Billionaire Blackmail | Inside the High-Stakes Plot

Summary

Podcast Summary: Crime & Justice with Donna Rotunno
Episode: Billionaire Blackmail | Inside the High-Stakes Plot
Date: May 13, 2026
Host: Donna Rotunno
Guests: Herman Weisberg (Private Investigator), Andrew Stoltman (Security and Investment Fraud Attorney)
Podcast Network: FOX News Podcasts

---

Overview

In this episode, Donna Rotunno examines a high-profile alleged blackmail and extortion case involving a billionaire co-owner of the Milwaukee Bucks. Joined by private investigator Herman Weisberg—dubbed the “Mistress Whisperer”—and Chicago-based attorney Andrew Stoltman, they dissect the legal, practical, and ethical complexities behind high-stakes extortion plots targeting the wealthy. The conversation explores how such schemes unfold, the blurry lines between settlement, extortion, and coercion, and the unique challenges of handling digital evidence and AI-manipulated content.

---

Key Discussion Points & Insights

1. The Modern Extortion Landscape

• Opening Theme (00:04–00:30):

  • Donna introduces the case: what began as an online flirtation led to a blackmail/extortion attempt against a billionaire, reflecting a broader trend targeting the wealthy.

• Professional Athletes as Targets (00:21):

  • Weisberg notes: "Professional athletes fall victim to this. Very often they're on the road... and the next thing you know, the person knows who they're targeting here."

---

2. Profile: Herman Weisberg, “Mistress Whisperer”

• Career Background (00:48–02:12):

  • Weisberg details his 20 years with the NYPD, especially his decade working closely with the Manhattan District Attorney on sensitive cases, and how discretion built his private investigation reputation.

• Reputation and Approach (02:22–04:27):

  • On his nickname:
    • "I despise the word 'Mistress Whisperer.' ... I would suppose I almost had just about a split of males and females both going down these bad paths." (03:40)
  • He emphasizes neutrality and strictly working through attorneys for legal and ethical reasons.

---

3. Case Anatomy: The Bucks Owner Alleged Extortion Plot

• Case Summary (05:50–07:07):

  • Outlines the suspected extortion: an online relationship escalates, mediation fails, financial demands increase after claims of STD transmission, legal counsel becomes involved, and ultimately, an indictment is issued.

• Investigator's Role (07:07–09:23):

  • Weisberg explains separating moral judgment from legal status:
    • "I’m in a kind of a no judgment business here... I look at this specifically as that they are a victim of attempted grand larceny by extortion." (07:29)
  • Discusses cultural perceptions of blackmail and why some perpetrators (notably from certain countries) don’t understand it’s a crime in the U.S.

---

4. Fine Lines: Mediation, Extortion, and Legal Settlements

• Handling Cases & Resolutions (10:45–15:20):

  • Weisberg recounts anonymized case studies, including an affair-turned-blackmail incident resolved through involving the perpetrator’s lawyer-parent—highlighting ways these cases can avoid law enforcement if the threat is contained.

  • Reference to the David Letterman case as the rare high-profile incident made public.

• Prevalence (15:20–17:31):

  • Weisberg reiterates, “I can’t believe how prevalent it is,” especially among people of means and public prominence, including athletes and executives.

---

5. Legalities: Extortion vs. Bribery vs. Standard Settlements

• Legal Differentiation (18:31–22:00):

  • Attorney Andrew Stoltman explains the razor-thin legal boundary:
    • “Extortion is threatening physical harm, and bribery is typically threatening to expose something that nobody would want out there about themselves.” (19:17)
  • Describes procedural norms: draft lawsuits are sometimes sent to prompt a civil settlement, but escalating demands and explicit threats (as in this case) cross into criminal conduct.

• Mediation Gone Wrong (22:00–23:46):

  • Stoltman unpacks the sequence: mediation, increased demands after additional allegations (STD), new lawyers making threats, and the defendant’s possible reliance on advice-of-counsel as defense.

---

6. Prosecutorial Hurdles & Defense Tactics

• Indictment and Legal Motions (23:46–26:15):
  • The woman faces charges of bribery, extortion, wire fraud, and evidence destruction. Defense is attempting to shift blame toward counsel—in the words of Stoltman, “a little bit of a pin the tail on the donkey.”
  • Destroying documents may lead to only minor penalties; focus is on getting more serious charges dismissed.

---

7. Digital Evidence, AI, and Authenticity

• Salacious, AI-Altered, and Manufactured Evidence (26:59–29:09):

  • Already wild claims in the Bucks case, including allegations of hidden cameras and AI-generated video.
  • “She might have been bluffing because the camera that they did find... apparently contained porn, but... some images of the Bucks owner's face superimposed.” (28:21, Weisberg)

• Validation and AI Challenges (33:14–34:52):

  • Weisberg and Stoltman discuss the necessity of computer forensics experts to authenticate digital materials and how the law lags badly behind technology.

---

8. Non-Disclosure Agreements (NDAs) and Their Limits

• How NDAs Differ (31:46–33:14):
  • Stoltman: “They really are only worth the paper they are written on. ... If there's just an NDA without the exchange of cash, that tends to make them less effective.”
  • Staggered payments over time are more likely to ensure continued silence.

---

Notable Quotes & Memorable Moments

• “I whisper to everybody that was violating the law... I almost had just about a split of males and females both going down these bad paths.”
  – Weisberg, (03:47)

• “I’m in a kind of a no judgment business here... I look at this specifically as that they are a victim of attempted grand larceny by extortion.”
  – Weisberg, (07:29)

• “You can't hold somebody up and say I'm going to tell your family and ruin you unless you give me a certain amount of money. It's a crime.”
  – Weisberg, (08:13)

• “Extortion is threatening physical harm, and bribery is typically threatening to expose something that nobody would want out there about themselves.”
  – Stoltman, (19:17)

• “I’m happy that prosecutors are bringing this because I happen to think stuff like this kind of has a prophylactic deterrent impact on other women or in some cases, men, coming forward and engaging in this sort of activity. ... If what is proven proves to be true, I hope the judge throws the book at the defendant.”
  – Stoltman, (31:08)

• “You have to be careful with those video cameras, because... the eye in the sky doesn’t lie.”
  – Stoltman, (27:09)

---

Timestamps for Important Segments

• 00:04–00:30: Episode and case introduction
• 00:48–04:27: Herman Weisberg’s background and approach
• 05:50–09:23: The Bucks owner's case — timeline and legal interpretation
• 10:45–15:20: Real-world extortion case studies and outcomes
• 18:31–22:00: Legal lines between settlement, extortion, and bribery (Andrew Stoltman)
• 26:59–29:09: AI, manufactured evidence, and credibility issues
• 31:46–33:14: NDAs and staggered payments as civil solutions
• 33:14–34:52: Digital authentication and law’s lag behind tech

---

Tone & Concluding Thoughts

Throughout the discussion, the tone remains professional, candid, and insider-focused, with Weisberg stressing discretion and nonjudgmental handling of clients, while Stoltman’s analysis brings clarity to complex legal distinctions. Both guests agree that technological advances and cultural gaps are making extortion cases more frequent, more complex, and more difficult to prosecute or defend.

Donna wraps up with an eye on the still-pending criminal trial and encourages listeners to send in questions—a reminder that in the world of high-stakes crime and justice, public understanding remains crucial.

---

For listeners:
This episode offers a deep, inside look at how high-profile extortion cases are navigated by both investigators and lawyers, highlighting the evolving risks in the digital age and the critical distinction between ethical legal tactics and criminal behavior.

Transcript

[A]

This is crime and Justice. I'm Donna Rotuno. What began as an online flirtation ended in a blackmail scheme for one billionaire sports team owner. The high stakes extortion plot is part of a growing trend targeting the rich and famous.

[B]

Professional athletes fall victim to this. Very often they're on the road and they respond back, and the next thing you know, the person knows who they're targeting here.

[A]

Before we begin, if you are enjoying the show, please hit the follow button. It's the best way to make sure you never miss an episode. Joining me now is private investigator Herman Weisberg. So, Herman, tell me a little bit about your work and what you do.

[B]

So back in 1990, I became a police officer with the NYPD. I spent 20 years working there, different assignments. Narcotics Intelligence Division. I was in undercover for a short time, and then I was fortunate enough for my last 10 years to be assigned to the Manhattan District Attorney Squad, which was a group of detectives working directly for the District Attorney at the time, Robert Morgenthau, legendary DA of Manhattan. And through those last 10 years, I worked a lot with prosecutors, which is a very kind of unique in the world of law enforcement to work directly with prosecutors. Usually there's a bit of an us against them mentality between detectives and prosecutors. You know, you very rarely get to work side by side. But I was lucky and got to do that. I got the attention of Mr. Morgenthau, as I suppose somebody that would keep his mouth shut, which he appreciated. And I handled some of the more sensitive cases that came through that office. So I got a, thankfully, a pretty good reputation for these things. And I left almost simultaneous to him leaving and retiring. And I started a company working for law firms and lawyers to handle some of the same cases that I handled back in law enforcement.

[A]

And that was back in the day when that office was actually prosecuting cases. I'm sure you'd love to go back to those times.

[B]

I think we all would to a certain degree. Right?

[A]

We all would. We all would. That's true. Herman. You have been referred to as the Mistress Whisperer. Tell me what that's all about.

[B]

Well, first I have to stop cringing like usual. I didn't give myself that name. I think it's an unfortunate and inaccurate.

[A]

Oh, I have a lot of names I didn't give myself, so I get it.

[B]

Yeah, well, yeah, I got kind of, you know, these extortion situations, I think very often. I mean, I just, I despise the word Mistress Whisper. I, I, I whisper to everybody that, that, that was violating the law. And who's the victims contacted the attorneys that I work with. But just to explain, a lot of times people don't realize that they've delved into criminality when they're dealing with certain situations. And because I know how to work a case and because I don't bluff, I basically used to when I first started out here, explain to a lot of people and come and visit with them and let them know that they're going down a course of criminal conduct and there's going to be a situation. And know what I'm talking about. Because I did this for 20 years and I've built a lot of successful cases of people doing even less than sometimes the people I'm talking to did. So a couple of attorneys and a couple of my clients. I don't know where it started calling me, you know, as compared to a horse whisperer, a mistress whisperer. But I can assure you there were just as many guilty male. I guess they're called misters. It's a male. Yeah. Mister and a mistress. Right. I would suppose I almost had just about a split of males and females both going down these bad paths.

[A]

So tell our listeners and our viewers who hires you? Why do they reach out to you in the first place? Are you reached out to by lawyers offices? Are you reached out to by individual parties? Kind of talk to us about how you get involved in these cases now that you're out of the law enforcement side of things and now on the. The private investigator side.

[B]

I'm glad you asked that, Donna. I exclusively work through council. If somebody calls my office with a situation, I tell them that, that I can really be effective, most effective working with your council, as opposed to me trying to do the job and then going with the results of my investigation to your lawyer. I'd rather work with them. Sometimes people say I don't have a lawyer and I can find the appropriate one for them. But in all cases, I think it's. I would say 90% of our cases come through lawyers. Sometimes it's white shoe firms that have nothing to do with criminal defense or criminal investigations. Then there's usually somebody in the firm that has a background as an AUSA or former prosecutor that will eventually get to someone like me. And if I'm lucky, they get directly to me. You know, it's built this business by keeping my mouth shut and not doing too many podcasts. But, you know, I've been doing it now for 16 years, so I feel like I. I got pretty good at editing Myself and making sure I never divulge any of my clients secrets or situations mostly, you know. And as you know if I get retained by counsel it falls under vel or the attorney client privilege. So I am bound by the same rules as attorneys.

[A]

So let's talk about what's going on here with the co owner of the Milwaukee Bucks and how you would approach a case like this. And just so everybody is aware of what's going on. The co owner of the Milwaukee Bucks was a victim in this alleged extortion plot that now has been indicted in New York and it is a case pending. There's a woman who was attempting to allegedly extort him, blackmail him for conduct that took place between the two of them. And then she started asking for lots of money. And there's a lot of different parts here where first they, they start communicating on their own. Then they decide to go to a mediator, he has counsel, she doesn't mediator makes some recommendations. She does not accept the mediators terms. After she finds out that allegedly she got a sexually transmitted disease from said co owner of the Milwaukee Bucks then begins to ask for more money and at that point she hires counsel, ends up now where we have this indictment. So talk to me about how your work would play into a case like this and how a lawyer's office would hire you and what they would ask you to do in a circumstance like this.

[B]

Okay. Yeah. And these are, you know, more prevalent than people think. They just mostly hopefully get, get handled discreetly and effectively, which is what I aim to do. But in a situation like this. Yeah, the, the, the victim here of the extortion and it's very, it's interesting to me because sometimes the victims, my clients get perceived as well, they were doing something wrong. So they're not really victims. But I separate that. I'm in a kind of a no judgment business here. I do criminal defense work such as you both do. And yeah, there are times where you know, people think that I'm working for a bad guy here. But I look at this specifically as that they are a victim of attempted grand larceny by extortion. And New York state has very. And the federal government in every state has rules against attempting to coerce somebody into giving them something material money usually by threatening to expose a secret. Whether it's true or untrue. You can't hold somebody up and say I'm going to do. I'm going to tell your family and ruin you unless you give me a certain amount of money. It's a crime. I find that culturally a lot of people from different cultures and people that come to this country don't really realize that there are, that this is a crime. I think this is more accepted generally in places like Asia. I found Russian people sometimes don't think of this as that much of a, of a real black and white kind of crime. You know, it's just, it, it's misperceived. Especially I found in China. I, I, there's definitely some confusion going on there when people come from China to this country and decide to blackmail somebody. I've confronted people like this and they're completely sometimes dumbfounded, confused.

[A]

Well, in the end, in these cases there's, there's kind of a fine line here between people settling out potential lawsuits before they get to that point and actually bribery or extortion.

[C]

Yes.

[B]

And that's why people very often the solution to this is really me telling someone that's committing this crime, don't trust me. Go to an attorney. Find out what you are doing from your own counsel who's going to tell you cease and desist from anything any further of this. Call up and apologize if you can. Because that fine line by time it gets to me in my office, by the time an attorney says it's time to call Herman and Sage Intelligence Group, it's, it's crossed over into criminality. I am not a thug. I'm not a hired thug that goes around threatening to go to law enforcement or anything like that. I take these investigations very seriously. I do a pretty comprehensive workup on this. And if the person is committing a crime and my client and the attorney deems it necessary or feasible for me to go and let this person, give this person one chance to, to back down and to let them real know that they're going down a bad path here and get, retain their own counsel if they feel like they're the victims of something. Go to your own lawyer and have your lawyer talk to the lawyer that I'm working for. That's sometimes the resolution on this which just shows you how confused that the, the bad actor is on some, some of these cases.

[A]

So walk me through some of your high profile cases and, and sort of the resolutions and how, how you get to that point and how the investigation helps lead to that resolution.

[B]

Again, I'm going to be editing myself. So if it's Steve, if I, if I'm stumbling, that's okay. It's because I, I'm very uncomfortable talking about people like this. I'm going To. I'm going to make sure that's okay. I appreciate.

[A]

I understand that.

[B]

Protect my clients first and foremost and past clients. I'll give you an example. I had a case where a man and a woman. The woman's married. The woman comes from a very successful family. She has a romantic affair with a young male that she met. Let's call it an activity like golf pro, tennis pro, something, it doesn't matter. Dance instructor. And they have this romantic liaison that goes on for a while. Suddenly, my client wakes up in the morning and says, I'm getting back together with my husband. I love my family. I love my old life. I don't want to see you anymore. I had a case where the person that was having the affair with her said, no, it's not over. And by the way, I've taken video and I've got pictures and I've got all of your text messages. And unless you continue this romantic affair and start paying my rent, I'm going to your husband, and your life's never going to be the same anyway. So neither of us. If I can't have happiness, neither can you. And this woman, I mean, she made a mistake. She was having an affair. It was bad. Again, that's not my job to judge these things. But at this point, she became the victim. So I tried very much to confront this young man and let him know that he was in the wrong. And he just refused to accept it. Kept threatening. I was lucky. I was in my background check, which I do on just about every one of my targets, to see if there's anything that I should know about any violence in their past. A bunch of different reasons for that. But in this case, I came across the fact that the young man's father was an attorney and pretty prominent attorney. I ended up going to the father and saying, listen, this is going to be bad. And you're going to, you know, your new client's going to be your son soon. Because if this continues, I have no choice. I'm going to law enforcement. He's not listening to me. Maybe he'll listen to you. That was a perfect resolution. It turned out to the combination of being an attorney and being a dad got this whole thing shut down clean. She didn't. The. The client didn't have to go to law enforcement, which would have exposed some of this situation. She would have had to tell her husband about the mistake that she made with a liaison, whatever you want to call it. She would have had to come clean to a lot of people. I'M very much happy with the results of that because the kid didn't end up going, the young man didn't end up getting himself into trouble with law enforcement. The woman was probably able to go back to her husband and family and hopefully is hopefully living a good life now. But you know, sometimes I think people's tell their, their lawyers, I don't want to go to the cops because that's just going to inflame this thing and it's going to be bad and I have to spill my secrets. I went back. Digress for a minute. The only public case, the only case that became public with me when I was still a detective with the Manhattan DA's office was David Letterman, who basically was extorted just like anybody else for having a, an affair. And the district attorney's office, as well as the Letterman decided, I'm going to come clean with this thing. And I don't, I will not accept being extorted. And that was that one case that I've done in my 10 years there that really, that outed itself and that, I think that was a good decision by the attorneys. But most of the cases that I had done were handled between me and the, the bad actor and me letting the bad actor know I've got a case against you. If you want to go forward, the only thing you're, you're not getting the money that you're demanding, you're not getting the, the, the continued romantic relationship that you're after. You're only getting one thing, and that is going to be a referral to law enforcement. So I think it's, you know, it's obvious which path you should take. But if you don't believe me again, go seek counsel. Go ask them if you've committed a crime. They're going to tell you the same thing. So, so yeah, sorry, that's the way I see these things go.

[A]

And how prevalent is this? And you know, cheating is the tale as old as time as we know. And so how often does this occur? Especially when, and obviously you're dealing with clients that have some means or otherwise. Nobody's asking for large sums of money. And you know, a lot of these people are titans in the industry. So, you know, how does that play into people being targets? And how often do we see this when affairs are present?

[B]

Oh, these are very varied cases. They go from somebody being drunk and you know, going on, you know, nefarious website like seeking arrangements or an escort site and just flirting with the idea and going back and forth and Texting. And then the person on the other end of the phone realizes, hey, you're a young professional. I don't think your company would like very much to get these texts, these lurid text messages that you've exchanged with me. All the way up to a sugar daddy sugar baby or sugar mama sugar baby relationship that lasts for years and then suddenly it's broken off these things. I want to bring attention to this and awareness to this. Donna, I don't like doing these cases anymore. I'd rather that people were aware of the fact. You're going to get yourself into trouble if you go around committing extortion. And you know, these also, you know, you talk about a small case. Professional athletes fall victim to this very often. They're on the road, they're 20 years old. They get hit up on their Instagram with a high. They're bored, they're not allowed to go out. They're sitting in a hotel room in some place they've never been to before. And even if they wanted to go out, they couldn't because they're, you know, they're being watched and they respond back. And the next thing you know, the person knows who they're targeting here. They get themselves into a thing where they exchange pictures or something like that. And there you go. Extortion is coming around the corner and you've got a very nervous person that's going to ruin his relationship with his girlfriend, wife, his family, his team. You know, it's just I can't believe how prevalent it is

[A]

what they did to your family. You're lucky to make it out alive.

[B]

Streaming on Peacock.

[A]

These men are going to come after me. Taking them out. It's my only chance.

[B]

Put a bullet in her head. From the co creator of Ozark.

[A]

Looks like a family was running drugs execution style. Killing is where for the keys.

[B]

Any leads on who they might have been running for?

[A]

The cartel killed my family. I'm gonna kill them.

[B]

All of them. Mia streaming now only on Peacock.

[C]

Zootopia 2 has come home to Disney Plus. Let's go get ready for a new case.

[A]

We're gonna crack this case and prove we're victorious partners of all time. New friends you are are Gary Desnake and your last name Desnake.

[B]

Dream team Habitats Zootopia has a secret reptile population.

[C]

You can watch the record breaking phenomenon at home.

[A]

You're clearly working at Zootopia 2.

[C]

Now available on Disney Plus. Rated PG.

[A]

I think it's a great time now to turn to Andrew Stoltman. Andrew is a security and investment fraud attorney based here in Chicago. So you've obviously listened to part of this conversation here with Herman, and I think now it's a good time to kind of talk about the legalities of this and the differences between bribery and extortion. And just your regular old, I'm going to file a lawsuit against this person, and prior to filing it, we're going to settle it out of court and do it ahead of time. So kind of walk us through that so our audience understands the difference, because I do think there's a fine line, and I do think that there's a lot of people, as Herman was saying, who really, truly don't understand the pitfall and the danger zone that they're walking into.

[C]

Yeah, absolutely. That. That's a real good point. You know, extortion is threatening physical harm, and bribery is typically threatening to expose something that nobody would want out there about themselves. And as a lawyer, you have to be real careful, because I've probably filed 2,000 different lawsuits or arbitration claims over the years, and it's not uncommon for us to send a draft copy of the complaint to the bad guy or bad company or whoever it may be beforehand and tell them, look, you have an opportunity to settle this. Now, obviously, the lawyer, with respect to the case that's at issue with respect to the buck's owner, made very specific allegations, very specific things that he was going to do if they didn't settle it. And that's where you get into the bribery. If you remember, P. Diddy had an opportunity to settle that very first lawsuit from Cassie Jenks, I believe her name was, and he didn't do it. The thing got filed, and then literally hundreds of other people came forward. He ended up. Ended up settling it the next day for a reported $10 million. So there's a smart way to do it. You have to be careful not to make an actual threat. And clearly, the defendant who's now, you know, released on bail, her lawyer didn't do it the right way.

[A]

And how does that play into. So she gets indicted, right? In this circumstance here that we're talking about, she gets indicted, and her lawyer is not indicted. And in reading the complaint, and, you know, you. You tell me you know this area of law better than I do, but it seems initially there was an agreement to go to mediation. So what that means is both parties agreed that there was some level of dispute and that they wanted to resolve it. Correct. So they go to mediation, and they say, we want to resolve it. It seems that they Have a deal. It seems that they've worked out a deal. And then next thing you know, she says, wait, I found out that I have an std, and now I want more money. And that's kind of when the wheels start to fall off. She reaches out. They reach out to each other without the mediator. Next thing you know, she's hiring counsel. So how is this situation? Because I find this a little bit more unique than your standard bribery or extortion case, because now you've started out with this mediation, and then you move into this lawyer getting hired, and the next thing you know, she's indicted. So kind of explain to me where it went wrong and why now, instead of just taking a settlement, we're now looking at this criminal indictment.

[B]

Yeah.

[C]

So at one point, the. The owner of the Bucks had allegedly offered $6.5 million to settle this case at the end of a mediation with a federal court judge. I think the individual who's now been arrested got cold feet because I think she realizes she could have got a lot more. So she seems to have backed out of the deal. I think she demanded $25 million after she found out about the alleged sexually transmitted disease. I believe her offer went up to $1.2 billion. And then you introduce a lawyer. And look, I don't know this lawyer from Adam, right. So I can't really cast aspersions on him, but these are really, really technical negotiations that take place. I question whether he has experience handling these sorts of negotiations. This is when he allegedly, on behalf of his client, starts making the threats that got her arrested. Now, look, her defense at trial is going to be, I relied on my counsel, I relied on my attorney to, To. To. To forward a settlement offer the right way without breaking any rules or any laws. Now, obviously, the lawyer is going to get up there and attorney client privilege is waived under this sort of criminal case. And he's going to say, no. She was the one who directed me to do this. He doesn't want to get in trouble, you know, with the bar or with federal criminal investigators. So he's going to say, no, Absolutely. This came from her. So she's in a tough position, but her number one defense is going to be, I relied on counsel to forward these settlement negotiations in a honest, professional way. Don't blame me. Don't throw me in jail. Look at my lawyer.

[A]

Well, it's really interesting because she's charged in a four count indictment, and those counts are just. So I make sure I get. Get it right. There's the bribery, there's the extortion. And then I think there's one other claim here, let's see, wire fraud. So she's, she's charged in these counts, and then there's a. Basically account saying that she destroyed and got rid of evidence. And so her lawyers, the Idala law firm in New York, who I know quite well, they filed a very interesting motion to dismiss the indictment. And this lays out this whole entire history with her lawyer. Now, what's. What I find interesting is they're not asking to dismiss count four, which is the count referring to destroying evidence. So obviously they, they must feel that either a, at least there's enough evidence to move forward to a trial, and they're not asking that, that the charges be, be dismissed. But, you know, is her defense more of a defense at trial, or does this motion to dismiss actually have any legs, given the way she hired counsel and the, the history of the settlement, communications here between the two of them?

[C]

Look, I mean, it's hard to get these charges dismissed. And call me a stickler, but I, maybe call me old fashioned, but I do hold lawyers to a higher duty of care than I do lay people. Lay people do stupid things every single day. Times a million lawyers are kind of held to a higher standard. So I personally think that this motion has some merit, meaning blaming, you know, blaming the lawyer with respect to what, you know, what transpired is a little bit of a pin the tail on the donkey. Now, ultimately, she's a client. She's ultimately responsible for everything that goes on. But, you know, I think she's willing to have the destruction of the documents claim remain in there, because even if she is convicted, that's. I don't want to call it a slap on the wrist, but it's relatively rare for you to get jail time, even rare to get significant jail time for the destruction of documents. We see it sometimes in political cases. So I think her current law firm is an excellent law firm. I think they're doing their job. They're trying to get the most serious claims dismissed and let the least serious claim stay in the case.

[A]

And let's talk about the legal line between consensual adult relationships and turning to this criminal extortion. Extortion or coercion. Right. There's, you know, there's this line, and obviously, as we were talking about with Herman, you know, he's obviously a very wealthy guy and, you know, he looked at $6.5 million as apparently throwaway money because that settlement didn't seem to be that difficult for her to get. And then, of course, she went back asking for more money, knowing that he had it. So kind of talk to me about, you know, how people become targets and what's the line here between this relationship and then this extortion and coercion.

[C]

There were allegations that she had a video camera in her tampon box in her bathroom. I mean, some really salacious kind of bizarre allegations have been made against her. Clearly she was filming these sexual relations without his knowledge. And, and, you know, I guess it's kind of common sense. You are a multi billionaire. You're very high profile. You kind of have to go into any relationship, especially from a woman who you met on LinkedIn, you know, kind of with, with both this up. So I, you know, this is obviously a smart guy. He's a pe, Private equity sort of sort of guy. He's worth billions. I, I'm almost surprised he'd get himself into this situation. But then, you know, you have a very attractive woman who reaches out to you. I'm sure she was very flirtatious. You got sucked into the vortex. But, boy, what a great warning for professional athletes, owners and billionaires and, and, and really, quite frankly, any sort of, you know, of man or woman out there, you just have to be so careful today. And obviously it needs to be a consensual relationship, but you have to be careful of those video cameras, because this is a saying that I'm sure Herman knows well, the eye in the sky doesn't lie. So you just. You have to be careful for sure.

[B]

I'm sorry, Herman.

[A]

Go ahead. I think you wanted to jump in here. Jump in. No, please jump.

[B]

I think one of the things that was very interesting in the complaint is she might have been bluffing because the camera that they did find, the phone that was hidden in the sanitary pad box, apparently contained porn, but it contained some images of the buck's owner's face superimposed. And that's why the eye in the sky doesn't lie. Probably worked before the artificial intelligence came to be. I think she superimposed. I think she was bluffing. Probably didn't have the salacious video that she wanted to have. And when the lawyer probably asked her, okay, let me see the videotape, she scrambled and superimposed his face to make it look like he was in a sexual act with her. That's the way I read the complaint. I don't know if anybody read that different than me, but that seems to be some of the evidence.

[A]

I did think that that was part of it, especially, you know, in terms of either destroying and, or manufacturing evidence. I did, I did think that that was, was definitely something that they were potentially intimating that way. And then they also talk about the fact that she threatened to reach out to his family members, his children, you know, and so there's, there's been all of these other threats. I think that, that lay here, which are really interesting. And, and I think that was done by her directly to him. And so I don't know. Andrew, tell me why. I mean, the, these cases, I think, are, can be tough for prosecutors. Obviously, if you have the paper trail and you have the text messages and you have the, you know, give me my money or I'm going to do A, B and C. Obviously, you know, that makes it a little bit easier. But there's also these other components here. If you, if you just looked at the complaint, you would not know about this history that they had or looking at the indictment, you would not know about the history that they had or with going to mediators and having these settlement conversations. And so how does, how does the history of this make these cases difficult? Or maybe not for prosecutors, but to me, it seems that it makes it a little bit harder when they've already started conversations about giving, giving you money.

[C]

Some question that this case has a lot more plot twists and turns, but, you know, I, I give the owner of the Bucks a lot of credit, too, for prosecuting this case. And obviously he has the financial resources, the NBA owner, every NBA team has, you know, typically at least one former FBI or law enforcement individual on the payroll. And so these cases don't come forward a lot because look what he was willing to pay at least $6.5 million to keep quiet. It is now out in the public. There are a lot of people laughing about this. I've seen some memes about it. There's nothing funny about it, right? This guy was extorted. He was bribed. But I am happy that prosecutors are bringing this because I happen to think stuff like this kind of has a prophylactic deterrent impact on other women or in some cases, men coming forward and engaging in this sort of activity. And, you know, it's such a black eye for, for, for Edens. Although now he kind of has more of a sympathetic audience. I'm happy that prosecutors are bringing it. I'm happy he decided to come to the authorities. And if what is proven proves to be true, I hope the judge throws the book at the defendant.

[A]

Let me ask you this, too. It made me start to think about NDAs. Right. You have these circumstances where, you know, usually men have a relationship with someone and then they don't want that relationship to go public. And then money is. Is passed across the table, and usually Gloria Allred's on the other side passing the NDA for the sign. So tell me about how that's a little bit different than what we're looking at here, because I think that's an interesting distinction that maybe people listening may. May want to know about.

[C]

Yeah, the NDAs are. They're becoming more common, but they really are only worth the paper they are written on. If there's just an NDA without the exchange of cash, that tends to make them less effective. I've historically structured those NDAs so the money spread out over many years. You know, maybe if you spread it over five years. Let's just keep the math simple for me. Say it's a hundred thousand dollars, $20,000 a year for five years, or $10,000 a year for ten years. If you keep that carrot dangling above the people's head in the form of money, you can really increase your odds of keeping everybody's mouth shut. There's some people who are simply, you know, I'm not a doctor, but I use this term loosely, crazy. And the fact that they signed an NDA claiming to keep everything quiet, it's meaningless. If there is exchange of money and it's spread out, you can kind of keep them quiet for a longer period of time, but it's tricky.

[A]

Herman, let me bring you back in about the AI component, because I think that's really interesting when we're talking about being able to authenticate digital evidence in court and what you really should have to prove to show that you're evidence is actually real and authentic. And I know, you know, there's metadata and there's ways. But talk to us about how you make sure that a video somebody tenders over. Especially as you said, in the world of AI, how can you make sure, especially when it's something coming from someone's own home, that that's actually proper in working order and accurate?

[B]

Yeah, it's. It's become more and more commonplace for. For us to be engaged with a computer forensics expert that can determine whether or not something has been altered or created by AI. That's. AI Security is a burgeoning field right now because of the dangers of what AI can do. We've all seen it. You can make it look like two people are kissing that have never been in the same room. And if you can do that, you can do a lot of things. So, yeah, that's become part of not every case. But on the high stakes case, you want to check immediately through an expert's eyes on whether or not something's been altered or created through artificial intelligence.

[A]

And Andrew, we know that the law never moves as fast as technology. And, you know, lawyers are constantly trying to find the right people to hire to do these kinds of things. And are you finding that the laws just have not caught up with where we are on the technology scale?

[C]

Oh, definitely. The law lags at least 10 years behind. I mean, sometimes it's a little bit quicker than that. But, you know, these politicians, they don't grasp a lot of the changes. They certainly don't grasp the technology. A lot of these laws then have to be reviewed by judges who know even less about technology than the legislatures who drafted the legislation. So, yeah, absolutely. The law is very much behind the field in terms of where everything is right now.

[A]

Well, I think this is going to be a really interesting one to watch. Herman and Andrew, thank you so much for your time today. We will definitely be paying attention and we will see if the judge grants any of the counts on the motion to dismiss and where this trial will end up and what counts are left. So great to have you both. Thank you so much. Thank you for joining me for another episode of Crime and Justice. Remember, we want to hear from you. Send us your thoughts, questions or theories, and we will answer them on air.