Sean Combs trial recap: Cassie Ventura pressed on drug use, Kid Cudi relationship, 'freak off' videos

Dawn Richard, a former member of the girl group Danity Kane, is expected to take the witness stand on Friday once lawyers finish questioning Ventura, prosecutor Maurene Comey said.

Richard last year filed a lawsuit against Combs, accusing him of groping, assaulting and imprisoning her.

The court is in recess until 9 a.m. EDT tomorrow.

Cassie Ventura was asked by the defense if she took a bad batch of MDMA at the InterContinental Hotel in Los Angeles before Combs was caught on security cameras assaulting her in 2016.

Ventura responded that she didn't recall exactly what she took or how the "freak off" began at the hotel.

That testimony bought an end to a grueling day of cross-examination that'll continue on Friday morning.

U.S. District Court Judge Arun Subramanian is urging Combs' lawyers to wrap up their questions for the eight-months-pregnant witness.

"We will try to narrow it down," defense lawyer Marc Agnifilo said. "This is a critical critical witness and I will come back in the morning and give you an estimate. It is an important witness and a very important case."

Cassie Ventura told the court that Combs expressed concern about getting caught in "the matrix," their code for getting too high, during "freak offs."

Ventura proposed a shorter "freak off" session at the InterContinental hotel to avoid getting too high before her film premiere.

“A matrix is like the high and we would be getting too high for anything sexual to happen. There would be no performance,” Ventura said during court.

Combs' videotaped assault on Ventura at a Los Angeles hotel was preceded by his repeated requests for a "freak off" that she expressed reservations about, the witness said.

Ventura said she wanted to devote her attention to the premiere of "The Perfect Match," a romantic comedy that included herself, Terrence Jenkins and Paula Patton.

Despite her concerns about performing a "freak off" during her promotional duties for the film, she agreed after he kept asking "over and over again."

Cassie Ventura confirmed to the court that there were never any drugs contained in the baby oil used during the freak offs with Combs.

Combs was accused in a lawsuit last year of spiking the lubricant with GHB, commonly referred to as a "date rape drug."

Combs once overdosed on painkillers and that drug dependence fueled some of the rapper's mood swings, Cassie Ventura said.

During this cross-examination by defense lawyer Anna Estevao, Ventura was asked if Combs ever overdosed and if she was ever addicted. Ventura answered "yes" to both.

And when the defense asked if Combs' mood swings were tied to pills, Ventura affirmatively replied, "It was a part (of it)."

Cassie Ventura testified that she sent a text message to Combs’ chief of staff about an incident in which he allegedly dangled someone over a balcony.

Ventura acknowledged hearing about Combs supposedly dangling Bryana “Bana” Bongolan over a balcony after the fact, but still reached out to a person in Combs’ inner circle.

“I did text that … there were other crazy things that happened,” Ventura told the court, adding she couldn’t remember the name of the person she sent the text to. "I saw what I saw, so I don't know." 

Cassie Ventura described Combs' reaction to her taking illicit drugs without him as "explosive."

Ventura added that he told his drug dealers in Los Angeles to stop giving her drugs.

Cassie Ventura told the jury Combs suspected her of being in a relationship with actor Michael B. Jordan.

Asked what Combs’ reaction was to the alleged relationship, Ventura said, “I wasn’t there to see it."

Ventura said she couldn’t remember if Combs tried to text her about him but “he did try to make contact.”

Cassie Ventura says that Combs kicked her in the back at his house after finding out that she was cheating on him with rapper Kid Cudi in 2011.

When asked by Combs' attorney if her relationship with Cudi "drove Mr. Combs crazy?" Ventura replied: "To my knowledge it wasn't good."

She confirmed that Combs was especially offended by the affair with Cudi because of his status within the music industry.

She added that suspicions and grievances over infidelity came up repeatedly throughout their relationship.

Cassie Ventura admits to keeping a burner phone while she was dating rapper Kid Cudi to keep the relationship private and away from Combs.

"I thought it would be way too dangerous if he found out," she said.

As she was dating Cudi, Ventura said she continued to have "freak offs" with Combs because to her it “was a job."

When Combs found out about Cudi — while going through her phone during one of the sex sessions — Ventura said Combs attacked her.

Cassie Ventura says that things got "a little scary" when Combs found out that she was cheating on him.

She also admitted to being upset when she found out that Combs was spending time with a woman named Gina in 2014.

Ventura said the infidelity prompted arguments.

Cassie Ventura testified that, during her relationship with Combs, she became jealous of his ex-girlfriend Kim Porter.

Ventura admitted to the jealousy after being asked by the defense attorney if Combs ever left a freak off with her only to visit Porter afterward.

Ventura agreed she was upset about not having the chance to form a relationship with Combs’ children despite having a relationship with him for seven years at that point.

Ventura also acknowledged it could be heartbreaking seeing Porter with the children and that she wanted to be part of Combs' family, not just his sexual fantasy.

“I had some jealousy,” Ventura said of Porter.

U.S. District Judge Arun Subramanian appears to still be agitated from the back-and-forth he had with Combs' attorneys prior to the break.

Subramanian's agitation stems from the speed with which the defense is questioning Cassie Ventura.

The judge sternly reminded the defense that it was given a day and a half to cross-examine Ventura, who is eight months pregnant, and that she would be done by the end of the week.

Combs' attorney, Marc Agnifilo, argued that Ventura should be able to come back Monday morning if needed.

The judge shot back: "In what universe did you not understand this is what was going to happen ... you’re not telling me this wasn't everyone’s understanding that this witness was going to be done this week?"

Ventura was reviewing exhibits in a side room while the exchange took place.

A photo from Manhattan federal court shows Janice Combs exiting the courthouse as the jury was on a lunch break today.

Justin Combs, Quincy Brown and King Combs also leave the courthouse.

The opening hours of Cassie Ventura’s cross-examination were a bit of a slog, with defense questions jumping around in subject and timeline and frequently interrupted by prosecution objections.

Those starts and stops appeared to hinder Combs’ lawyer, Anna Estevao, from smoothly making the defense’s case that Ventura was often a willing participant in the witness’s seemingly abusive relationship with the defendant.

And Ventura appears to have caught on to the defense’s line of questioning.

She’s often interjected qualifying terms such as “at that time” to frame her relationship with Combs as a complicated one that could toggle between caring and violent.

U.S. District Judge Arun Subramanian called for a lunchtime recess and asked jurors to return to the courtroom at 1 p.m. ET.

Subramanian told lawyers he wasn't happy with the pace of Ventura's examination because he wants the eight-months-pregnant woman to be done sooner rather than later.

When the defense said they would need all day today and all day tomorrow, Subramanian angrily responded, "That is the exact opposite of what I was told." 

"This witness needed to be off the stand by the end of the week. So what happened?" the clearly perturbed judge said.

Cassie Ventura alleged during testimony that while Combs was a wealthy businessman and record executive he was doing so under the influence of drugs.

“He needed to recover,” Ventura told the courtroom, referring to Combs’ alleged drug abuse.

Ventura also accused Combs of also using ecstasy and cocaine.

Asked whether she thought Combs was a drug addict, Ventura responded, “I would say he was an addict.”

She answered “yes” when defense attorneys asked if Combs would become angry or volatile during withdrawals.

“I’m not a doctor, coming off of certain pills he would be pretty irritated,” Ventura testified.

Combs needed to be constantly updated about Cassie Ventura's whereabouts, perhaps concerned she was stepping out on their relationship, the witness said.

When asked what would trigger a spike in telephone calls from Combs, Ventura said it could be for any number of reasons.

"Could be anything from not telling him where I was, angry about me, could be anything, maybe he assumed I was cheating," she said. "I don't know."

When asked if she believed the volume of calls spiked when Combs theorized Ventura was cheating, she said: "Yes."

The defense asked Cassie Ventura to confirm that Combs both built up and knocked down her confidence, citing text messages between the pair.

Ventura agreed, also acknowledging that Combs called her "a queen."

"Words were helpful," she said. "He’s got that inspiring energy inside him."

Cassie Ventura testified that she understood how filing her 2023 lawsuit accusing Combs of rape and sexual abuse could ruin his career.

Asked by defense lawyers what happened to Combs’ career after she filed, Ventura responded, “That’s a lot.”

Prosecutors objected to that question. Defense lawyers then rephrased, asking if she understood how the publicity surrounding the lawsuit ruined his career.

Ventura responded: "I can understand that."

Cassie Ventura testified she was dating rapper and producer Ryan Leslie when she met Combs.

When Ventura signed with Bad Boy Records in 2006, she was platonic with label boss Combs and dating Leslie, the witness said.

Ventura was about three years into her relationship with Leslie when she went to Miami to see Combs, leading to the first time she and the defendant had intercourse, the witness admitted under cross-examination.

She confirmed that a flyer was made to advertise a club appearance she was making to give the impression of a professional reason to travel to Miami, so as not to make Leslie suspicious.

The defense is asking Cassie Ventura about her initial success in the music and modeling industry, in what appears to be an effort to paint her as being independently rich and famous and not under Combs' control.

Ventura was asked to confirm that she was becoming a wealthy celebrity with a thriving music and modeling career on her own, before she began dating Combs, her then-boss. She acknowledged that she was "doing well" during that time.

His attorney asked her: "You were an up-and-coming star?"

Ventura replied: "I guess you could say that."

Cassie Ventura told Combs in a 2009 email that having "freak offs" was the next step in their relationship.

But she also mentioned that she went back and forth about the idea and needed to trust him more to be sexually free.

“In order for me to be more open with the things we do in bed, I need to feel safe, like home…like this is my husband, and this is the only man that will ever have this aggressive sexual side of me,” she wrote in the email to Combs. “When we used to freak off when we were so in love there were no questions asked, it felt right. Like it literally made sense for the next step in our sex life together.”

When asked by the defense if "freak offs" were an important part of her relationship with Combs, Ventura responded, "It was an integral part."

The defense asked Cassie Ventura if she deleted the sex videos she had of Combs on her devices, which she confirmed.

They then showed an email exchange between Combs and Ventura in August 2009, confirming what appears to suggest the existence of the videos and the pair's illicit drug use.

Ventura emailed Combs: "Do you have any pills on you."

Combs replied: "Imma do it again."

Ventura responded: "I just deleted the video off of my camera, it was so dope."

The defense, in its ongoing effort to paint Cassie Ventura's relationship with Combs as consensual, has spent the morning presenting the witness with endless emails and text messages the couple exchanged about their sex life.

The missives have been detailed and graphic.

“I’m so horny,” Combs wrote in one of the tamer messages, with Ventura responding: “Omg I was just about to text you the same thing.”

Or when Combs said, “I can’t wait” for one of their “freak offs,” Ventura shot back: “I can’t wait either.”

Sean “Diddy” Combs is seen in the sketch taking notes during the morning arguments in his sex trafficking trial in New York City today.

Judge Arun Subramanian just abruptly called for the court to go into a 10-minute recess after Cassie Ventura could be seen whispering to him.

The sudden recess came just as Combs' attorneys were showing the court explicit emails and texts between her and Combs from 2009.

An extremely graphic message from Ventura to Combs drew an objection from prosecutors, which the judge sustained.

The emails and texts appear to be an effort on behalf of Combs attorneys to undermine Ventura's repeated claims that she did not want to participate in the "freak offs."

Ventura testified that she wanted to please Combs at the start of their relationship, so she agreed to take part in his "freak offs" — drug-fueled intercourse, often with sex workers as the rapper watched.

"Yes, at the time, I wanted to make him happy," she said.

Combs' lawyers then produce a series of texts and emails in which Ventura discusses the freak offs, including one where she writes "i am always ready to freak off Lol."

But when the defense again asked if she wanted to make him happy by participating in the "freak offs," she clarified, "No, it was a lot more than that."

Even though Combs had six children at the time of their relationship, Ventura admitted in emails of the time she wanted to have a child with him.

When asked by Combs' attorney why she wanted to spend so much time with Combs, Cassie Ventura replied: "Because I fell in love with him."

"He was charismatic — big personality, larger than life," she said. "The beginning of the relationship was really fast, fast paced, scary. But the more time I spent with him, his real personality came out — sweet, attentive."

Ventura also acknowledged that at the beginning of their relationship, the pair was reluctant to be public about their romance.

The defense appears to hope it can blunt some of the horrific details of Combs' abuse of Cassie Ventura with evidence their relationship had better days.

"I love you so much it makes me cry," according to a message Combs sent on Aug. 12, 2009, to Ventura, known as "Babygirl" on her Blackberry.

Then on April 4, 2010, Combs said his relationship with Ventura meant everything to him.

"Love my baby …i love you so much it consumes my life how did it happen," Combs wrote in an email.

Ventura responded: "I wonder the same thing who was i before we decided to be together."

As the cross-examination begins, Sean Combs' attorney asks Cassie Ventura to confirm if she "knew the real Sean."

"Yes," Ventura replies.

"The Sean other people didn’t see," Agnifilo said.

"Correct," Ventura replied.

Combs' former partner, a key government witness, took the witness stand for her third day of testimony.

In the opening moments of cross-examination, Ventura answered most questions with simple yes/no responses about their relationship of 11 years.

The witness is wearing a light colored blouse with a coat.

The defense wants to show that Ventura was a willing participant in this relationship and might have been involved with others.

“A large part of the defense is the infidelity on both sides and the fact that Mr. Combs understood that Ms. Ventura was having other relationships with other men," defense lawyer Anna Estevao, who will lead the cross-examination, told the judge outside the ears of jurors.

Prosecutors said they hope to have the eight-months-pregnant Ventura off the stand as soon as possible.

“This witness is very, very pregnant,” said lead prosecutor Maurene Comey. "We are afraid she could have the baby over the weekend. We want her off the stand before the weekend."

The cordial relationship between prosecutors and defense attorneys during pretrial hearings is quickly evaporating.

Courtroom tension dramatically increased this morning during arguments, outside the presence of jurors, over which text messages the defense can introduce to show Ventura’s relationships with other men.

The Combs-Ventura relationship was one that took place over text messages, “they texted about everything,” defense lawyer Marc Agnifilo said.

Cassie Ventura, the R&B singer and Diddy's former partner, is set to undergo cross-examination today. She has already delivered two days of emotional testimony, alleging that Combs subjected her to years of physical abuse, sexual coercion and manipulation through threats and surveillance.

Cross-examination of a complainant in a case involving sexual abuse and domestic violence is always a challenge for defense attorneys. But the defense must carefully attack Ventura’s credibility and the consistency of her accounts when they begin their cross-examination.

You can expect defense attorneys to explore whether the drugs she took at these “freak offs” have affected her memory. They will also question her financial motives, although the government elicited testimony yesterday that Cassie has already received her $20 million settlement from Combs in the civil case.

U.S. District Court Judge Arun Subramanian hopes to have proceedings start at 9:30 a.m. today, in what figures to be a long day of the defense cross-examining key government witness Cassie Ventura.

Combs’ defense has already conceded that the rap mogul has a bad temper and has been violent under the influence of drugs or alcohol.

But his attorneys will still want to put a dent in Ventura’s lengthy testimony about years of abuse she suffered while dating Combs.

In the Sean "Diddy" Combs trial, social media is flooded with thousands of opinions from people following the proceedings with heavy focus on the testimony of Cassie Ventura. NBC News' Maya Eaglin describes what people are saying and how the jurors will see evidence the public will not.

06:45

Jurors spent all of Wednesday hearing troubling details of Combs’ relationship with Cassie Ventura, which included incidents of emotional, physical and sexual abuse.

When Assistant U.S. Attorney Emily Johnson asked Ventura why she put herself through this grueling process, the witness said she owed it to herself.

“I can’t carry this anymore, the shame, the guilt, what’s right is right and what’s wrong is wrong, people aren’t disposable,” the witness said.

At least 18 brands and organizations have already cut ties with Sean "Diddy" Combs since the allegations against him went public, before a verdict in his case has been reached. Molly McPherson, a reputation and crisis strategist, spoke with NBC News' Gadi Schwartz about the possibility of Combs' reputation being repaired depending on the outcome of the trial.

04:07