
Today, Combs' personal assistant took the stand to tell the jury what he says Combs made him do in a workplace overshadowed by drugs, guns, and threats. NBC News correspondent Chloe Malas is outside the courthouse in Lower Manhattan to tell us all the details. Hey, Chloe. Hey, Andrea.
Chapter 2: What did Combs' personal assistant reveal?
This is the second day David James, that is Combs' personal assistant during the mid to late 2000s, took the stand. Yesterday, you told us he seemed emotional, maybe overwhelmed at times. How was he today?
Today, he was not crying on the stand. He was in what appeared to be the exact same outfit, but maybe he's just a simple guy. So he said he's from Flint, Michigan, and that he's just a guy who's a hard worker, and that when he signed up to be Combs' assistant, that he knew that it was going to be rigorous. He... Talked back a lot to Mark Agnifilo, who's one of Combs' defense attorneys.
He made quips. He elicited laughs. I actually even saw him make diddy laugh at one point when talking about having done ecstasy at a New Year's Eve party and that the ecstasy made him dance and do something called diddy bopping.
So we should say, Chloe, that James was testifying under what's called a proffer agreement, meaning the prosecution granted him immunity to talk about any crimes he may have been involved in. So yesterday, he talked about his interactions with Cassie. Today, both the prosecution and the defense sort of set Cassie aside, and they wanted to talk to him really about his...
job than what he did for Sean Combs.
He said that he got Combs' ecstasy, that he would be an intermediary between one of Combs' drug dealers. He talked about everything, like running to Duane Reade, which is a pharmacy here in New York, and getting him snacks and, you know, getting all of his facial products that he needed and that he used just for men. He would go to these hotel rooms and set everything up before Combs got there.
One of the things that Combs always wanted with him was Heinz ketchup, especially when he traveled, because it turns out that ketchup is not the same everywhere you go, and that he always wanted Combs to feel comfortable in whatever city that he was in.
There was something that was said that I thought was really interesting, something that security... said to this assistant about being tired?
Yeah, he said security would often kind of joke and say, you know what rhymes with tired? Fired. And that this was part of the job and that if you wanted to keep the job, that you did what was asked of you.
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Chapter 3: What illegal activities did Combs' assistant discuss?
Exactly. And this morning before the jury came in, the prosecution, they made the argument to the judge that this incident shows that Combs' criminal enterprise, it existed. And an inside look into how it actually works.
This personal assistant is really giving us, in his words, an inside look into Sean Combs' life. He also testified about an incident involving his personal chef, an incident that Combs allegedly wanted help covering up.
Yes, and we expect to hear from the chef herself about this, but David James claims that on one occasion he returned to Combs' home and that Combs said to him, I need you to go down to the police station, file a police report, and say that... Jordana put her hands on me. And... This is the chef? This is the chef.
And so he believed the implication was that Combs wanted him to file a police report to say that, listen, she was the aggressor, not me, because he was worried that it might leak out to the media. But again... The dots were not connected for us. David James wasn't there to witness what happened between the two, so how would he know?
The personal assistant, Chloe, can't testify about what he heard or what he was told because that's hearsay. But you're saying the suggestion is that he knew something bad happened between Combs and that chef.
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Chapter 4: What was the incident involving Suge Knight?
Exactly. So the implication is that he was aware that Combs had hit this chef first and that he knew that by filing this police report that he would be filing a false one. And so he didn't want to commit something illegal, although we've heard him knowingly commit other illegal activity today, but he didn't want to do this.
And we're going to hear more from the chef we expect to find out her version of these events.
I am interested in hearing that. Before lunch, Cassie Ventura's mother took the stand. It was pretty quick because the defense decided not to cross-examine her.
Yeah, I was really surprised by that. But after talking to several different defense attorneys, they all said that they weren't surprised. What would she say? You know, I didn't call the police because I was afraid for my daughter's life. What was interesting is she talked about Cassie having come home to Connecticut in 2011 over the holidays and that she was shocked.
to learn that her daughter was in a physically abusive relationship and that she saw bruises all over Cassie's body. And that's when she took out her Kodak digital camera and started taking photos. And we have those photos now. We see bruises on her arms and her legs and on the top of her buttocks. And it's really jarring.
Yeah, the photos are everywhere online, and there's one in particular that was above her eye, above her eyebrow that looked pretty bad. Cassie's mother also says that she got an email from Cassie in December of 2011. Can you tell us about that? Yeah.
Yeah, it was right before her mother took these photos. She got an email that we saw today with the subject line videos from Cassie. And she said, Sean is going to release these videos of me, two explicit videos. And he's upset that I'm dating Scott Mascuti, a.k.a. Kid Cudi. And these videos might be dropping. And the mom said that when she got that email, she was, quote, physically sick.
She's saying that Sean Combs was actually demanding money from them?
Super unclear. This is something that a lot of people are talking about today. Cassie's mom claims that Diddy demanded that she and her husband pay $20,000 to him. So they took $20,000 out of their home equity line of credit. They wired it over to someone at Bad Boy Entertainment and that it was because Diddy felt he had spent all of this money on Cassie and that he wanted to be repaid for it.
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Chapter 5: What allegations were made about Combs and his chef?
But something that's really important to point out is that she says, OK, she paid this $20,000, but that within four to five days, the money was back in her account. So bizarre.
When we come back, a male stripper testifies that in 2012, he agreed to dance for a woman named Janet and her husband. But when he arrived, he was greeted by Cassie Ventura. Welcome back, Chloe. So just before lunch, a witness came to the stand with a very unusual professional name. The Punisher.
He's an exotic dancer, Sheree Hayes, and he says he was a stripper. Not an escort, but that he was hired to set up a sexy scene for a husband and a wife. And that on the first occasion of what we now call freak-offs, that he didn't know that it was Cassie and Diddy, but that later he saw Diddy's face. Because remember, they wore costumes and wigs and all sorts of things to hide their appearances.
And that... Diddy would sit in the corner and masturbate, which was what we heard before, while he told them to cover themselves in baby oil and that he would watch.
Has anyone ever said why these people needed to be covered in baby oil at all times during these freak-offs?
I think it just went to his fetish. He wanted people glittering and shimmering, and that's why, you know, during these Homeland Security raids on his homes, they found about 1,000 bottles of baby oil. Even in New York, when he moved here to turn himself in, essentially, to the feds amid this investigation, they found more baby oils.
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Chapter 6: How did Combs allegedly influence his assistant's actions?
Even though he'd already seen these criminal indictments, he clearly loves baby oil and brings it everywhere.
Oh, my. Yeah. So two things that are really important about his testimony for the prosecution. First, he was clear in court that this was a commercial transaction. He says he got paid. And the other important thing is that he traveled for these encounters.
I mean, if there's something that's very clear at this point, Andrea, it's that Combs... paid people for sex, and these individuals at times would cross state lines. So how is he going to get out of that? I mean, we heard in the openings his legal team saying that he was paying for people's time, not their sex. Will the jury believe that?
We'll have to see. He also describes Sean Combs as directing Cassie, calling all the shots.
Yeah, he also says that Cassie always had a general awareness that Combs was in the room. But I mean, obviously, he's telling them what to do. And he's also in there masturbating. But I guess he's saying, although it appeared to be consensual, she would like look over to him before he would perform oral sex or actually have sex with her sort of to get his approval. But it was a glance.
It wasn't necessarily like a verbal cue.
When he was asked if he ever saw Cassie refuse to do any of these things.
He said no.
He said no. Yeah, which goes to the defense's case.
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