Law&Crime Sidebar - P. Diddy: Porn Addict or Predator?

Episode Date: September 25, 2025

Sean "Diddy" Combs was back in court Thursday for a pre-sentencing hearing, arguing his prostitution conviction should be tossed out! What exactly did his team say, how did he look, and could we see a new trial ordered right before he's officially sentenced next week? Law&Crime’s Jesse Weber and court reporter Elizabeth Millner break down the latest in the Sean Diddy Combs case, including his defense's arguments for a lesser sentence and powerful letters of support submitted to the court.PLEASE SUPPORT THE SHOW:Use the code JESSE to get 10% OFF on select Plaud productsPlaud NotePro: https://bit.ly/4pfGqQ7HOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger, Christina O'Shea, Alex Ciccarone, & 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.

Wondery Plus subscribers can binge all episodes of this Law and Crimes series ad-free right now. Join Wondery Plus in the Wondery app, Apple Podcasts, or Spotify. Sean Combs was back in court today, arguing his convictions should be tossed out. What exactly did his team say? How did he look? What can we expect next? And by the way, this is all in anticipation of next week when he's going to officially be sentenced. Is that even going to happen anymore? And what will that sentence be? could he be going to prison for the next few years? Welcome to Sidebar.

Presented by Law and Crime, I'm Jesse Weber. A big hearing has just wrapped up in the Sean Diddy Combs case that we need to talk about. He is trying to get his convictions thrown out. Now, this is in advance of next week where the rat mogul turned convicted felon is officially going to be sentenced on two charges of transportation to engage in prostitution. This comes after his bombshell trial a few months back. The trial where a jury of his peers may have found him guilty of those charges, but not guilty of sex trafficking and racketeering conspiracy, which, by the way, carried really significant prison time. Here, for the charges that he was convicted of, he faces a maximum of 10 years in prison on each charge, although most legal analysts would suggest that is highly unlikely that that's what he would receive. I will tell you that, but federal prosecutors, they have previously.

suggested four to five years in prison. They may ask for even more. Combs defense team has asked for around 14 months. And after already sitting in federal lockup at the Metropolitan Detention Center since September of 2024, he's always been denied bail. If the judge sides with the defense's recommendation, then Combs would be essentially released immediately. And by the way, just real quick, we're going to talk about what happened today. But I want to highlight something about the sentencing before we talk about what happened today. So his attorneys submitted a 182-page sentencing memo laying out their argument for a lesser sentence. They go into Combs' history and upbringing by discussing how his father was shot to death, that this had a tremendous impact on Sean Combs' life, how he has had this dedication to his family and career and built a family for his colleagues and friends out of his business, how he has been an inspiration to others, that if you have to consider different factors like drug use,

and addiction and certain medical conditions that were redacted in this filing. But that may all play a role in his anger. And we know the defense definitely tried to explain away a lot of those angry moments, right? The infamous Cassie Ventura beating that video back in 2016. The defense went into what he was convicted of, how it doesn't warrant significant prison time, that Cassie Ventura and Jane, the key victims and accusers in this case, were part of a consensual sexual relationship with Sean Combs. That's the argument. I mean, and remember, he wasn't convicted of sex trafficking, despite the evidence of freakoffs and wild king nights.

So the defense hammers home that there was no force, fraud, or coercion, that the male escorts that make up the transportation to engage in prostitution convictions, they were freely consenting to what happened. They argue, quote, this is the only case we've identified where the government claims professional consenting adult males were Man Act victims. The Man Act refers to transportation to engage in prostitution. They emphasize, and by the way, this comes up again today, that Combs didn't earn any money as part of this prostitution. They emphasize how the guidelines, say, six to 12 months should be the sentence,

how the court cannot use any evidence from the racketeering or sex trafficking parts of the case in sentencing him for prostitution, that it would be unconstitutional. They fought back on the enhancers that prosecutors have argued for a more strict sentence. They can't argue fraud, coercion, that Combs wasn't a leader or organizer. And again, they say, look at what he was acquitted of. That would suggest that. And they argue, look, he has already experienced enough punishment by sitting at the notoriously bad MDC for over a year. So they argue for a 14-month sentence.

And by the way, in anticipation of sentencing, people have submitted letters of support for Sean Combs to the court. You have a letter from his mother, Janice Combs, who writes in part, I'm writing this letter to implore your honor to please have mercy on my son. Sean has always been a loving and caring son. On December 21st, I will be 85 years old. Goes on, I would like to be able to spend the last few years of my life with my son, Sean. Unfortunately, my son has made some terrible mistakes in his life, which I know he recognizes.

His adopted sister, Keisha Combs, wrote, I pray that this moment is not the end of Sean's story, but a turning point toward a more purposeful and honorable life. You even have letters from fellow inmates. You have one from a Raymond Castillo who writes, Mr. Combs has saved me, not only striving to better himself, but to better everyone he encounters as a whole and leave a positive impact in everyone's life.

Even behind bars and with limited resources, I have witnessed this man do magical things. In a place of segregation, I have seen Mr. Combs bring unity to all races and ethnic groups, no matter the background as a united front. You have another inmate who writes, because of Mr. Combs, everybody in the unit is treating and acting positively towards each other. And for many people, that's a step forward in becoming a better person for when they get

out of prison. So with all of that in mind, right, that's sentencing. Is it even going to happen or is his conviction going to be thrown out? Because we got to talk about what happened in today's hearing, where Combs tried to get those convictions thrown out. And for that, let me bring on once again, Law and Crime Networks reporter to Elizabeth Milner, Elizabeth, so good to see you, get a chance to talk about this again. It's been a few months.

Thank you so much. First of all, it was a crazy scene getting in. There was a lot of people who tried to, right? You were there since like 6 a.m. Yes, I was there bright and early 6.30 a.m. got there and there was already a line. Now, it was mainly a lot of press, but then we had this moment where we could just, like, put our names down on the list, come back later. And then when I came back, it was just so many more people.

And I was surprised to see how much interest they had for just kind of what I felt to be like a standard procedural hearing. So many people, I think, wanted to get one of their final glimpses of Sean Combs before they eventually, or before he eventually learns his fate. Yeah, and how did he look? Because they, we have the courtroom sketches, in my opinion. He looks skinnier. Yeah, I was thinking that, too. No, I don't want anyone to mistake what I had said like I had did last year with astonishingly thin, none of that.

But I did feel like he did look slimmer from trial, but I did think he was kind of in an oversized MDC jumpsuit, which I was really surprised he was wearing as opposed to kind of this. what had been ordered by the judge, which was the sweaters, the slacks, all of that stuff. So he came in in the tan khaki suit. He kind of beamed up with smiles. I was surprised given how long it's been since he's seen probably all of us, but I think it was more so the smiles for his family. His family was there. His family was there, and the entire family, too. So that included Keisha Combs, the Wanda Lane, who's been kind of taking care of the twin girls while Sean Combs has been incarcerated.

Sarah Chapman, who is the mother of Chance Combs, Chance Combs was there, the twins were there. Janice Combs, Sean Combs's mother was there, Charlooshy, who's been a fixture every single day of trial. You had him on sidebar. I've interviewed him. And so he was there as well as Quincy Brown, Justin Combs, Christian Combs, and Christian Combs's girlfriend. So it was a really pretty stacked.

And that was just excluding, or that was just including the family, there were still some loved ones there to support too. Let me ask you something. Have you ever walked out of a meeting and you thought, wait a minute, what do we just decide after all of that? Or maybe you sat through a really good discussion, but you kind of lost track of the action items, later on. Look, I've been there. No shame in saying it. But that's why I want to bring your

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And right now, you can get 10% off of Plaid's other features, Note Pin, with code Jesse. Just click the link below or scan the QR code on screen. Okay, so we have to talk about what the main argument was today. The main argument centered around this motion for judgment of acquittal. It's basically when defense attorney, defense counsel says, look, there was not enough evidence to convict this person. And this is regarding the two convictions that he got, right, two charges of transportation to engage in prostitution. I mean, it basically says what it is. It's transporting people across state lines for the purposes.

And international lies. And internationalized for the purposes of sex work. There doesn't have to be force, fraud, or coercion. It was literally transporting men, Cassie, Jane, that's it. Okay, first issue I understand was about the timing of that motion, right? What happened there? Yeah, so initially the government was kind of making the argument here, and it was first starting off with Meredith Foster,

because I think a lot of people have to remember the lead prosecutor in this case, Maureen Comey was no longer there because she's been dismissed from her job, which has been reportedly nothing to do with this case or anything like that. That's another story for another day. But Meredith Foster was making these arguments for the government, And it seems like at first they were kind of talking about challenging the jury instruction, particularly. And they cited some cases, one from 2025 USA versus Kelly, and how the defendant in that case argued on appeal that it was unconstitutionally vague for Mann Act and RICO conspiracy. But the government was pretty much arguing that this should have been raised pre-trial.

They were citing cases from 2003, 1973, just about the broader concerns. But the government was saying it felt like the defense was kind of taking a second bite of the apple. They were encouraging, or the government was saying that the defense is encouraging the defendant to raise these claims afterwards. It says that the defense didn't raise these issues until even after trial, and it says that it should have been kind of raised during the indictment phrase, during the indictment phase. Whereas Alexandra Shapiro, who was making the defense arguments, she was saying that the law on Rule 12 is extremely restrictive. And she says that there's no way to make this argument at an earlier point because this was kind of a result of the acquittal because he was found not guilty of RICO, conspiracy and sex trafficking, victim one, and Jane, victim one being Cassie Ventura. And so the defense was saying that they were unable to make that argument any earlier.

And so they were kind of trying to do it now because that was the most appropriate time for them. You put that to the side about the timing of. The judges, okay, put the timing aside. I go now to the substance, whether or not there are substantive real grounds to throw these convictions out. One of the arguments, and I have to say a lot of these have actually been consistent with arguments that were made in prior filings by the defense. One of them is, and if I'm understanding correctly, Sean Combs didn't make any money off of this prostitution

or he didn't pay for it himself, right? There's like a commercial aspect argument. What did they say? Yeah, so initially they were going to be asking kind of four questions and that both sides had to answer these questions. So this was brought up during question, too, about whether or not the Mann Act prosecution had a financial motive and whether or not the defendant kind of

falled under the second liability, which is something I completely didn't know about because I'm not a lawyer or anything like that. But it was interesting kind of hearing those arguments. So the defense starting off, that also being Alexandra Shapiro, she was saying that the statute should be construed narrowly to Pimson prostitution.

She said that Mr. Combs was an alleged consumer and that this is just kind of a wire type of case. And it seemed like that's what the defense's whole argument was, that he was just financially giving the money, but it wasn't that he was necessarily making the money. And so the judge said, well, why wouldn't Combs be liable for willfully, under that willfully causing theory? And the defense said, no, because it's talking about the transportation aspect and the mens rea is that people would engage.

Intent. Yes, exactly. And the intent that people would engage in prostitution. You can't say that he's willfully doing that necessarily because he, in essence, was just watching two people have sex pretty much. And so the defense was talking about the money aspect and how they previously argued that, you know, the money was for time. It wasn't necessarily for sexual purposes. It wasn't that typical pimp prostitute situation like that they were trying to make that comparison to. And so the defense was saying that it seems to imply that Sean Combs' conviction was based off the money transaction. Because if you remember from those summary flight charts, it was very easy for the jury to draw those conclusions about this is how much money was paid.

This is what this, when this flight happened. And we, the jury found an essence. that when these hotel nights were happening, that this was for the, pretty much, the process of transporting people across state lines for the purposes of prostitution. Whereas the government was saying that the conviction should still stand that the defense is challenging the vagueness

and the definition of prostitution specifically. And so the government said that this issue isn't whether the defendant himself engaged in prostitution and specifically in sexual acts. It's whether the defendant transported a person across state lines or international lines for the purposes of sex. And so the government argued that he facilitated the transportation with intent, and even though Cassie and Jane, and that's kind of where that first liability, secondary liability come in, where Cassie and Jane were the ones that the government was kind of saying were the ones who were contacting these entertainers or these escorts.

But it was Diddy or Sean Combs who had that second liability because he watched, but he also provided the money. Like he ate it and abetted it in a way. Yes, exactly. Because it's not like a traditional case where someone had this organization. organization that was shipping off prostitutes to different people and this wide network. Yeah, but that's not necessarily what's required of this law. It's did you transport people across lines for the purposes of sex work? And I hear that, and I hear that argument. And yeah.

Oh, I was going to say, and the defense kind of, you know, brought it back too later where they were saying that the government hasn't raised to the jury, the secondary liability. And that speaks volume. So Alexandra Shapiro making that argument. And she says that they don't contest that the money came from Sean Combs. That's what I thought was interesting in their argument. Don't you remember during the trial? How much evidence was there that the money that came from him or he was on the phone or there was voice notes or messages, right?

That he was directing all of it. Exactly, exactly. And so in kind of that last hurrah to save this argument, the defense said that the Man Act actually historically is an embarrassment to the United States because that's where they kind of brought in that racial undertone that it was founded under. Can you explain that? They've said consistently it's racist. What did they say about that? And then we'll get into the constitutional arguments, which I think are really interesting. But before that, what did they say about it being racist? Well, this is an argument that they've made previously, right?

This is an argument that they've been making for months on end where essentially the law was drafted a long time ago in different times and different ages, where it's really just kind of talking about the slave trade and transporting persons across. state lines. And so what the defense was pretty much saying that the purposes of this law in general in the 2025 lens is not intended for what it was at and initially made for. And so what they're saying is nowadays that the DOJ Department of Justice is pretty much only prosecuting where it is kind of that typical sex trafficking in a way people across state lines or minors. And so I think the defense's whole point that they were trying to drive home was that these were consenting adults

who were coming across state lines and what i thought was interesting to jesse is i'm wondering if the money transaction wasn't there if there was if the prosecution wasn't able to find these money points would we even be sitting here today commercial can just mean something of value so if the escorts were receiving something of value to engage in this work or the argument would be jane or cassie were receiving something of value in exchange like a fancy gift Yeah, I think they can make that argument, but you also do have money trail. Yes, you do have the money trail. I mean, they did make their argument in prior filings suggesting he's a prominent black man

who's being prosecuted for this, that it's not a tag along of, like you see in other cases, of a large sex trafficking network. He was convicted of that and that alone, and it does raise the question if all they ever had were those charges and not racketeering and not sex trafficking, would they have even brought this case. Yeah, and that's what the defense also pointed out today too. We have to get into this First Amendment argument. Now, I've talked about this on a previous sidebar because it was in one of the defense's filings. This is a novel argument. This is very interesting. They're basically saying he is protected by the First Amendment and that this is simply voyeurism? Explain

this to us. Yes, and so that came up in question four, which was answered before question three. just a little bit out of order. But the question was whether the records show, if every time an escort traveled across state lines or international lines, were these encounters, hotel nights, freakoffs, were they always filmed. And so, and the other part two of that question was, does it even really matter?

And so the government, in essence, was saying that, no, it doesn't really matter, and that escorts were routinely filmed and that the evidence at trial showed that, while he frequently filmed the hotel nights or the freakoffs, they also talked about the exhibits showing the sex tapes and those exhibits, also correlate with the travel records, but the government says it's irrelevant, especially to

talk about it because the Mann Act is all about transportation and not necessarily filming. And so the government said that the act that violated the law was transportation. So when he transported the individuals across state lines, it was for the purposes of sex, that he's not just this amateur porn producer, whereas the defense says, well, it doesn't matter if he always filmed the freak officer or not, that he was a producer and a consumer of pornography or amateur porn, as they had called it. And that's protected by the First Amendment. And so Alexander Shapiro, she said that he had a right as a consumer in order to, I guess,

take part in them in a way, I should say, and that adults have the right to consume pornography. Jane even brought it TV, something that we heard during testimony during the trial, so that way they could watch it during their movie nights, just videos of them in their hotel nights. And so the judge was like, well, what does this really have to do with, the conviction for First Amendment issue, and then the defense kind of brought up only fans and just in essence that it's not illegal to consume it because he wasn't necessarily partaking in it.

But I thought it was kind of an interesting argument. I think their strongest part is not every encounter was filmed, right? If you're saying, well, he was just filming it's for personal use, well, not every one of them was filmed. And they say it's about criminalizing, traveling for prostitution, traveling for commercial sex. They talked about the Supreme Court case, O'Brien,

And that's where the Supreme Court upheld a federal law that said it was illegal to destroy draft cards. There was no First Amendment protection. And the court created what's called the O'Brien test for determining whether expressive conduct or symbolic speech does it merit being protected by the First Amendment. The government would need to show significant government interest here. So here, what do they say? What is the government's interest in policing this, in criminalizing what he did? What is it? It's that just to regulate?

Well, honestly, first, Jesse, you should have been inside that courtroom to give us all that little, like, rundown of what O'Brien meant. Because I truly was like, O'Brien, O'Brien. Write down O'Brien if I could find it in my notes because, again, no phone, no computer, nothing. Wasn't able to Google it. But the government said that regulating prostitution is of government interest. They say it's important to discourage violence against.

women, illegal drug use, preventing sexual assault. And they say within all 50 states, there are laws regulating prostitution in all 50 states, depending on which state you're in, determine if there is a substantial issue. And so the government was arguing that prohibiting transportation can help with the goal of thwarting prostitution. Because I know people in the defense specifically have kind of just been chalking up the case to this is just a private matter. This is what's going on and the government's trying to police what's going on in adults' bedroom. And so the defense said, well, this is expressive conduct that's protected by the First Amendment and that the DOJ, the Department of Justice, and their policy confirming as such.

That's what the defense was arguing. And so the defense argued that the DOJ, they prosecute cases with minors and specifically with sex workers. Because again, remember, even though they call the men entertainers or escorts, the defense has been very adamant that these men were not prostitutes. And even the ones that testified, the Punisher as well, or Cheray Hayes and Daniel Phillips, they had testified that they were paid for time, that they weren't necessarily prostitutes, but did admit that they do, you know, do specialized events in those, that sort. But the defense said that these were consenting adults. It occurred in the privacy of hotel rooms or in someone else's home. It wasn't like that they were at a massage parlor or a room kind

of in, you know, that I'm talking about. And so the defense argued that this was pretty much a private matter. And so the government came back and said that this was laid out in several previous submissions that the defense put in and that they were all denied. But it was interesting just kind of hearing those arguments about O'Brien and learning more about O'Brien today. Did you glean anything from the judge, Judge Arun-subramania, about which way he's going to rule on this? Because I understand he didn't make a decision. But he did like, didn't he at one point he's like, if you have a businessman who, you know, pays for his client to be with a prostitute, And the client participates in sexual acts with this prostitute.

Is the businessman liable, or is this businessman a prostitute? Is it transportation doing a job? Exactly. Or in a way. Yeah, and it's interesting. And he asked that because he did. And what was the response? But also, did it give you a sense that he's not believing the defense's arguments?

Well, I think there were little tidbits where I felt that way sometimes. And I feel like Judge Arun Submarini, and he does a very great job in really just kind of fleshing out what both sides want. He's always doubling and asking questions, making sure like, okay, if I'm understanding this correctly, you want this and this. So to answer your first question, the defense said that no, it's not prostitution.

And again, they believe that that's where their client's position really is. And so I felt like from what I could think, you know, because I'm not in the judge's mind or anything like that, it seems like he's leaning toward maybe possibly leaning towards no on the defense motions. I feel like sentencing.

will go on as usual on October 3rd, and the reason I say that is because he said, I'll see you guys next Friday. So I think he already has, in his mind, that sentencing will go forward. But whether or not he'll side with the defense at sentencing or the government at sentencing will be interesting. So two points there. A, he said what, that he'll make him a decision, he might make a decision on this soon, but nothing today about sentencing. Nothing today about sentencing, not even a time. We don't even know the time yet. But it is October 3rd. It is October 3rd. And you're going to be there. And I will be there. And I will be there. And one thing I will say about sentencing, and I think that this might work to the advantage of the prosecutors, the disadvantage of the defense.

Yes, they can make the argument that these charges, these convictions are minor, considering what we're talking about with racketeering and sex trafficking, what he was acquitted of. But I've always said, I think it's the amount of times. The amount of times that he did this. It wasn't a one-off. It was multiple times with multiple sex workers. And did anything come out today about that? Did they mention that the prosecution? Yeah, absolutely.

The government, kind of in their last part of their arguments overall, they were pointing out that Sean Combs also had a history of violence during this breakoff. You talked about the 2016 Intercontinental Hotel incident and what happened there, what happened as late as June of 2024 with Jane. And so the government in their last kind of argument to the judge before we were all dismissed was that Sean Combs had planned these out. He had coordinated these all for his sexual pleasure. So while the defense was kind of pointing out that it was maybe Jane or Cassie who had been in communication with these escorts or entertainers,

they said it was all because it was at the direction of Sean Combs for his sexual pleasure and sexual gratification. And the government said, don't forget why we were here. This has been going on for years. 15 years they pointed out, 2009 to 2024. So it seems like for me and again, not a lawyer or anything like that, But it seems like when the judge takes into consideration, the sentencing, he might take into consideration the full scale of everything from the trial and not specifically the flight logs or that some seemed more willing to participate

than in other time. So it'll be interesting to see. We'll see if we're right or wrong. Yeah, come next week. We shall. Elizabeth Milner, great to see you again. Thanks so much. Thank you.

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 podcast. You can follow me on Instagram or X. I'm Jesse Weber. I'll see you next time.