Rotten Mango
I Watched Diddy’s Lawyers Question Cassie For 16 Hours - This Is EVERYTHING That Happened
Wed, 21 May 2025
The energy in the courtroom has shifted. Sean Combs no longer looks like a statuesque wax figurine. He is now much more animated, literally jumping out of his seat to look at the evidence screen, there is almost an air of anticipation. But why?For the past 2 days Cassie Ventura, a government witness and victim in this case, has been testifying against Sean Combs. Now, the defense will begin their cross examination. Sean Combs’s attorneys will attempt to poke holes in Cassie’s story, discredit her, and show the jurors that she “wanted freak offs.” Everyone seems to be under the impression that the defense has very slim evidence to accomplish this. Then why is Sean Combs so happy? Do they know something we do not?
Chapter 1: What happened during Cassie's cross-examination?
I think every single person I know in existence, on a personal level, taken it upon themselves to send me anything that is related to Sean Combs. The amount of AI-generated TikToks that my parents send me asking me if I'm safe, if I'm going to be okay in the next two months, it's getting out of control.
But an interesting series of TikToks have actually been circulating in the Rotten Mango group chats. In short, it is always somebody very passionate in front of a camera, seemingly very frustrated because nobody else thinks the way that they think. One person says, why the hell didn't Cassie leave? Like, you guys need to stop acting like we have this invisible line in the sand.
Like, we're not allowed to ask, why didn't you leave? She's putting up with the bullshit because she thinks the good shit outweighs the bullshit. Y'all are going to stop making people acting like they're crazy for pointing that out. At the end of the day, though, at what point are we saying you're a willing participant or not? Like, we can't ask common sense questions.
Chapter 2: Why did Sean Combs seem more animated in court?
Another person on TikTok compares her to Ghislaine Maxwell, the counterpart of Jeffrey Epstein. No, bro, she's got favorite escorts. She's picking out different escorts. And come to find out, she's been cheating on her husband throughout this. No, bro. Cassie's husband is finding out that he's getting cheated on in the most diabolical ways in the courtroom. That he's walking out.
Side note, that is factually incorrect. That is not why he walked out. And y'all are acting like this is grape? She was a willing participant. I can't stand how we are framing Cassie as this super victim when she's picking out the escorts that she wants. She's one of the most freaked out people in Hollywood. And y'all think that women just aren't on that?
You hear a woman being part of stuff like this and you think, oh, there's no way she could have wanted that. Actually, bro, yeah, she's a ringleader. We saw the text messages. She's setting this shit up. That's so nasty, bro. Everybody up there freaked out and the women too. Another one is focused on Cassie's husband, Alex Fine, with one TikTok saying, She cheats on you and he takes you back.
Y'all work this shit out. And then years later down the line, you have to find out how and exactly what way she was cheating on you. You find out not only was she cheating on you with one dude, she was getting double, quadruple teamed. And not to mention she had an affair with the man that she said abused her. And then women on TikTok are going to gaslight you for taking on her bullshit.
That is why women don't get the respect that they beg for in society because they don't tell the truth under any circumstances Unless it benefits them the comments under that read 1 billion women versus accountability another reads Cassie got away got married and still went back to Diddy and women are gonna keep moving the goalposts for her actions and
Another says, if your girl is praising Alex Fine and saying things like, every woman needs Alex Fine, you gotta run. I will say, many of the comments in these videos and the videos themselves are misquoting or miscontextualizing statements and or questions from the cross-examination against Cassie Ventura. Here is a full recap on the 12-hour long cross-examination of Cassie Ventura.
We would like to thank today's sponsors who have made it possible for Rotten Mango to support the Joyful Heart Foundation. They are working to transform society's response to SADVCA and support survivors' healings. This episode's partnerships have also made it possible to support Rotten Mango's growing team.
We'd also like to thank you guys for your continued support as we work on our mission to be worthy advocates. As always, full show notes are available at rottenmanglepodcast.com. A few disclaimers before we get started. Regarding content, there are themes of DV, essay, and sex trafficking. Please watch with caution.
Many of the quotes and statements included have been shortened and condensed for brevity or rearranged because... I mean, if you look at the transcripts for Cassie's cross-examination, I think it's almost 1,000 pages. OK, no, I want to say it's like a good 600 pages. It's a thick stack, and they keep jumping back and forth. The timeline was so confusing.
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Chapter 3: What controversial TikToks are circulating about Cassie?
There are these like five windows on the side of the courtroom that are massive. And the second one near the front, the curtains are clipped closed with like a giant binder clip. The courthouse, I think, spends all of their money pumping the AC. It's like negative 10 degrees in there. Cassie even mentioned that she might be a little bit chilly. The judge is always asking people if they're chilly.
Everybody's cold and the freaking curtain is binder clipped.
Why don't they bring it up?
They do. They say it's a... I talked to Officer Riz who basically controls the courtroom and he said it's either going to be snowing or it's going to be so hot everyone's going to be sweating. Like there's no... I think it's very hard to control.
I see.
Sean Combs walks into the courtroom. He's wearing this sandy colored sweater with a collared shirt. He looks anxious but not in the bad way. Like that's the best way we can describe him.
This is like before the cross. Yeah, before the cross. The direct has happened.
The direct lasted two days, it's happened, and now we're heading into the cross-examination. So this means that Combs' defense team are going to be grilling, poking holes into Cassie's story. I'm going to go into what all the steps mean in a second. But he looks like something is going to happen. He looks almost anticipatory. It's anxious because you're anticipating something.
Side note, he is also not allowed a belt for obvious reasons. And his pants are always dangerously close to just like giving the press a sight of something that we did not ask for. And you can just tell it's going to be a big day. Because in walks Karen Agnifilo. Mark Agnifilo's wife, also Luigi Mangione's representation, counsel. And she brings her mom, her elderly mother. Karen's mom?
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Chapter 4: How did the defense try to discredit Cassie's testimony?
What?
Cassie messages Combs. I want to spend time with my baby. Okay, well let me know either way so I can plan my night. Love you so much. You look so sexy today. Hello? Well, hit me when you have time. Thank you, baby. I love you so much, and you look so sexy today. So what are you planning to do so I can plan the rest of my night? Baby, I want to F-O so bad, but I don't want to fuck myself up.
What am I to do? After the messages are read out loud, Esteveo lets it sink in for a second. So at this point, this is the fifth text message to him suggesting that you guys get together, right? Sure, yeah. And after he was asking you multiple times what you wanted to do, it was up to you, right? Yeah. And he again says, what would you want to do, right?
And then you say, I don't want you thinking I don't want to, right? So after this, she's like, I don't want you to think that I don't want to F-O. Yeah. As in, you don't want him to think that you don't want to have a freak-off. Correct, because he's been asking me over and over again. After you have asked him over and over again. Yeah, I guess.
It's just like, you know, when you're with somebody, you know how they speak and you know what they mean when they text certain things. It's like that. Esteveo mentions that Sean texts back. Thanks, babe. I love you. You look beautiful. Proud of you. Have a great day. And then no response. What are you doing? I just got out of a spiritual therapy session. What are your plans?
With the messages up, Esteveo says, because at this point, he's asking you what you want to do, right? Because at this point, you have proposed a number of things. You've proposed a freak-off. You've proposed going out with your girlfriends. You've proposed just being you. I'm assuming that means staying in, right?
This is the message at the top where you say, baby, I want to F-O so bad, but I don't want to fuck myself up. What am I to do, right? Yep. And this is the one that you were asked about in your direct testimony, right? Yes. And this is the one when you were asked why you sent this message, right? You said you were doing damage control because you didn't want him to ruin your movie premiere.
Because remember, after the Intercontinental Hotel incident, she's got a movie premiere where she had to put a lot of makeup on. And that's the same one where she's like asked about, oh, how was your chemistry with your co-star? And she's like, he's a friend, he's a friend, he's a great friend. Right. And at that point, Mr. Combs has sent you a number of loving messages, right? Yeah. Right.
And he's participated in a promotional event for your movie, right? A luncheon? I think he just came, but yeah, he came. That went smoothly, right? Sure. And it was supportive of whatever decision you wanted to make in terms of how you two spend your time together, right? Yeah. And then he says, so what would you want to do? And that's when you say, we can have fun.
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Chapter 5: What were the emotional impacts of the texts shown in court?
Wait.
Alex Fine and Sean Combs make prolonged eye contact. I would even consider it glaring. And so much is said through that look. Nothing great. But immediately after, Brian Steele and Mark Agnifilo start comforting Sean Combs like he just saw the boogeyman. And my researcher, like patting his back, like talking to, almost like they're giving him a pep talk.
They're both leaned into the sides of his face. Like it's okay. Like that's the vibe. I don't know if they said it's okay, but that's the vibe.
So they saw the exchange of the look.
And they're both like comforting him. Like he just saw the boogeyman. That's the feeling. Like they're really comforting him. I've never seen them comfort him like this. They'll hug, they'll like tap each other on the back. But this was like calming someone down, comforting. I don't know. It was weird. It was weird. Now, there were moments where I think the defense
We're trying to prove a lot of points. But it really depends on how the jurors are receiving this information. It's hard to say because I do think there is a small discrepancy between what the internet thinks and maybe what the jurors think. The jurors, a lot of them have poker face.
But there will be times where I feel like they are not responding the way the internet is responding to some things that are said.
Such as?
I think a lot of the text messages did not sit well with some of the jurors is the feeling I got. I really have no way to prove it. It's just like an intuitive feeling that my researchers and I felt. It would be like moments where a vulgar text message would be shown.
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Chapter 6: Did Cassie feel safe in her relationship with Sean Combs?
I think it also probably connects to the fact that Sean Combs had hired Alex Fine as her personal trainer, and then they ended up getting married. Again, I think every single person is going to have a different reaction to this. That's the point that the defense is trying to establish from the court's perspective. Like, being in the courtroom, that was the perspective.
They also bring up the fact that she was in South Africa filming a movie called Honey 3, and that's when she started dating Michael B. Jordan. And that she had another brief relationship with someone who was an NBA star. She doesn't know if he still is. Esteveo brings up another celebrity.
He found out that you were dancing with another person in the entertainment industry and was upset and took your phone, right? I honestly don't know. Do you remember the occasion when he suspected of you dancing with Chris Brown? I do. Which, side note, weird connection, Mark Geragos was Chris Brown's attorney during the incident with Rihanna.
And he is technically a long-term attorney for Sean Combs. So just like random attorney connection. I do, but I was not, he thought you were right. I don't know. Defense Exhibit 1303A is received into evidence. Esteveo leans towards the podium. I'll read Mr. Combs' message. Can I not get a chance to make things right? It seems like you're blaming everything on me. It's like you have anger to me.
I haven't taken care of you. Cassie responds, I'm not running around telling our business, but my family knows because I need their support right now. You took care of me materialistically, not where I needed it. I have lived in this bubble by myself for too long. I'm too dope. You may not be happy, but maybe it's because you surround yourself with people that always take from you.
I don't need you taking care of Kim, Sarah, and Gina. I needed to love you and put me first. I just don't trust anymore. The last shot put the nail in the coffin. I promised myself I wouldn't be with you anymore if you did that to me again. You lied to me. When I think to Burning Man a year ago, all the things I found out that you paid for and continued happening, I just love myself more.
I'm not blaming you, maybe I didn't try, but you wanted me to be a machine and forgive you every time, and she never went away. When you're talking about the last shot put in the nail in the coffin, that she never went away, you're talking about Gina, right? I would think so. Combs is slowly nodding his head during the sign of questioning. Now, Cassie was really collected for
like her 12-hour cross-examination, there are parts where she would be waiting and awkwardly kind of smiling at Esteveo. She seemed very genuine, like she wasn't like throwing daggers at Esteveo. When it was quiet, she would just kind of awkwardly sit there and smile. At one point, Esteveo asks her if a personal assistant ever came into the hotel room during a freak-off.
Cassie's like, to my knowledge, they set up and helped clean up after freak-offs. I don't know if they ever came in during. You would remember if an employee came into the room while you were in the middle of a session with an escort, right? Maybe. I don't know. I was high as well. I had my privacy invaded quite a bit while I was in that relationship, so I can imagine.
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Chapter 7: What was the significance of the text messages discussed in court?
What do you want to do tonight? I don't know. What are the options? Am I meeting you in the Hamptons or will we be in the city? In city, whatever your heart desires. Well, I get in kind of late. We can just go to bed. You'll probably be tired. I doubt that. I'm going to sleep on the plane. LOL. So what do you want to do, woman? And no, I'm not asking you to FO. I want to know what you want to do.
Get something to eat, smoke, take a walk. He says that there's a party tonight, I'm horny as fuck also, but the way, and please sleep on the plane, smiley face, and it looks like I have off tomorrow and I need some Valium, which there's a pack in my top drawer. She doesn't respond, he texts hello. This part, I think it's intriguing. Cassie likes to eat, smoke, take a walk.
I feel like Sean is always texting her that he's horny.
Yeah.
Like, all the text messages. I feel like I have not seen many text messages where there's a lot of depth in their conversations, or at least both ways. She tells him where the pills are, and she just briefly says, Let's go out and have some carefree fun. We will play it by ear. When are you on your period? What's carefree fun? I'm skipping it, just taking it as it comes. Are you on it now? No.
Good. Are you horny? Yes. How horny? What you be thinking about when you're horny? Cassie responds, I think about the way you're on top of me and the way you look at me and talk to me like that. I love looking up at you and hearing you moan. He responds, you like it when I moan. I'm a moan more for you, just for you. I love it, lol. That's what I really think about.
I love the way you talk to me when you're on top. She does not mention, I love jumping into a gallon of baby oil in hotel rooms with strangers. She mentions her relationship with Mr. Combs, which she, again, said in the direct. One of my favorite times is when we FO'd and then we made love after. I also liked it when we made love before and then, you know, it was just in the next room.
Then he came in and I blindfolded you. She responds, yeah, I liked those times. I love it when we make love after. The last time was so good. I get the point that the defense is trying to make, but also I don't get the point that the defense is trying to make with these specific text messages. He even texts Cassie, so what do you want to do, woman? I'm not asking you to F-O.
Again, it sounds like he knows that any time he asks, maybe she has like a, I don't really want to type of reaction.
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Chapter 8: How did jealousy play a role in Cassie's relationship with Sean?
I didn't just leave you. I said goodbye a few times. I want to be there for you, but needed to get to grandma. My flight was delayed, so I'm taking off now. I need to be real with you. I know how crazy and painful this all is. And you want my support, but you've compared me to Gina the other day and the babysitter, whom he's allegedly sleeping with at the time.
And there's last night and you posted that Kim was your soulmate. What was the 11 years all about? 11 consistent years. I know you're going through a lot, but that hurt my feelings. I love you, but I'm going to my family right now. I'll probably make it Saturday with my dad. I'll hit KK, Christina Coram, the chief of staff. Hit me if you need me. Love you.
So Esteveo and what they've been arguing since the defense opening statement is that Cassie did not leave Sean Combs because she realized that he was abusive and that he r-worded her. They're trying to argue that her final straw in leaving was that he called Kim Porter his soulmate online. He let you go, right? You never saw him again after that, right? I didn't see him again.
I don't know about letting me go. That's different. You never saw him again. Yeah. And you got married. I did. To the love of your life. Correct. And over the years, has Mr. Combs reached out to you? Yes. So they start reading text messages from Combs to Cassie. Checking on you. Seeing how you're doing. Hope you're well. Sending you love and light. Hope you're well. Congratulations, Cass.
I'm truly happy for you. You're going to make a beautiful mother. God bless. This one, Cassie does respond. Thank you. God bless. Sending you love and light. Hope all is well. I had a dream about you last night. Shaking my head. What a difference a year makes. Really happy for you. Have a blessed day. Just sending love. Later, he sends another one. Congratulations. I'm really happy for you.
I know you're so happy. You deserve it. Love. Then March 2020, he texts, Miss my best friend. Hope you are well. Frankie is so beautiful. Love. Miss you too. And thank you. Hope you're taking care of yourself and the family as well. Thank you so much for responding. It really means a lot more than you know. I'm so happy for you. The kids are good. Mom is good. I hope your family is well also.
I miss you guys. Sending you nothing but love and light always. Please know I'm always here if you need me. Cassie responds, I've been reflecting a lot, like a lot. The turns of life are so crazy, but I'm happy everyone is good. Please send my love to them, and if I can express anything, take care of you. I'm trying, just had another operation. This is going to be my last, lol.
Not entirely sure what that is referring to. Shit has definitely been rough without your friendship. I pray for a day that I can sit down with you and let you know all the things I've reflected on. You were there for me throughout everything. You were my ride or die. 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. Don't ever forget that love. Sorry, I needed a second to gather my thoughts. The things you said blew my mind a bit. First, I don't hate you. I never have.
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