DIDDY REPORT 
Key things to know from the cross-examination of Cassie Ventura today
Cassie Ventura faced cross-examination from Sean “Diddy” Combs’ legal team today in his federal criminal trial.
Ventura, a former girlfriend of Combs and one of his accusers, has been on the stand since Tuesday afternoon. The prosecution’s star witness testified about the beginning of the relationship and her participation in “Freak Offs,” which is what Combs called the drug-fueled sex performances he orchestrated.
In court, the jury saw affectionate messages between Ventura and Combs, but also texts that showed Ventura’s frustrations and hesitancies.
Combs has pleaded not guilty to racketeering conspiracy, sex trafficking and transportation to engage in prostitution and could face up to life in prison.
Here’s what to know:
- Start of relationship with Combs: Ventura testified that she loved Combs and believed he loved her. Ventura said she fell in love with Combs’ “real personality.” Asked about her desire to make the music mogul happy, and if that included agreeing to “Freak Offs,” Ventura responded, “There’s a lot more to that.”
- Early “Freak Offs”: Jurors saw text messages from 2009 that Ventura confirmed reflected the “open communication” between the pair. She said that at the time, she felt comfortable expressing her needs to Combs regarding the “Freak Offs.” In the messages, Ventura said she needed to “feel safe” to be more open sexually. However, in other messages, Ventura told Combs a recent “Freak Off” left her feeling “dirty and grimy” and noted their early intimacy felt different when they were “so in love.”
- Defense strategy: The jury also saw messages from March 2017 when Ventura told Combs, “I love our (Freak Offs) when we both want it.” She testified that those were “just words at that point.” The defense tried to use these and other messages from the beginning of their relationship to characterize Ventura as a consenting adult, not a victim of coercion, attorney and legal affairs commentator Areva Martin said.
- Other relationships: Ventura described arguing with Combs about his relationships with other women, particularly a woman called “Gina” in 2014, and testified that she “had some jealousy” toward Kim Porter, who shared three children with Combs. Meanwhile, Ventura said Combs was suspicious of her having relationships with other men, including celebrities, and said she took lengths to protect the rapper Kid Cudi from Combs.
- Drug use: Ventura testified that she and Combs were both doing a lot of drugs during their relationship and that she experienced adverse side effects. Ventura said Combs was “explosive” at times when he’d find out she was doing drugs with her friends or took his drugs without him knowing. The defense attorney also asked a lengthy line of questions to suggest Combs was reliant on opiates and any withdrawal from them would negatively affect his mood.
- Testimony timing: Judge Arun Subramanian told attorneys he wanted to have Ventura off the stand tomorrow and the defense should finish its cross-examination before lunch. Prosecutor Maurene Comey said yesterday in court that the prosecution is worried Ventura, who is heavily pregnant, “could have the baby over the weekend.”
What it was like in court as Sean Combs watched Cassie Ventura’s cross-examination
Sean “Diddy” Combs did “not look happy” during his federal criminal trial in New York today, according to a CNN correspondent who was in the courtroom.
Cassie Ventura, his ex-girlfriend, was answering questions from his lawyers on cross-examination about their relationship and the “Freak Offs” he organized. The jury also saw a slew of text messages between the two, some of them explicit.
“He was passing a ton of notes to his defense, he had a very serious look and he was fixated on his defense attorney who was cross-examining Cassie today,” CNN entertainment correspondent Elizabeth Wagmeister said.
As for Ventura on the stand, Wagmeister said her demeanor had changed from the last two days, when she was facing questions from prosecutors.
Wagmeister said Ventura’s hours of testimony recounting graphic details have been “grueling for her,” but today “she was much more at ease and even laughed a few times on the stand.”
Combs’ defense attorney laughed with her in some of those instances, Wagmeister said, adding that those were moments that “kind of humanized” Ventura and helped her as a witness.
Prosecutor expects to question Ventura for another hour after defense finishes cross-examination
Prosecutor Emily Johnson said she expects about an hour of redirect-examination whenever the defense team finishes its cross-examination of Cassie Ventura.
Judge Arun Subramanian told the defense that they should be able to finish cross-examination with the balance of the trial day tomorrow. Defense lawyer Marc Agnifilo said they’d do their best, but still made no promises that cross-examination could be finished in that timeframe.
Subramanian has noted that he does technically have authority to cut off cross-examination when it’s amounted to the duration of the direct testimony.
The prosecution and defense teams plan to convene at 9 a.m. ET tomorrow before Ventura’s testimony continues.
Jury dismissed for the day
The jury has been dismissed for the day. Testimony is expected to resume again tomorrow morning.
Defense walks through messages Ventura and Combs exchanged before hotel assault
Defense attorney Anna Estevao is going through more messages between Cassie Ventura and Sean “Diddy” Combs from March 3, 2016, which led to the “Freak Off” before the eventual assault in the hotel hallway.
Some of these messages were shown to the jury by prosecutors during Ventura’s direct-examination.
After going back and forth about potential plans with her friends, Ventura messaged, “We can have fun, I don’t want you thinking I don’t want to.” She told Combs to set it up.
The defense attorney suggested Ventura proposed and encouraged the “Freak Off.”
Ventura pushed back, testifying that messages from Combs repeatedly asking about her plans for the night was his way of posing a “Freak Off.”
She said when you’re with someone for so long, “you know what they mean when they text certain things.”
In some of the messages, Combs indicated they should do the “Freak Off” sooner rather than later since Ventura had events for a movie premiere coming up.
Combs’ lawyer suggests he was going through withdrawal before 2016 hotel altercation
Defense attorney Anna Estevao is suggesting Sean “Diddy” Combs was going through withdrawal in the days before the March 2016 assault at the InterContinental Hotel.
Combs’ attorney reviewed a series of text messages from March 3 between Combs and Cassie Ventura in which the couple discussed Combs having symptoms that Estevao suggested are consistent with withdrawal.
Ventura testified that she does not remember Combs going through withdrawal at that time. She acknowledged the texts appear to suggest he was sick at the time.
Cassie Ventura is back on the stand after short break
The jury is back in and Cassie Ventura is back on the stand after court took a short break.
Defense asks Ventura to confirm baby oil was not laced with drugs
Defense attorney Anna Estevao asked Cassie Ventura to confirm the Johnson’s baby oil they used during “Freak Offs” was never laced with any drugs.
The defense attorney also asked her to confirm that filling a baby pool would take a lot of baby oil and might explain why Sean “Diddy” Combs was keeping lots of baby oil on hand.
Judge Arun Subramanian sustained an objection to that question.
Large amounts of baby oil were recovered during searches of Combs’ residences in Miami and Los Angeles in March 2024, according to an indictment at that time. Law enforcement seized “various Freak Off supplies,” including drugs and more than 1,000 bottles of baby oil and lubricant, at his homes, according to the indictment.
The jury is taking a break
The jury was just dismissed for a short break. Testimony will resume soon.
Defense returns to Ventura’s previous testimony on incident concerning Suge Knight
Defense attorney Anna Estevao returned to Cassie Ventura’s previous testimony about the time Combs’ rival Marion “Suge” Knight was nearby and he and his security guards “quickly packed up and drove down there.”
Estevao pointed to a report from investigators after they met with Ventura in June 2024, which said she told them she was brought along in the car and cried. Ventura said that was incorrect.
“I didn’t go in the car with them,” she said.
During her testimony yesterday, Ventura said Combs was “rivals” with Knight, the former rap mogul who was sentenced to 28 years in prison for a fatal hit-and-run incident on the set of the movie “Straight Outta Compton.”
Combs overdosed on painkillers in 2012, Ventura confirms
Sean “Diddy” Combs overdosed on painkillers in February 2012, Cassie Ventura confirmed while testifying.
Ventura said that on that day, they had a “Freak Off” and went to a sex club before Combs went without her to a party at the Playboy Mansion.
Later that night, she took him to the hospital, where they learned he’d experienced an overdose, she testified.
“From what he told me, he took a very strong opiate that night, but we didn’t know what was happening, so we took him to the hospital,” she said.
Defense attorney Anna Estevao has asked a lengthy line of questions to suggest Combs was reliant on opiates and any withdrawal from them would negatively affected his mood.
“He was extremely dependent on his opiates right?” she asked Ventura.
“For a time,” Ventura said.
“He was very upset if his opiates were taken away from him?” Estevao asked.
“I guess so,” Ventura said.
Ventura details side effects from drug use
Cassie Ventura said that in early 2017, she got very sick from her drug use and began to look for help.
“I lost all sense of smell and taste when I woke up, and I had numbing in my arm,” she said. She said she also experienced some dissociative side effects from ketamine use.
Ventura confirmed that Sean “Diddy” Combs noticed some of her symptoms and suggested she see doctors.
She said that she didn’t tell Combs everything about her drug use throughout their relationship, but she added that they were both doing a lot of drugs.
Defense suggests Ventura didn’t personally witness Combs dangle her friend over balcony
Defense attorney Anna Estevao suggested that Cassie Ventura didn’t personally witness Sean “Diddy” Combs dangle her friend, Bryana “Bana” Bongolan, over a balcony at Ventura’s apartment as she’s previously alleged.
“Isn’t it true you learned about this incident after the fact?” Estevao asked.
“I saw what I saw,” Ventura responded.
Estevao showed Ventura a text message she sent Comb’s chief of staff Kristina Khorram shortly after the incident telling her that she learned of the altercation after the fact.
Ventura told the prosecution during her testimony yesterday that she woke up to find Combs holding her friend over her balcony railing before throwing her onto the patio furniture.
Estevao asked Ventura if she was on drugs that night. Ventura testified she couldn’t remember if she’d done drugs before falling asleep earlier that day.
Ventura describes some of the times Combs was “explosive”
Cassie Ventura said Sean “Diddy” Combs was “explosive” at times when he’d find out she was doing drugs with her friends or took his drugs without him knowing.
“If we weren’t getting high, or if I wasn’t doing it with him, it was a problem,” she said.
Combs used industry clout to control Cassie Ventura’s career and avoid consequences, music editor says
Sean “Diddy” Combs controlled Cassie Ventura’s career through her record deal with his company and his clout in the industry as a whole, Jem Aswad, executive music editor at Variety, told CNN today.
By 2011, Ventura had only made one album, even though she signed a 10-album deal with Combs’ label, Bad Boy Records. Aswad described Ventura as a “mid-level star at the time.”
He said that while most record companies signed similar long-term deals, seven albums was usually the standard. Aswad said Ventura’s terms were “very restrictive,” adding that a deal like that “locks you up for your career and then some.”
And Aswad said that, despite Combs developing a reputation around the industry for having a temper and even being violent, the fear he struck in others insulated him from consequences and kept certain things from coming to light.
“He was one of the most powerful people in the music business for 20-some years because he was so wealthy and because he had so many people who were willing not only to do what he wanted, but were very afraid to speak out against him. Now, I’ve been in the industry, ever since he first started coming around basically, and you heard about his temper, you heard people were afraid of him, the violence was a matter of public record. I did not hear about ‘Freak Offs,’ I did not hear about a lot of these things that are coming to light now, and neither did a lot of people that I know,” Aswad said.
Ventura says her friends knew about abuse because they sometimes witnessed it
Cassie Ventura testified that her friends knew that Sean “Diddy” Combs physically abused her — sometimes because they witnessed the abuse themselves, she said.
She said she also told her parents and brother about the abuse at different points.
Actor Michael B. Jordan’s name was just brought up by the defense
At the time, Sean “Diddy” Combs was also suspicious that Cassie Ventura was starting to date actor Michael B. Jordan.
When asked about it, Ventura said she didn’t know how Combs reacted to this news because she wasn’t with him to see it.
Defense attorney Anna Estevao moved on from that line of questioning without expanding on that purported relationship with Jordan.
Ventura describes how she broke up with Combs in 2015
Cassie Ventura testified that in 2015, she broke off her relationship with Combs for a time while she was in South Africa filming a movie.
She said she broke it off with Combs by sending a video of him with another woman at an event to a text chain with Combs and some of his closest staff. Ventura said she felt betrayed by them for not telling her.
Ventura said she also blocked Combs’ phone number for a time while she was filming.
Ventura’s testimony sets up arguments on both sides during the rest of the trial, expert says
Cassie Ventura’s answers to questions from both the prosecution and defense are setting up the more fleshed out arguments lawyers will make over the next several weeks of Sean “Diddy” Combs’ criminal trial, a trial consultant told CNN.
First, the testimony will be bolstered by expert witnesses for each side, Richard Gabriel said.
The prosecution will bring experts who likely argue that, “psychologically, this does meet the threshold for coercion and sort of her being under the thumb of Sean Combs,” Gabriel told CNN. Meantime, the defense’s experts will likely say it does not, and argue her “independence and her ability to leave” the relationship.
Secondly, the lawyers will take what Ventura says on the stand and argue the actual legal statutes. They will need to explain to the jury how her testimony does — or doesn’t — meet the legal definition of what Combs is accused of, Gabriel said.
Jurors “fundamentally have to get their own gut feeling as to whether there’s real participation on her part,” he said.
This sentiment was underscored during a conversation between the lawyers and the judge earlier today about how much longer Ventura would be on the stand. Defense attorney Marc Agnifilo stressed to the judge that the defense believes Ventura is the most important witness in the case.
Ventura says Combs often brought up her relationship with Kid Cudi
Throughout her relationship with Sean “Diddy” Combs, Cassie Ventura said he would often bring up her relationship with rapper Kid Cudi, who was identified by name in court.
“He brought it up quite a bit,” she testified.
She confirmed that when she would accuse him of cheating on her, he would often bring up her relationship with Kid Cudi in response.
Ventura says Combs often brought up her relationship with Kid Cudi
Throughout her relationship with Sean “Diddy” Combs, Cassie Ventura said he would often bring up her relationship with rapper Kid Cudi, who was identified by name in court.
“He brought it up quite a bit,” she testified.
She confirmed that when she would accuse him of cheating on her, he would often bring up her relationship with Kid Cudi in response.
Ventura is back on the stand
Cassie Ventura has returned to the stand to resume her testimony.
Court takes steps to have Cassie Ventura’s testimony conclude before baby arrives
The court in Sean “Diddy” Combs’ trial has taken a number of steps to have Cassie Ventura’s testimony completed by Friday — hopefully before the pregnant pop singer gives birth.
Ventura is due to deliver her third child next month.
The prosecution called Ventura to the stand Tuesday as its third witness and ended its direct examination Wednesday at 4:15 p.m. ET, leaving about 45 minutes until the expected end of court. Defense attorney Marc Agnifilo asked the court to begin cross-examination Thursday morning rather than right away, but prosecutor Maurene Comey resisted.
“This witness is very, very pregnant. We are afraid she could have the baby over the weekend,” Comey said, according to a court-provided transcript of the Wednesday exchange. “We want her off the stand before the weekend and we believe 45 minutes could make a difference.”
Judge Arun Subramanian ultimately decided to wrap up for the day.
He has told the defense team they need to complete their cross-examination of Ventura around lunch Friday, saying direct took a day and a half, so the defense will get a day and a half. He left open the possibility of granting additional time if there’s something that “really needs to be done” after lunch tomorrow.
Court has condensed its lunch breaks, generally an hour long, to about 30 minutes, and Subramanian has proposed ways the defense might streamline its questioning as it goes through a slew of exhibits. After lunch today, Ventura was given an iPad to review material on, as part of the effort to speed things up.
Agnifilo said the defense is trying to streamline the process, but stressed the belief that Ventura is the most important witness in the case.
“That is the cross-examination that is required of a critical witness in a trial that involves a life sentence,” he said.
Combs seen passing sticky notes to lawyer during Ventura’s testimony
While the defense questioned Cassie Ventura about text messages, Sean “Diddy” Combs was seen writing on orange sticky notes and passing one after another to his attorney sitting beside him.
Combs also spoke during the break briefly with the attorney handling the cross-examination.
Message shows Ventura’s frustration over her difficulty forming a relationship with Combs’ children
By 2013, Cassie Ventura had been in relationship with Sean “Diddy” Combs for about seven years, she testified. But, she said, she still hadn’t been able to form a relationship with his children.
Ventura expressed her frustration over not being able to spend time him and his children in a July 2013 message she sent to Combs, which was shown to the jury this afternoon.
The message, in part, references other divorced celebrity couples and how they spend time together with family. The message went on to say:
“I’ve been at the edge of tears this whole week. I don’t think that you sympathize with my feelings. I understand you feeling like you need to protect your children but after a while… It’s like for what? They’ve never known you and Kim [Porter] to be together. Unless there’s something that I just don’t know about. They were babies when we started dating.”
Jury takes a short break
The jury was dismissed for a short break.
Cassie Ventura rushed down the aisle to exit the courtroom.
Ventura says she got a burner phone to hide new relationship from Combs
Cassie Ventura testified that Sean “Diddy” Combs introduced her to rapper Kid Cudi around 2011 so they could work on music together.
Ventura said she began dating Kid Cudi while she was on a break with Combs.
She testified that she got a burner phone to communicate with Kid Cudi because she didn’t want Combs to find out about the relationship.
“I thought it would be way too dangerous to tell him about that,” she said.
Ventura said Combs eventually found out about the relationship when he went through her phone during a “Freak Off.” She said that she was still having “Freak Offs” with Combs while they were on a break because “it was a job.”
Ventura said Combs lunged at her when he found out, but he didn’t make contact with her.
Ventura says women on social media often claimed to be in relationships with Combs
Women on social media would often claim to have a relationship with Sean “Diddy” Combs, his ex-girlfriend Cassie Ventura testified.
“It happened often enough that I don’t know that I would remember every single one,” she said.
Defense attorney Anna Estevao asked if Ventura would react when she saw Combs with other women.
“Yes, mainly Gina,” Ventura responded. She confirmed that a woman called “Gina” was the main problem in their relationship.
The defense is using texts to characterize Ventura as a consenting adult, legal expert says
Sean “Diddy” Combs’ defense attorney Anna Estevao has spent the day questioning the prosecution’s star witness, Cassie Ventura, with a focus on certain text messages from early in her relationship with Combs that appeared to reflect the “open communication” between the pair.
Attorney and legal affairs commentator Areva Martin told CNN this line of questioning was “expected” from the defense during cross-examination, and was something Combs’ attorneys had established from their opening statement.
“A big part of their case is trying to get this jury to believe that Cassie Ventura was a consenting adult in these sexual acts, these ‘Freak Offs’ that we’ve heard so much about during her direct testimony,” Martin said.
Martin continued: “So a lot of what the defense has been doing today during this cross-examination is showing text messages and getting Cassie Ventura to acknowledge that, according to these text messages, she was a willing participant in some of these ‘Freak Offs.’”
What the defense hasn’t yet done is make the “connection between those text messages in the early stages of the relationship and the violence that we heard so much about during the direct testimony yesterday,” Martin said.
Martin added that, upon redirect, the prosecution may “try to link the violence that happened later in the relationship to her participation, and make the argument still that she was being coerced into these commercial sex acts.”
Ventura addresses defense, saying she feels “there’s a lot we skipped over”
Defense attorney Anna Estevao reviewed some text messages with Cassie Ventura from a 17-page text exchange between her and Sean “Diddy” Combs.
In the thread, the couple was planning for Combs to join her in New York City for the weekend. The jury also saw texts between them planning to see “The Book of Mormon,” and about escorts and a sex club.
When Estevao moved on to another exhibit, Ventura said, “This isn’t about what I feel is relevant right now, right, because there’s a lot we skipped over?”
Estevao didn’t acknowledge her question.
Ventura says she felt “some jealousy” of Combs’ former partner Kim Porter
Cassie Ventura is now testifying about other women Sean “Diddy” Combs spent time with while the two of them were dating.
Ventura testified that she “had some jealousy of Ms. Porter,” referring to Kim Porter, who shared three children with Combs. Porter died in 2018.
Ventura confirmed that it would upset her when Combs would spend holidays with his family and Porter, even though the two were no longer in a romantic relationship.
Ventura also testified that she learned Combs was spending time with a woman called “Gina” in April 2014.
“I was really upset,” Ventura testified. She said Combs denied the relationship to an extent, but added that she and Combs argued multiple times about him getting back together with Gina.
She said she also argued with Combs about other women.
Ventura said Combs was also suspicious that she was romantically involved with other men.
Defense reads texts from Combs to Ventura in which he wrote about “surprise package coming from out of state”
The jury is seeing messages of Sean “Diddy” Combs and Cassie Ventura planning and preparing for a “Freak Off.” Ventura confirmed that there were times Combs picked up supplies and contacted escorts for them.
In an exchange from 2017, Combs told Ventura he was making plans for a “Freak Off.”
Defense attorney Anna Estevao read aloud some of his texts:
- “Didn’t hear from you so I just put some plans in motion let me know to stop”
- “Surprise package coming from out of state”
- “Just let me know if I’m headed in wrong direction so I can cancel”
More messages about “Freak Offs” presented to jury
Messages about “Freak Offs” between Cassie Ventura and Sean “Diddy” Combs are being read and shown to the jury now.
In one conversation from March 2017, Ventura told Combs to stop playing the victim. “That’s all you wanted and that’s why I was upset,” Ventura wrote, according to the messages read aloud in court. “I love our [Freak Offs] when we both want it,” she wrote.
Ventura testified that “I would say that loving ‘Freak Offs’ were just words at that point.”
Defense is trying to paint the picture of a more complicated relationship between Combs and Ventura
In its cross-examination, the defense is trying to argue to the jury that Cassie Ventura and Sean “Diddy” Combs’ relationship was more complicated than what the prosecution painted it to be, a CNN reporter in the courtroom said.
Prosecutors, during their direct examination of Ventura, have alleged that Combs committed a “sex trafficking crime,” CNN correspondent Kara Scannell explained.
“Combs’ defense is that there there was domestic violence in this relationship, he’s not running away from it, but he says it wasn’t sex trafficking,” Scannell said.
The defense is arguing that many of the fights between Combs and Ventura came because of infidelity on both sides. In response to their questioning, Ventura testified that drug use made both of them irritable.
“That’s another way that the defense here is trying to create a more complicated scene than what the theory of the prosecution’s case is,” she said.
The defense also asked Ventura about if Combs’ staff knew about the “Freak Offs.” This goes to the racketeering charge against Combs, in which the prosecution alleges he was using his businesses and his enterprise to commit these crimes, Scannell said.
Ventura testified today that she didn’t tell Combs’ staff about the sexual encounters, but yesterday she detailed how some of Combs’ assistants and other personnel would help make arrangements for escorts and hotel rooms.
Cross-examination has resumed
The jury is back in the courtroom.
Defense attorney Anna Estevao is continuing her cross-examination of Cassie Ventura.
Judge says he wants to have Ventura off the stand tomorrow
Judge Arun Subramanian told the defense team they need to complete their cross-examination of Cassie Ventura before lunch tomorrow, but he left open the possibility of granting them additional time if needed.
He said he wants to have Ventura off the stand tomorrow.
“The direct took a day and a half, so the defense will have a day and a half. So you have today, you have the morning tomorrow,” Subramanian said.
“If there’s something that really needs to be done after the lunch break, then you can have some additional time at my discretion,” he added.
Defense attorney Marc Agnifilo said the defense is trying to streamline its questioning but stressed their belief that Ventura is the most important witness in the case.
“That is the cross-examination that is required of a critical witness in a trial that involves a life sentence,” he said.
The judge has returned to the bench
The judge is back on the bench.
The defense gave Cassie Ventura an iPad with exhibits it intends to question her about on cross-examination to review ahead of time in an effort to speed up proceedings.
The defense is questioning Cassie Ventura about her 11-year relationship with Combs. Catch up here
Cassie Ventura, the former girlfriend of Sean “Diddy” Combs and one of his accusers, faced cross-examination by the defense today about her turbulent relationship with the music mogul.
Ventura testified about falling in love with Combs and her involvement in his “Freak Offs,” as the defense showed the jury a slew of past messages between the pair.
Here’s what Ventura has said so far today, as court takes a break:
- Falling in love with Combs: Ventura confirmed she was in a relationship with Combs for 11 years and testified that she loved him and believed he loved her. Ventura said she fell in love with Combs’ “real personality.” Asked about her desire to make Combs happy and if that included agreeing to “Freak Offs,” which is what Combs called the drug-fueled sex performances he orchestrated, Ventura responded, “There’s a lot more to that.”
- Jury shown sexually graphic text messages: Some graphic texts reviewed by the jury came as Ventura and Combs were planning a “Freak Off.” Ventura also asked Combs if he had “any more pills” in texts shown by the defense. Ventura testified that she was using opiates like Norco around the time of the messages, and later said the two took various drugs together, including MDMA.
- More on “Freak Offs”: Jurors saw text messages from 2009 that Ventura confirmed reflected the “open communication” between the pair. She told the defense that at the time, she felt comfortable expressing her needs to Combs over participating. In the messages, Ventura said she needed to “feel safe” to be more open sexually. She told Combs a recent “Freak Off” left her feeling “dirty and grimy” and noted their early intimacy felt different when they were “so in love.” Ventura confirmed she and Combs had conversations about the “swingers’ lifestyle” but that “Freak Offs” were “very different.” Ventura testified that she did not want Combs’ employees to know about “Freak Offs” and she never told her friends about them.
- Combs’ behavior: Ventura confirmed her previous testimony that Combs would regularly call her incessantly if she didn’t answer the phone or otherwise set him off. Ventura previously testified that Combs had strong opinions about her physical appearance and controlled what she wore.
- Previous relationship: Ventura testified that she met Combs through Ryan Leslie, a music producer she dated for about three years. Leslie was about 10 years old than her, Ventura said, meaning Combs was the second older man she’d dated at that point.
Editor’s note: If you or someone you know is struggling with intimate partner violence, there are resources available, including the National Domestic Violence Hotline. If you or someone you know is struggling with mental health, help is available. Dial or text 988 or visit 988lifeline.org for free and confidential support.
Combs was addicted to “success,” Ventura says
Cassie Ventura testified that Sean “Diddy” Combs was very busy successfully running his companies and managing his career during their relationship. She testified that he remained busy even when they were having frequent “Freak Offs,” consuming lots of substances, and recovering from those events.
Ventura confirmed that she believed Combs was an addict, and defense attorney Anna Estevao asked what he was addicted to.
“Success,” Ventura responded.
Estevao went on to ask what substances Combs was addicted to.
“I think it varied over the years,” Ventura answered, adding that at one point he was addicted to opiates.
She confirmed that Combs was more irritable and angry when he was withdrawing from opiates. Ventura testified that she was also addicted to opiates for a period.
She said they took various drugs together, and that Combs’ drugs of choice were ecstasy and MDMA. She said she didn’t believe he was ever addicted to those drugs, and that they were “party drugs,” in contrast to opiates, which they took more regularly.
Defense says it will try to finish Ventura’s cross-examination by tomorrow
Before breaking for lunch, the prosecution and defense had a discussion about timing.
Sean “Diddy” Combs’ lawyer Marc Agnifilo said defense attorney Anna Estevao is going to try to finish cross-examination of Cassie Ventura by the end of the day Friday.
Judge Arun Subramanian proposed how the defense team might streamline the questioning. Estevao said she has “many” exhibits to go through with Ventura.
Assistant US Attorney Emily Johnson said it’s always been planned that Ventura needs to be off the stand by the end of the day tomorrow.
Agnifilo flagged that the prosecutors opted not to call Ventura first.
Court is taking a lunch break
The jury is breaking for lunch now. Testimony is set to resume at 1 p.m. ET.
Ventura details the influence Combs had on her physical appearance
While she was being questioned by prosecutors, Cassie Ventura testified that Sean “Diddy” Combs had strong opinions about her physical appearance and controlled what she wore.
Ventura said during cross-examination that she would send him photos of her clothing.
“Do you believe that Mr. Combs has good taste?” defense attorney Anna Estevao asked.
“I think he does, yeah,” Ventura responded.
Estevao also asked Ventura if she thought Combs had an impact on fashion and culture. Ventura agreed he did.
Combs would call incessantly if she didn’t pick up her phone, Ventura says
Cassie Ventura confirmed her previous testimony that Sean “Diddy” Combs would frequently call her incessantly if she didn’t answer the phone.
She said there were “a million things” that could trigger this, and she gave an example of not telling him where she was.
Defense attorney Anna Estevao asked why she thought Combs was concerned about this.
“I think because he would assume I was cheating,” she testified, but added that he would call her for other reasons too.
Ventura says she didn’t want Combs’ staff to know about “Freak Offs”
Cassie Ventura testified that she didn’t remember any of Sean “Diddy” Combs’ employees walking in while they were having a “Freak Off,” and she said she never talked to any of his staff about them.
Ventura said she “definitely didn’t” want his employees to know about them.
Ventura said Combs’ assistants would often set up the hotel rooms before a “Freak Off,” and they would, at times, come in a hotel room while they were staying there. But, she added, she doesn’t have a specific recollection of a staff member in the room when she was actively in a “Freak Off” with Combs and an escort.
Ventura acknowledged that she never told her friends about the “Freak Offs.”
Ventura says she and Combs had conversations about the “swingers’ lifestyle”
Cassie Ventura confirmed that she and her then-boyfriend Sean “Diddy” Combs had conversations about the “swingers’ lifestyle,” and eventually she saw it in person at the sex clubs they went to.
Defense attorney Anna Estevao asked if the “Freak Offs” were related to the “swingers lifestyle.”
“Related in a sexual way, yeah,” Ventura said. “But they’re very different.”
Why the prosecution asked Ventura about her civil lawsuit against Combs before the defense could today
Cassie Ventura testified yesterday during her direct examination that she and Sean “Diddy” Combs agreed to settle the civil lawsuit she filed against the music mogul in 2023 for $20 million.
The defense just raised the subject again today, with attorney Anna Estevao asking Ventura if she thought it would be fair to say Combs’ career was ruined after the lawsuit became public. “I could understand that, yeah,” Ventura replied.
CNN legal analyst and former federal prosecutor Jennifer Rogers told CNN the prosecution would have seen this line of questioning coming, and there was a strategy behind bringing it up during direct examination yesterday, before the defense cross-examined Ventura.
“Prosecutors always do what we call ‘drawing the sting,’ so if you know there’s a good point for cross-examination, you always bring it out on direct so the jury isn’t surprised and they don’t think, ‘Oh, prosecutors didn’t tell us about this,’” Rogers said. “So you’re kind of signaling to the jury, ‘We know about this but we still believe our witness.’”
Rogers said that Ventura “told this story in her lawsuit; she got $20 million as a result of that story, that’s essentially the same story that she’s telling now, so what was her incentive in bringing it in the first place? That’s the bias point.”
“It’s a really good point for them,” Rogers said, adding she expects the defense to “hit it hard.”
Ventura alleged in her lawsuit that Combs raped her in 2018 and subjected her to years of repeated physical and other abuses over the course of their relationship, which Combs denied.
The civil suit is separate from Combs’ ongoing federal criminal trial.
Ventura more open than Combs about expressing her feelings in messages, she says
The jury next saw an email Cassie Ventura sent to Sean “Diddy” Combs in October 2007, a few weeks after her 21st birthday party.
Ventura testified that the email demonstrates open communication between her and Combs, but said it was “usually a one-way street.” She said that she would send messages being open about her feelings more often than he would.
In the email, Ventura wrote: “We’ve only really had one week of each other just together and I can say that it’s been the best and worst.”
She wrote about the things she liked about Combs and dreaming of “a beautiful future together.”
“Who knew I’d fall so fast?” she wrote.
She also wrote about some negative feelings she had about their relationship, and she indicated she felt that her friend may be better suited for Combs. “It’s hard for me to handle that,” she wrote.
“On the other hand you’re constantly weary of me… I’m sneaky. I never seem to make the right decisions to you. I’m a spoiled brat, I’m dramatic, disrespectful and for some reason, you just don’t trust me,” she wrote.
Ventura told Combs she needed to “feel safe,” text messages show
The jury viewed text messages between Cassie Ventura and Sean “Diddy” Combs from December 2009 that Ventura confirmed reflected the “open communication” between them.
She told defense attorney Anna Estevao that at the time, she felt comfortable expressing her needs to Combs over participating in “Freak Offs,” drug-fueled sexual performances orchestrated by Combs.
Ventura wrote in the 2009 message that she needed to “feel safe, like home” to be “more open with the things we do in bed.”
She continued: “The last time was a mistake but since has made me feel a little dirty and grimy as opposed to sexual and spontaneous. That’s the only reason why I go back and forth in my mind with wanting and not wanting to do it.”
Ventura wrote that “when we used to Freak Off when we were so in love, there were no questions asked,” but she did not feel that same level of love “anymore at least.”
Ventura testifies Combs was the second older man she dated
Cassie Ventura testified that she met Sean “Diddy” Combs through Ryan Leslie, a music producer that she dated for about three years beginning when she was 18 or 19.
Leslie was about 10 years old than her, Ventura said, meaning Combs was the second older man she’d dated at that point.
Ventura and Combs had a platonic relationship when she first signed to his company, Bad Boy Records, she confirmed. He supported her after a bad TV performance, and that meant a lot to her, she said.
Following her 21st birthday, Ventura said she wanted to join Combs on a trip to Miami, but she was still dating Leslie, so she testified she used a flyer for an event as an excuse to go on the trip.
Ventura gives more details about her 21st birthday
Cassie Ventura testified it was “fair to say” that she was a celebrity in her own right by the time she was 21 years old.
Sean “Diddy” Combs brought other celebrities to her 21st birthday party, which was held at a night club in Las Vegas, she said.
When defense attorney Anna Estevao asked Ventura how a 21-year-old could attract celebrity guests, Ventura said, “That was all him, I didn’t know them.”
Ventura testified during the prosecution’s direct-examination that she ran away when Combs kissed her for the first time at her 21st birthday party.
Ventura says she was using opiates around the time she sent text messages
The jury saw another message exchange between Sean “Diddy” Combs and Cassie Ventura from August 2009 where she talked about wanting more pills and deleting a video.
In the texts, Ventura asked Combs if he had “any more pills.” Ventura testified that she was using opiates like Norco around the time these messages were sent.
In the same text messages, Ventura also mentioned deleting a video, but she testified that she wasn’t sure what kind of video she was referring to in the messages and couldn’t be sure it was a “Freak Off” recording.
Defense attorney Anna Estevao asked if Ventura preferred to have “Freak Off” videos recorded on her devices. Ventura said, “I didn’t want them to be recorded at all.”
Jury shown sexually graphic text messages Combs and Ventura exchanged in 2009
The jury is seeing more sexually graphic text messages Cassie Ventura and Sean “Diddy” Combs exchanged in August 2009.
The messages are a continuation of texts that were shown before Ventura, who is being cross-examined by the defense team now, asked for a short break. Those texts came as they were planning a “Freak Off,” which is what Combs called the drug-fueled sex performances he orchestrated.
Ventura returns to the stand
Cassie Ventura is back on the stand where she’s under the defense’s cross-examination.
The scene inside the courtroom right now
During this break requested by Cassie Ventura, defense lawyer Karen Friedman Agniflio, who is married to Sean “Diddy” Combs’ lawyer Marc Agnifilo, is at a divider and conferring with five attorneys from the defense team. She is speaking the longest with Anna Estevao, who is doing the cross-examination.
Earlier, Combs gave a heart-shaped hand gesture to Karen Friedman Agniflio’s mother, who is seated beside her.
Combs is wearing a beige sweater, white collar and gray pants. His three sons and mother are in the courtroom this morning, and he tapped his chest when he made eye contact with them.
Ventura requests a break
Cassie Ventura has asked the judge for a quick break.
The jury has been viewing text messages between her and former boyfriend Sean “Diddy” Combs while they were dating.
Defense attorney asks Ventura about her desire to make Combs happy
Defense attorney Anna Estevao asked Cassie Ventura a series of questions about how she had earned Sean “Diddy” Combs’ trust and about how she wanted to make him happy.
“And to make him happy, you told him that you wanted to do ‘Freak Offs?’” Estevao asked, referring to the drug-fueled sex performances Combs arranged.
“There’s a lot more to that,” Ventura responded.
Ventura recalls what made her fall in love with Combs
Cassie Ventura testified that she fell in love with Sean “Diddy” Combs’ “real personality.”
Defense attorney Anna Estevao had asked Ventura what made her fall in love with Combs, prompting Ventura to say that she hadn’t “thought about it in a while.”
“The beginning of the relationship was really — we spoke about it already — it was really fast, fast-paced, scary but the more time I spent with him and got to know him, his real personality — at least what I thought was his real personality — and I liked what it was,” she explained.
When asked what about his personality she liked, Ventura said, in the beginning of their relationship, he was “very sweet” and “attentive.”
Ventura also described Combs as having “a charismatic big personality that everyone really loved.”
Ventura testifies she wanted more time and attention from Combs when they were dating
Cassie Ventura testified that she often wanted more time with Sean “Diddy” Combs while they were in a relationship.
The jury saw a message Ventura sent Combs in April 2010:
“I haven’t talked to you AT ALL, I know you can take 3 minutes out of your day to talk to me and you don’t even try. You’re in too much of a rush to get me off of the phone. That’s not being in a relationship with someone that you love and are in love with. I am really hurt by the way you deal with me, I don’t need your money, I need some attention. I am thankful, but I can pay for these things myself.”
Here are some of the text messages Ventura and Combs exchanged
The jury is being shown a series of text messages between Sean “Diddy” Combs and Cassie Ventura.
Ventura testified that one exchange was sent via Blackberry about two and a half years into their relationship. Some of that exchange read as follows:
Ventura: Going to sleep now so it can be tomorrow faster. I love you
Combs: love my baby
Ventura: 🙂
Combs: I love you so much it consumes my life…
Ventura: I wonder the same thing for myself like who was I before we decided to be together
Combs: I never knew it could be like this
The jury also saw texts from August 2009, in which Combs told Ventura “I love you sooooo much it makes me cry.” In that exchange, Ventura called Combs “Pop Pop.”
Earlier this week, Ventura testified that she called Combs “Pop Pop,” which was the name she called her grandfather.
Jury sees emails between Combs and Ventura
The jury saw emails between Sean “Diddy” Combs and Cassie Ventura from January 2008.
Ventura read the emails aloud on the witness stand.
Combs said, “It makes me so happy that you would fly to ATL just to see me. I’m a very lucky man, I love you, I miss you, can’t wait to hold you.”
Ventura responded, “I’m a very lucky woman. I miss you so much. I’d fly wherever you needed me, whenever. I love you.”
Ventura testified that early on in their relationship around this time, she and Combs would often send each other loving messages.
Ventura says she felt hurt more at the beginning of their relationship when Combs cheated
Cassie Ventura confirmed that she was with Sean “Diddy” Combs for 11 years despite his flaws because she believed he truly loved her.
“So when he cheated on you, it really hurt?” Estevao asked.
“I would say not every time,” Ventura said, adding that she spent more time feeling hurt in the early stages of their relationship.
Ventura confirms she knew a version of Combs other people didn’t see
Defense attorney Anna Estevao asked Cassie Ventura if she remembered calling Sean “Diddy” Combs “larger than life” during her testimony. Ventura confirmed she did.
“But to you, he was Sean” and “you knew the Sean that other people didn’t see?” Estevao asked. Ventura confirmed.
Estevao asked if Ventura always knew that she was special to Combs.
“No, I don’t think I always knew,” Ventura responded.
“You sometimes knew?” Estevao said.
“Sometimes is fair,” Ventura replied.
Ventura’s voice was soft — almost a whisper — as she answered these questions.
Defense asks Ventura if she and Combs were in love during their relationship
Defense attorney Anna Estevao began her cross-examination of Cassie Ventura by asking about the couple’s love during their relationship.
Estevao asked: “You and Sean Combs were in love for 11 years right?” to which Ventura responded, “Yea.”
Estevao: “You loved him?”
Ventura: “I did.”
Estevao: “And you believe that he loved you as well?”
Ventura: “Yes.”
Jury enters the courtroom
Defense attorney Anna Estevao will be cross-examining Cassie Ventura for the defense.
The jury is now entering the courtroom.
Combs’ family arrives at court
Members of Sean “Diddy” Combs’ family, including his sons and mother, have arrived at the courthouse in Manhattan.
Combs is already inside the courtroom.
His twin daughters Jessie and D’Lila Combs were traveling yesterday for their high school prom in the Los Angeles area this weekend, according to a source close to the family.
Cassie Ventura’s husband Alex Fine is also in the room.
Attorneys are still debating
Attorneys are still debating evidentiary issues about exhibits the defense wants to show the jury during Cassie Ventura’s cross-examination.
Defense says it wants to use “colorful” text messages during cross-examination
Prosecutors and defense attorneys are arguing again about what text messages the defense can show the jury during cross-examination of Cassie Ventura.
The defense says it wants to use some “colorful” text messages between Ventura and Sean “Diddy” Combs from points in their relationship when Combs thought Ventura was seeing other people.
The judge is on the bench
Judge Arun Subramanian is on the bench ahead of day four of Sean “Diddy” Combs’ federal sex trafficking trial.
The prosecution and defense will discuss a text message issue before the cross-examination of Cassie Ventura begins about 9:30 a.m. ET.
The jury is not in yet.
What to expect in court today
This morning, Cassie Ventura — the former girlfriend of Sean “Diddy” Combs and key witness in the case against him — will be cross-examined by the defense.
She has already spent nine hours on the stand providing her testimony, and she now will face questions from attorneys representing Combs. Defense attorney Anna Estevao said she expects cross-examination to stretch into Friday.
While talking about what exhibits the defense might submit into evidence yesterday, Teny Geragos — a criminal defense attorney representing Combs — said Ventura’s direct examination went differently than what was expected and the legal team would adjust their strategy accordingly. It followed the jury seeing photos of Ventura’s injuries and hearing her say Combs attempted to blackmail her by threatening to release videos of “Freak Offs.”
Combs’ defense is that the “Freak Offs” were consensual sex acts and the physical violence between Combs and Ventura went both ways driven in part by infidelity.
Here’s what a legal analyst told CNN about the possible strategy adjustment.
8:06 a.m. EDT, May 15, 2025
Here’s a recap of Cassie Ventura’s second day on the stand
During her testimony yesterday, Cassie Ventura revealed, in detail, numerous occasions that her relationship with Sean “Diddy” Combs became physically violent.
At one point, Ventura broke down in tears as she talked about going to rehab and trauma therapy in February 2023. She said she was having flashbacks during a shooting for a music video with another artist. She also said she was suicidal.
Here are details of Ventura testimony during her direct examination yesterday:
- Details of a violent relationship: Ventura testified that the first instance of violence with Combs left her “shocked” and further described multiple violent encounters with him — including being beaten after a party at a Los Angeles club, Combs’ security chasing her when she attempted to escape, and a 2018 encounter where she said Combs raped her in her living room. Ventura said she felt trapped, citing Combs’ access to guns and past threats and that Combs continued to threaten her after their relationship ended.
- Violent behavior toward others: Ventura said she also witnessed Combs become physically violent with other people, including some of his employees. She said she recounted a time she saw Combs punch someone in the head. Ventura also described seeing Combs hold her friend over the balcony railing at her Los Angeles apartment early one morning. Ventura later said an altercation with Combs led to the end of a 17-year friendship with her best friend in 2018.
- Kid Cudi relationship: Ventura said Combs lunged at her with a wine opener after learning she was dating rapper Kid Cudi during a “Freak Off” in 2011. Combs told Ventura that Kid Cudi’s car would be blown up, she testified. Ventura alleged in her civil claim that it was “around that time, Kid Cudi’s car exploded in his driveway.”
- Witnesses to violence: Ventura testified that early on in their relationship, Combs’ security personnel and driver saw him physically abuse her. In later years, she said assistants, including one named “Mia,” witnessed the abuse Ventura endured and some assistants told her they quit after witnessing the violence.
- Ventura sought help for her drug use: Ventura said she was ”heavily dependent on opiates” throughout her relationship with Combs. She said she sought professional help for the opiate use five or six times during the span of the relationship. She said she last did drugs in 2022 and she no longer uses narcotics.
- Lawsuit settlement: Ventura said she received a $20 million settlement after filing a civil suit in November 2023.
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