From disturbing footage to allegations of physical violence to damning texts, we are breaking down some of the biggest blows to the defense so far in the Shaun Diddy Comb sex crimes trial. As we are in the heart of week two, we discuss these potential losses for the defense. But don't be so quick to think that this is a straightforward conviction.
Welcome to Sidebar, presented by Law and Crime. I'm Jesse Weber. We're now in week two of the Shaun Diddy Combmes criminal sex crimes trial and one of the things that I have been wondering has been some of the pieces of evidence that have proved potentially problematic for the defense.
Meaning, are there defense losses? And by the way, this is coming from somebody who said that I think the prosecution's case is not a slam dunk. It's complicated when you talk about racketeering and sex trafficking.
Those elements are not so straightforward. It's not just the jury accepting that Combmes allegedly beat an alleged victim up or sexually assaulted them. These aren't state charges.
These are federal charges. They're very, very specific elements that the prosecution needs to prove. Like for sex trafficking, you need to prove that Commes recruited, harbored, transported, maintained victims to engage in commercial sex acts by using force, fraud, and or coercion.
racketeering conspiracy. The top count, criminal enterprise, pattern of racketeering activity with at least two underlying crimes like forced labor, kidnapping, arson, sex trafficking, bribery, criminal agreement to do this, it's high burden. It's a high burden.
Can the prosecution meet it? But putting all of that to the side, the prosecution has been quite deliberate and methodical in what witnesses they have called and the evidence they have presented. So with that, I want to touch upon five of the biggest blows to the defense so far.
Five of potentially the biggest losses so far to them. So for that, I'm not going to do it alone. So for that, I want to bring on trial attorney Andrew Stoleman to talk more about this.
Andrew, thank you so much for coming here on Sidebar. Appreciate you taking the time. Anytime.
Thank you. So, first before I go into the losses or potential losses to the defense, you would agree with me this is not a slam dunk clear case for the prosecution, at least with respect to the racketeering and sex trafficking charges, right? Yeah, there's no question.
With respect to the most serious charges, which are the racketeering and the sexreated charges, I it's an uphill climb for prosecutors. And so I was a little surprised when these when these charges got filed at the federal level. And so I'm really watching this carefully.
Prosecutors have scored some points, but they still have a really long way to go. Yeah. Because you a lot of this this alleged activity, this alleged behavior would have made up state charges for assault and battery and potentially rape and things of that nature.
But you know, there's statute of limitations issues. So how do you transform it into a federal case charges like this? But I want to talk about the defense and I want to talk about some problems for the defense.
So number one, physical violence. It seems to me the prosecution has done an exceptional job of proving physical violence. And when we talk about force, right, and force, fraud, and or coercion in the sex trafficking count or using force to cause victims to engage in freakoffs, right, Cassandra Venturine testified that Combmes would kick her, stomp her head, drag her.
The 2016 tape of Combmes appearing to beat her up at the LA Intercontinental Hotel. There were photos of her alleged injuries. Text messages from Cassie to Combmes can also arguably prove this.
For example, there's one that says, "I'm not a ragd doll. I'm somebody's child. " Another message, "You are sick for thinking it's okay to do what you've done.
Please stay far away from me. " Dawn Rashard testified that she observed Combmes physically abusing Cassie, told her to leave, but apparently was afraid to get involved for her own safety, that she saw injuries on Cassie. Cassy's former best friend, Carrie Morgan, testified she saw Combmes be violent with Cassie in two separate incidents.
Daniel Phillip, a man allegedly hired by Combmes to have sex with Cassie, testified he saw Combmes drag her into a room and then heard slapping sounds. The defense even conceded that Combmes was violent and seemingly admitted he engaged in domestic violence. So, Andrew, if I'm correct, and tell me if I'm wrong here, but if I'm correct, why is this so vital to the case?
And am I right that this could be a loss for the defense? Absolutely. There are jurors on this case who have probably made up their mind already simply based off of the video of him beating his girlfriend in the hotel room.
There are a lot of jurors who just look at testimony, they look at evidence, they look at the video, right? There's the old saying, the eye in the sky doesn't lie. And when they saw Combmes smacking her, kicking her, hitting her, there are a lot of jurors out there that probably said guilty at that point, even before they heard all the evidence, it's not a good look.
It's a horrific look. And one of the things you do as a criminal defense attorney is you try to create sympathy for your client in the eyes of the jurors. Now, we don't know a lot about these jurors.
It seems like they skew male. They're a little bit older, but there are a whole bunch of people out there that have convicted Shawn Combmes as soon as they saw that video of him beating his girlfriend. So, you're talking from an emotional standpoint, right?
Not necessarily looking at the elements of the charges, right? Because that was going to be one of the big concerns of the uh defense is about this tape, and I'll talk about the tape in a moment, but what you're saying is not even a legal point of view. When the jury hears about this alleged violence, they may want to convict him because of that.
Not necessarily because it's racketeering or sex trafficking. Yeah, absolutely. And the more conservative the jurors are, the more likely they are to simply shut down, have that curtain go in front of them, and disregard the jury instructions, disregard the rest of the the testimony, the defense's case, and say, "This is a bad dude who beats up women, and there's no question in our mind that he's doing it because we've seen him doing it.
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shouldn't happen, but happens all the time. And it would be very difficult to know unless jurors came out after a verdict and said, "Yeah, we convict him because we didn't like him. We convicted him just because we're like, we need we want to hold them accountable.
" I don't really know if it matched up to the elements. I don't know if the prosecution met their burden, but you know, unless they came out and said that, but do you think from a legal point of view, the physical violence or the alleged physical violence, has it established the elements of sex trafficking? Has it helped prove the racketeering charge?
If so, how? Not at all. You know, and I think Diddy's lawyers did a pretty good job in their opening statement saying, "Look, he's basically a bad guy and he did this stuff, but that's not sex trafficking.
Hiring a prostitute is not sex trafficking. Beating up your girlfriend, it's not sex trafficking. Wait a minute.
Wait a minute. The physical violence, doesn't it go to force, fraud, coercion? If you tie it to this pattern of sex sex acts, right?
So the 2016 tape, talk about it. I mean, if you're saying that was after a freakoff, okay, if you're saying this is the environment she was around or allegedly around, not only violence but threats of violence, doesn't that feed into a sex trafficking count? remember it's the idea of transporting her uh work, you know, having these these uh sexual episodes with sex workers who are getting paid freakoffs happening in multiple locations.
I mean, that doesn't the physical violence doesn't support sex trafficking in in a vacuum. It does, but the defense has done a good job of introducing some of the text messages from Diddy's girlfriend talking about how she likes these freakoffs, how she wants another one, right? Expressing affection.
And if you're trying to establish coercion, I think those sorts of text messages are are harmful to the prosecutor's case and and I would expect that to be the central point of the defense case. Consent, consent, consent. These were willing participants.
They came back time and time again. Even after they were free and clear, they still came back. So I think it goes to the consent related issue on the coercion charges.
Sure. They definitely have an argument to that. The counterargument would be yes, she agreed at the beginning.
Yes, she agreed 95 times, but the five times she didn't, that's a problem for the defense. And for the racketeering, I would make the argument, you know, one of the means and the methods of racketeering, right? This criminal enterprise that was in, you know, Combmes used his businesses and his resources and his wealth and his associates to further criminal activity.
One of the means and methods of this criminal enterprise was using violence or threats of violence to engage in a pattern of conduct whether it's kidnapping or arson or sex trafficking. And I think it's not just solely about, you know, using uh threats or violence to force Cassandra Ventur, allegedly force her into sex acts, but it goes to this criminal enterprise more easily digestible and understandable for the jury. No.
Yeah, I would agree with that and that's clearly the angle that the prosecutors are are going down, the track they're going down. But that kind of leads to the second point, which is the credibility of some of these witnesses. I mean, there's the old saying, conspiracies crafted in hell don't have angels as witnesses, right?
We have witnesses in this case. Prosecutors called a male escort, right, to substantiate some of these allegations. Uh Diddy's girlfriend got a reported $10 million plus payout with respect to uh being silent uh and not f or excuse me not filing the charges against him.
So you're absolutely right, but the credibility of these witnesses is crucial in this case and I think that's one of the areas where the prosecutors have an uphill climb. Let me real quick about the settlements. So, she settled with Shawn Combmes for reportedly $20 million, then cooperated with the the government.
Not sure why she didn't. It's not like she was in the middle of litigation and then, you know, a favorable verdict would help her a lot. I mean, I don't know what the incentive would be for her to help.
And then with the $10 million with the Intercontinental Inter intercontinental hotel, I imagine the prosecution can say, "Yeah, she deserved it. Nobody called police. The tape was essentially hidden.
" How does that affect her her credibility? I'll give you a quick point on that as we talk about it. No, great point.
That's what the prosecutors are going to argue. I I guess Diddy's lawyers are going to come back and say, "Look, this is an ex-girlfriend. She's now married.
She's upset with him. She got a huge payout. " You know, attack her credibility.
Will it be effective? I don't know. But I think that's the route they're going to take.
So, in the ve veil of, you know, we're talking about potential losses to the defense. I mean, we know that as soon as it came out that this footage of the March 2016 alleged t attack on Cassie by Combmes that that would come into evidence, right? Some form of it, whether it's cell phone videos of the surveillance footage, different angles of the surveillance footage.
This was something that Combmes team had tried desperately to make sure a jury would not see. As soon as we knew it came in, it was going to be a problem for the defense. It's horrifying to say the least.
And again, the prosecution has asserted, and so is Cassie, that this was after a freakoff. So arguably, you have a straight road, more straightforward road to sex trafficking, right? Force, commercial sex acts.
But Andrew, if the argument comes out, well, you know, why didn't Cassie leave 11 years of abuse, sex trafficking, she never left, called police, reported him. Well, fear of physical violence. Look at the tape.
If she didn't do what he wanted, that's what was in store for her. Can't the prosecution make that argument? They absolutely can make it and they will make it.
But I I just think the length of the relationship that she had with Diddy, the text messages that she sent expressing, you know, affection and and and wanting to participate in some of these freakoffs. It's not quite the openandsh case. I think it's probably going to be enough to have these jurors say, "Yeah, you know, he's guilty on these charges.
" But it's still an uphill climb for prosecutors. It really is. This is not an easy case for them.
What do you make of the defense saying, "Well, you know, Combmes was maybe going through drug withdrawal. He was irritable. " And if that's some sort of I mean, they said in their opening statement that that tape, the 2016 tape was indefensible.
And yet they're making the point about talking him withdrawing from drugs and what state he was in. What do you make of that defense? It it's a that's a double-edged sword because if I'm the jurors, I'm sitting there thinking, well, this aberrant, disgusting, horrific behavior.
Why did a guy who's worth a couple hundred million dollars and famous and had so many women uh liking him engaged in this sort of activity? Well, you know, the jurors could possibly say he was on drugs. Uh he was an alcoholic.
He was a drug addict. whatever the case may be. But I it it certainly doesn't excuse his behavior.
I think the defense team might be arguing this in part if he is convicted to be able to argue to the judge, look, you didn't have the proper uh mental state, the mena to commit these crimes. Therefore, don't sentence him to the maximum. But it's a it's a double-edged sword.
They're kind of dancing on the head of the pin with that argument. Now, let me move on to another potential loss for the defense, another potential blow to the to the defense's case. So, a big part of the prosecution's case is establishing that Combmes used not only violence and threats, but blackmail and financial control to get Cassie to do what he wanted.
Again, important for sex trafficking, also part of racketeering. Cassie had testified that Combmes paid for her rent, gave her cash, controlled her career. In fact, Comb's former assistant, David James, testified that Cassie told him, "Man, this lifestyle is crazy.
" And he told her, "You should leave or why don't you leave? " And she responded, "I can't. I can't get out.
" Citing how Combmes pays for her life, controls her music career. And he testified, "I just didn't think that she could easily leave. " Carrie Morgan testified to the same thing, too.
Uh, this is Cassandra Ventura's former best friend. And then I'm reminded about the allegation that she made, Cassandra Ventura made about the plane incident where Combmes allegedly showed her freakoff videos on a plane. She testified she felt trapped.
Then after they landed, he wanted a freakoff and when they landed, they had a freakoff. To me, it feels like the most straightforward potential argument for sex trafficking. So, you have a travel element, you have a coercion element or threat element, you have a se a freakoff.
So, you have this commercial sex act element. Andrew, do you think that this is a blow to the defense, this idea of con uh control and that she can't leave? Yeah, that might be the best argument that prosecutors have because it's it's straightforward.
It's basic. The jury can understand it and intuitively it makes sense. That's where you can leverage the defendant's wealth against him with respect to these charges.
And I think that's probably reality. I I haven't seen the full testimony with respect to everything he has lavished on her. I'm certain it's going to be more fully developed during this case.
But I think that's a great great argument for prosecutors. And you know, she also had apparently sent him a message. Please delete any video out of your phone if you have them.
Too many people have access to your stuff. Uh by the way, Mr James had testified that Combmes had told him and said that he called Cassie moldable and said and Combmes said that I got her right where I wanted her. She's young.
So Andrew, you know, you're hearing the prosecution why they they would want the jury to hear that evidence. The defense seemed to suggest, well, there were alternative interpretations here, like he wasn't controlling her. He wasn't controlling her appearance, for example, to dominate her, but was providing constructive feedback because he was a fashion mogul.
So, this idea again of I, you know, 17-year age difference, started young with her, allegedly taught her a lot of I hate to say this, but she even testified that, you know, introduced her to certain sex acts. this idea of having control over her finances, career, moldable defense saying there's alternative interpretations here. How do you see it?
Yeah, there certainly are alternative interpretations, but I think the jurors are going to look at it and just kind of see through it. This is powerful powerful testimony and evidence, right? because uh Patty is so wealthy, because he's, you know, in the music industry so substantially, uh because of her background, all of that kind of feeds right into the juror's wheelhouse in terms of what was going on.
I think that might be the reason. If Diddy is convicted, I think that might be the reason why he's convicted because it's a really powerful argument. And then you had Don Rashard, again, this former member of Danny Kane, who testified to witnessing the alleged abuse of uh Cassie, testified to feeling that Combmes was threatening, that he allegedly made a statement to her that she should keep quiet about Comb's alleged abuse, saying where he comes from, people go missing if they talk.
And she interpreted that as quote that we could die. And so she was concerned for her safety to not intervene. There was also testimony that Combmes himself and was and his team would constantly keep tabs on Cassie, too.
Carrie Morgan testified that Combmes tried to use a hammer to break into Cassy's apartment. So, this all goes to the idea of an environment of violence, an environment of threats, an environment where it's not so easy to speak up, not so easy to leave. Do you think that this is a problem for the defense to overcome?
Yeah, it's certainly a problem. But someone like Don Richards, I mean, she has a lawsuit pending against Diddy. And I would I would expect that to be a central argument throughout the case that all of these witnesses who have lawsuits pending uh against Diddy have an agenda.
They have an incentive to convict him. Now, will that be enough for jurors to say, you know, her credibility isn't substantial enough for me to believe her? I I I don't know.
But it's certainly an attack angle for the defense. Oh, I will tell you the cross-examination of Dawn Rashard was something. You know, keep hitting her on inconsistent statements that she made, allegedly bringing up details now when she's testifying.
Um, there was testimony about, you know, why did you seem to try to work again with Diddy or stay in contact with Diddy? Um, you know, a financial incentive, a lawsuit, always an important area for cross-examination. But I do want to move on to another part, another potential blow to the defense.
So I think the prosecution has done an effective job at showing, you know, did Cassie really consent to all of this? She testified to getting urinated on. Daniel Phillip testified that Combmes directed he and Ventura uh to roleplay during these sexual sessions, the freakoffs, and what to do.
And I think there's evidence to establish that while she may have initially agreed to the freakoffs and even encouraged them and set them up. That was not all the time. You have this alleg you have this alleged text from her to Comb saying this is all we do.
There's another time when she said she wanted to talk to Combmes about freakoffs and he guessed quote now you don't want to do it anymore. Oh, I already know you so predictable. So having the jury believe that these freakoffs, maybe not all of them, but a portion of them were non-consensual is going to be key to this defense.
Do you think that this is a blow to the defense as I've outlined it? I that's so hard to say. I mean, these some of these jurors may be sitting there thinking, look, if she didn't want to partake in this activity after the first one, she should have left the second one, third one, fourth one, fifth one.
And I get the argument that look, Diddy was controlling her through finances, through money, through through through coercion, and I get it. But I I just think it's going to be hard for these jurors to think after partaking in so many of these that she was being forced into them. Look, I think the allegations with respect to the urination, I mean, it's so disgusting.
It's it's it's so deprived that I have a feeling some jurors are just going to look past so much more of the evidence and say, "This guy is guilty. " But I I I think that kind of gets to the argument that the uh prosecutors have an uphill climb on some of these charges took place so many times and some of these are going to say if she wanted to leave she could have and she I I think a lot of this comes down to psychological evidence. We uh did a whole other sidebar on this about how the prosecution is going to call their own uh forensic psychologist to testify about uh or psychologists to testify about their reasons why victims don't leave their abusers and coping strategies and things of that nature.
And you know the prosecute the defense excuse me is going to call their own witness to rebut that. But there's problems. I mean there's other evidence.
the messages. One message from Cassandra Venturine to Combmes that says going to FO on Tuesday. There's a conversation where it appears Combmes is saying how his favorite times are when they foed and then made love afterwards.
To which Ventur responds, "Yeah, I like those times. " Combmes writes, "Anything you need me to get or set up in case we want to fo? " And Ventura Fine responds, "Oh, hit whoever would turn you on to see me with.
" And there's another message. Wish we could have foed before you left. My period is over.
So, I agree with you. Those could be problematic for the prosecution's case and definitely something the defense is honing in on. Okay.
Now, going to a potential blow to the defense. I have to say Combmes is facing two charges of transportation to engage in prostitution. Okay.
And these charges are with respect to two different victims, including victim one, Cassie Venturfine. And just let me read what it says in the indictment. Combmes transported, aided, and emedded and willfully caused the transportation of female victims and commercial sex workers in interstate and foreign commerce on multiple occasions with the intent that they engage in prostitution.
Now, for purely purposes of alleged facts matching up to the elements, if you take as true what we've heard so far, it seems to me at least, Andrew, the prosecution could easily convict Combmes of this because Ventura testified that freakoffs would happen with Combmes NML escort in New York, Miami, LA, Eitha, Spain, Turks, and Caos. She explained how escorts were paid to have sex with her. She was shown photographs of alleged sex workers like one called the Punisher.
How at least one escort was used in multiple cities. There is a lot of talk about traveling. Daniel Phillip testified about being paid to have sex with Cassie while Combmes watch.
I mentioned before the plane incident with allegedly being shown videos of freakoffs. They land and then they have a freakoff presumably with a sex worker. That's you don't need force, fraud, or coercion.
It's like transporting people for purposes of prostitution. Andrew, to me, that feels like the toughest case for the defense to to fight against as of all the charges. Yeah.
And it's basic stuff that these jurors can follow. They can understand. Uh it's not very complicated.
It's bad. It's disgusting. So, those are the sorts of facts that these prosecutors just love jamming down the throats of the defense.
and quite frankly the jurors as well because that's that's about as solid as it gets. So these prosecutors obviously want to play this up because it is nefarious. It is bad and it is very important in this case.
It's potentially 10 years in prison. That's what what we're talking about with that charge. And look, I think the defense is trying to say this is what they came out in their opening statement that he was paying these people for their time and experience.
I don't I don't think that goes very far. Maybe they're trying to say, you know, he wasn't instrumental in it, but I, you know, time and experience. I I don't know exactly what that defense means.
Yeah, I agree. And look, I I kind of call that the red face defense. As a defense attorney, a lot of times you present an argument and it just doesn't really pass the red face test.
You're hoping one or two jurors may buy it, but that is very much an uphill climb for Diddy and his team. And look, to be clear, this episode was dedicated to potential losses or blows to the defense, but you articulated it so well. This is not a slam dunk case for the prosecution.
This is a high burden for racketeering, for sex trafficking. There are people scratching their heads and still trying to understand how this, you know, matches up to it. I think this is a case that's going to be maybe won or lost in closing arguments, right?
I I think that this is about how it's properly articulated, laid out, what the jury instructions are. I think it comes down to the very end of this case. Boom.
That's it. And and you know, it it's prosecutors have a 95% win rate in federal court and and the New York prosecution team, of course, are like the New York Yankees or the prosecutor's office, right? But in the same sense, we know we have a long track record of celebrities being found not guilty on some really heinous, horrific crimes, right?
OJ Simpson is the quintessential example, but obviously Michael Jackson and so many others. When you have the resources of Diddy, you can afford the top flight legal teams, you can afford uh the uh the consultants with respect to the juries, you can have the top expert witnesses, and obviously that makes a huge huge difference. So, a lot of people have written this case off and said to themselves, "Wow, you know, Diddy's guilty.
" Well, he's clearly guilty of being a scumbag, right? I don't think there's any question about that. But there we we still have a long way to go.
We are probably in about inning two of a nine inning ball game and Diddy is in this case. Andrew Stolman, thank you so much for coming on. I really, really enjoyed the conversation.
Would love to have you back. Thank you. And that is 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.
