Sean Combs: A personal assistant and The Punisher take the stand.

Summary

Dateline: True Crime Weekly – Episode Summary Episode: Sean Combs: A Personal Assistant and The Punisher Take the Stand
Release Date: May 21, 2025
Host: Andrea Canning
Produced by: NBC News

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Introduction

In this gripping episode of Dateline: True Crime Weekly, host Andrea Canning delves deep into the high-stakes racketeering trial of Sean Combs, widely known as Diddy. Released on May 21, 2025, the episode titled "Sean Combs: A Personal Assistant and The Punisher Take the Stand" provides an in-depth look at the allegations against Combs, featuring testimonies from key witnesses that shed light on the inner workings of his alleged criminal enterprise.

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David James’s Testimony: The Personal Assistant’s Account

Timestamp [00:01 – 07:22]

David James, Sean Combs’ personal assistant from the mid to late 2000s, takes the stand under a proffer agreement, granting him immunity to discuss any illicit activities he may have been involved in.

Chloe Melas, NBC News correspondent, reports from outside the courthouse:

[01:02] Andrea Canning introduces David James as "Combs' personal assistant during the mid to late 2000s."

David presents a multifaceted image of Combs, intertwining both the glamor and the alleged dark side of his professional life.

Key Points from Testimony:

1. Illegal Activities and Coercion:

   • James details how Combs allegedly pressured him and others to protect his reputation, even through illegal means.
   • He mentions procuring ecstasy for Combs and acting as an intermediary between Combs and drug dealers.

2. Daily Operations:

   • James describes his duties, such as fetching facial products specifically for Combs and ensuring Combs felt comfortable in any city by providing his preferred Heinz ketchup ([02:25]).
   • He recounts an incident where Combs allegedly ordered him to locate Suge Knight with the implication of potential violence ([04:11]).

3. Interactions with Security:

   • Security often joked about the threat of being fired if tired, emphasizing the high-pressure environment ([03:13]).
   • James was subjected to lie detector tests after accusations of theft, which he claims he passed ([03:34]).

4. Cover-Up Attempts:

   • James testifies about an incident involving Combs’ personal chef, where Combs allegedly instructed him to file a false police report claiming that Jordana (the chef) was the aggressor ([06:05]).

Notable Quote:

[05:30] "No one fired a gun that night, but Combs had people willing to do illegal things for him." – Andrea Canning

James’ testimony paints a picture of a controlled environment where Combs exerted significant influence and maintained strict oversight over illicit activities.

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Cassie Ventura’s Mother’s Testimony: Unveiling Abuse

Timestamp [07:22 – 09:34]

Cassie Ventura’s mother takes the stand briefly, with the defense choosing not to cross-examine her. Her testimony focuses on the alleged physical abuse Cassie endured at the hands of Sean Combs.

Key Points from Testimony:

1. Discovery of Abuse:

   • Cassie’s mother recounts visiting Cassie in Connecticut during the 2011 holidays, where she observed bruises and signs of physical abuse ([07:31]).

2. Evidence of Abuse:

   • She revealed that Cassie took photographs documenting her injuries, which are now publicly available, showing extensive bruising ([08:10]).

3. Emails and Financial Demands:

   • An email from Cassie in December 2011 threatened the release of explicit videos unless demands were met ([08:25]).
   • Cassie’s mother claims that Combs demanded $20,000, which was briefly withdrawn from their home equity line of credit and sent to Bad Boy Entertainment. Remarkably, the money was returned to her account within days ([08:59]).

Notable Quote:

[08:53] "When I got that email, I was physically sick." – Cassie Ventura’s Mother

This testimony highlights the personal turmoil and alleged coercion Cassie and her family experienced, adding a deeply emotional layer to the prosecution’s case.

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The Punisher’s Testimony: Unveiling Sexual Exploitation

Timestamp [09:34 – 13:05]

An exotic dancer, known professionally as The Punisher (Charay Hayes), testifies about his encounters with Sean Combs and Cassie Ventura in 2012.

Key Points from Testimony:

1. Sexual Encounters:

   • Hayes describes being hired to create a provocative setting for a couple, only to find Cassie Ventura instead of Janet and her husband ([10:04]).
   • He recounts witnessing Combs in compromising positions, including masturbating in the corner and instructing participants to cover themselves in baby oil ([10:45]).

2. Use of Baby Oil:

   • The Punisher explains that baby oil was used to create a glittering effect, aligning with Combs’ fetish for shimmering appearances. Authorities discovered extensive quantities of baby oil in Combs’ properties during raids ([10:51]).

3. Commercial Transactions and Travel:

   • Hayes emphasizes that these encounters were commercial transactions, with Combs paying him and having him travel across state lines for these activities ([11:18]).
   • He clarifies that while Combs’ defense claims these were consensual transactions, the prosecution sees them as part of a larger pattern of exploitation ([12:03]).

4. Control Over Cassie:

   • Hayes states that Cassie always sought Combs’ approval before engaging in sexual activities, suggesting manipulation and control ([12:08]).

Notable Quote:

[12:44] "This was all consensual," – Defense’s stance as highlighted by Andrea Canning.

Hayes’ testimony is pivotal in illustrating the alleged misuse of power and the orchestrated nature of Combs’ interactions with Cassie, challenging the defense’s narrative of consensual relationships.

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Upcoming Developments

As the trial progresses, significant events are anticipated:

• Testimony from Kid Cudi (Scott Mascudi):

  • Known for alleging that Combs "blew up his car" out of jealousy over a brief relationship with Cassie Ventura, Kid Cudi’s testimony is expected to be a major turning point in the trial ([13:05]).

• Further Witness Accounts:

  • The prosecution aims to establish a comprehensive view of Combs’ criminal enterprise, reinforcing the argument that he orchestrated illegal activities through coercion and manipulation.

Notable Quote:

[13:21] Andrea Canning hints: "We're in for another wild ride tomorrow."

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Conclusion

This episode of Dateline: True Crime Weekly intricately weaves together testimonies that depict Sean Combs not just as a music mogul but as an alleged orchestrator of a criminal empire fraught with drugs, coercion, and exploitation. The personal accounts of David James, Cassie Ventura’s mother, and The Punisher collectively build a narrative that challenges Combs’ defenses, setting the stage for a dramatic continuation of this high-profile trial.

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Notable Quotes with Timestamps

• Andrea Canning [05:30]: "No one fired a gun that night, but Combs had people willing to do illegal things for him."
• Cassie Ventura’s Mother [08:53]: "When I got that email, I was physically sick."
• Defense’s Stance [12:44]: "This was all consensual."

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Further Information

For more detailed coverage and updates on the Sean Combs trial, visit NBC News: Diddy on Trial.

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Produced By: Franny Kelly, Alison Orr, Liz Brown Kurloff
Music By: Jesse McGinty
Executive Producer: Paul Ryan
Senior Executive Producer: Liz Cole

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Stay tuned for the next episode of Dateline: True Crime Weekly for continued coverage of this landmark case.

Transcript

[Andrea Canning]

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 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 Melas is outside the courthouse in lower Manhattan to tell us all the details. Hey, Chloe.

[Chloe Melas]

Hey, Andrea.

[Andrea Canning]

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?

[Chloe Melas]

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 Homestead assistant, that he knew that it was going to be rigorous. He talked back a lot to Mark Agnifolo, 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. Yeah, 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 Boppin' so we.

[Andrea Canning]

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 and what he did for Sean Combs.

[Chloe Melas]

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 was 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.

[Andrea Canning]

There was something that was said that I. That I thought was really interesting. Something that security said to this assistant about being tired.

[Chloe Melas]

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.

[Andrea Canning]

One of the things almost sounds like, I don't know, some reality show or something. The lie detector tests were part of the job.

[Chloe Melas]

Well, he said that on two different occasions he was, I guess, considered a suspect when there were some things stolen. One time a watch of Combs they couldn't find. And another time money was gone. And so we don't know if other people were questioned, But I'm assuming that they were. And that the way that Combs would deal with something like this is not only have security go to wherever he was and search his things, but also subject him to a lie detector test. And he says that he passed both.

[Andrea Canning]

Let's get to the heart of what the personal assistant says Combs made him do that might have broken the law. We talked about the illegal drugs. What else are we talking about here?

[Chloe Melas]

He talked about a time in 2008 when he was in Los Angeles and he went to a very famous diner called Mel's Diner with some. Somebody who had worked on Combs security team, that guy's name is Drock. That it was well after midnight and that when they pulled up, that's when the head of security saw a very, very famous rap executive named Suge Knight. Suge Knight. If you know about the east coast, west coast rap war, you also know that it's not a secret that he and Combs didn't like each other. He goes on to say that he and Drock left Mel's Diner, went back to Combs home. That's where he found Combs arguing with Cass. And that Combs told David James to get into this black Escalade. And that Combs then had three handguns sitting on his lap. And that he was told to just drive and go back to the diner and find Suge Knight. And that they never found Suge Knight, but that he was under the impression that they were going to try to kill Suge Knight. And again, these are David James claims. So Combs team has pointed out that his story has not stopped, stayed straight when he's talked to prosecutors before his testimony today. And Combs team really pushed him on the details, which he does seem to be foggy on. But then again, it was 2008. We're in 2025 now. Yeah.

[Andrea Canning]

So to be clear, Chloe, no one fired a gun that night. But the prosecution is trying to show that Combs had people willing to do illegal things for him.

[Chloe Melas]

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.

[Andrea Canning]

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.

[Chloe Melas]

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.

[Andrea Canning]

This is the chef.

[Chloe Melas]

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.

[Andrea Canning]

So how would he know the personal assistant, Chloe? He 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.

[Chloe Melas]

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.

[Andrea Canning]

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.

[Chloe Melas]

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.

[Andrea Canning]

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?

[Chloe Melas]

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, upset that I'm dating Scott Mascudi, AKA Kid Cudi, and these videos might be dropping. And the mom said that when she got that email, she was, quote, physically sick.

[Andrea Canning]

She's saying that. That Sean Combs was actually demanding money from them.

[Chloe Melas]

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 paid $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. But something that's really important to point out is that she says, okay, she paid this $20,000, but that within four to five days, the money was back in her account.

[Andrea Canning]

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.

[Chloe Melas]

Professional name, the Punisher. He's an exotic dancer, Charay 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. Cause, 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.

[Andrea Canning]

Has anyone ever said why these people needed to be covered in baby oil at all times during these freak offs?

[Chloe Melas]

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 a thousand 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 oil. So even though he'd already seen these criminal indictments, he clearly loves baby oil and brings it everywhere.

[Andrea Canning]

Oh, my. So two things that are really important about his testimony for the prosecution. First, he was clear that 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.

[Chloe Melas]

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.

[Andrea Canning]

He also describes Sean Combs as directing Cassie, calling all the shots.

[Chloe Melas]

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.

[Andrea Canning]

When he was asked if he ever saw Cassie refuse to do any of.

[Chloe Melas]

These things, he said no. Right?

[Andrea Canning]

He said no. Yeah. Which goes to the defense's case.

[Chloe Melas]

Yes, it does. And also, he says that he never saw Cassie take drugs or appear to be really under the influence of anything. And he said that he didn't take drugs and that I think the most he said that he saw there was weed and alcohol.

[Andrea Canning]

So this is really how the defense handled him then is they went back to their. The theme of this with the defense, and that's that everything is consensual.

[Chloe Melas]

Yeah. And actually with some humor. I mean, some of the testimony is just so outrageous and the way that these witnesses are handling it with their own self deprecation, I mean, it's honestly, if there were cameras in the courtroom, everyone would have a field day with all of this.

[Andrea Canning]

Yeah. And I feel like, Chloe, we're in for another wild ride tomorrow. Is that right?

[Chloe Melas]

Yes. Kid Cudi. Remember, he is the musician who says that Combs blew up his car because he was jealous that he was dating Cassie for a brief period of time. So this is gonna be interesting. I mean, it's the first major celebrity besides Cassie that we've seen testify.

[Andrea Canning]

Big day tomorrow, Chloe. Thank you as always. And we will talk to you next time.

[Chloe Melas]

Bye, Andrea.

[Andrea Canning]

Thanks for listening. We'll be back with a new episode tomorrow night. And if you want to read the latest developments and analysis from inside the courtroom, check out the NBC newsletter. Diddy on trial go to nbcnews.com diddy to find that. On Trial is produced by Franny Kelly with help from the Dateline True Crime Weekly team. Our senior producers are Alison Orr and Liz Brown Kurloff. Her original Music by Jesse McGinty. Paul Ryan is executive producer and Liz Cole is senior executive producer of Dateline.