“The Trial Of Sean Combs” Episode Eight | Diddy’s Defense Grills Cassie

0:10 Get ready to dive deep into one of the most gripping legal battles of our time. I'm your host, Jim Chapman, and today we're unraveling the high stakes drama surrounding one of the music industry's most enematic figures, Sean Diddy Combs, in a case that has captivated millions. The courtroom has become a battleground for fame, fortune, in the dark secrets that lurk beneath the glittering surface of celebrity life. As the gavel comes down, we'll explore the allegations, the testimonies, and the shocking twists that could change the course of Diddy's legacy forever. Was this case merely a clash of lifestyles or something much more sinister? With each episode, I will bring you exclusive insights, analysis, and witness testimony accounts that will leave you on the edge of your seat.

1:23 So buckle up as we embark on this thrilling ride through the trial of the century, where the stakes are high, the drama is real, and the truth is anything but certain. This is the Trial of Sean Combs. Let's get started, and this is the third day of testimony. Four Cassi Ventura. The prosecution wrapped up the direct examination of Cassie yesterday May fourteenth, and as I'm recording this on May fifteenth, the defense has their shot at Cassie during cross examination.

2:14 Very highly anticipated aspect of the trial taking place today. Cassie entered the courtroom at eight point fifty am and she took her place at the witness box. She's wearing a double breasted black suit jacket and that is over. A light colored shirt. And Combe's defense attorney Anna Festivo will be handling the cross examination for the defense. And I want to say this right off the bat, I knew the strategy would come into play. There would be no way a man was going to cross examine Cassie for the defense. Think about how that would come off to the jury, considering what she's been through with a particular man named Diddy in Another strategy deployed by the defense was that they requested the judge grant their request to have Cassie seated in that jury box prior to the jury coming into the courtroom. This is the first time that's occurred now.

3:15 That was due to the fact that she was pregnant, no doubt, and they didn't want the jury to garner sympathy for her because she's pregnant now. And I don't get why they would want to do that, but I mean, come on, for two days now, she's been walking in there pregnant. The jury has been seeing her walk in You're not hiding anything from them. I mean, she's obviously pregnant. And let me tell you a little bit about the defense attorney Anna Estivo. She's known for handling white collar crimes. She's not necessarily used to handling crimes of this level, criminal charges of this level, I should say. And a Steve O opens her cross examination of Ventura with this question, quote, you and Sean Combs were in love for eleven years, right?

4:04 And Cassie replied yes, Steve, and then said you loved him, And Cassie said I did. And as STEVO said, and you believe that he loved you as well? And Cassie said yes. And Steve O asked Cassie if she remembered calling Sean Combe's quote larger than life during her testimony, and Ventur confirmed she remembered doing that. Then, as Steve O says, but to you, he was Seawan and you knew the sean that other people didn't see, and Ventura confirmed that. And what she doing here, She's getting Cassie to say yes over and over and over again, trying to mentally make her agreeable. Steva then asked Ventur if she always knew that she was special to Combs, and Ventura responds, no, I don't think I always knew, And as Steve O says, you sometimes knew, Inventur replied, hmmm, sometimes it's fair. And Ventur's voice at this point in the trial very soft, almost a whisper, as she answers these questions. And as Steve Ovin says, so when he cheated on you, it really hurt, right, And Ventur responded with I would say not every time, and she added that she spent more time feeling hurt in the early stages of the relationship. The Journey then gets shown some emails from early on in the relationship between Cassie and Cones,

5:37 and she had Cassie read those emails out loud, and Cassie read them and it's quote, it makes me so happy that you would fly to with Lana just to see me. I'm a very lucky man. I love you, I miss you. Can't wait to hold you. Obviously come saying that to Cassie. In Ventur responded in that email, I'm a very lucky woman. I miss you so much. I'd fly wherever you needed me whenever. I love you. Ventura then testified that early in their relationship, around this time, she and Combs would often send each other loving messages. Then the jury shown some other text messages from around the same time period. Ventura says, going to sleep now so it can be tomorrow faster.

6:23 I love you. Combs responds, love my baby, and then Ventura sends a smiley face emulgy and comb says I love you so much it consumes my life, and Ventura says I wonder the same thing for myself, like who was I before we decided to be together, and Combe says I never knew it could be like this, And obviously they're trying to paint a picture of a loving relationship right. The jury also saw texts from two thousand and nine in which Combs told Ventura, quote, I love you so much and may makes me cry, and in that exchange, Ventura responds with love you.

7:05 Pop Pop, which we. Now know was the name of our grandfather. And some freaky thing only known to Sean Combs. He wanted her to call him that as well. Steve then asked Cassie why she fell in love with Combs, and Ventura described the beginning. Of the relationship. She said, when she was nineteen, he was in his mid thirties. It was fast paced and scary, but she said, his real personality, or at least what she thought was his real personality, that came out, and she said, I liked who he was. She said Combs early on was sweet and attentive. So the defense they've spent at this point, like a half hour establishing this love connection, if you will, between Cassie and Diddy. And then the defense presents a message to the jury from cas too Diddy. This is in twenty ten, and it stated, quote, 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 someone that you love and are in love with. I'm really hurt by the way that you deal with me. I don't need your money, I need attention. I am thankful, but I can pay for these things myself. The defense asked Cassie at that point what she meant by all that, and Cassie said she

8:36 often wanted to spend more time with Sean Combes while they were in a relationship. The defense attorney then says, so to make him happy, you told him that you wanted to do freak offs. Right. Cassie replied, No, There's a lot more to that, and it's at this point the defense emits some messages into evidence from Cassie to Ditty from two thousand and nine, in which Cassie and Diddy were discussing a potential freak off with an escort named Jules who he's come up again and again during this trial, right, Cassie said in one of the messages, quote, I'm always ready to freak off, laugh out loud, unquote. And obviously it's the goal of the defense to establish there was nothing coercive about freakoffs between Shawn Combs and Cassandra Ventura. They want to make sure that during today's testimony they paint her as a willing participant who was not coerced in any way. Cassandra Ventura then whispers to the judge and he calls a ten minute break. Now, during this break, Seawan Combes. He's sitting between his lawyers. He's wearing a sand colored sweater and a collared shirt, and he has been really more fidgety today than he was the last two days. He's leaning back and forth in his chair, and he continuously, it seems like, take his black framed glasses.

10:05 On and off. And during the break, Combs hands a note to his lawyer that was leading the cross examination of Cassie Comb's sons. At this time, they're in the courtroom, three sons and his mother, Janis Combs all in that spectator's gallery. And after that break, Cassie returns to the witness box. She's clutching what appears to be a chain of beads and it has a tassel on the end, and she's watching the jurors as they file back into the courtroom after that break, and at that point, the defense picks up again with these sexually explicit messages that Cassie, in showing Comb's would text back and forth in anticipation of a freak off. In two thousand and nine, Combs wrote her quote, I can't wait, and she replied I can't wait either.

10:56 The jury then saw another message exchange between Diddy and Cassie, and this was in August of two thousand and nine where she talked about wanting more pills and she talked about deleting a video. In the text, Ventura asked Comes if he had quote any more pills. Ventura testified that she was using opiates like Norco around that time that these messages were sent. In the same text messages, Ventur also mentioned deleting a video, but she testified she wasn't sure what kind of video she was referring to in the messages and couldn't be sure if it was a freak off recording or some other video that was totally innocent. Now, Defense attorney Estevo then asked Ventur if she preferred to have freakof videos recorded on her devices or on his devices, and her response, and this was a great response, was I didn't want them recorded at all.

11:55 So then the. Defense focuses on a message that Ventura sent to Combs in two thousand and nine that expressed some conflicting feelings about the freak offs. She wrote, in part, when we used to freak off. When we were so in love, there were no questions asked. It felt right, like literally made sense for the next step in our sex life together. I get nervous that I'm just becoming the girlfriend that you get your fantasies off with, and that's it. I don't get the other part anymore, at least in Combe's defense then asked Ventur if her hesitation reflected in the message came from a concern that she wouldn't be seen as his full girlfriend because of her participation in these sex encounters with escorts, and she said, quote, I think that's a way to look at it.

12:48 I guess yeah. She was also asked if Sean was the first older man that she dated, and Ventura testified that she met Sean Combes through Ryan Leslie, who was a music producer that she dated for about three years, and this started when she was eighteen or nineteen. She said Leslie was about ten years older than her, meaning Combes was the second older man she dated at that point. Now, I'm not sure where the defense was going with that. I guess because Cassie, under the prosecution direct testimony, was alluding to the fact that she was very young and naive when she started dating Seawan Combs. And the only thing I can come up with regarding their point is that, hey, you already dated.

13:38 A dude ten years older than you before this. So they continued on that line of questioning and following her twenty first birthday. As we learned under direct examination, Ventura said she wanted to join Combs on a trip to Miami and she was dating someone at that time. She had mentioned well that person was Leslie. She testified she the flyer for an event as an excuse to go on that trip. She actually told her boyfriend at that time that Sean Combs had arranged a concert or something there in Miami and she was going to sing at this concert, and they even made up a fake flyer for that. At that point, the jury viewed some other text messages where Cassie wrote about some negative feelings she had about their relationship, her in Sean, and in that text message she indicated she felt that her friend may be better suited for comb She said, quote, It's hard for me to handle that. On the other hand, you're extremely weary of me.

14:42 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. The jury then viewed some text messages between Cassie and showing from December of two thousand and nine that vent Turk confirmed reflected the quote open communication between them. She told defense attorney is Steve O that at that time she felt comfortable expressing her need to combs over participating in freak offs. In one message from two thousand and nine, Cassie wrote that she needed to quote feel safe, like home and to be more open with things we do in bed. She continued, quote 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 or not wanting to do it. She went on to write, when we used to freak off, when we were so in love, there were no questions asked, but she did not feel the same level of love anymore at least and from there a Stevo brought up that lawsuit in twenty twenty three that was settled for twenty million dollars, and she asked, Cassie, you understand that his career was ruined at that point, right, and Cassie replied, I.

16:08 Can understand that. Yeah. So the defense then moved on to talk to her about the swinger lifestyle, and Cassie confirmed that she and Sean Combs had conversations about the swinger lifestyle and eventually she saw it in person at the sex clubs. That they went to together. And as STEVEO asked if the freak offs were related to that swinger's lifestyle, and she said related in a sexual way, yeah, but they're very different. The defense then asked if any of Come's staff knew about the freak afs outside of security, and Cassie Ventura testified that she didn't remember any of Shawing Comb's employees walking in while they were having a freak off. She said she never talked to anyone on the staff about it, and she went on to say she definitely didn't want any of his employees to know.

17:05 About any of that stuff. Ventura said Come's assistance would often set up the hotel rooms before freak off and they would at times come into a hotel room while they were staying there, but she said, I don't have a specific recollection of a staff member in the room when the freak off was going on, and I have no idea if they knew or not. She also acknowledged she never told any friends about the freak alls. The defense then asked Ventura about her testimony that Combs would sometimes call her incessantly. A Stevo asked if those calls were triggered by fears of infidelity. Was he worried about her cheating on him? Cassie responded with, that's one of the reasons, And then Cassie was asked about her testimony that Sean Comes frequently weighed in on her appearance, including her hair, her clothing, and body piercings, those nipple piercing specifically. Steve has said many people respected his perspective in this regard, true, to which Cassie answered, from my perspective, yes, And what the defense is trying to do there is basically say, hey, he wasn't trying to control you regarding your appearance and suggesting you wear heels and things like that. He just had great style and people respected his opinion when it came to style, and look, that's a good point. He was known for his style, and the defense team is not a joke, y'all.

18:34 They're going to pick up every little crumb of doubt that they can. The defense then asked Cassie about shaw Combe's drug use, which she already testified was a central element in those freak offs, and Cassie agreed that Comes, at least at one point, was an attic, testifying he often took opiates, and she admitted that she did as well. She said that multiple times she witnessed him going through what's known as opiate withdraw and she admitted that caused him to be more irritable. And what the defense is trying to do there is attribute his abusive behavior to drug addiction, basically saying he was on all these drugs and he didn't know what he was doing, which don't mean a hell of beans to me. It doesn't mean you're not responsible for it because you were on drugs, But it seems to be a heavily focused route that the defense is taken. And at this point there's kind of a tense back and forth between prosecution and the defense team about how long the cross examination of Cassie is going to take. The defense said it intended to finish by the end of the week, but it can't make any promises, and the judge is kind of pissed about this. He said that there have been discussions for weeks now about how Ventura, who keep in mind, y'all, she's like can deliver at any time. She's in her

20:05 third trimester, she's due this upcoming month. But I mean, the clock's ticking, and when you have this kind of pressure on you, you have to testify. In a case of this magnitude, it can bring on a baby, right, So the judge says she needs to be off the stand by the end of the week, and it's at this point they. Break for lunch. After lunch, the judge address the length of time Cassie was to testify. He said he wants to have Ventura off that stand tomorrow. Quote, the direct took a day and a half, so the defense will have a day and a half. So you have today and you have tomorrow morning. If there's something that really needs to be done after the lunch break, then you can have additional time at my discretion.

20:53 So this judge is. Very firm on them wrapping this up by Friday. After or just prior to lunch. The defense then picks back up with the government exhibits that are already in evidence more messages between Ventura and Combs, and the defense points to additional text in which Combs and Ventura seemed to agree that they enjoyed freakoffs in a twenty seventeen message, saying quote, when we both wanted. When asked about the message, Cassie responded, I would say that loving fos freakoffs were just words at that point. In an older exchange, Combs wrote quote, I want a freak golf right now, to which Ventura responded, Lol, me too, and then added, well, I want to have fun with you. And the defense then started focusing on how the couple communicated about planning a freak golf. They reviewed a text message chain in which the planning of a freak off was discussed with I'm saying, quote have fun impress me. And to give you some context on that, this is when Cassie was about to leave her apartment and visit a sex shop for supplies. She texted and let Sean know that's what she was about to do. And when I say supplies, I mean supplies for the freak off. I guess baby oil and whatnot, and that's when he responded back with

22:25 have fun. Impressed me. The defense then noted that Ventura had not said no at any point in that text exchange, and Cassie replied, you're correct. Defense attorney Esteve o them right aloud some of Diddy's other texts related to the freak Offs, and I'm going to read you. Two of those. One said quote, didn't hear from you, so I just put some plans in motion. Let me know to stop, and then the second one said, surprise package coming from out of state. Just let me know if I'm headed in the direction so I can cancel. The defense then brought up a text chain referring to a freak Off in Castie messaging Ditty saying quote, I'm too excited, and when they asked her why, she said that if she didn't like freak offs, she testified that quote, I probably would have been excited to see him and have fun with him. But the defense underlined that in the text chain it seemed to them that she was just excited in general, and then shockingly to me at least. The defense raises the subject of kim Porter, who y'all was the on and off girlfriend of Sean Combs, the mother of three of his children, and she died in twenty eighteen.

23:46 After all this shit came out with Diddy, a lot of people questioned the manner in which she died and thought there may be something more sinister to it. So the defense asked Cassie about kim p and specifically what her feelings were toward kim Porter, and Cassie testified, quote, I had some jealousy of miss Porter. The defense then pressed a little further and said, did y'all argue a lot over infidelity, to which she agreed. She said they would argue about that, and she said it was a little scary, she said, when they thought about his but even more scary when they fought about her own alleged transagressions, if you will. And it's at this point Cassie starts appearing very frustrated for the first time in this trial, after the defense reads a message Cassie sent to Shawn Combs and said, quote, wish we could have f oed before you left, and of course that stands for freak off.

24:49 And then the defense. Attorney moves on to recount Cassie's relationship with rapper Kid Cuddy and if you'll remember, that was the guy who had. His car blown up. Cassie confirmed that during that relationship she used a burner phone or a secret second device. When she dated Kid Cuddy, she claimed that it was while she was on a quote break from her relationship with Shawing Combs, and she admitted that she was continuing to have freak offs with Combs, saying it was a quote job and that she didn't know if he considered them to be on a break or not, because I assume that Comb's is claiming he had no idea they were on a break and that she was cheating on it. Cassie said she did not tell Combs about the new relationship because she thought it would be way too dangerous. And then the defense went deeper into what they characterized as Cassie's jealousy issues, and they asked her specifically about social media. Cassie said women on social media would often claim to have a relationship with Seawan, saying it happened often enough that I don't know that I remember every single one. The defense they move on and they get on to more messages, and one specifically related to Cassie having difficulty over not being afforded more time by Combs when he would spend time with his children. They showed one text message chain where Cassie said, quote, I've been at the edge of tears

26:22 this whole week. I don't think you sympathize with my feelings. I understand your feelings like you need to protect your children, But after a while, it's like for what they've never known you and come to be together unless there's something I don't know about. They were babies when we started dating, and again I was a little brought back by what the point was here. The only thing I can derive is that they're trying to again hammer down. The jealousy stuff with Cassie. So the defense brings up Kid cutting again and they characterize Combs meaning the defense team as I rate. And they asked Cassie if she would agree with that characterization, and she said yes. She said in part because kid Cutty was considered a celebrity like Sean Combs was, and she also said that issue would come up repeatedly throughout the rest of their relationship. She said later in twenty fifteen, she was filming a movie in South Africa, and she learned that Combs had been spending time with one of his on again, off again girlfriends, and that pissed her off so much she cut off contact with him for a while. And she said, I actually started dating Michael B.

27:45 Jordan at that time, And the defense didn't really press this. They just kind of moved on. It was apparent they didn't want to talk about Michael B. Jordan, but they did return briefly to the topic of freak golfs, and the defense asked Cassie if her what they termed as sexual marathons with Shawn Comb's were a chance to do drugs together in a safe, confined space. Inventor agreed that they tried many substances, including psychedelics, and they experimented with drugs together both during freak offs and elsewhere, and the defense attorney said, so you were able to keep up with him in a way that most other people could not as it relates to drugs. Vent Tur replied, surprisingly.

28:29 So yeah. She went on to say that Shawn Combs react explosively when he found out that Cassie was doing drugs with her friends and not him. She said, quote, if we. Weren't getting high, or if I wasn't doing drugs specifically with him, it was a problem. Steven then moved into another line of questioning and brought up that friend of Cassie's that Cassie had testified in direct examination she had seen being dangled over a balcony by Sean Combs. If you'll remember that friend of hers, well, that friend's name was Brianna Bigolin. I believe it is how you pronounced that.

29:10 Steve O asked her, quote, isn't it true you learned about this incident after the fact? Remember Ventura said she was there. Ventura responded, quote, I saw what I saw. And then as Steve O shows Ventura a text message that she sent Combe's chief of staff shortly after the incident, telling that chief of staff that she learned of the altercation after the fact. And y'all that's a problem because she testified yesterday she was there when it all went down. Steve then asked Ventur she was on drugs that night. Ventura testified she couldn't remember if she'd done drugs before falling asleep earlier that day. And then if Steve O asked Cassie if she had any side effects from her drug use, and Cassie said in early twenty seventeen, she got very sick from her drug use and she began to look for help. Quote, I lost all sense of smell and taste. When I woke up, I had numbing in my arm. She said she also experienced some disassociative side effects from ketamine use. The defense then says, did Shawn Combs notice some of your symptoms and suggests that you go see doctors? And Ventur confirmed that he did.

30:31 She said that she didn't tell Combs everything about her drug use throughout their relationship. They were both doing a lot of drugs, but he did indeed ask her to go see a doctor. And what they're trying to do there is trying to show that Combs cared about her, which I think is a major stretch. The defense then shifted back to twenty twelve from twenty seventeen, and they asked Ventura to recall a time that Shawn Comb's overdosed on opiates while at the Playboy mansion, and Ventura said that on that day they had a freak golf and then they went to a sex club before Combs went without her to a party at the Playboy mansion. Later that night, she said she took him to the hospital where they learned he experienced an overdose. Quote 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. The defense then asked he was extremely dependent on his opiates, right, and venturre responded for a time, as Steve O then said, he was very upset if his opiates were taken away from him. Correct, and Ventura said, I guess so. And as Steve O said, did there ever come a time when you and he were not dependent on painkillers? And Ventur went on to say that they obtained a plant medicine in Mexico, which was a lie in the United States, to try to

32:02 help them detox and she said that plant medicine worked, but only temporarily. So the defense at this point is highlighting that Shawn Combs apparently had this long time dependency on pills and that it had prominent effects on his mood. The defense then asked Cassie directly, we would like to dispel any widely circulated rumors were there drugs in the Baby Wild that was applied at the freak offs, and Cassie responded, no, never. So the defense then returned to Ventura's previous testimony on an incident concerning sug Knight. In direct examination, Cassie testified that sug Knight was nearby one day when she and Shawan Combs were having a freak off, and he and the security guards quickly packed up and drove to go find sug Knight. Well A Stevo pointed to a report from investigators after they met with Vin Tura in June of twenty twenty four, which said Cassie told police that she was brought along in the car and she was crying in the car when they went to go find suge Night. And she said that was incorrect.

33:19 I didn't go in that car with them. So what are they trying to do there? They're trying to point out you said one thing here, now you're saying something else three years ago, putting doubt. It's all about putting doubt in that jury's mind. The defense then brings up that twenty sixteen Hotel Hallway incident again, and they make suggestions into why Combs reacted the way that he did. The defense reviewed a series of text messages between Combs and Cassie just days prior to the incident, in which Cassie told Combes to quote stay hydrated and get some rust ventura. She pushed back on that, though she testified she did not remember Comb's going through any sort of withdrawal during that time, which was what the defense was leading up to, she did acknowledge the text appeared to suggest he was sick at the time, and of course, being sick and going through withdrawals from opiates are obviously two different things. And this is a good example of the defense just trying to sprinkle a little doubt in a juror's mind. They don't need them all, he's want to sprinkle a little doubt and say maybe he was going through withdrawal.

34:32 Symptoms and didn't know what he was doing. Right, And continuing on that line of questioning the defense, they present some other messages leading up to that incident in that hotel hallway. So those other messages, and I'll give you some context. This is after going back and forth about potential plans with some of her friends, casting message Sean and she said, quote, we can have fun. I don't want you thinking I don't want to unquote, she told co to set it up, and the defense attorney suggested that Ventura was proposing and encouraging a freak off at that hotel, and Ventura pushed back again on that. She testified that messages from Combs repeatingly asking her plans for the night was his way opposing a freak off to her, not the other way around. She went on to say, when you're with someone for as long as me and Sean were together, you know what they mean when they text certain things. And it's at that point the judge says, you got a two minute warning, and then we're adjourning court, and so they had time for one final question, and it was about that twenty sixteen Intercontinental Hotel incident, and they said, quote, do you recall the beginning of the freak off session? And Ventura responded she did not, but guess she had taken some MDMA or ecstasy or something. And then the defense followed that up with do you think it was bad at your drugs?

36:01 And Ventura said, I have no idea, and with that court adjourned. So in my mind all day long, she testified today, absolutely grilled, and I think the defense. Their whole goal here. Is to excuse the stuff that Sean Combs did relative to abuse. They're gonna blame that on the drugs. Look, they produced some messages where, if I'm a grror, I would have a little doubt in my mind at this point as to whether Cassie wasn't on board with him Freakoffs, because they got a lot of text where she's just not only I guess, being cool about the freak Alls, but she's actually shopping at one point for freak All supplies.

36:49 So it ain't looking good from that standpoint. Because coercion is one of the things they have to prove right now, it doesn't look like he coerced her into these freak afts. Necessarily, Cassie will be coming back tomorrow, Friday, May sixteenth, to conclude her testimony. As the judge said, it better be done by lunch, So look for that update to drop as soon as I can drop it. Thank you so much for listening. Check out the Patreon for commercial, free early releases, bonus episodes, files, and even quarterly gifts for our top tier members on Patreon, and until next time for exposed scandalous files of the elite.

37:32 I'm your host, Jim Chapman, much love,