Cassie Ventura’s Final Day on the Stand – May 16, 2025 | P Diddy Trial

Get Every Detail In This Gripping Courtroom Drama

May 19, 2025

Dear Permission to be Powerful Reader,

A courtroom sketch shows Casandra “Cassie” Ventura on the witness stand, facing an intense cross-examination.

Dressed in a tailored pinstriped suit, the 38-year-old singer sits visibly pregnant – eight-and-a-half months along – as she recounts the darkest moments of her relationship with Sean “Diddy” Combs .

It is Friday, May 16, 2025, Cassie’s fourth straight day of testimony in Combs’ federal sex-trafficking and racketeering trial, and the atmosphere in the Manhattan courtroom crackles with tension.

Cassie’s voice trembles at times, but she remains determined. Her husband, Alex Fine, watches from the gallery, silently supporting her .

Judge Arun Subramanian has made it clear that Cassie’s testimony must conclude today – mindful of her advanced pregnancy – and urged the defense to wrap up its questioning by day’s end . The stage is set for a dramatic culmination of an already harrowing week.

Cross-Examination: The Defense Challenges Cassie’s Credibility (Morning)

Defense attorney Anna Estevao resumes her cross-examination with a cool, methodical tone. She paces before the witness stand, intent on chipping away at Cassie’s credibility.

Estevao’s questions zero in on a violent incident from March 2016 at the InterContinental Hotel in Los Angeles – an episode jurors have seen on surveillance video, showing Combs dragging a hooded Cassie through a hallway.1

Estevao (defense attorney): Ms. Ventura, didn’t you tell investigators that Mr. Combs had “blacked out” during that 2016 incident?2

Cassie (softly): I believe he was intoxicated3.

Everyone’s definition of “blacked out” might be different, but… yes, he was very intoxicated.

Estevao nods and immediately shifts to a piece of evidence. She retrieves a printed text message and approaches the witness.

Estevao: I’d like you to read aloud the text you sent Mr. Combs on March 10, 2016, a few days after that hotel incident. Take your time, but please, read it exactly as you wrote it.

Cassie’s hands shake ever so slightly as she takes the document. In a steady voice, she reads her own words from years ago:

Cassie (reading her 2016 text):

“When you get fucked up the wrong way you always want to show me that you have the power and you knock me around. I’m not a rag doll, I’m someone’s child.”4

The courtroom falls silent except for the scratching of pens as everyone notes the stark language. Cassie’s emphasis on “I’m not a rag doll, I’m someone’s child” hangs in the air. Combs sits at the defense table a few yards away, expressionless, as his ex-girlfriend’s message condemning his violence is entered into the record.

Estevao presses on, unfazed by the emotional weight of the quote. She produces another set of text exchanges, this time aiming to show the jury a different side of Cassie.

Estevao: You referred to that night as “Friday at the InterContinental.”

In fact, in another message you told him, “We need a different vibe than Friday at the InterContinental,” didn’t you?

Cassie: Yes, I did text him that. I was referring to that night.

Estevao: And Mr. Combs replied, “Fuck Friday, I don’t even want to do that again,” to which you responded, “LOL true,” correct?5

Cassie: (swallowing) Yes. He said he didn’t want to repeat that, and I—I agreed in that text.6

The defense attorney lets that sink in: after the alleged assault, the couple exchanged apologies or at least mutual acknowledgment that it was a night to forget. It suggests, Estevao implies, that Cassie stayed with him by choice even after the violence.

Now Estevao pivots to the subject of the trial’s most salacious allegations – the “freak offs.”

These were, according to Cassie’s prior testimony, twisted sexual encounters orchestrated by Combs in which he would watch her engage in sex with hired escorts. Estevao’s aim is to show Cassie as a willing participant rather than a victim.

Estevao (arching an eyebrow): Ms. Ventura, you’ve testified about so-called “freak offs” – group sex sessions with male escorts that Mr. Combs allegedly forced on you. But isn’t it true that in the beginning, you were enthusiastic about these encounters?

Cassie tenses at the suggestion, and a few jurors shift in their seats. Estevao doesn’t wait for Cassie to answer before drawing the jury’s attention to a new exhibit – a transcript of a 2010 text conversation.

Estevao: Let’s look at your own words from June 2010. You texted Mr. Combs that you wanted to talk to him about the “freak offs,” adding, “It’s not a big deal.” Did you write that?7

Cassie: (hesitating) I may have… if it’s there, I must have.

Estevao: It is there. And Mr. Combs replied, “Now you don’t want to do it anymore. Oh, I already know. You so predictable,” to which you answered, “I wasn’t going to say I didn’t want to do it anymore.” You were reassuring him, weren’t you?

Cassie: I was trying to… navigate his moods. I didn’t explicitly tell him I wanted to stop at that time.

Estevao smiles thinly and reads another line from the 2010 exchange.

Estevao: In that same text thread, Mr. Combs wrote, “I’m not going to play no games with you and you ain’t gonna keep shutting me down,” and you replied, “I’m not shutting you down. I never do. If anything, it’s always the other way around.” Those are your words, correct?

Cassie: Yes. That’s what I wrote.

From the defense table, Combs’ attorney Mark Geragos observes impassively as Estevao systematically lays out Cassie’s past messages. Estevao continues:

Estevao: You even suggested bringing another woman into these sessions at one point, didn’t you?

Cassie: Yes, I did suggest that, I… I thought maybe it would please him in a different way .

Estevao (nodding): So you were actively participating and making suggestions for these “freak offs,” correct?

Cassie: (quietly) At first, I was trying to do what would keep him happy. I didn’t know how to say no…

Estevao steps closer to the witness box, voice rising slightly.

Estevao: You didn’t know how to say no? Or you didn’t want to say no? You were an adult, free to leave at any time, weren’t you?

Cassie opens her mouth but falters. Before she can frame an answer, Estevao presses on, changing tack:

Estevao: Let’s talk about your behavior outside of Mr. Combs’ presence. You were recorded threatening a man over a certain video, were you not? A DJ in Miami?

Cassie blinks, realizing what’s coming next – one of the most embarrassing episodes related to the “freak offs.” The defense team has just played an audio recording for the jury: Cassie can be heard in a heated confrontation with a DJ who claimed to have seen an explicit video of one of her freak-off encounters.

Over the courtroom speakers moments ago, Cassie’s own angry voice rang out: “I’ve never killed anybody in my life but I will kill you.”8 In the recording, she was threatening this DJ because she feared the existence of a secretly recorded sex tape.

Now Estevao pounces on that recording:

Estevao: That was you on the tape saying, “I will kill you,” correct? Threatening to kill a man over a sex video?

Cassie (sighing, ashamed): It was me. I said, “I’m going to kill you.” I was terrified… I was desperate to keep that video from getting out .

Estevao (with a hint of sarcasm): Terrified that your reputation would suffer? You weren’t being forced in that video, were you? That was a consensual encounter with a male escort, Jonathan Oddi, and you were worried it might go public.

Cassie’s eyes glisten as she explains herself to the jury:

Cassie: I was worried about the video going public – yes . I was afraid of what Mr. Combs would do if that tape got out, and I… I wasn’t thinking. I said something horrible because I was so scared.

Estevao allows herself a small satisfied smile, having shown the jury Cassie’s capacity for anger and the lengths she went to hide aspects of the “freak off” life. Now the defense lawyer moves to another line of attack: Cassie’s motivations and financial incentives.

She holds up a document – Cassie’s 2023 civil lawsuit, which was settled out of court.

Estevao: Ms. Ventura, you sued Mr. Combs in 2023 and ultimately received $20 million in a settlement, correct?

Cassie: We reached a settlement, yes. I can’t comment on the amount… but it was widely reported.

Estevao: After securing that money, you canceled a planned concert tour, didn’t you? You were scheduled to tour in late 2023, but you called it off right after getting the settlement. Isn’t it true you no longer needed the money from touring?

Cassie (firmly): That wasn’t the reason why I canceled . I was overwhelmed by everything – the lawsuit, the publicity… (her voice breaks a little) It wasn’t about the money.

Estevao raises an eyebrow but continues coolly. She now references a series of text messages exchanged after Cassie and Combs had broken up – messages suggesting amicable feelings.

Estevao: You remained in contact with Mr. Combs even after your relationship ended, didn’t you? In fact, you had dinner with him in Malibu and even went home with him afterward, after the alleged rape in 2018 – correct?

Cassie: (looking down) I did have dinner with him that one time… I was confused. I… we did end up at my place.

Murmurs ripple through the courtroom at this admission that Cassie voluntarily met with Combs after the events she described as rape. Estevao seizes the moment:

Estevao: You also sent him friendly messages. For example, in August 2018, you wrote to him, “Hit me when you can ❤️,” did you not?

Cassie: I don’t recall that exact message… I might have, I was trying to keep things calm between us.

Estevao: And in later messages, you told him you didn’t hate him and that you “wouldn’t be at this point” in life without him, correct?

Cassie: (quietly) I did say I don’t hate him. I told him I have love for what we had in the past .

Estevao: In fact, Mr. Combs texted you “We’re honestly lucky to be alive… I’m glad you found someone. You deserve the world.” He was practically wishing you well in your marriage, wasn’t he?

Cassie: He… he did send that text. I didn’t respond by meeting him, though. I kept my distance after that.

Estevao: When he said you were “lucky to be alive,” you understood he meant because of your heavy drug use together, right?

Cassie: Yes – we did a lot of drugs back then . Surviving that… It’s something we both acknowledged.

At this point, Estevao glances at the clock. It’s approaching midday. She shuffles her papers, perhaps sensing the judge’s impatience to move things along. She decides to finish with a flourish that brings the focus back to the trial’s core allegations.

Stepping closer to Cassie one last time, Estevao’s tone is sharp:

Estevao: Ms. Ventura, you claim you were a victim, but isn’t it true that you stayed with Mr. Combs out of jealousy and choice? You chose to endure this because you didn’t want to let him go. Every day for over a decade, you made a choice to stay – isn’t that right?

Cassie’s attorney leaps up: “Objection!” The prosecution objects to the argumentative characterization, and Judge Subramanian sustains the objection with a curt nod. Estevao purses her lips, realizing she’s gone as far as she can for now.

Estevao (softly): No further questions, Your Honor.

She returns to the defense table. Cassie exhales shakily and takes a sip of water. It’s clear from her reddened eyes that this gauntlet of cross-examination has been grueling. A court officer offers her a tissue, and she dabs at her eyes, determined to maintain composure. The worst is over – but the most emotional moments are yet to come on redirect.

Lunch

After a brief lunch recess, the prosecution begins its redirect examination, aiming to clarify Cassie’s statements and rehabilitate her credibility. Assistant U.S. Attorney Lauren Mack leans forward with a gentle tone:

Prosecutor (AUSA Mack): Cassie, earlier you acknowledged sending some texts that sounded cooperative or even enthusiastic about “freak offs.” Let’s talk about that. In the beginning, were you open to these “freak off” sessions?

Cassie: At first, yes. I was open to trying them in the very beginning because I wanted to please him .

Prosecutor: How did your feelings change over time?

Cassie: Over time I grew to dread them. I told him on multiple occasions I didn’t want to do them anymore .

Prosecutor: If you tried to refuse a “freak off,” what would happen?

Cassie pauses, her eyes welling as memories flood back.

Cassie: I felt like I couldn’t refuse. If he wanted a freak-off, then any work I had would just… take a backseat . I had to do freak offs – there was no real choice. And if I tried to leave before he said it was over, he would get violent .

She glances at the jury, her voice cracking slightly. “He would get violent if I tried to stop,” she repeats quietly, and jurors recall the video of the InterContinental incident – a stark confirmation of her words.

Prosecutor: Cassie, you mentioned you felt you “had another job” during those years. Can you explain what you meant by that?

Cassie’s face flushes with emotion. She knows this is the heart of it – how those “freak offs” consumed her life and identity.

Cassie: My music career… it changed after I started dating him. My whole life became about keeping him happy. He made me turn down opportunities, cancel appearances – everything was about serving his needs . Honestly, it got to a point where organizing those “freak offs” was my job. Basically… basically a sex worker, is what I felt like .

A stunned hush falls. Cassie’s blunt description — “basically a sex worker” — prompts an immediate reaction.

Estevao (jumping up): Objection! Move to strike.

Judge Subramanian, eyebrows raised at the remark, addresses the jury:

Judge: The objection is sustained. The jury will disregard the witness’s last characterization.

Cassie presses her lips together, fighting back tears. The prosecutor nods and continues, careful to draw out Cassie’s meaning in acceptable terms.

Prosecutor: Let’s focus on facts. Mr. Combs required you to be available at any time for these sessions, correct?

Cassie: Yes. His moods affected my whole life – my career, how I felt about myself, my self-worth . If he was in the mood for a freak-off, everything else in my life had to stop. I had to do it, no matter what.

Prosecutor: What did you have to do to prepare for a “freak off”?

Cassie (sighing deeply): I had to get myself ready from head to toe, get the room ready… arrange the escorts, all of it . He brought me into a world I didn’t know or understand . I never imagined my life would involve… that kind of degradation.

Prosecutor: Did you want to be with those other people – the escorts?

Cassie: No. I only ever truly wanted to be with him. I was in love with him and terrified of losing him or angering him . That’s the only reason I went along with it in the beginning. I thought if I did what he wanted, he’d be satisfied and not… hurt me.

Her voice hitches on that last phrase. She pauses to compose herself, one hand resting on her swollen belly unconsciously . The prosecutor gives her a moment.

Prosecutor (gently): Cassie, can you explain to the jury why you stayed as long as you did, under those conditions?

Cassie nods through tears. This is the crux of her story – the mix of fear, love, and control that kept her ensnared.

Cassie: I was worried for my safety. I was worried for my career. But I also… I was in love with him. I worried that if I didn’t do what he wanted, he wouldn’t want to be with me anymore . I know that sounds strange given everything, but that was my mindset. He had broken down my confidence so much that I believed I had no other choice.

Several jurors exchange glances, some visibly moved by the raw honesty of Cassie’s admission. Even a few observers in the gallery wipe their eyes. Cassie’s husband watches intently, his hands clasped tightly in front of him.

The prosecutor’s voice hardens a bit as she turns to the physical abuse component:

Prosecutor: Did Mr. Combs ever physically harm you during these “freak offs”?

Cassie closes her eyes for a moment, then answers:

Cassie: Yes. He beat me more than once during them . If I didn’t perform how he wanted or if I displeased him somehow, he… he would hit me. I remember once I had a urinary tract infection and was in pain, but he still demanded a freak-off and got angry when I wasn’t responsive enough .

Her composure finally cracks as she relives these traumas. Cassie’s voice breaks and tears spill down her cheeks.

Cassie (through tears): It made me feel like dirt. It made me feel worthless … like I was just there to be used.

She sobs softly, and the prosecutor steps forward consolingly.

Prosecutor: Cassie, take your time. You’re doing great.

Judge Subramanian leans forward, concern on his face, but Cassie raises a hand indicating she can continue. She sniffles, regaining just enough steadiness to proceed. The prosecutor decides to address the defense’s implication that money motivated Cassie.

Prosecutor: Earlier, the defense suggested you got a $20 million settlement and that’s why you stopped your tour. What would you say to anyone who thinks you went along with abuse for a payday?

Cassie’s teary eyes flash with resolve. She answers hoarsely but forcefully:

Cassie: I’d give that money back in a heartbeat if it meant I never had to endure those “freak offs” in the first place . If I never had to have “freak offs,” I would have had agency and autonomy… and I wouldn’t have had to work so hard to get it back, to feel like a human being again .

Several jurors nod subtly, empathy etched on their faces. In the gallery, someone lets out an audible sniffle at Cassie’s declaration. Even Combs, who has maintained a stoic demeanor throughout, shifts in his seat, folding his arms tightly.

Prosecutor: Cassie, just to be absolutely clear – do you have any doubt about what happened on the night in 2018 that you described as rape?

Cassie meets the prosecutor’s gaze, then the jury’s, with unwavering certainty:

Cassie: No. I have no doubt. He raped me .

Her simple answer resonates in its finality. The prosecutor nods, having allowed Cassie to reaffirm her truth.

Finally, the prosecutor glances at the defense table as if to preempt any suggestion that Cassie bears hatred or vendetta.

Prosecutor: How do you feel toward Mr. Combs today?

Cassie takes a deep breath, wiping her tear-streaked face. Her answer is thoughtful, not spiteful:

Cassie: I don’t hate him… I have love for the past and what it was . But I also have a lot of pain for what he did to me. I’m here because I want to finally break free of that pain – and to make sure no one else has to go through what I did.

With that, the prosecutor concludes:

Prosecutor: Thank you, Cassie. No further questions.

Cassie sinks back in her chair, emotionally exhausted but relieved. The judge turns to the defense table.

Judge: Ms. Estevao, anything further?

Recross and Conclusion

Estevao rises once more for a brief recross-examination, her expression measured. She knows the jury has been moved by Cassie’s testimony, but she makes one last attempt to mitigate the damage.

Estevao (coolly): Ms. Ventura, you testified that you initially agreed to those “freak offs” because you loved Mr. Combs. You knew they were his preference in the bedroom, didn’t you?

Cassie bites her lip. There’s a pause. She answers quietly:

Cassie: Yeah. I knew it was something he liked sexually .

Estevao: And you wanted to make him happy at first, correct?

Cassie: At first, yes.

The defense attorney nods, having gotten Cassie to reaffirm that the origin of these acts was tied to consensual experimentation, even if it later devolved.

Realizing there is little more to gain without appearing callous, Estevao yields.

Estevao: No further questions.

At the judge’s indication, Cassie slowly rises from the witness stand. For a moment, the courtroom observes the pregnant young woman standing tall after days of gut-wrenching testimony. Judge Subramanian offers a solemn nod:

Judge: Ms. Ventura, you may step down. Thank you.

Cassie steps down carefully. As she walks past the defense table, she does not spare a glance at Sean Combs. Combs himself sits rigidly, jaw clenched, staring ahead at nothing.

Cassie exits the courtroom aisle where her husband stands waiting. Though not a word is exchanged here, the relief on Cassie’s face is evident as she grasps his hand briefly.

In the hushed courtroom, the jury watches this silent moment of closure. They have witnessed four days of testimony filled with lavish excess and brutal abuse – freak-off orgies, threats, blackmail, violence, and heartbreak. As court adjourns for the day, the jurors are left with Cassie Ventura’s final words echoing in their minds:

“I had to do freak offs… It made me feel like dirt… I’d give that money back if I never had to have ‘freak offs.’”

Her ordeal, laid bare in vivid detail, has transformed the sterile courtroom into a stage of human tragedy and resilience.

The dramatic crescendo of May 16, 2025 will loom large when it comes time for the jury to render judgment on Sean “Diddy” Combs.

Until next time,

Dancer, Writer, Buddhist.

https://au.rollingstone.com/music/music-news/cassie-ventura-sean-combs-trial-testimony-last-day-76909/

https://toofab.com/2025/05/15/everything-cassie-said-freak-offs-violence-blackmail-diddy-trial/#:~:text=Right%20off%20the%20bat%2C%20she,what%20that%20meant%20was%20different