Law&Crime Sidebar - Johnny Depp's Lawyer on 5 Bombshell Moments in P. Diddy Sex Trafficking Trial

Episode Date: May 23, 2025

The second week of Sean “Diddy” Combs’ federal trial is in the books. As the prosecution prepares another round of witnesses, Law&Crime’s Jesse Weber sits down with attorney Ben Chew, who famously represented Johnny Depp in civil court, to discuss the most major moments so far.PLEASE SUPPORT THE SHOW: Get 15% off OneSkin with the code SIDEBAR at https://www.oneskin.co #oneskinpodHOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger, Christina O'Shea & Jay CruzScript Writing & Producing - Savannah Williamson & Juliana BattagliaGuest Booking - Alyssa Fisher & Diane KayeSocial Media Management - Vanessa BeinSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Personal assistance, freak-offs, alleged blackmail, celebrities, extreme violence, and drugs, guns, and baby oil. If you thought week two of Sean Diddy Come sex crimes trial wasn't going to be explosive, you'd be wrong. We are catching you up on some of the major moments that happened in court. Welcome to Sidebar, presented by Law and Crime. I'm Jesse Weber. Well, after an explosive

first week in the Sean Diddy Combs criminal trial with opening statements, testimony that included the star witness in this case, Cassandra Cassie Ventura Fine, we entered week two. And I would describe week two so far as, because at the time of this recording, we haven't quite finished it up yet. We're recording Thursday morning, so just entering into testimony of day nine. But it seems to me the theme for week two was corroboration, meaning corroborating the testimony of Cassie. And also, too, trying to prove the finer points, the finer elements of the racketeering charge. And we're going to go over those big moments from week two. But yes, Combs is accused and charged with racketeering conspiracy, that he formed this criminal enterprise engaged in a pattern of a legal activity,

that he entered into a criminal agreement to further the interests of this criminal enterprise, that this included the repeated abuse, threatening, coercion of women into these sexual performances known as freak-offs, makes up the sex trafficking charges too, and he also faces charges of transporting victims and commercial sex workers for the purposes of prostitution. And a lot happened this week. A lot happened this week. So, to get into a recap and analysis of week two, let me bring in a claim trial attorney, Ben Chu, who, as we know, famously represented Johnny Depp in his high-profile celebrity trial against Amber Heard. And as we will talk about later, one of the witnesses that testified in that trial actually testified in this trial.

But we'll save that for the end. Ben, great to see you. Thanks for coming here on Sidebar. You're most welcome. Nice to be here. Thank you, Jesse. You got it. So let's talk about another celebrity who took the stand this week. Okay, started off Dawn Rashard from Danity Kane. Now, she filed her own lawsuit against Ditty, too. Okay. Now, she actually, returned to the stand, continued her testimony from the week prior, and she claims that she witnessed Diddy attack Cassie, including hitting her in the head with a skillet. She claims that Diddy punched Cassie at a dinner that was attended by other high-profile people like Usher and Jimmy Iveen and Neo. She claimed she observed injuries on Cassie. She claimed that Diddy made a

perceived threat to her, quote, he said you could go missing that we could die. She testified that Combs had drugs and guns, but on cross-examination, she was pressed about why did she try to stay in contact with Diddy to work with him? She was questioned on perceived inconsistencies between her testimony and things that she said in the past to authorities. It was a really tough cross-examination by Sean Combs' defense counsel Nicole Westmoreland. Ben, how do you think she helped the prosecution and was she reliable? I think she did help the prosecution and what you suggested earlier in terms of corroboration, all these witnesses seem to be confirming the testimony of Cassie Ventura.

And of course, she had the ultimate confirmation in the video, which was so powerful and kind of indelible, probably in the juror's minds. I agree with you. I think the cross-examination did score some points. But when you have the quantity of witnesses saying essentially the same thing, I think it's pretty powerful for the prosecution. And she furthered certain points, right? the idea of why Cassie couldn't leave.

Well, maybe this helps support Cassie couldn't escape, right? She testified that she saw staff members there. They didn't intervene in what was going on. And I wonder if it supports also the force component of sex trafficking, right? You know, this idea that force was used as a way to induce Cassandra Ventura into these sexual episodes, these freak-offs. And then I also wonder if the repeated physical violence and the threats goes into the pattern for racketeering. because the racketeering charge takes up so many pages of the indictment. I don't care which indictment you're looking at.

There's multiple superseding indictments. And it focuses on Combs, not just allegedly abusing or attacking, named victims, right? Like alleged victim number one, Cassandra Ventura, but other people and other women. And I think that she goes to support that, right? Completely. And I think particularly the danger and the threat element seems to be a recurring theme, the violence, the threat of violence, the threat of violence. the threat of violence and the apparent basis of the threat, I think, I think helps the prosecution a great deal. Also, real quick, totally off topic, but I want to thank our sponsor, OneSkin

for this episode. You know, being on camera as much as I am, having the right skincare products matters, that you matter to you too. Our skin changes as we get older. There's dryness, there's deeper wrinkles, but that's why we have One Skin. So One Skin was founded by an all-woman team of scientists who developed the proprietary OS01 peptide. So this peptide, targular cellular senescence. It is a key hallmark of aging. It's scientifically proven to decrease lines and wrinkles, boost hydration, help with thinning skin. They have over 4,000 five-star reviews for their full line of face, body, sun, travel-sized products. And one of the things I like about OneSkin is how easy it is to integrate into my daily routine. Just a few simple steps,

good to go. So for a limited time, you can try OneSkin for 15% off when you use the code sidebar at checkout at one skin.co. That's 15% off at oneskin.com with code sidebar. Remember to tell them that we sent you there when they ask where you heard about them. Invest in the health and longevity of your skin with one skin. I'll tell you what, your future self, definitely going to thank you. How bad is the cross-examination for her though? Because she apparently allegedly told different versions of stories like the egg story. So one story, apparently she said Did he just threw eggs at Cassie? Then she testifies and said she saw Diddy hit Cassie with the skillet. You know she filed her own lawsuit. There was an instance where she was questioned how on

March 18th, 2025, she didn't say anything about people go missing. And the defense asked her, you said Mr. Combs made a death threat, one that you didn't recall seven times. Do you think this hurts her? Yeah, I do. I mean, I think the defense definitely scored points. Well, then we had Kerry Morgan. So it wasn't just Don Rashard who testified. We had Kerry Morgan used to be best friends with Cassie. She too claimed she observed Diddy be violent with Cassie, including allegedly dragging her by her hair in Jamaica, kicking her in another incident, that Cassie lost her spark while she was in this relationship with Diddy, that he spoke down to Cassie regarding her appearance and her behavior, that he would constantly call Morgan looking for Cassie,

even Christina Corum, Combs' former chief of staff, would reach out. But she also testified that she too was an alleged victim of Combs' abuse. She testified that she was at Cassie's house when Diddy showed up, choked her, hit her in the head with a wooden hanger, says she had a concussion from that. And she even claims that she was paid $30,000 by Diddy and signed an NDA and that this actually went through Cassie. And she claims she's no longer friends with Cassie after all of this. Quote, the reason I stopped speaking to her was because she was not supportive of me after that incident. I draw my line at physical abuse. Now, she was cross-examined too. And the cross was interesting because it focused a lot upon whether it was

jealousy fueling Combs violence rather than a need to control Cassie for purposes of sex trafficking, whether Cassie was jealous of the love that Combs had for the late Kim Porter. So, Ben, it seems to me she hits a lot of different potential elements of the charges here. But of course, it does become a question, is what she's describing domestic violence or is what she's describing sex trafficking and racketeering? Yeah, and it could be both. I mean, that's where it becomes dicey for both the prosecution and in the defense. and will it matter to the jury or will just the fact of the violence and the threats

kind of overtake the nuances of the line between domestic violence and conspiracy and racketeering? Do you think that this testimony from Kerry Morgan and Dorn, Richard, helps establish that he was operating a criminal enterprise filled with threats and fear and violence? Do you think it helps that? I think it helps, but I still think that they need to do more on the technical elements of those crimes. And I suspect that we are going to be seeing that as the trial progresses. I think the control aspect is key for sex trafficking, right? So when you talk about sex trafficking,

it's harboring, maintaining, transporting somebody for purposes of commercial sex. So if you're talking about sex with sex workers, and also using force, fraud, or coercion to induce that person to engage in this behavior. The idea of controlling is very, very important. The $30,000, though, you know, one of the things we talk about is the underlying crimes for racketeering, to prove racketeering, they need to prove at least two predicate crimes. $30,000. Is that bribery? Well, it certainly, it certainly suggests the criminal aspect as opposed to the jealousy aspect, because that's the only thing that would explain the financial, why pay? That's a great point. And, well, you know, he could say, I didn't want to be embarrassed.

I didn't want to be embarrassed. It was not to cover up a crime. I didn't want to be embarrassed. I didn't want to embarrass anybody. But we move on to two other ways. witnesses. So you want to talk a little bit more about racketeering? I think that these witnesses could be arguably the most important witnesses as of yet for racketeering. Maybe. David James George Kaplan, so the former assistance to Diddy. So if you're talking criminal enterprise and a conspiracy and a criminal agreement to commit racketeering activity and that Combs used his staff to commit crimes and cover them up, you need the inner circle to testify, right? So David James testified that he was told when he was first brought in, quote, this is Mr. Combs.

kingdom, we're all here to serve in it. Okay. Testified about helping to prepare hotel rooms for what prosecutors allege were elaborate sexual encounters, freakoffs, right? Clothing, toiletries, food, drinks, a medicine bag. Then there were these so-called personal items like baby oil, lubricants, condoms. Interestingly, he would be reimbursed for getting the food and the drinks through official bad boy entertainment channels, but the personal items, those payments were apparently made in cash, stacks of bills that James says did he kept in a Louis Vuitton bag and personally hand out, and that Combs allegedly blackmailed him, blackmailed him with footage he had of James, high on drugs, that he was forced to take lie detector tests as part

of his job, how Combs brought three guns with him to confront rival Shug Knight at a diner. And he talked about Cassie, too, said that at one point he said to her, why doesn't she just leave Combs, to which she allegedly responded that Diddy controlled her career, paid her allowance, paid her rent, and then he even testified that Combs told him privately, Cassie was very moldable. Then you had the other former assistant, George Kaplan. So he testified to cleaning up hotel rooms after these sexual events, talking baby oil, liquor bottles, drugs all around, and he was told that this was done to allegedly protect Diddy's public image. So it's kind of interesting when you think about a criminal enterprise and there needs to be a common purpose.

testified to receiving drugs for Combs at one point, testified to the demands of the job, how he was under constant threat of being fired. Ben, I laid a lot of it out. You think these witnesses help prove racketeering? Absolutely, Jesse. I think that I think they're very strong. They were, they're right next to him every day. And it continues the theme of threats and money, which I think is very helpful to the prosecution. And what you mentioned about the accounting for it, that the company paid for the food and the drinks and he paid cash for the other the drugs, etc. shows a consciousness of guilt. It's nothing spontaneous. That suggests more the criminal aspect of it. So I think that part of it was powerful. Yeah, not that as if it was just,

hey, this is his private sex life. You know, there's nothing nefarious going on to pay in cash when you could have used company resources to pay or reimburse, it's interesting to think about. And also there's that corroboration again of maybe why Cassie couldn't leave and corroboration that these freakoffs even existed. Although I will tell you, Kaplan testified he was given immunity. James talked about a proffer agreement. Help or hurt their credibility. Well, it hurts their credibility a little bit, but that's that's fairly standard in these criminal cases, as you know. So the defense scores are a few. points about that, but I think ultimately, I think the testimony was strong.

It's not a shocker considering we're talking about a racketeering conspiracy and Sean Combs is the only defendant, right? If you're talking about him being leading a criminal enterprise, no one else is charged. Of course, you're going to expect the people who testify against him have some sort of protection. Yeah, but the jury has to weigh and assess that. So now I want to get into something else. I want to get into the testimony of what was found, A, when Combs was arrested in New York in September 2024, what was found in his hotel room at the Park Hyatt, and B, what was found at his Miami property when it was raided by the feds last year. So let's start with the hotel room.

So again, he comes to New York voluntarily to surrender himself to authorities. He knew he was going to be arrested. He knew he was going to be charged. Probably did this because he thought it would help him make bail, which, by the way, he was never granted. But apparently, and as documented in photos, in that hotel room were medications. There were baggies of a pink powder that tested positive for ketamine and MDMA. This is the testimony of one of the witnesses.

There was lubricant. There was several bags and bottles of baby oil. There was a fanny pack with $9,000 in cash. There was a lighting device. There was evidence that a woman was staying there too. Ben, is this bad? Does it look like he's continuing purported freakoff? even right to tell the moment of his arrest?

And if so, why would he bring this stuff? Well, absolutely. It makes it seem far less like a personal choice and much more like a systematic enterprise, the lighting in particular, the drugs, all of this is consistent with the prosecution's theory. Why would he bring it knowing, I mean, if you know, here's the thing, right? Cassandra Ventura talked about Freakoff's in her lawsuit, right?

I think he knew that she was cooperating with the government. If he knew he was being investigated for this, why allegedly bring the very materials of the crime with you when you're arrested? Well, it may be his perception of invincibility that he had been doing these things for a long time. He's a very possible, very powerful person. People in his organization touted to him. So that could explain it. Could be hubris. Could be that he just thought that he would never really get.

caught. But then we heard from an agent with Homeland Security, okay, testified about the raid that was conducted on Combs Miami Mansion last year, okay? Found a Gucci bag filled with ketamine and MDMA, bottles of lew, baby oil, a handgun in a suitcase, cell phone stuffed in a boot, AR-15 assault rifles with defaced serial numbers, platform heels, lingerie, condoms, sex toys. Across examination, the defense counsel seemed to criticize the level of force. for the search. They question whether Diddy's fingerprints or DNA were even on the handguns, Ben, what's the value of all this? Well, the value, I think, goes to just the volume of materials suggests that this was more than just his personal use. And I think the most damning was the AR-15. I mean,

I could see a jury understanding why somebody, like Diddy, would want to have his own firearm for protection, though he has guards really to do that. But the AR-15s really suggest something more nefarious. There's no real reason that anybody should have an AR-15 legal or not. I mean, I think that begs a lot of questions. Look, I think they need to prosecutors, they need to convince this jury that we're dealing with the mafia, right? Because that was what RICO was first established for, organized crime. And if you go into his mansion, he's got guns and he's got paraphernalia, that's how they do it. They need to convince this. this jury that he's ahead of a criminal enterprise.

Now, it doesn't have to have a charter. It's not a criminal organization where you need a charter or bylaws, but you know, some association in fact. And if you build up the power, the influence, you build up the resources, that's how they do it. Not saying they're going to get it, but that's how they do it. I think that's important. Now, we have talked a lot about Cassie and the witnesses who helped her credibility.

Who I haven't talked about yet was her mother, Regina Ventura. She too testified this week, and she testified to seeing injuries on Cassie, took photos of them. She testified that Combs threatened to release sex tapes of Cassie because she was in a relationship with Kid Cuddy, that Diddy was demanding $20,000 because he was angry for all the money that he spent on Cassie when she's now in a relationship with Kid Cuddy. So what does Regina do? Well, she claims she testified that she took out a home equity loan to pay it. But the money was actually returned to her and I will tell you it was some explosive testimony. The defense didn't even question her, Ben, which I thought

was interesting to considering what she was alleging yeah i thought the testimony was very strong i can understand why they wouldn't want to cross-examine her in any depth because she's such a sympathetic witness they might have asked the one word one one one sentence question you're cassie ventura's mother right i mean just to remind the jury that that she obviously would would do anything for her daughter. But I think they were right not to go after her very strongly because I think it would really poison the jury. It may be. You could be 100% right. I mean, there were avenues for her them to question her about. I mean, it's a serious allegation that Combs was blackmailing, right, Ventura. And blackmailing is a very important theme in a sex trafficking case. So

interesting that they didn't question her about it. Now, let me tell you who we heard from also. We heard from another witness named Sherey Hayes. Now, he is not only known as Sherey Hayes, he is also known by his stage name, The Punisher. So this is a stripper who says that he was hired by Didy and Cassie to perform for them numerous times, including, by the way, at a Trump Tower Suite, where apparently Cassie was wearing a robe and a wig, and Combs was there in the room naked. He was handed $800 in cash. Testified, he performed for them eight to 12 times, and that Combs was directing these encounters, which is, what, by the way, Cassandra Ventura had testified to. But here's the thing. He also testified, it never seemed to him that Cassie was uncomfortable during the freakoff sessions. And he even

testified, it seemed like it was consensual as far as he was concerned. So, Ben, why would the prosecution call him then? I had that same question because I think he was more helpful to the defense than he was to the prosecution. But again, I guess the money angle goes more to the racketeering and less to the personal. But I think he was a mixed, a mixed blessing for the prosecution. Or they're just trying to establish, hey, you know what, transportation to engage in prostitution, right? Because Cassandra Ventura is being shipped to all these different places and having relations with sex workers of some kind or people being paid for sex. There you go. Or maybe it's just to establish, sometimes I forget about it. But in every case, you just have to establish a fact.

You have to establish a freak off a curd. Yes, you can have Cassie testify about it, but you have the escorts have the sex workers testify there was a freak off i was part of the freakoff they need to establish that as a matter of fact for the jury that's a great point and and he helped them do that for sure okay ben you know how i'm going to talk about now i got to talk about dr don hughes so this is a board certified forensic and clinical psychologist who testified in your trial the amber heard johnny dep trial she testified on behalf of amber heard side and she was called here, and it seemed the reason that she was called was to have the jury try to understand how is it possible that Cassie can claim she was a victim of sex trafficking and forced to

perform in non-consensual freak-offs, but she didn't leave Combs in their long relationship. Why did it appear that she set up the freak-offs? Why did it appear that she paid workers? You have text messages where she's seemingly encouraging the freak-offs. Well, could there be psychological issues at play? And Dr. Hughes testified. about power dynamics, how abusers trap victims, including through love bombing, you know, including showering them with gifts and compliments. There's trauma bonding can cause someone to stay, a victim being financially dependent upon their abuser, the effects of psychological abuse and sexual abuse, that traumatic memories can be buried down, may take therapy to resurface for someone

to understand what exactly happened to them. And she even testified, if you're going against someone who has wealth, access, and privilege, who's going to protect me? But on cross-examination, she was questioned about the fact that she didn't examine Cassie. Okay, she's providing general opinions. I mean, she even described it as general subject matter testimony, that she's a paid expert, admitted to 60% of her income comes from courtroom testimony. She was asked about malingering, so that's about someone faking symptoms. She was also asked about financial motivations like maybe Cassie suing Diddy. So, Ben, look, you might be a little bit biased here,

but what are your thoughts on the testimony of Dr. Don Hughes? I thought that the cross-examination, in my opinion, was devastating. As you pointed out, the fact that she didn't have any interaction with either of the two, either with Diddy, which you would understand, but none with Cassie. So she's violating the Goldwater rule, which is you don't form an opinion without actual firsthand knowledge. I thought that was very damning as far as. her testimony. Also, the fact that she had only testified as an expert on behalf of the alleged

victim, I think that also showed that she had a bias and that she came across a bit as a hired gun. Well, let me ask you this from a point of law. There were certain things she couldn't testify to. Okay, so she couldn't come in and talk about coercive control. That was litigated before she couldn't testify about it. Witnesses can come in and provide general, like she says, general subject matter testimony without talking about the specifics of the case or talking about the specifics analysis of the people in the case, right? They could provide general subject matter testimony. Like, for example, in a use of force case, somebody could talk about use of force without talking about the particulars of that case. That's permitted, right? Sure. And I understand why they

tried to do it. I just don't think in this case it was particularly effective. And I think more convincing was the fact witness who testified that Cassie was somewhat passive in nature. I think that's something that the prosecution can certainly argue that she's not the type of personality who would push push up against somebody as powerful as did he. You know, it's interesting. I had this conversation yesterday. I wonder, and this is what somebody was questioning me about, would the jury look at the fact that they're calling Dr. Hughes and saying prosecution doesn't feel confident enough in its case for us to believe that Cassie was a victim. They need to call a doctor to explain why she did what she did.

That shows a weakness in their case. Or is it, listen, we have to explain to this jury how someone in Cassie's position who described vile things happening to her coming out, testifying against him now, I don't know if she necessarily has a financial motivation to go after her because she already settled her lawsuit. Why cooperate with the government? What is the reason that she's coming out now unless, of course, she really was a victim? It might not look like it in certain scenarios, but she was a victim. So you see what I'm saying?

I wonder that balance for the jury, do they say calling Dr. Hughes shows a weakness in the prosecution's case or, yeah, makes total sense because it has to explain why she stayed. There has to be an explanation there. Yeah, I think that's right. I mean, I think she checks the box. So the prosecution and closing argument can say you heard from Dr. Hughes that this is not a typical behavior in a victim, it seems counterintuitive, but it's actually the norm. So they've got that piece now for their closing argument. But of course, the defense has a piece as well

to say, well, this is a hired gun. This is somebody who always works for the alleged victim. This is somebody who had no contact with either side. And then making your point that they realize that their case is so weak, they have to bring on this hired gun. So I think there's fodder for both sides for closing argument. I think this whole case is going to come down to closing arguments. I've said it before,

I said it again. I think it's all how it's articulated, how the jury understands the jury instructions, the elements of these crimes, whether or not the burden was met, I think it all comes down to that. But Ben Shue, so good seeing you.

Thank you so much for taking the time and breaking down the big moments from week two. Thanks so much, Jesse. And that's all we have for you right now here on Sidebar, everybody. Thank you so much for joining us. And as always, please subscribe

on YouTube, Apple Podcast, Spotify, wherever you should get your podcasts. I'm Jesse Weber. I'll speak to you next time. You can binge all episodes of this long crime series, ad free right now on Wondery Plus. Join Wondery Plus in the Wondery app, Apple Podcasts, or Spotify.