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Brian Buckmire
Hi, I'm Brian Buchmire, an ABC News legal contributor and host of Bad the Case Against Diddy. You're about to hear our latest episode following everything going on in Sean Combs trial from the prosecution and the defense. Remember to hear all of our updates on this case follow Bad the Case Against Diddy. We're dropping two new episodes every week, including one that's not available anywhere else. Now, here's our episode. This episode is brought to you by Lifelock. Not everyone is careful with your personal information, which might explain why there's a victim of identity theft every five seconds in the U.S. fortunately, there's LifeLock. LifeLock monitors hundreds of millions of data points a second for threats to your identity. If your identity is stolen, a US Based restoration specialist will fix it, guaranteed, or your money back. Save up to 40% your first year by visiting lifelock.com podcast terms apply. A warning that this episode includes discussion of violence, sexual assault and suicide. So please take care when listening this week, USA v. Sean Combs has been mostly about one witness, singer Cassie Ventura, who was in a romantic relationship with Sean Combs for over a decade. Cassie brought the first civil lawsuit against Combs in 2023. It included allegations of sex trafficking and was settled quickly with no admission of guilt. This week we learn through her testimony the amount of that settlement. $20 million. For a long time, that lawsuit was the only look we had into her experience with Sean Combs. I remember when we were researching earlier episodes of this podcast, the lawsuit was one of the very few sources of information we had to draw from to try to understand her, her side of things. And now here's Cassie Ventura sitting in court, very pregnant, answering question after question, testifying to how she believes Sean Combs held her career back. How she started off participating in orchestrated sex performances called freak offs because she wanted to please Combs. How she says leaving a freak off early led to Combs beating her in the hallway of the Intercontinental hotel back in 2016. The jury saw videos of that incident captured by the hotel's surveillance cameras. Combs denies the federal charges of sex trafficking, racketeering, conspiracy and interstate transportation for prostitution. He's facing and he's pled not guilty. Under cross examination, the defense asked Cassie to read texts she'd sent to Combs. Texts they say show her willingness, eagerness and agency in the relationship. The defense also questioned whether her reluctance to participate in Combs freak offs was because she wanted their relationship to develop more and to be more than their sexual encounters. In other words, was the story more about jealousy and infidelity than the serious charges Combs is facing. One of the people keeping an extremely close eye on everything happening in the courtroom is my colleague Tonya Simpson. She's a coordinating producer for ABC's investigative unit. We're going to talk about what she heard and observed while sitting in the courtroom when Cassie was on the stand. I'm Brian Buckmire, an ABC News legal contributor and practicing attorney. You're listening to Bad Rap, the case against Diddy, this episode, Star Witness. Tanya, you and I have both been in court every day. I think we've been like line buddies as well for a while. We've heard some really incredible testimony. And I say incredible not because it's like amazing, but just almost beyond belief. Most notably from Cassie Ventura, Diddy's ex. We'll get into that in a minute. But listeners might be surprised to learn we can't take any electronic devices into the court with us. So we have to take notes. The old fashioned pen and paper. How's your wrist holding up, by the way?
Tonya Simpson
You know, my wrist is doing okay. My fingers were getting a little sore on the first day. I was starting to get a dent on one of my fingers from the pen. So I actually bought cushions to put on my pens while I'm writing. And that has helped a lot.
Brian Buckmire
And I know you guys can't see us, but Tonya's flipping through his book. One, some of the nicest writing I've seen.
Tonya Simpson
Thank you.
Brian Buckmire
Two, very small writing. And so you're like squeezing things into the margins just to make it fit, but it's still just covering the page.
Tonya Simpson
Yeah, yeah. I am a very meticulous note taker. Shout out to my grade school teachers for the penmanship.
Brian Buckmire
Okay, so Tanya, let's dive into these notes of yours and see what you think about this case. What have been some of the more compelling points each side has made this week or things that stood out to you? Maybe more so in Cassie's testimony.
Tonya Simpson
Sure. I think one of the first things that stood out for me and Cassie's testimony is when prosecutors asked her to walk through the hotel video. It was interesting to see her watching that video. I was paying very close attention to her face. I was also looking at Sean Combs face while she was watching Cass. Even Tour's husband has also been in the courtroom. I noticed him watching Diddy watching Sean Combs while the video was playing. But it was interesting to hear Cassie talk about everything that led up to what we saw in the video. And Then everything that came after she explained that they were at the hotel, they were in la, she was getting ready for a big movie premiere. And she talked about how she didn't necessarily want to do a freak off that weekend, but she felt like she needed to because she wanted her premiere to go smoothly. She talked about the fact that that was one the only times that she had ever actually tried to leave a freak off. And Cassave Ventura claimed that the reason she tried to leave that freak off is because at some point she was hit in the face, she had a black eye, and she knew she had this movie premiere coming up and she didn't want to get any more injuries before she had to hit that red carpet.
Brian Buckmire
You mentioned Cassie Ventura's husband, Alex. Fine. And I know that you and I are very close. I think you're just a little off to my side and maybe one row behind. I'm curious if you saw what I saw. I saw him staring at Sean Combs as well. But did you see the side of his face and his ear turn red as if he was getting heated?
Tonya Simpson
He turned very, very red. And when he would look at Sean Combs and kind of look at Sean Combs family, it was a very pointed stare. It wasn't a glance. He would look at them for stretches of time, like a few seconds, maybe even a minute or so.
Brian Buckmire
Yeah, I was like, I've seen that glare.
Tonya Simpson
Absolutely. I also thought it was interesting that from the moment that Cassie came into the courtroom, she would glance at her husband Alex when she walked in. While she's being questioned, she is looking very pointedly at the prosecutor. She does not look at Diddy. She is not looking over at the defense table in between questions. I've seen her glance at the jury. I've seen her look deeper down at her hands or at the screen in front of her, even when there's nothing on it. But it's notable that she hasn't made any eye contact with Sean Combs. So, Bryan, one of the legal issues that has come up this week is exactly what to do with these explicit videos and still images from the freakoffs that prosecutors presented as evidence in the case of how to present them, who gets to see them. ABC was actually part of a coalition of news organizations that argued that the media, or at least a small pool of journalists, should be able to see these videos so that we can describe what's in it, report on it, but not to actually publish the images or videos. The judge said no. So only the jurors, the witness, Cassie, were Able to look at these still images on screens in front of them. The attorneys had hard copies of the images in a binder. I wonder what you make of that decision.
Brian Buckmire
I understood why the judge came to the conclusion that they did. There are competing constitutional rights in the courtroom at any given time. Privacy rights of the alleged victim, constitutional rights of the defendant, but also constitutional rights of the public and the media. And I think when all of these butt heads, the court errs on the side of the protect the person who has gone through these alleged acts. While they are allegations, there are documentations and photos of them as well. And I think the belief is that we as journalists can have the ability to articulate what we saw and heard in court sufficiently enough to inform the public without, as the court suggested, re traumatizing Cassie or anyone else who takes the standard. We do have the opportunity, because we're in court, to see how the jury and people in the courtroom react. So how did they react when they saw some of these very graphic pieces of evidence and also hear the testimony?
Tonya Simpson
There were definitely reactions from the jury during some of the really graphic points. At one point when Cassie was describing being urinated on, I saw several jurors look down at the floor and shake their heads. They looked a little disgusted. During Cassie's testimony, when jurors were given the opportunity to see still images from videos of freakoffs, there were a couple of jurors I noticed, would look at the screens in front of them and look away pretty quickly, like they didn't really want to look closely. Something else that I noticed during Cassie's testimony that wasn't as graphic. The jurors are riveted. Their eyes are on her. A lot of times in court, kind of it looks like a tennis match. The jurors will look back and forth between the prosecution or the defense attorney and back to the person they're questioning. During Cassie's testimony, most of the jurors have been locked in. I've seen some of them leaning in. They're taking a lot of notes during these graphic sections of the testimony. Not a lot of note taking. Not a lot of looking at Cassie. It is a lot of looking down, looking uncomfortable, like I said, looking a little disgusted and even a little sad for her.
Brian Buckmire
Tonya, in the morning, Cassie came across as very stoic and matter of fact, in a way, to me, that was a little jarring. I think if anyone is describing the sexual abuse and the trafficking or the allegations thereof, you would be trepidatious, you would be shocked. You would Say it as a shocking thing, but she talked about it as plainly as I'm talking about. Yeah, you're wearing a green sweater. Yeah. You have headphones on. And she was just matter of fact. But in the afternoon when the testimony got very dark, things changed, right?
Tonya Simpson
Yeah. During the morning it was a lot of what I would say, technical questions, the kind of the who's the what's the where. And you're right, she was soft spoken, but it was very monotone where she kind of ticked through some of the names and the places that the freak offs would happen. Wednesday afternoon they asked her questions about how she was feeling and questions about her going to rehab and going to trauma therapy after her and Sean Combs relationship ended. And we saw a very different Cassie. It started with her getting choked up a little bit when she talked about feeling like she has ptsd. And then she started sobbing when she recounted a story of how she didn't want to live anymore. At one point, at one point she apologized to the prosecutor and said, I'm sorry, I just need a minute. The prosecutor offered her a box of tissue and gave her a second before they continued. But you could tell that it was a really hard thing for her to talk about. And yeah, I think that was one of the most emotional moments that we saw from Cassie during her testimony.
Brian Buckmire
When we come back, what are the stakes for the prosecution in having their star witness testify at the very beginning of what's expected to be a long trial?
Tonya Simpson
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Brian Buckmire
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Brian Buckmire
I'm back with Tonya Simpson. She's the coordinating producer for ABC's investigative unit and someone who's been in the courtroom paying very close attention to what's unfolding. And we're debriefing on what we observed.
Tonya Simpson
So I am not a lawyer, even though I've been spending a lot of time in court these past couple months. So I'm excited to be sitting down with someone who is, because I really wanna get your take on something. Again. Incredible testimony from Cassi Ventura. But how do you think that her testimony fits into the prosecutions to charges against Sean Combs?
Brian Buckmire
So I think when I watch trials, I watch them a little differently than the average person, which I also think is somewhat at a bit of a disadvantage. Because at the end of the day, it's not an attorney who decides guilt or innocence. It's everyday citizens who sign up and choose to be jurors. But when I listen to the testimony and I watch the jurors, I'm thinking, here is the square hole. This is the peg that the government is trying to fit into it. And is it fitting? Is a square peg too big? Is it a circular peg? Is it a triangular peg? Whatever it is. And I would say in the first day of Cassie's testimony, it didn't feel like this peg was fitting correctly into the hole. And the reason for that is, is as a former public defender at the Legal Aid Society in Brooklyn, I've represented people who have been victims of domestic violence, victims of sex trafficking, people who have sex trafficked others. And as I listened to it, I was like, does this sound like domestic violence or does it sound like trafficking? And then the first day, I was like, these sound like the elements of a crime that would be more in line with domestic violence from the facts that we were hearing. But on the second day of testimony, that's when I started to hear testimony and evidence and. And also the way that Cassie was talking about Sean Combs, I was Like, I've heard this tone before. I have heard this type of conversation before. I have heard these elements before. And that's when I started to piece together. I think they're getting closer to the trafficking allegations now. I say closer because they still need to have individuals come forward and testify to say, I was part of this criminal enterprise. Sean Comb did this intentionally for the purpose of trafficking. This wasn't just a violent relationship. I think they still need a lot of pieces, but I'm starting to see the pieces align with what the government is accusing in the second day of testimony.
Tonya Simpson
And I also think in my non expert, non legal opinion, I think that Cassie's testimony has done a lot for the charge of transportation to engage in prostitution. She has testified about multiple escorts that they hired and how these same escorts, they would see them in different cities in different states. She talked about how they would arrange travel for some of the escorts. At one point internationally, she says they flew an escort to Ibiza for a freak off. I want to get your thoughts on that. And also, what about the racketeering?
Brian Buckmire
So I always hate to look over a defense attorney's shoulder and be like, this argument doesn't really make sense. But when the defense made the argument that this is not transportation for the sake of prostitution, because Sean Combs was paying for the time of escorts and dancers, because he was just believing he was paying for their time, wasn't paying for sex, I kind of looked over at people and be like, come on now. This, come on now. I think I made this.
Tonya Simpson
Is that what you got face? Is there more coming face?
Brian Buckmire
I'm like, come on now. And the defense that they were making, I just didn't think really worked out. And it just seems like an easy layup for the government in the way they're presenting this case. So I don't see an argument to combat what you're articulating. And I agree. The easily laid out facts that make out that charge, when it comes to the racketeering, I think that's more difficult for the government. There are a lot more moving pieces that you have to fit into place. And if one moving piece doesn't fit correctly, the whole structure can fall. And I see the defense having much more opportunities to poke holes in that case or to make that structure fall when it comes to the sex trafficking charge, when you're arguing this is simply just domestic violence and the racketeering, when you're saying there is no criminal enterprise here.
Tonya Simpson
So Cassie Ventura was considered, I think, pretty much by everyone to be the government star witness, a key witness. She is one of the first people to testify. Are there pros and cons to having your star witness testify during the very first week of what is being estimated to be an up to eight week trial? Six to eight weeks.
Brian Buckmire
So the pro of having your star witness testify so early, and I don't even think they really had a choice with this. Cassie Ventura is very much pregnant to the point that I think her due date must be very soon.
Tonya Simpson
Eight and a half months.
Brian Buckmire
Yeah. And so I think for her health, the health of her child, the health of her family, I think the government's doing the right thing by getting her in and out of here as quickly as possible. So it's not really a choice in terms of strategy here, but if it was a choice and it was strategy, I think it's good in the sense of you set the tone and the tenor of the case very quickly. You understand what happened to your star witness or the alleged victim, however you want to describe them or what perspective you're looking at it. And hopefully that carries on throughout the trial. The difficulty or the downside of that is when you get to a point where you're doing your closing argument some eight weeks later, the end of June, beginning of July, you've got to keep telling people, remember what I said two months ago, remember this, remember that. And jogging their memory and trying to piece it all together can be difficult. And I think it might also amount to a little bit of a longer deliberation time because then the jury's got to get in there. They got to request testimony from two months ago.
Tonya Simpson
Hopefully their notes are as good as mine are.
Brian Buckmire
I mean, with your handwriting, we should just photocopy it and send it to the jurors. At this point, I think it would work out much better. But that's kind of the downside there. Thanks to ABC coordinating producer Tonya Simpson for joining me for this episode. Tanya, I'll be seeing you back in the courtroom. Before we go, if you or someone you know is a victim of sexual assault, please call the National Sexual assault hotline at 1-800-656-HOPE or go to rainn.org that's it for this episode of Bad the Case Against Diddy. Make sure to check out a new special from ABC News called Diddy on Trial that's now streaming on Hulu. Nightline co anchor Byron Pitts sits down with Charlucci Finney, a music producer and longtime friend of Combs, in his first network interview. Here's a clip from the special I.
Tonya Simpson
Never received a dollar from him as a payroll.
Brian Buckmire
That's my brother. Blood make you related, but loyalty make you family. You can find Diddy on trial from Impact by Nightline only on Hulu. If you have something you're curious about in the Diddy trial, leave a voicemail for me at 646-504-3221. You might even hear me answer it next week on the podcast. The number again is 646-504-3221. You can also find it on our show Notes. Thanks to everyone who's called in to ask your questions so far. The Case Against Diddy is a production of ABC Audio. I'm Brian Buckmire. Our podcast production team includes Vika Aronson, Nancy Rosenbaum, Audrey Moztek, Amirah Williams, Tracy Samuelson and Sasha Aslanian. Special thanks to Stephanie Maurice, Kaitlyn Morris, Liz Alessi, Katie Dendos and the team at ABC News Live. Michelle Margulis is our operations manager. Josh Cohan is ABC's director of podcast programming. Laura Mayer is our executive producer.
Tonya Simpson
We interrupt this program to bring you an important Wayfair message. Wayfair's got style tips for every home. This is Nicole Byer helping you make those rooms flyer. Today's style tip when it when it comes to making a statement, treat bold patterns like neutrals. Go wild like an untamed animal. Print area rug under a rustic farmhouse table. From wayfair.com Ooh, fierce. This has been your Wayfarer style tip to keep those interiors superior. Wayfair Every style, every home.
Brian Buckmire
Yeah, the NBA playoffs are here and it's about to be. Ridiculous. Unbelievable, Unfair, fair, downright nasty, straight up, can't miss, don't blink, Grab your popcorn and strap in. Cinema this isn't about who's next. This is about who's now. This time it's different. The NBA Playoff is presented by Google. Continue on ESPN and abc.
Podcast Summary: 20/20 – "Star Witness"
Episode Release Date: May 16, 2025
Host/Author: ABC News
Podcast: 20/20
Episode Title: Star Witness
In the "Star Witness" episode of ABC News' 20/20, host Brian Buckmire delves into the high-profile trial of Sean Combs, commonly known as Diddy. The trial has garnered significant attention, primarily due to the testimony of Cassie Ventura, Diddy's ex-girlfriend and a pivotal witness. The episode provides an in-depth analysis of the prosecution and defense strategies, courtroom dynamics, and the broader implications of the case.
Cassie Ventura's involvement in the trial stems from a civil lawsuit she filed against Sean Combs in 2023, alleging sex trafficking. The lawsuit was settled for $20 million without any admission of guilt from Combs. Her testimony in the current trial sheds new light on her experiences and the allegations against Combs.
Key Points from Testimony:
Career Hindrance: Cassie claims that Combs deliberately hindered her career growth.
“How Combs held her career back.” ([01:30])
Orchestrated Performances: She participated in orchestrated sex performances, known as "freak offs," to please Combs.
“She started participating in orchestrated sex performances called freak offs because she wanted to please Combs.” ([02:05])
Abuse Incident: Cassie alleges that when she attempted to leave a freak off early, Combs assaulted her in the hallway of the Intercontinental hotel in 2016.
“Leaving a freak off early led to Combs beating her in the hallway.” ([03:00])
Settlement Details: The $20 million settlement provided the first substantial insight into her allegations against Combs.
Tonya Simpson, ABC's coordinating producer for the investigative unit, provides firsthand observations of the courtroom proceedings. Her insights highlight the emotional and psychological toll the trial has on those involved.
Notable Observations:
Cassie's Demeanor: Initially stoic and matter-of-fact, Cassie's demeanor shifts as the trial progresses, especially when discussing personal trauma.
“During the afternoon, Cassie started sobbing when recounting her struggles.” ([11:39])
Husband's Reactions: Cassie’s husband, Alex Fine, exhibits visible signs of frustration and anger towards Combs and his associates during the trial.
“He turned very, very red and gave Sean Combs a pointed stare.” ([06:49])
Juror Engagement: Simpson notes the jurors' reactions—ranging from discomfort to intense focus—during graphic testimonies.
“Jurors were riveted, leaning in, taking notes during graphic sections.” ([09:46])
A significant point of contention in the trial is the presentation of explicit videos and images from the "freak offs." The prosecution sought to display this evidence to the jury, but the defense argued against its public dissemination.
Court's Decision:
Implications:
The jury's responses to the testimony and evidence are varied and indicative of the case's emotional weight.
Key Reactions:
Discomfort and Disgust: Jurors visibly reacted with discomfort during graphic testimonies, such as descriptions of sexual abuse.
“Jurors looked down and shook their heads when Cassie described being urinated on.” ([09:46])
Focused Attention: Despite some discomfort, many jurors remained intensely focused on Cassie's testimony, taking detailed notes.
“Most jurors were locked in, leaning in, taking notes during graphic sections.” ([09:46])
Brian Buckmire and Tonya Simpson analyze the prosecution's strategy, particularly focusing on the strength of Cassie's testimony in supporting the charges against Sean Combs.
Prosecution's Strategy:
Defense Arguments:
Challenges and Prospects:
The decision to have Cassie Ventura testify early in the trial carries both strategic advantages and potential challenges.
Advantages:
Setting the Tone: Early testimony from a key witness like Cassie helps establish the prosecution's narrative and highlights the core allegations against Combs from the outset.
“Setting the tone and tenor of the case very quickly.” ([19:22])
Efficiency Due to Health Concerns: Cassie's advanced pregnancy necessitated her early appearance in court to ensure her well-being and that of her child.
“For her health and her child's, getting her in and out quickly was paramount.” ([19:51])
Challenges:
Memory Retention: As the trial extends, keeping the jury's attention on early testimonies can be difficult, potentially requiring repeated emphasis on initial points during closing arguments.
“Jogging the jury’s memory over several months can be challenging.” ([20:52])
Prolonged Deliberations: Extended trials may lead to longer jury deliberation periods as jurors attempt to piece together information presented over weeks.
“Longer deliberation times due to the trial’s duration.” ([20:52])
The "Star Witness" episode of 20/20 offers a comprehensive examination of the Sean Combs trial, emphasizing the pivotal role of Cassie Ventura's testimony. Through detailed courtroom observations and legal analysis, the episode highlights the complexities of prosecuting high-profile cases involving serious allegations like sex trafficking and racketeering. As the trial progresses, the strategies employed by both the prosecution and defense will continue to shape the jury's perception and the ultimate outcome of the case.
Notable Quotes:
For those interested in following the latest developments of this case, ensure to stay tuned to ABC News' 20/20 for comprehensive coverage and in-depth analysis.