Sean “Diddy” Combs’ federal sex-trafficking and racketeering trial finished its second week of testimony on Thursday, with the jury hearing a wide range of evidence as prosecutors try to prove that, over two decades, the rap and fashion mogul abused women, engaged in the trafficking of sex workers and turned his music and fashion empire into a criminal enterprise. 

Combs’ defense countered these allegations this week with strategic cross-examinations of most of the witnesses brought by federal prosecutors, aiming to discredit and minimize their allegations, testimony and expert witness status as Combs maintains that he is innocent of all charges in the case. 

Sharp and tough questioning has pervaded the trial, which is expected to last for five more weeks and, if it ends with a guilty verdict from the eight-man and four-woman jury, could result in the onetime high-flying superstar of the rap world in prison for life. Here is a look at some of the most compelling exchanges and moments from this week at the Daniel Patrick Moynihan United States Courthouse in lower Manhattan. 

The Ex-Assistant and the Kompromat

On Tuesday, Combs’ former assistant David James testified about a number of experiences he had during his time working for the mogul. One exchange he had with Combs following an office party may back up the claim that he was prone to holding onto compromising footage of people as a form of security, threatening to release it in order to keep them in line. 

Cassie Ventura testified last week that a similar threat hung over a lot of their relationship, with Combs threatening to release “freak-off” footage of her with male sex workers that she believed could destroy her career. The practice is also in line with what Rodney “Lil Rod” Jones, who worked as Combs’ videographer while living with him and producing his music, stated in his civil complaint against Combs last year. Here’s a look at what James said in court this week.

James: A few days later, we made it back to New York City, we were in the executive office and he called me into his office. He was reviewing footage from the party.

Prosecution: Can you explain what you mean by footage from the party?

Yeah, so we’d have a videographer who basically recorded everything for his parties, and Mr. Combs was reviewing the footage to see what people were doing at the party, things like that.

What, if anything, did Mr. Combs say to you about this video?

He was kind of like, I heard about it at first. And he says, “Yo, playboy, is that you dancing around the party,” and I said, “Yeah, that was me dancing around the party.” And he said, “Were you on ecstasy that night?” And I said, “Yes, sir, I was.”  And he kind of nodded his head and he said, “Okay, I want to keep this footage in case I ever need it.” 

The Mogul and the $20,000 Demand 

This week, the jury and public learned, as Combs became privy to Ventura’s affair with rapper Kid Cudi, he demanded that her mother, Regina Ventura, who took the stand to testify this week, pay him $20,000 in compensation for the investment that he’d made in her as an artist signed to his Bad Boy Records label. 

Regina Ventura testified that she paid the money for the safety of her daughter following her dealings and relationship with Combs. Days after the $20,000 was paid to Combs, it was returned with no comment or explanation from Combs to his on-off girlfriend’s mother. 

Notably, Combs’ defense team declined to cross-examine Regina Ventura. Here’s a look at her exchange from the stand with the feds.

When did you meet Sean Combs? 

2006. My daughter signed with his Bad Boy Records. He was her boss. Then they started dating. They moved to L.A. 

Read this message from December 2011.

Casandra wrote to me. She said Sean Combs threatened to release a sex tape and go after her and Mr. Mescudi. 

How did you react?

It made me sick. Sean Combs demanded $20,000, he said to recoup losses due to Mr. Mescudi, from my husband and myself 

Why did you take a loan to pay Sean Combs? 

For the safety of my daughter.

The Punisher and the Freezer Meat

Tuesday saw colorful testimony from Sharay Dashawn Hayes, the sex worker known as “The Punisher,” who discussed his work with Ventura and Combs at “freak-offs,” over several occasions. And for a man known as “The Punisher,” he was quite candid about a topic that might embarrass some men and certainly runs counter to his moniker. 

Hayes work at “freak-offs” ended when his issues around erectile dysfunction in 2015 apparently frustrated Combs to the point that he was no longer hired, Hayes told the court this week. The mogul’s “assertive, aggressive” tone as he demanded that Hayes and Ventura have penetrative sex in front of him, which was delivered in close proximity, threw him off and “startled” him, he said. 

While this, Hayes says he believed, was what ended his professional relationship with the couple, his story has a happy ending. He eventually wrote a book, called In Search of Freezer Meat, which he described as “a men’s self-help book that chronicles me developing and ultimately curing my erectile dysfunction by way of a penis implant.”

Here’s a look at Hayes’ exchange with Assistant U.S. Attorney Meredith C. Foster.  

Why did you have these performance issues? 

Just, you know, me personally, a sexual scenario with a woman’s partner present, actively giving directions and stuff, like that was not the norm for me. So it created some discomfort that could affect me and my performance.

What would you take to address these performance issues during these encounters? 

Oh, I tried Cialis, Viagra, the corner store pill, anything that I thought could possibly help me perform. It was a lot of pressure.

Approximately when was the last time you had a sexual encounter with Ventura and Combs? 

March of 2015, somewhere around that time. 

Can you describe what happened during that encounter? 

Similar scenario where we started out interacting on the couch. This is specifically, I believe I mentioned earlier that there was a time that Mr. Combs came, intervened, he put — threw condoms on the couch, and he expressed he was ready for us to begin penetration. His interaction and him being in close proximity was not the norm, so it kind of threw me off and startled me, so I struggled with getting an erection and I couldn’t perform. 

What did he say? 

He said I’m ready — as he presented the condoms, he said ‘I’m ready to see you fuck her.”

And what did he do with the condoms?

He threw them on the couch where we were interacting. 

What was his tone when he said I’m ready to see you fuck her? 

Assertive, aggressive. 

How did she react? 

She reacted kind of startled, similar to myself. 

And did you and Ms. Ventura engage in penetrative intercourse after this? 

We attempted to, but like I said, I struggled to achieve an erection and maintain it, so it was a failure. 

And what happened at the end of this encounter?  

Eventually, another similar scenario, Mr. Combs left the room, Ms. Ventura followed him, she might have returned a few minutes later, and I was still instructed to finish. So I believe I masturbated to a point of orgasm. Shortly after they both left the room and she returned with money to pay me. We had a conversation where she was thanking me for my — for being private and, you know, respecting their privacy in terms of our interactions.

The Porsche and the DNA

As Scott “Kid Cudi” Mescudi shared from the witness stand as he testified on Thursday, one detail from defense attorney Brian Steel took the rapper by surprise. Following the bombing of Mescudi’s Porsche outside his Hollywood Hills house in 2012, police launched an investigation. But according to Mescudi, he never learned anything about the incident from local police.

But Steel had some information to share with Mescudi as he cross-examined the witness. It turns out that DNA from a female was discovered on the vehicle during the investigation. Given the nature of DNA, it’s hard to say if this could point to the gender of the culprit who wrecked the vehicle with a Molotov cocktail, it was compelling enough to be noted by police and mentioned by Steel in court. But it certainly provided a genuine moment of surprise this week and might send amateur internet sleuths down a rabbit hole over the weekend. 

Here’s how the exchange went down on Thursday between the defense, the prosecution, Mescudi and the judge overseeing the proceedings. 

Defense Attorney Steel: You knew that DNA was collected, true? 

Mescudi: Yes. 

Steel: You know that DNA comes back to a female, right? 

Mescudi: You said what now? 

Steel: The DNA comes back to a female. 

U.S. Attorney Johnson:  Objection. 

Judge Arun Subramanian: Grounds?

U.S. Attorney Johnson: Hearsay, speculation, foundation. 

Judge Subramanian: Mr. Steel, maybe you can ask some more questions. 

Steel: Sure. And were you aware that the results came back from the DNA that it came to a female? That’s my question. 

Johnson: Same objection. 

Judge Subramanian: Sustained. 

Steel: Do you know that there were results from the DNA? 

U.S. Attorney Johnson: Objection. 

Judge Subramanian: That’s overruled. 

Mescudi: I tried to reach out to the police. I didn’t hear any follow-up about any of the fingerprints or anything.