Crime Fix with Angenette Levy - 11 Shocking Moments in Cassie's Emotional P. Diddy Trial Testimony

Episode Date: May 19, 2025

Sean "Diddy" Combs' legal team chose attorney Anna Estevao to cross-examine Casandra "Cassie" Ventura about her relationship with Combs and the "freak offs" the two arranged with male escorts. Estevao grilled Ventura about emails and text messages she exchanged with Combs, her willingness to participate in "freak offs", her claim that Combs raped her and a recording of her threatening to kill someone who claimed to have seen a video of a "freak off." Law&Crime's Angenette Levy goes through the details with criminologist Dr. Meghan Sacks in this episode of Crime Fix — a daily show covering the biggest stories in crime.PLEASE SUPPORT THE SHOW: If you received Depo-Provera birth control shots and were later diagnosed with a brain or spinal tumor called meningioma, you may be eligible for a lawsuit. Visit https://forthepeople.com/lcdepo to start a claim now!Host:Angenette Levy  https://twitter.com/Angenette5Guest: Dr. Meghan Sacks https://www.youtube.com/@WomenandCrimeProducer:Jordan ChaconCRIME FIX PRODUCTION:Head of Social Media, YouTube - Bobby SzokeSocial Media Management - Vanessa BeinVideo Editing - Daniel CamachoGuest Booking - Alyssa Fisher & Diane KayeSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can binge all episodes of this law and crimes series ad-free right now. Join Wondery Plus in the Wondery app, Apple Podcasts, or Spotify. Cross-examining Cassie, Sean Diddy Combs' lawyers went at Cassie Ventura with the couple's text messages about freak-offs, their love for one another, and threats of murder as Combs casts the violence and freak-offs as domestic violence and consensual sex, not sex trafficking. I go over the grilling of Cassie Ventura in Combs' trial and whether Combs' team got their job done. Welcome to Crime Fix. I'm Anjanette Levy. Cassie Ventura is the government's star witness in its

sex trafficking in Rico case against Sean Diddy Combs. Ventura, whose stage name is Cassie, was on the stand for four days in the Southern District of New York as the federal government works to prove that Sean Combs used his companies to commit a number of crimes and that Cassie Ventura and other women were sex trafficked by Sean Combs to meet his sexual desires and fantasies. Combs, for his part, says any sex the women had with male escorts that he hired was consensual. The freak-offs were sometimes days-long, drug-fueled sex encounters where Ventura and other sexual partners of Sean Combs had sex with these male sex workers as Combs watched and sometimes masturbated. The encounters were often videotaped, and Combs kept those tapes, according to federal prosecutors. Cassie Ventura testified that she and Combs were together for 11 years, and there's a 17-year age difference

between the two of them. Cassie was also one of his recording artists. Now, at first, she said she was open to these freak-offs, but later, she said she felt she had no choice in taking part in them. A centerpiece of the government's case, of course, is that 2016 video of Combs chasing Ventura out of a hotel room in Los Angeles, hitting her and kicking her as she tried to leave. Ventura also testified that she felt forced to take part in the freak-offs, even when she was suffering from urinary tract infections, some she would get so often that antibiotics wouldn't even work to treat them any longer. On direct examination, Assistant U.S. Attorney Emily Johnson asked Ventura about that civil lawsuit that she filed against Sean Combs,

which really started this entire federal investigation into the rap mogul. It was settled within a day. Ventura said she agreed to drop the suit in exchange for $20 million. Combs' team will say this is largely about money and there was no sex trafficking. Attorney Ana Estiveo was chosen to cross-examine Ventura, so let's get right into it. Estiveo started by asking, you and Sean Combs were in love for 11 years, right? Cassie responded, yeah. Estiveo continued, during that time you loved him. Cassie responded, I did, yes. Estiveo asked, and you believed that he loved you as well. Cassie responded, yes.

Estiveo then went on to ask, and during those 11 years, you took care of him. Cassie responded, in the ways I could, yes. Estiveo asked, and you believed that he needed someone to take care of him. Cassie responded, I don't know. Estiveo followed up and you believed that he needed someone to take care of him. Cassie responded, I don't know. Estiveo followed up, in some ways? Cassie answered, in some ways, I guess, yeah. Estiveo then got Cassie Ventura to admit that she left Combs, but always returned to him. Estiveo asked, you said on direct that you were very jealous.

I think insanely jealous is the phrase you used. Cassie responded, I did. Estiveo asked, and he gave you a lot to be jealous of, right? Cassie responded, I mean, it's all relative, yeah. Estiveo asked, but for 11 years you put up with that jealousy, right? Cassie responded, not the whole time, no. Estiveo asked, you were on and off during the relationship, but you kept coming back to him for 11 years. I wouldn't use the word coming back. You would continue to get back together with him for 11 years. Cassie responded, yes.

Estiveo then asked, despite his imperfections, maybe not strong enough. Cassie responded, yes. Estiveo said, his flaws, right? Cassie responded, yes. Thisiveo said, his flaws, right? Cassie responded, yes. This is another law and crime legal alert. If you receive Depo-Provera birth control shots and were later diagnosed with a brain or spinal tumor called meningioma, you may be eligible to take part in a lawsuit. Morgan & Morgan is investigating claims that patients were not properly warned about this risk. It's free to check, takes just a few minutes, and you don't pay unless Morgan & Morgan wins. So scan the QR code on your screen, click the link below, or go to ForThePeople.com

slash LC Depo to see if you qualify. Estiveo also had Ventura read from emails and text messages that showed Combs and Ventura appeared to love one another. Estiveo asked, can you read the second message from the top out loud, Miss Ventura? This is from Mr. Combs to you. Cassie responded, you want me to read it out loud? Estiveo says, yes, just the text of the message itself. Cassie responded, it makes me so happy that you would fly to ATL just to see me. I'm truly a lucky man. I love you. Missing you. Can't wait to hold you. Cassie responded, Estaveo then asked, Cassie responded,

Estaveo responded, thank you. There were other emails, some from 2009, in which Sean Combs called Ventura BG, which she said stands for baby girl. Ventura read from the message, going to sleep now so it can be tomorrow faster and you can be home. I love you. Then Estiveo read Combs' part. Love my baby. Ventura responded, smiley face. Estiveo then read Combs' part again. I love you so much. It consumes my life. How did that happen? Cassie responded, I don't know. I wonder the same thing for myself all of the time. Like who was I before we decided to be together? Combs' part, I never knew it could be like this. How do you have me this way? Cassie responded, LOL, what do you mean? I'm so happy that we fell in love.

Combs' part, we are so in love, we don't do anything else. Now, Anna Estiveo is trying to show with all of these messages that Cassie Ventura loved Sean Combs, that they loved one another, and that she wanted his attention. She asked Ventura to read a message from 2010. Ventura loved Sean Combs that they loved one another and that she wanted his attention. She asked Ventura to read a message from 2010. Ventura stated, So you hung up. It's like I need to have something written out to say to you with no breathing room or you'll get mad at me and hang up. I haven't talked to you at all. I know you can take three 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 the phone. That's not being in a relationship with somebody that you love and are in love with. I'm 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. Estiveo asked, I believe you testified on direct examination that you frequently wanted more time with Mr. Combs, right? Cassie responded, yes. Estiveo then asked, and it was important to you to get your special time with him? Cassie responded, yeah. Ventura said she loved Combs because he was sweet and attentive. Estiveo confirmed that Ventura once told Combs that he made her a better woman, daughter, and person. Then the testimony turned to the freak-offs. The defense says Ventura was a willing participant in the freak offs, not a sex trafficking victim. Estiveo read from a text from Combs where he said to Ventura, you tell me the day you choose. Ventura responded, it can be whenever. Combs responded, name the

night. Ventura responded, I feel like the weekend, like a Friday night would be best because we'd want some time to recover for work or the work week, right? This upcoming weekend, the 8th, is the only one I have until the 28th. Estiveo responded, okay, I'm on it. That was Combs' part. Then Estiveo pivots using some of Cassie's own words against her regarding that March 2016 incident at the Intercontinental Hotel in Los Angeles. Estiveo quotes Cassie Ventura, you say, baby, I want to F-O so bad, but don't want to F myself up. What am I to do, right? Ventura responded, yup. Estiveo then asks, when asked why you sent this message,

you testified, I definitely didn't want to mess myself up, mess up my body for my premiere by partying, but I was telling him that I wanted to have a FO with him. That's what you testified to, right? Cassie responded, right. Estiveo then said, you said that it was a bit of damage control ahead. I personally felt like if I sort of initiated go along with creating this, then my premiere wouldn't be ruined, right? Cassie responded, yup. Estiveo then asked, so you testified you were trying to get ahead of it in a way, right? Cassie then responded, yes.

Estiveo then said, you said he would have just made it miserable for me. I never really had like the chance to or opportunity to enjoy the things that I'd worked really hard on. So it just felt like I was just what you're trying to play a balancing act a bit, right? That's how you testified about this message? Ventura responded, yes. But ultimately, it was Cassie who set up that freak-off that she was later punished for trying to escape. Estiveo asks, And then what do you say?

Ventura responds, So let's do it. Can you set it up, though, so I can just run home and grab stuff? Estiveo says, And then he says, Start at 7 or 8 o'clock and end at 4 a.m. at the latest. Take a Xanax and or Ambien and go to sleep. We'll be okay. And you rest tomorrow and all day Sunday. You'll be good and drink a lot of water. We'll be good.

But we won't have hours to be caught in a matrix. If we do it, I want you to call Garen and see what he has so he can really be a turn-on. But if we're going to do something, the sooner the better. Did I read that right? Toward the end of that line of questioning, Estiveo tries to get Cassie to admit the batch of drugs that night that they were using was among a bad batch. Estiveo asks,

the drugs that you and Mr. Combs took that day were a bad batch of MDMA, right? Emily Johnson, the assistant US attorneyS. attorney, then objects. The court overrules the objection. Estiveo asks, they were a bad batch, right? Cassie responds, I have no idea. I don't know. Anna Estiveo asked Cassie Ventura about her meeting up with Sean Combs on September 27,

2018, after they had broken up. Estiveo refreshed Ventura's recollection that she had indeed seen Sean Combs that day. By that point, Ventura was dating her current husband, Alex Fine. Ventura confirmed that she and Combs had sex, and this is the defense trying to show that Ventura was not being held hostage by Sean Combs and sex trafficked against her will.

Estiveo asks, and that night when you were having intercourse with him, did you receive a FaceTime call? Ventura says, I did. Estiveo responds, and did you answer that call? Cassie Ventura responds, no. Estiveo asks, did you recognize the caller ID to be your now husband? Cassie Ventura responds, I did. Estiveo asks, and Mr. Combs noticed this call, right? Cassie Ventura says, yep. And Estiveo asks, and he noticed the name that was, or the alias that was popping up on your phone, right? Ventura responds, yep. Estiveo asks, and this was in the middle of your evening with Mr. Combs? Cassie Ventura responds, correct. The questioning about this

night continued, with Estiveo appearing to imply that Ventura may have made up a claim that Sean Combs raped her when she told Alex Fine that she had sex with Combs that night. Estiveo asked Ventura, you told your now husband that Mr. Combs raped you, didn't you? Ventura responded, I did. Estiveo responds, that evening, right? Ventura says, that evening? Estiveo says, in September. Ventura responds, no, that wasn't the evening when I was raped. Estiveo asks, your husband punched a wall at a certain point, right? Ventura responded, he did. After an objection, the questioning continued. Estiveo asked, when you informed him that Mr. Combs raped you, correct? Ventura responded, yes, I think. I don't remember exactly when that was. Estiveo asks, your husband learned of your sexual intercourse with Mr. Combs, right?

Ventura responded, right. Estiveo asks, and you told him that Mr. Combs raped you, right? Ventura responded, right. Estiveo asked, and you told him that Mr. Combs raped you, right? Ventura responded, right. Estiveo asked, and when your now husband learned about it, he punched a wall, right? Ventura responded, I believe so. Estiveo also seemed to question Ventura's memory of the date when the rape by Combs took place. Then she turned to other text messages that showed Ventura continued to talk with Combs. Estiveo asked, and after your breakup, you're telling him that you feel lost without him, right? Cassie Ventura says, yep. Estiveo asked, and after your dinner in September, you don't see him for a number of

weeks, correct? Ventura responded, correct. Estiveo asks, and that's because you had broken up with him, right? Ventura responded, yeah. Estiveo asks, a month after this, on November 15th, 2018, Kim Porter passed away unexpectedly. Isn't that right? Ventura responded, yup, it is. Estiveo responds, and you went to the memorial service for Miss Porter, correct? Ventura responded, yup, I went. Ventura said she went to the memorial for Kim Porter that was held in Georgia. Estiveo read from a message Combs sent to Ventura said she went to the memorial for Kim Porter that was held in Georgia. Estiveo read from a message Combs sent to Ventura in 2020, and part of it read, I pray for a day that I can sit down with you and let you know all the things that I've reflected

on. You were there for me throughout everything. You were my ride or die, and I've got nothing but love for you always. My heart is filled with joy to know that you don't hate me, and I hope you're taking care of you also. I thank God for the time that we had together, and you're one of the greatest women in the world, and don't ever forget that. Love. Ms. Ventura, you were also friends with Mr. Combs throughout your relationship, right? Ventura responded, right. Estiveo then asked, you didn't only consider yourselves romantic partners, correct? Ventura responded, correct. Estiveo confirmed with Ventura that in the fall of 2023, she was planning to go on tour,

but then after settling her civil suit with Combs for $20 million, she canceled the tour. Estiveo also played a recording of Ventura threatening a man who claimed he saw a video of her in a freak-off. Ventura said in the recording, you're lying about my effing life. I want to kill you, cut you up, and put you in the effing dirt. On Redirect, Assistant U.S. Attorney Emily Johnson asked Cassie Ventura whether there were times throughout her relationship with Sean Combs in which he was loving toward her, and she said there were times, but that those times never lasted. They also discussed the freak-offs again. Johnson asked, how did Sean's moods affect your career?

Ventura responded, it depended on if he was in the mood to have a freak-off. My work would take the back seat, so that would be my career not being paid attention to because I had to do other things. Johnson asked, what other things did you have to do? Ventura responded, I had to do other things. Johnson asked, what other things did you have to do? Ventura responded, I had to do the freak-offs. Johnson asked, and what kind of preparation did freak-offs entail? Ventura responded, a lot. Me getting myself ready, head to toe, getting a room ready, setting up entertainment, yeah. Johnson asked, when you say setting up entertainment, what are you referring to? Cassie said, to escorts. Johnson also asked Ventura about how Combs' moods impacted how she felt about herself. Ventura said Combs' lifestyle was chaotic and she sought his approval. When asked, she said she wanted to have sex with

only Combs, not other men. Ventura also said that Combs expected her to send him messages pretty much constantly to keep him sexually excited. She said the amount of music she put out once she started dating Combs changed because she had to focus her attention on him and he was in charge. When Ventura said her music career suffered because she had another job as a sex worker for Combs, the defense objected and moved to strike the answer. The judge granted the motion to strike the sex worker answer. Johnson then continued, how many times did Sean insist you have a freak off when you still had a UTI? Cassie Ventura responded, all the time, frequently. Johnson asked, and did Sean beat you during freak offs? Cassie Ventura said yes. Johnson asked, once or more than once? Ventura responded, more than once.

Johnson asked, how did you feel during the freak-offs when Sean beat you? Ventura responded, worthless, just like dirt, like I didn't matter to him, but that I was nothing, like absolutely nothing. Ventura went on to say that she didn't want to do the freak-offs anymore, but felt she couldn't say no. So I want to bring in Dr. Megan Sachs. She's a criminologist and also the co-host of the Women in Crime podcast. Dr. Sachs, I want to know, what is your gut reaction, your first reaction upon reading about the cross-examination of Cassie Ventura? Did the defense do what they needed to do to impeach her or to

make her look like somebody who was obliging in this? She's not a sex trafficking victim. She's just somebody maybe who had some regrets. That's a really good question. The defense, I first want to say, had a tough job here. And I think they probably knew this was going to be especially difficult. Cassie is almost nine months pregnant. So they have to cross-examine a woman who's in a delicate state. They can't look like they're attacking a pregnant woman. And nobody wants to see that, right? Nobody wants to feel that kind of attack. So they had a balance here. And look, they used what they had.

They pointed out text messages in which you can see Cassie is loving and she expresses her affections for Sean Combs. She also does express in the text messages seemingly at times a willingness to participate in these freak-offs, as they're called. And I'm saying seemingly, and what seems via text is not always what is. I think that one of the things they probably didn't do i think they were trying to um diminish her credibility with claims of her false timelines and um when she said that she had suffered a forcible rape at the hands of sean combs i think they tried to trip her up well didn't you say this actually happened at a different time and and so i think they were trying to take away from her credibility i don't think they did that i don't think they diminished her credibility um but what they may have done was you know show somewhat of what or what the jury

might perceive as um a willingness to participate and that's only in the mind of the jurors, but that might have been part of what they did. The forcible rape, let's go back to that part of this, because it's interesting they're going there. And that to me, the government will say, this is part of Sean Combs treating her basically like property and like a sex worker. And when, when they tried to, when Cassie said in her, um, redirect that she basically had this other job, you know, she wasn't his girlfriend and his, uh, you know, recording artists. She was a sex worker. The defense objected the, the judge struck that answer from the from the record. So he told the jury to disregard that, which I found very interesting.

But they're trying to establish that Sean Combs viewed her as basically property, as like almost like somebody who is there for his pleasing. The defense did try to say not only did she have the timeline wrong, but I think that they're trying to imply that maybe she made it up or was trying to turn a consensual sex encounter into forcible rape because she wanted to tell her now husband, Alex Fine, that so that he would be more understanding of her having sex with Sean Combs while they were dating. Did you kind of get that from that exchange as well? I absolutely got that. I absolutely believe they were trying to demonstrate that this was a consensual relationship or a consensual encounter. Their question about didn't you have a consensual relationship or didn't you have a consensual encounter. Their question about didn't you have a consensual relationship or didn't you

have a consensual sexual encounter after this forcible rape was meant to undermine the allegations that this was anything but consensual because Cassie says, yes, there was a consensual sexual encounter afterwards. So I think the defense is saying, well, wait a second, if someone was sexually assaulted, would they really go back and have another consensual encounter with the same person? That simply doesn't make sense. They also followed up with, well, surely in your next round of messages with him, you would have then said, I cannot believe you assaulted me, or how could you have raped me? Did you not say this? And she says, no, I didn't say that. So yes, I cannot believe you assaulted me or how could you have raped me? Did you not say this? And she says, no, I didn't say that. So yes, I think they are very clearly trying to show

that this encounter was consensual and that perhaps Cassie just could not tell her then boyfriend and now husband this. I think that was the goal. That's what I got completely. These relationships, I mean, obviously she was with Sean Combs for 11 years. That's a really long time. There's this huge age difference. She said she wanted to please him in more ways than one. Obviously she said she loved him, but then there's this whole messiness too, about she got mad because he put on after Kim Porter passed away, he put on Instagram or Twitter or something that she was my soulmate. And that really upset Cassie. And she went to the memorial service in Georgia and then she left and then she never saw him again. I mean, there is some I mean, obviously, the defense had some fodder here for cross-examination.

And then she you know, the stuff about the civil suit and her, you know, writing the book and then going and filing this suit for 20 million dollars. Or she filed the suit and then settled it for 20 million dollars within a day. I'm sorry. So they did have some fodder here for cross-examination. They did. I want to say something about victims and about offenders and something I say in my classes a lot. Most victims are imperfect and most offenders are not monsters. So things are not going to be neat and clean like everyone wants them to be. Cassie is not, you know, a perfect victim in in the regards that we want. Our society kind of loves to see a perfect victim. She's a human being with emotions. She was really, if you look at it, under the control or at least in this power dynamic where she didn't have power. But, you know, she did love Sean Combs. She was in this relationship.

She's trying to normalize things that happen as well. And that's very common for victims in long-term abusive situations to try to normalize it. Well, he loves me. I love him. We're in a relationship to fear losing him. There was a lot of her identity tied to him. And as she becomes, you know, as he becomes more powerful too, she loses power in the relationship. And so there's a panic, you know, there's something she's grasping onto. And I think people should realize

that this is not a clear cut situation of how victims will behave in these relationships. And remember, he may be an offender, possibly, allegedly, but he's not a complete monster. There are moments of love and tenderness and happy times in the relationship, and he treated her at some times well. So this is not an easy straight line. Now, in terms of the book and the money,

that I do think is, you know, it's a smart defense tactic. They established with Cassie that she wasn't really, she didn't have that much source of an income before. You know, what was she kind of doing with, in terms of income? How was she being supported? Wasn't she supporting her family? Maybe her husband didn't draw a huge income. And then all of a sudden her money problems disappear with a $20 million settlement from Sean Combs. That's what they were trying to show that there was a financial motivation here. Whether or not that impacted the jury, you know, we can't say for sure now, but certainly they did their job and everyone knew

they were going to bring that into this equation. Yeah. It'll be interesting to see how, how it works out. I mean, in fairness, you know, Cassie held her own. I think she answered that. I mean, I think her answers were very genuine and, you know, she could only explain it like, yes, she got a settlement, but it wasn't about the money. It didn't guide her decisions. As I understand it, her testimony was quite credible, at times vulnerable. Of course, there were moments where I'm sure she was embarrassed. There were moments of tears. I don't know that the issue here will come down to her credibility or will it come down to what the jury understands? Can they differentiate? Can they see the difference between domestic violence and sexual trafficking? I don't know if they can also, sex trafficking is incredibly complicated

and it's kind of new in its evolution. Just as of 10 years ago, we were still treating trafficking victims as sex workers. And I still, that mindset still kind of permeates. So will they be able to get past some of these older notions? I think maybe that becomes more of a central question here. And will they again, will they see this as trafficking or will they see this as this guy is kind of vile? He's definitely abusive. He's definitely violent. And he's actually he's sexually deviant by most standards. But is that trafficking? And I think that's going to become the central question. I think that's an excellent point. Excellent point. Thank you so much, Dr. Megan Sachs. I appreciate it. Oh, sure. Thanks for having me. And that's it for this episode of Crime Fix. I'm Anjanette Levy. Thanks so much for being with me. I'll see you back here next time.