Cassie Faces Cross-Examination by Diddy’s High-Powered Legal Team — And Her Testimony Is Being Put to the Test
The courtroom battle between Cassie Ventura and Sean “Diddy” Combs entered a new phase today as Cassie took the stand for cross-examination, facing off against the music mogul’s team of elite, high-priced attorneys. With a reported million-dollar defense team at his side, Diddy’s legal strategy is clear: poke holes in Cassie’s powerful testimony.
And from the very first day, the pressure is showing.
Cassie, who delivered emotional and detailed testimony during direct questioning, is now facing intense scrutiny as defense lawyers challenge her timeline, memory, and motivations. Legal experts say this phase of the trial could be crucial, as the defense attempts to cast doubt on her credibility before the jury.
While Cassie remains composed, courtroom insiders say there have already been a few shaky moments — moments the defense may use to weaken the emotional impact of her earlier statements.
As the trial continues, all eyes are on Cassie — and whether her voice can remain steady under the weight of relentless legal pressure.
Stay with us as we break down what happened during day one of cross-examination, and what it could mean for the rest of the case.
Here’s the full transcript of the testimony:
[Before the cross examination] Ventura’s lawyer Wigdor: I have a right to be part of the meet and confer about which evidence she can be questioned about; she is the only victim witness that has standing under Rule 412. Judge Subramanian: We have to move forward
Judge: Other issues, Ms. Slavik? AUSA Slavik: As we noted in our email to the court early this morning [Note: The judicial documents are not being put in the public docket] Judge: We might get a sign from Ms. Estavao [who will cross Cassie] that it’s not an issue
AUSA Slavik: The defense last night dumped 400 exhibits on us. This cannot continue throughout the course of the trial. Judge: Ms. Estavao? Combs’ lawyer Anna Maria Estavao: We have been working tirelessly in response to Ms. Ventura’s testimony
Judge: Mr. Agnifilo, I thought you were going to take his off my plate Combs’ Agnifilo: I will keep trying. This is the main witness, she stands by herself. That said, we have been doing this all night, until 3 in the morning. We flagged exhibits for them
AUSA Slavik: There are two dozen exhibits that the government has objections to, they are listed in the chart Judge: Just the ones in the chart? [Again, these judicial documents are not going into the public docket. Not the case in many other SDNY trials]
Judge: Bring the jury in. [Jury enters] Combs’ lawyer Estavao: Ms. Ventura, you loved Mr. Combs, correct? Ventura: I did. Estavao: For 11 years, you took care of him? Ventura: In some ways. Estavao: You called him larger than life? Ventura: I did.
Combs’ Estavao: Others called him Diddy or Puff Daddy, but you called him Sean, right? Ventura: Yes… Estavao: You knew a version of him the rest of the world couldn’t see, right? AUSA: Objection! Judge: Overruled. Ventura: In ways.
Combs’ Estavao: You kept coming back to him for 11 years? Ventura: I wouldn’t say “coming back.” Estavao: You believed he loved you too. Ventura: I did believe he loved me too. Estavao: So when he cheated on you it hurt? Ventura: Not every time
Combs’ Estavao: Bring up this Defense Exhibit- AUSA: Objection. Not in evidence. Judge: That’s true – this is not in evidence. Estavao: Ms. Ventura, read it just to yourself… Why did you send this message? Ventura: To let him know I was going to dinner
Combs’ Estavao: What was going on when these messages were sent? Ventura: I’m not sure. Estavao: What was going on in your relationship then? Ventura: It was early. We were loving. Estavao: I offer it AUSA: Objection, being offered for the truth. Overruled
Combs’ Estevao: Please read Ventura: I wrote, “I love you, smiley face, I’ll fly anywhere for you, I love you, Cass.” Estevao: This 2009 email AUSA: Objection, hearsay Judge: Ms. Estevao, ask more questions. Estevao: From Blackberry what is BG? Ventura: Babygirl
Combs’ Estevao: What did you write? Ventura: “You hungry, Pop Pop?” Estavao: And Mr. Combs wrote to you, “We are so in love we don’t do anything else.” How long had you been seeing each others? Ventura: Like two and a half years
Combs’ Estevao: Please read this, 1364. Ventura: “I haven’t talked to you at all, you don’t even try. You rush me off the phone. I’m really hurt. I don’t need your money, I need some attention.” Estevao: You wanted your special time with Mr. Combs? Ventura: Yes
Combs’ Estevao: You testified that you told him, I love you so much you make me a better woman Ventura: I definitely wrote those messages Estevao: You wrote, I can’t wait until we have a baby of our own – you knew that he had six children at the time? Ventura: Yes
Combs’ Estevao: So now, these messages about freak off… When you say, you know it doesn’t matter to me, you mean, weekend or weekday, either is fine? Ventura: That’s what it says. Estevao: Mr. Combs says, Maybe we can call Jules, can you do it. Yes.
Combs’ Estevao: This was an explicit message from you about the anticipated upcoming freak off? AUSA Johnson: Objection!
Judge: We will take a recess
10:48 am – they’re back Judge: Ms. Estevao, you may proceed. Combs’ Estevao: Ms. Ventura, this is from Mr. Combs to you – you respond with an extremely explicit message, right? Ventura: Yes. Estevao: This is two days after the planning of a freak off, right? Yes
Combs’ Estevao: He said, I want to see – how did you reply? Ventura: “I can’t wait either.” Estevao: You wrote, “I feel like I want to f*ck,” right? Ventura: That’s what it says. Estevao: Mr. Combs says, I’m so horny I can’t concentrate – what do you say?
Ventura: That I’ll go to Duane Reade for candles and then set up the room. Combs’ Estevao: Did you understand that he was going to take another video of you? AUSA: Objection! Speculation! Judge: Ms. Estevao, you can move on. Estevao: You ask, any pills on you Yes
Combs’ Estevao: What pills were you taking then? Ventura: Opiates. Estevao: You deleted videos on your devices, right? Ventura: Yes. Estevao: What did you write? Ventura: That I need to feel this this is my husband, the only one who will see this side of me
Combs’ Estevao: Were you afraid that Mr. Combs was only seeing you for sex in this way? Ventura: That was a concern. Estevao: You still were not public in your relationship with him? Ventura: Correct. Estevao: Were freak offs important? Ventura: Integral to us
Combs’ Estevao: Who was at your 21st birthday party in Las Vegas? Ventura: Britney Spears, Dallas Austin. Estevao: How did you get them there? Ventura: They came for Sean. Estevao: You’re very beautiful and charming Ventura: Thank you Estevao: It’s true
Combs’ Estevao: Who is Tommy Mottola? Ventura: A well known producer. Estevao: You were an up and coming star? Ventura: I guess you could say that. Estevao: After you signed with Bad Boy, things were still platonic? Ventura: Yes
Combs’ Estevao: You had rough performance? Ventura: 106 and Park, it did not go well for me. Estevao: How did he help you after that? Ventura: We did a YouTube video, he said, Everybody makes mistakes. Estevao: What was wrong? Ventura: I couldn’t hear myself
Combs’ Estevao: You were dating Mr. Leslie – how much older than you was he? Ventura: Ten years. Estevao: Then you traveled to Miami with Mr. Combs – the flier of the event was just a cover, to spend time with Mr. Combs, right? Ventura: That’s true.
Combs’ Estevao: You had a tattoo of Mr. Leslie’s initials on your body, right? Ventura: Yes. Estevao: How many tattoos did you have then? AUSA: Objection. Relevance. Judge: Overruled. But let’s keep it moving Ventura: 3 Estevao: The one on your arm? A: No Regrets
Combs’ Estevao: Mr. Combs taught you how to do oral sex? Ventura: He did. Estevao: Look at this. Tell me when you’re ready… Can you read it? Ventura: You can read it. It’s making me laugh. It’s from 2007. Estevao: You wrote, I feel protected, you are sweet
Combs’ Estevao: You wrote, I see that Kerry is better fitting for you. I’m hurt that you think I’m malicious. You’re very important to me. X. Cass. Ventura [laughs] Estevao: What were you trying to convey? Ventura: It’s like a journal entry.
Combs’ Estevao: You discuss Kerry Morgan – did you think Mr. Combs was attracted to her? Ventura: There was a point in the very beginning. Estevao: Did that complication carry on in your relationship? Ventura: Not really. Kerry was just always with us
Combs’ Estevao: I’d like to start asking about freak offs. Sometimes you wore a wig and a mask? Ventura: Yes. Estevao: The general public did not know – AUSA Johnson: Objection! Judge: Rephrase. Estevao: No one knew until November 2023, in the public Yes
Combs’ Estevao: Fair to say his career was ruined after your lawsuit? Ventura: I could understand that. Estevao: Let’s read these messages. Mr. Combs wrote, When are you on your period? Ventura: No now. Estevao: “What you be thinking about when you horny?”
Combs’ Estevao: Ms. Ventura, if you don’t want to read the answers, I can read them. Ventura: Thank you. Estevao: The o has lots of ooooo’s after them, right? Ventura: Yes. Estevao: After a freak off you’d make love with Mr. Combs? Ventura: Yes
Combs’ Estevao: Your period, Mr. Combs is asking you when you’re on it, right? Ventura: Yep. Estevao: He’s asking in the context of when to meet up and have sex? Ventura: Looks like it. Estevao: Sometimes you watched him with a female? Ventura: 2 or 3 times
Combs’ Estevao: Did you talk with Mr. Combs about the swinger’s lifestyle? Ventura: That no one talks about it. Estevao: Were you keeping freak offs secret from your friends? Ventura: Yes. Estevao: His assistants help him? Ventura: With everything
Combs’ Estevao: You would remember if an assistant came in during one of your sessions with an escort? Ventura: Not necessarily. I was high. Estevao: So you don’t remember much. Ventura: I had my privacy invaded a lot during that relationship.
Combs’ Estevao: This is from July 2012. You say to Mr. Combs, “I’m horny and bored.” This was after a freak off, right? Ventura: There are a lot for texts here [Said to be 25 pages – where will defense exhibits ostensibly entered into evidence be available?]
AUSA Johnson: I would ask that the witness be allowed to read the entire document Judge: How many pages? Combs’ Estevao: Eight. AUSA: We don’t have a copy for the witness Estevao: We’ll show it on the screen [But not in the public gallery]
Combs’ Estevao: You said Mr. Combs often put you down. But he also sent you encouragement and called you a queen, right? Ventura: Yes. [Sidebar] Estevao: What would trigger Mr. Combs’ incessant calls to you? Ventura: Anger, doubt about where I was
Combs’ Estevao: If he suspected you of cheating, he’d call you incessantly? Ventura: That was one of the reasons. Estevao: Because he thought- AUSA Johnson: Objection! Judge: That’s sustained.
Combs’ Estevao: Do you believe Mr. Combs has good taste? Ventura: I think he does. Estevao: He’s had an impact on fashion? Ventura: People like his style. Sean John. Estevao: Did you consult with him on your look? Ventura: Sometimes I got advice I didn’t ask for
Combs’ Estevao: He still ran his companies even while having all these freak offs, right? Ventura: He did. Estevao: What was he addicted to? Ventura: Success (laughs) Estevao: What substances? Opiates? Ventura: Yes. He told me. And I saw it.
Combs’ Estevao: Did Mr. Combs’ mood depend on whether or not he was withdrawing from opiates? Ventura: He was more irritable, I would say. Estevao: What other drugs was Mr. Combs’ addicted to AUSA: Objection. No foundation Judge: I’ll ask if I want the grounds.
Judge: Sustained. Re-phrase. Combs’ Estevao: What was his drug of choice? Ventura: Ecstasy or MDMA. Estevao: Opiates daily? Ventura: When he was doing them. Estevao: You saw him withdraw? Ventura: Yes.
Judge: We’ll break [Juror leaves; witness leaves] Judge: Ms. Estevao, where are we in your cross? Estevao: We have a lot of exhibits. Let me confer over lunch. Judge: Non-responsive. Will you finish today or early tomorrow? Agnifilo: To the end of tomorrow
Agnifilo: We might not be able to finish tomorrow. This is the most important witnesses. Judge: For months we said, this witness had to be off the stand by the end of the week. AUSA: Our direct was a day and a half. Limit them to that.
Judge: Show Ms. Ventura the exhibits in advance. Maybe just ask her question, rather than these exhibits. We have a timing concern. Agnifilo: They called two witnesses to start. That wasn’t our choice. It’s a critically important witness. Judge: Streamline things.
Judge: We’ll break
1:10 pm they’re back Judge: Ms. Estevao, has the witness had a chance to review the exhibits? AUSA: They are lengthy. Judge: We’ll do the best that we can. I was told this witness would be off the stand by the end of the week. We let the jury go early yesterday
Judge: If there’s something that really needs to be done on cross after lunch tomorrow, I may allow it. We have ot leave time for re-direct. This witness is being responsive.
Ventura enters, jury enters. Combs’ Estevao: Let’s turn to GX 411. AUSA Johnson: It’s not in evidence yet. Estevao: So B-414, page 3 and 4. You wrote, “I love our FOs, when we both want it.” You felt that? Ventura: Loving FOs were just words at that point.
Combs’ Estevao: Mr. Combs wrote to you, I want to freak out right now. And you wrote that you wanted it too: “LOL me too.” Ventura: I texted more than that Estevao: But you did text that to him. Mr. Combs’ wrote to you, Jules is available, if you are into it.
Combs’ Estevao: You could have said yes or no, and you said, Love you. Ventura: There was no yes or no. Estevao: Bring up B-420 on page 2. Mr. Combs wrote, Do I have your permission to set up freaky fun. You wrote, Ovulation. Ventura: Yes.
Combs’ Estevao: Here, what do you say? Ventura: I asked, Which hotel – I must have called him in between. I don’t want to assume anything. Estevao: He said Montage, you said, you could also go to Pleasure Chest. What would you get there? Ventura: Sexual supplies
Combs’ Estevao: What supplies? Ventura: Lubricants, outfits. Estevao: He says, Have fun, impress me. You say, OK. He says, Can we kiss a lot. What do you say? Venture: Yes. Estevao: You wrote, I left the iPad Ventura: I don’t know whose iPad this meant
Combs’ Estevao: Mr. Combs’ wrote, I’ve be there right after my session. This was in June 2017. Do you remember arguments you were having at that time? Ventura: Not specifically. Estevao: Here you say, the game starts at 10 pm, no breaking character to 8 am
Ventura: This was a game a friend of mine told me, a way to rekindle your romance Combs’ Estevao: By doing something different in the bedroom Ventura: It’s a whole getting into character thing Estevao: Mr. Combs says, let’s get some outfits and go to sex club
Combs’ Estevao: Mr. Combs wrote, Surprise package coming from out of state.. Why can’t I reach you? What do you say? Ventura: I was getting my brows done. Estevao: Did you come to know Mr. Combs was leaving to freak off to go see Kim Porter? Ventura: Yes
Combs’ Estevao: How did you find out about Gina – how did you feel? Did it upset you? Ventura: Yes. Estevao: It prompted arguments? Ventura: It did. Estevao: And he thought you were not faithful – what were his reactions? Ventura: It was scary
Combs’ Estevao: Mr. Combs wrote to you, let’s do something different in NYC this weekend… FYI Dave hit me. What does hit mean? Ventura: Reached out. Estevao: And Daniel contacted you. Did this mean you might have a freak off? Ventura: Might.
Combs’ Estevao: He tells you, You better put me on VIP vibrate alarm or something. He’s frustrated you don’t answer his texts fast enough? Ventura: Right. Estevao: You tell him to come to NYC understanding there could be a freak out Ventura: Maybe
Combs’ Estevao: You also saw the Book of Mormon? Ventura: Yes (laughs) Estevao: Masked Pleasure, if that a sex club? Ventura: I would assume. Estevao: He asks Are you ready for tonight. What do you say? Ventura: Yes, I just have to get some things
Ventura: This is not about what I felt, right? Because you are skipping over a lot here… Combs’ Estevao: What did you write? Ventura: As much as you think you’re Bruce Willis, you’re not. Your kids were babies when we started dating
Combs’ Estevao: If you saw him on social media on vacation with, it was heartbreaking? Ventura: It could be. I was seven years in…. Estevao: And what about this, about Gina… You wrote, I don’t want to be a side piece. But I’ll treat you as a king
Combs’ Estevao: You wanted to be the main girlfriend? Ventura: In 2013, yes. Estevao: You saw social media posts of Mr. Combs with other girlfriends and got angry, right? Ventura: Can I speak? I was jealous of certain situations.
Combs’ Estevao: Did there come a time he suspected you were in a relationship with someone in the industry – Mr. Mescudi? Ventura: Yes. Estevao: Mr. Combs thought it could be good for your career if you collaborated with Mr. Cudi – I mean, Mr. Mescudi Ventura: Yes
Combs’ Estevao: Why did you begin your relationship with Mr. Mescudi? Ventura: We enjoyed each other’s company. Estevao: You were in a relationship with Mr. Combs? Ventura: We were on a break. Estevao: But you were still doing freak offs with him? Ventura: Yes
Combs’ Estevao: After Mr. Combs found out by going through your phone, you went to see him – you knew he was upset, he previously attacked you Ventura: Yes. I thought I’d be safer with other people there.
Last updated: 2:25 PM ET
