Dateline: True Crime Weekly
Sean Combs: A personal assistant and The Punisher take the stand.
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
Full Episode
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.
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.
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