In Sean "Diddy" Combs trial, Cassie Ventura's cross examination focuses on their relationship, drug use, texts

They questioned her about their nearly 11-year off-and-on relationship, and displayed many messages between the two. A lot of time was spent on messages that were sexually explicit, loving, and at times full of jealousy. They also honed in on drug use, pointing out specifically that Ventura often did drugs without Combs.

Read a full recap here.  

Ventura is expected to be back in court Friday for additional cross-examination. 

Earlier Thursday, the judge told Combs' defense team that unless there was a compelling reason, cross-examination should end Friday at noon, so there's an opportunity for prosecutors to re-direct, and then Ventura can be done. 

Alice Gainer has been reporting on the trial the entire time. Here's some of what she saw in court Thursday. 

The defense shared additional messages showing a loving relationship between Combs and Ventura. 

At one point, Combs allegedly sent her a message about attending spiritual therapy, and calling it a process. 

Other texts leading up to the 2016 hotel incident were shown, with Combs allegedly texting Ventura messages like thank you, I love you baby, you look so sexy today, and more. In the texts, Combs allegedly tells her it's up to them what they do. She replied she didn't want him thinking she didn't want to do a "freak off." 

Ventura testified she told them after he had asked her over and over. 

Texts allegedly showed Combs appreciated explicit messages Ventura sent him, and asking what she was doing that evening. 

He wants to know what you want to do so he can plan his night, the defense said. 

The key words there are plan his night, Ventura replied. 

Ventura was asked about an incident in which Combs allegedly threw a wooden hanger at her friend, which resulted in their friendship breaking up. 

I don't think I ever said I saw it, Ventura said on the stand. She was in the bathroom at the time, and said she heard it. When she came out, her friend was hurt. 

The incident took place when Ventura was dating the man who is now her husband, and she hadn't told Combs about him, Ventura said. 

Ventura said the friend who was struck with the hanger made a legal demand against her, which she paid because she felt responsible, and the two haven't been in touch since. 

Defense attorneys spoke again about the incident on a balcony in which Combs allegedly hurled a friend of Ventura's into patio furniture. 

The defense asked Ventura: Didn't you learn about his balcony incident after the fact?

I saw what I saw, Ventura replied. 

Ventura was then asked what it's like to take too much ketamine.

You disassociate, you're not there, Ventura replied. 

Ventura was asked if she and Combs referred to themselves as "get high partners," and she said they did. 

The defense asked if she did drugs with a friend, and if that friend provided her with opiates. Ventura said yes, and that she was highly addicted to them at the time. 

Ventura agreed with the defense's statement that Combs was not happy about her opiate addiction, which she thought was hypocritical. 

Asked if she tried cocaine with her friend, Ventura replied she'd tried everything. 

The defense asked if Combs told her to stop doing drugs with her friends. 

Ventura said he did, and that if the two of them weren't getting high together it was a problem. 

He only wanted you to get high with him, not her friends, the defense asked. 

Yes, Ventura said. 

Asked what Combs' reaction was when he found out if she took drugs without him knowing it, Ventura replied "explosive." 

Ventura was asked if, in 2016, Combs told drug dealers in Los Angeles not to sell her drugs as part of an effort to stop her from using drugs. She replied that happened at some point, but she didn't know if it was in 2016. 

Ventura said there were times when the two of them would discuss getting off drugs, but they didn't go to rehab, and there was a cycle of relapse. Ventura testified they were both addicts at that time. 

The defense attorney then asked whether part of "freak offs" was doing drugs and being able to experiment. Ventura said yes. 

Ventura agreed that she also took drugs while partying at Burning Man, and had many friends who did drugs, and was part of a drug party culture. She was asked if that was part of what drew her and Combs together. 

Drugs became a thing over time, Ventura said, adding that the "freak offs" lasted for days because of drugs. 

Ventura was asked if the "freak offs" wasn't just sex, but also using drugs, listening to music and hanging out, and to have her time with Combs. She said it was. 

Ventura was asked who in her family knew about incidents of abuse, and when. She said her mother and father found out about it in 2011, and Combs came to Connecticut to speak with her parents about problems with their relationship. 

Asked if her friends knew about the physical abuse, Ventura responded "unfortunately, yes." 

Ventura testified she witnessed Combs abusing other people, and becoming inebriated and abusive. 

Ventura testified that she found out Combs was continuing to date another woman while she was working on a movie. 

She testified she was beginning a relationship with actor Michael B. Jordan.

Ventura said she broke up with Combs by sending a video of Combs with the other woman to him and other members of his staff in 2015. She testified she sent it to all of them because she was hurt, and had been spending all of her time with them, and felt they were all part of her family. 

"Everybody was lying," Ventura said on the stand. 

Ventura was asked about her relationship with Kid Cudi, using a burner phone for that purpose, and whether she felt justified in cheating with Cudi because Combs had been cheating. I guess, she replied. 

The defense asked Ventura if, after she broke up with Cudi and got back together with Combs, when she would accuse Combs of cheating, would Combs always reply by saying she had an affair with Cudi?

Not always, but yeah, Ventura replied. 

The jury was seated Monday before opening statements began. It includes 12 members and six alternates. 

The jurors are eight men and four women and they range in age from 30 to 74. One is a social worker, another is a scientist and some are retirees.

Potential jurors filled out questionnaires about how much they may have already known about the case. They were also asked if they were familiar with a list of some 190 celebrities, if they had been victims of sexual assault, and if videos of sexually explicit content or physical violence would make it impossible for them to be fair and impartial. 

At one point, Ventura allegedly sent the following text to Combs: "You're making me look like a side-piece and that's not what I thought I was."

She explained that in 2013, she thought she was Combs' main girlfriend.

Asked if she had previously testified she was insanely jealous when she saw social media posts of him with other women, Ventura replied, sure. 

Ventura testified she was aware Combs had relationships with other women, and that she was very upset when Combs wouldn't break off his relationship with one of them. 

She testified that his seeing other women prompted arguments between the two.     

After lunch, the jury was shown additional texts allegedly sent between the two. 

Combs: I want a freak off right now

Ventura: Lol me too. Well I want to have fun with you

In another message, Combs allegedly asked her permission to set a "freak off" up, and Venture allegedly replied "yes." 

The defense continued to say the cross-examination will be long. 

The judge told them he wants the cross wrapped by noon Friday, unless there is a real reason for it to go longer. 

That way re-direct will happen Friday afternoon. 

The jury then came back in after lunch, and the questioning of Ventura resumed. 

During the lunch break, the judge asked the defense when they will finish their cross-examination. The defense replied they thought they'd need all day Thursday and Friday, saying they had a lot of material to go through, and that Ventura was the most important witness in the case. 

The judge the said that Ventura needed to be off the stand by the end of the week, and that had been discussed for months prior to trial.

Prosecutors said their direct examination took less than two days, probably only a day and a half. The prosecutors asked the court to limit the length of cross-examination to the length of direct examination. 

The judge said the court has limited time, and wondered if there was a way to streamline her questioning. 

The defense complained that prosecutors didn't call Ventura as their first witness, saying it was their choice not to call her first. Prosecutors replied the first two witnesses had scheduling issues, which is why they went first. 

The defense asked Ventura about sending pictures of her outfits to Combs, and asked if she thought he had good taste. The defense asked if she was aware he founded the clothing line Sean John, and that it was very successful. 

The defense then asked Ventura if she'd say Combs was an addict. 

She said she would. 

"What was he addicted to?" the defense asked. 

"Success," Ventura said. 

She was asked if Combs was addicted to opiates, and she testified that at a point, he was, and that withdrawal is painful and makes people ill and they can't do normal things. 

Ventura testified that Combs' primary drug of choice was ecstasy or MDMA. She added that she took opiates daily, and that she witnessed Combs go through withdrawal from opiates. 

The jury then went on lunch break. 

Ventura was shown additional text messages, and agreed they exchanged messages of love and affection. She said Combs often put her down, and often built her up. 

"Often encouraged you to be the best artist and woman you could be?" the defense asked.

"Yeah," Ventura replied, adding that Combs had inspiring energy. 

The defense then said it had 26 more pages of messages, and the judge called a sidebar. 

The defense then showed more messages between Combs and Ventura, some of which are explicit and suggestive. 

"One of my favorite times is when we FO'ed and then made love after," Combs allegedly messaged her. 

The questioning turned to conversations about swingers. Ventura asked if the "freak offs" were related to a swingers lifestyle.

In a sexual way, yeah, but "they're very different," Ventura replied. 

Ventura testified that she wasn't aware of whether Combs' personal assistants were aware of what went on during a "freak off," even though they would help set up hotel rooms for them. Ventura testified she had no specific recollection of one of Combs' employees walking in during one of them. 

She was asked if she told any employees about them, and whether she wanted any of the employees to know about them. 

"I definitely didn't," Ventura said. 

Here's a courtroom sketch of Cassie on the stand Thursday by artist Christine Cornell. 

Ventura again acknowledged she was worried that the release of "freak off" videos would cause her career to suffer. 

She was then asked, from her perspective, what happened to Combs after she filed her lawsuit, and whether it would be fair to say his career was ruined. 

The government objected to the question, saying it called for hearsay and speculation, but was overruled. 

The defense again asked: You understand his career was ruined, right?

"I could understand that," Ventura said. 

"I just want to be uncontrollable," Ventura wrote in a message to Combs. 

The defense then began reviewing how Ventura met Combs through a producer, and started to detail how the sexual history between the two began. 

Ventura giggled on the stand as she read a 2007 message she wrote before the message was read to the jury. Ventura said she was giggling because the message was from 2007. 

We only had one week together and it's been the best and worst, Ventura wrote in the message. I've never felt so safe and loved. I feel protected in your arms. You're one of the sweetest most sincere people. Grateful you've chosen to be part of my life. 

"Who knew I'd fall so fast," Ventura wrote. 

The message went on to say Combs might be weary of her, and she might be being sneaky. 

Ventura referenced being called a spoiled brat, dramatic, and disrespectful. She wondered if a friend of hers might be better for Combs, and that she might make more sense for him. 

"I'm hurt you think I'm a malicious person," Ventura wrote. She added she felt sad Combs didn't feel like she's the right one, and that she really does love him, and that he's very important to her. 

Ventura was asked about the "sneaky" remark, and whether it referred to her cheating on her then-boyfriend with Combs. Ventura said that could be. Asked whether she thought Combs had an attraction for her friend, Ventura said there was a point in the beginning, but she doesn't remember ever talking about it. 

The defense started to discuss Ventura's 21st birthday.

Ventura testified Britney Spears and Dallas Austin attended her party because of Combs

The defense asked Ventura about her successes up until then. 

Ventura said she had put out an album and that it did well. She was asked if she said she was a celebrity in her own right, to which she replied yes. She had been modeling for some time. 

The defense attorney then told Ventura she was very beautiful and charming.  

Thank you, Ventura replied. 

It's true, the defense attorney said. 

Questioning returned to Ventura's comment of the "dope" video, and more messages with explicit content were shown. 

In one message about the "freak off," Ventura wrote that she goes back and forth in her mind with wanting to and not. 

You're showing you feel two ways about the "freak offs" with Combs, the defense asked. 

Yes, Ventura replied. 

She was asked if she was afraid Combs was only seeing her for sex in this way, and only fulfilling that part of his sex life. She said she didn't remember that specific message, but it did sound like she was worried about it.

The defense asked if her hesitancy was whether she'd just become the girlfriend to fulfill his fantasies and not his true girlfriend. Yeah, I guess so, she replied. 

You say that's the only reason why I go back and forth in my mind, the defense asked. 

That's what it says, Ventura said. 

The defense asked if Ventura was afraid at the time if she was just being treated as someone to fulfill his fantasies. She acknowledged that was a concern. 

They did not go public until two and half years later. 

In a message, Ventura allegedly asked if she wrote to Combs if he had any more pills on him. Ventura told the court she wasn't sure which kind. 

What kinds of pills was she taking around that time in 2009, the defense asked. 

Opiates, Ventura said. 

Was Combs taking opiates at the time?

Ventura testified she didn't know how much or what his intake was. 

Cross-examination resumed after a short break. 

The defense showed some explicit messages from 2009 Ventura sent to Combs, including one sent ahead of a "freak off." 

In one message, Ventura wrote to Combs that she deleted a video from her phone that she called dope. She was asked if that was a video from a "freak off," and Ventura replied that she didn't know. 

Ventura was asked if she typically deleted videos she made with Combs. Sexual ones, Ventura replied. 

The defense displayed messages showing the two of them coordinating a "freak off." 

In the below exchange, Jules refers to a person who participated in "freak offs." 

Combs: "Friday it is. I wish we could get Jules here." 

Ventura: "LOL maybe we could we don't know him that well though."

Combs: "Wanna call him and feel him out?"

Ventura: "Yeah, I can do that."

Ventura was asked to confirm if she wrote to Combs that Combs made her a better woman, daughter, sister and so on. 

Yes, Ventura said. 

That she couldn't wait until they had a baby of their own for Father's Day, that she loved Combs will all her heart?

Yes, Ventura replied. 

Ventura confirmed she felt the relationship was special because not a lot of people got that time with Combs, and that she really fell in love with him, and was like a shadow for a little while. 

Ventura testified her relationship with Combs was much different than any relationship she'd had before, and that it was passionate. 

Ventura agreed it was fair to say Combs trusted her with his secrets, and that she earned his trust. 

"You told him you wanted to do freak offs?" the defense asked.

"No, there's a lot more to that," Ventura replied. 

Ventura was asked what she meant when she said he was a larger-than-life personality. 

"He's a charismatic, big personality that everyone really loved," Ventura said. 

What made Ventura fall in love with him, the defense asked.

Ventura said the beginning happened very fast, but the more time she spent with him and got to know him, what she thought was his real personality came out, and she liked who he was. 

Ventura called him "sweet, attentive." 

You stated when you really care about someone and you're in love you don't want to disappoint them, the defense asked, along with whether that's how she felt about Combs at the time. 

Yes, Ventura replied. 

The defense showed additional texts between Combs and Ventura. 

"I love you so much it makes me cry," one read.

"I'm so happy we fell in love," read another. 

I don't need your money, I need some attention Ventura wrote in an email to Combs. I'm thankful but I can pay for these things myself. 

Ventura was asked if it was important to her to get more special time with Combs. Yes, she replied. 

Ventura is wearing a light-colored blouse and a blazer on the stand, with her hair pulled back into a ponytail. 

Estevao asked Ventura if she knew she was special to Combs, which is why it hurt so much when Combs lied to her and cheated on her. Ventura said yes. 

"You kept coming back to him for 11 years," Estevao said. "You put up with all that because you thought he truly loved you too." 

Not every time, Ventura said. 

Some text messages between them were displayed. One from Combs to Ventura said he was happy she'd fly to Atlanta just to see him, that he was a lucky man and he missed her and loved her. 

I'm a very lucky woman, she replied. I miss you so much. I'll fly for you whenever you need. 

Thursday's court proceedings got started with cross-examination of Cassie Ventura. 

Defense attorney Anna Maria Estevao began her questioning of Ventura by asking if she had been in love with Combs for 11 years and whether she took care of him. Ventura replied yes to both questions. 

Ventura agreed that Combs was larger-than-life to her, and said she knew the real Combs, the version he wouldn't let the rest of the world see. 

Dozens of people have filed civil lawsuits against Combs, but most of those allegations are not part of his federal criminal trial. 

While Ventura has been publicly identified in the case, three other women are also expected to testify. Their names are not being released to the public, and they will testify using pseudonyms. 

The indictment refers to them as Victim-1, Victim-2, and Victim-3. They are expected to be called to the stand as the trial progresses.

Sean "Diddy" Combs faces several federal charges. 

He was initially indicted on racketeering conspiracy and sex trafficking charges last September. Additional charges were later announced, including sex trafficking allegations from as recently as 2024.

Prosecutors say Combs led a criminal organization involving sex trafficking and traveling across state lines to engage in prostitution, arson, bribery and obstruction of justice. 

The superseding indictment said he used force, threats and coercion to cause his alleged victims to engage in commercial sex acts. It also said he subjected the victims to violence, threats of violence, threats of financial or reputational damage and verbal abuse.

The indictment specified at least three female victims.

Combs has pleaded not guilty.  

If convicted, he could be sent to prison for decades. 

The trial of Sean "Diddy" Combs is taking place in federal court, so there's no broadcast of the proceedings allowed.

Sketch artists are allowed in the court, however. 

CBS News New York's Alice Gainer has been at court since the start of the trial and will be providing updates to this live blog all day. 

Some of the details from Ventura's testimony are disturbing. 

Wednesday, she told the jury that after a break-up, she was raped by Combs in 2018.

Jurors were shown images from the so-called "freak offs," where Combs allegedly directed Ventura and male escorts to perform sex acts. 

She also testified about years of psychological and physical abuse during their decade-long relationship, including the video of Combs attacking her at a Los Angeles hotel in 2016.

For more details of Ventura's testimony, CLICK HERE.

CBS News New York's Alice Gainer has been following the case from the start and will be at the courthouse each day providing real-time updates. Watch her recap from Wednesday, the second day of Ventura's testimony. 

Casandra Ventura, who performs under the name Cassie, rose to fame with the single "Me & U" on her self-titled debut album. The song landed the No. 1 spot on the Billboard Hot R&B/Hip-Hop chart in 2006.

In her testimony, she said she signed with Bad Boy Records when she was 19, and Combs first kissed her on her 21st birthday. She and Combs dated off-and-on for more than 10 years, from about 2007 to 2018.

Ventura is now married and pregnant with her third child. 

CLICK HERE for more about Ventura and the other accusers.

Three witnesses have testified in the case so far.

Israel Florez was the first on the stand. 

Florez worked as the security manager at the hotel where Combs was caught on video attacking Ventura in 2016. He testified Combs offered him a stack of cash as a bribe and asked him not to tell anyone about the incident. Florez said he rejected the bribe. 

Daniel Phillip told jurors he was paid to have sex with Ventura while Combs watched. He also testified he was present when Combs threw a bottle at Ventura and dragged her by her hair into another room, where he described what sounded to him like Combs hitting Ventura. 

Ventura has testified about her relationship with Combs. She alleged that Combs suggested she have sex with other men while he watched, and that he provided drugs for "freak offs." She accused Combs of repeatedly beating her, and testified that arranging the "freak offs" became her job. 

She went on to accuse Combs of raping her in 2018.