The Rise and Fall of Diddy - Bad Boy For Life?: 8

Episode Date: November 4, 2025

In the final chapter of Sean “Diddy” Combs’ federal trial, both sides make their closing arguments: one painting a picture of criminal enterprise and coercion, the other insisting on chaos, not conspiracy. Jurors weigh surveillance footage, text messages, and seven weeks of explosive testimony. Then comes the moment everyone’s been waiting for. What happened inside that jury room…and what does it mean for Diddy’s future?Featuring interviews with: Elizabeth Millner, Dan Abrams, Ira Jettleson, Matt Murphy, Mackenzie Joy Brennan, and Will Korman—-Host - Jesse WeberReporter - Elizabeth MillnerExecutive Producer - Jessica LowtherWriter and Producer - Cooper MollAssociate Producer - Tess Jagger-WellsEdit and Sound Design - Anna McClainGuest Booking - Diane Kaye & Alyssa FisherAdditional Production Support - Juliana Battaglia & Stefanie DoucetteLegal review - Elizabeth VulajKey art - Sean PanzeraSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Listener discretion is strongly advised. Sean Diddy Combs entered a Manhattan federal courtroom facing charges that could have resulted in a life sentence. The indictment was sweeping, racketeering conspiracy, sex trafficking by force, fraud, or coercion, two counts of transportation to engage in prostitution. Prosecutors described a structure built around Combs' fame and wealth, a network of staffers and enablers who arrange freak-offs, distributed drugs, and managed anyone who might pose a threat. They said this wasn't a series of isolated incidents.

It was a coordinated enterprise. The defense told a very different story. They acknowledged excess and dysfunction, but denied any criminal conspiracy. They claimed the government had stretched blurred relationships and private chaos into a federal case. Over seven weeks of testimony, jurors heard from nearly a dozen witnesses. They viewed surveillance footage, read explicit text messages, and followed a timeline that stretched back more than a decade. And once the lawyers made their final arguments and the jury began deliberating, everything came down to one question.

Was this the collapse of a criminal enterprise, or just the unraveling of a complicated life? I'm Jesse Weber, and this is the rise and fall of Diddy, the federal trial. In a federal criminal trial, the judge delivers a set of legal instructions before the jury begins deliberating. These instructions define what the charges mean. They tell jurors what the government has to prove, how to interpret evidence, and what the law actually requires. In the Sean Combs case, those instructions became a battleground of their own. The defense wanted precision. They asked for language that narrowed the path to conviction, that emphasized intent and required jurors to connect every dot. The prosecution wanted room to

maneuver. They pushed for wording that allowed inferences, context, and broader interpretations of how criminal conspiracies work. One flashpoint was the definition of conspiracy under racketeering law. The defense wanted the jury to be told that all members of the group must share a common goal. Prosecutors argued that co-conspirators do not need to know the full scope of the enterprise or even each other to be criminally liable. Judge Arun Suburmanian sided with the defense on that point. He declined to expand the instruction and said further clarification,

can come in closing arguments. Another fight came down to just one word. Long crime reporter Elizabeth Milner recalls that the prosecution wanted the jury to consider whether a person's behavior, rather than their statements, could show agreement to join an illegal scheme. The judge says that he will change the sentence in context of conspiracy actions may speak louder than worse.

So they're just adding little things here and there where it doesn't seem either prejudicial to the defendant or that way they can make it very, simple for the jury to understand this. The phrase, actions speak louder than words, was included in a section about evaluating conspiracy, a small change, but one that could affect how jurors weigh direct evidence versus circumstantial evidence. The instructions on forced labor triggered another key dispute. The government wanted to include language stating that sexual services can qualify as labor. They cited a precedent from the R. Kelly trial.

But the defense pushed back, calling the proposal prejudicial and confusing. The judge ended up overruling the government's objection because he said that the concern is that the jury may be confused, that sexual services automatically count as laboring services. While the judge sided with the defense, it would not be hard-coded into the law read to jurors. He said prosecutors could argue that point in closing. And the sex trafficking instructions brought even more disagreement. prosecutors wanted to clarify that a completed sex act is not necessary, that payment does not prove consent, and that prior consensual sexual activity does not eliminate the possibility

of trafficking. The defense argued that this language implied guilt and undermined the presumption of innocence. Again, the judge declined to include all of the government's proposed language. Finally, there was the Man Act. The government successfully persuaded the judge to change one key phrase. Instead of saying someone was transported with intent that the person would engage in prostitution, the instruction would now say to an act of prostitution. They wanted that specific language to be changed to an act of prostitution because they say they didn't want to imply that the person who was transported and in some instances of prostate lines was a sex worker. That shift made it easier for prosecutors to argue that intent

existed, even if the victims themselves didn't consider the acts to be prostitution. So the judge ended up siding with the government here, but it seems like that was the biggest thing from both sides to really hammer out. Throughout the entire back and forth, Judge Suburmanian walked a careful line. He tried to make the instructions fair without overcomplicating the task ahead for the jury. Milner wondered if they were keeping up. Will this all click with the jury that this means this and this means that? But we'll have to wait and see what their reaction is once they ultimately sit down, get those closing arguments, and then get those instructions before they go into that

room and deliberate. By the time it ended, every word of the law the jury would be expected to follow had been scrutinized, negotiated, and locked in. The ground rules were set. Now it was time for the main event. the final chance for each side to make their case. The first to stand before the jury was assistant U.S. attorney, Christy Slavic. Your first great love story is free when you sign up for a free 30-day trial at

audible.ca. slash Wondery. That's audible.ca. slash Wondery. Prosecutor Christy Slavik stood at the podium. Sleeves rolled up, pacing, and confident. This was her moment to tie it all. together. Her task was to convince the jury that what they had seen the past seven weeks was not just troubling or disturbing, but criminal. Her strategy was simple. Paint Sean Combs as the head of a coordinated operation. The beginning of the closing argument by the prosecution is that Sean Combs has a small army of personal staff. No one could stop him. He used his inner circle and money to cover up his crime and even referred to his assistance as foot soldiers and other things like

that. So really pointing out how those who were in Sean Combs' inner circle helped fill this case of racketeering conspiracy against the defendant. Then Slavic reminded jurors of the testimony from Cassie Ventura. They talked about 2011 where Sean Combs attacked Cassie after he found out she was sleeping with Kid Cuddy, 2013 when Sean Combs attacked Cassie in her apartment when Cassie was with Nia and Deontay, 2013, again that same year where Sean Combs assaulted Cassie in Jamaica because that she was taking too long in the bathroom. 2015, where Sean Combs beat up Cassie at a Las Vegas party,

and DRock actually ended up crying after seeing Cassie's injuries. And then, of course, the 2016 incident that happened at the Intercontinental Hotel. She shifted to Jane, the choking, the dragging, the slap that echoed through the testimony of multiple witnesses. Slavic argued that physical violence was not separate from the sex trafficking. They went hand in hand. They were saying that Sean Combs groomed. Jane into sex trafficking. So they say that first stage, again, being the drugs, the

outfits, putting pornography on something that kind of didn't enjoy it according to her testimony. But she said the second stage was the fantasy talk and how the fantasy talk pertained to being with other men and that Sean Combs made it happen eventually. And then third stage was using a payment of rent, that payment of rent was used as leverage. Slavic told jurors that violence was not an unfortunate side effect. It was part of the machinery, a way to break down resistance and ensure obedience. Then came the drugs. Slavic described them as an essential ingredient of every freakoff.

She listed all the drugs out because drugs was something that was very common throughout all the testimony that the witnesses had. So she talked about cocaine, meth, ketamine, oxycodone, Xanax, MDMA, GHB, 2C, and mushrooms as well. She called them chemical handcuffs. used to keep women compliant, awake, and disoriented. Slavic also leaned into Dr. Dawn Hughes' testimony to reinforce her narrative of trauma bonds, manipulation, and power imbalance. To kind of help paint the picture a little bit more in these summations, the question always is, why didn't she leave?

Then she pointed outward to what she said Combs thought he could get away with. They also point to the June 18, 2024 incident that happened at Jean's house where she was physically assaulted. And then at the end of it, when she said she was forced to do a hotel night, even after being assaulted, Sean Combs said something to her saying, is this coercion? And I think the government was really pointing out that coercion was the specific word that Sean Combs used. She shifted focus. Jurors weren't just asked to consider what happened behind hotel doors. They were also shown what came before, who arranged the travel, who paid for it, and who benefited. The government called it coercion.

In terms of Calgary related to Cassie, the government says that the defendant told Cassie to book travel for these escorts and that these escorts would travel to places like a visa as an example or New York City. The flight logs were back. Government exhibits that mapped out movements from one city to another, from Los Angeles to New York, from Atlanta to Miami. They brought back that flight summary chart again, something that I think works in their favor because the jury can take this back when they go to deliberations and really see everything. laid out in a way like a road map. One name came up again and again, Jules. They point to one specific instance, starting in August of 2009, August 26 of that year, where Sean Combs coordinated with Jules, Jules being the escort that C.N. Sean Combs used often during their freak-offs, but I think also notably he was the escort

that was inside that hotel room during the March 2016 incident at the Intercompanmental Hotel. The government said Combs didn't just use Jules. He moved him, booked his flights, paid his drivers. They brought up flight records, including a $419 flight to get Jules over to New York City from Los Angeles. Also a $220 limo service that was also paid for by Sean Combs. And that Sean Combs even texted Jules that he'll tip him more if he can make it out to New York City because, again, he's traveling from L.A. So there's the transportation right there. And then the government points to the defendant paid for Clayton Howard, aka Dave, another escort that was used to fly.

him to Los Angeles from New York City. And so the government, again, relying on flight records, that summary chart that was shown towards the end of the trial, just saying that the defendant is guilty on count three in every single one of these instances. And it's a lot of instances on that specific chart. Count five pointed to Jane. The government says that the defendant transported escorts or entertainers, as Jane calls them to Miami, to Los Angeles, to New York. The government said that Jane, although she set up the travel and paid for the flights, She was always reimbursed by Sean Combs. More names followed.

Jessica, Paul, Reggie, flights to Turks and Caicos, texts to an escort agency rep. We also talk about how Jessica Ruiz, the travel agent, also set up travel because, of course, that's her job, but the account holder being assigned to Sean Combs. And so the government even talked about the defendant transporting an entertainer or Paul, somebody that Jane and Sean Combs used during their hotel nights to Turks and Kings. And he was traveling from Los Angeles for these hotel nights or Wild King nights, whatever you want to call them. The paper trail led to Las Vegas. The government said the defendant directed Jane to have hotel nights with three escorts, that Reggie, an escort or entertainer or whatever.

We want to call them that he flew out from Vegas to Los Angeles. So again, transporting Reggie over from Vegas to Los Angeles. According to prosecutors, this wasn't casual or spontaneous. it was structured, documented, financially backed, and when paired with the travel records and texts, it became a charge that jury could trace step by step. I think it's probably one of the strongest charges that the government has and their holster here.

If I was somebody who didn't know this case at all, and I was coming in for the first time listening to these closing arguments, I feel like the government has a really strong case on all counts. Christy Slavic ended her closing with a forceful call to action. She said the jury had seen the pattern, the violence, the enterprise. G told them it was time to hold Combs accountable. But the defense still had its say. And when Mark Agnifalo stepped up, he didn't just dispute the government's case.

He tried to dismantle it piece by piece. Literally one of the first lines he said in his closing argument was this is a tale of two trials. The first trial is about witnesses and videos and texts and evidence. He said the second trial was just the word of mouth by the prosecutors. He was saying that this case is badly exaggerated. He says it's made up, in other words. He was saying that the evidence shows that Sean Combs is a self-made successful black entrepreneur. He's done something that's hard to do and that's have wonderful, successful, legitimate businesses.

He says how many government witnesses said that they were moved by Sean Combs, that being with him was like drinking from a fire hose. Magnifalo said the government had distorted reality, trying to turn personal chaos, into federal crime. Yes, Combs had his demons, but mistakes, he argued, didn't amount to a criminal enterprise. He opened with what he was willing to admit. If domestic violence was a charge here, he would have pled guilty to it. Then he pivoted, arguing the prosecution had inflated consensual acts into allegations of trafficking and cast emotionally complex relationships as evidence of coercion. He challenged the credibility of the government's key witnesses.

arguing their stories conflicted with texts, timelines, and common sense. When he turned to Mia, he suggested her version of events was crafted, not candid. But Agnifilos said the biggest problem wasn't anyone witness. It was the lack of something much larger. There is a gaping lack of evidence. He says that he was trying to do this enterprise by what, having sex with his girlfriends? He told jurors that the so-called enterprise was nothing more than a high-profile while entourage, people doing their jobs, not committing crimes.

On the trafficking charges, Agnifalo said what looked extreme from the outside was simply part of a world built on sex, ego, and blurred lines. He didn't deny it was messy, but he said it wasn't criminal. Mark Ignifalo is like, okay, I suppose you can sex traffic your girlfriend if you sell her into prostitution, they're swingers, this is a lifestyle. Again, that was a common theme throughout his closing, was that this was just an alternative. lifestyle, that these were just swingers, and these were just people who were engaging in threesomes, that they were adults, that they were making these choices.

And he was saying that this was what people do who are in love. They do things that maybe they don't necessarily want to do, but they do it because they love their partner, and that doesn't amount to sex trafficking. As he neared the end, Agnifalo made a sweeping accusation. This wasn't about justice, he said. It was retaliation. He says the government targeted Sean Combs because of Cassie's lawsuit. He says that's what makes this different from any other case, especially ones that he has defended, where he says, okay, today you, you being the jury, are the United States of America.

I'm asking you to acquit Sean Combs on all counts and return him to his family who's been waiting for him. Mark Agnifalo gave the jury an alternative story. He asked them to look past the headlines and the accusations and see the messiness as just that. Messy, not criminal. but the prosecution still had the last word. In their rebuttal, Assistant U.S. Attorney Maureen Comey stood before the jury one last time

and didn't hold back. She accused the defense of trying to distract of blaming the victims, of turning the trial into a referendum on the women and the government instead of on Sean Combs. She went as far to say, He is not a god,

pushing back on the defense's portrayal of Combs is untouchable, misunderstood, and above the law. Comey reminded jurors of the women who testified, the abuse they described, and the fear that lingered long after they left. She said this wasn't about lifestyle. It was about power, violence, and a man who didn't take no for an answer.

And then she brought it home. This ends in this courtroom, she said. Hold him accountable. The arguments were over. The evidence had been laid bare, the stories told, the counter-narrative sharpened. Now, it was out of the lawyer's hands. Twelve jurors would step into a room, shut the door behind them, and decide whether Sean Combs was guilty of some of the most serious federal charges imaginable.

When the jury left the courtroom, they carried more than just a verdict form. They carried the weight of a case that had promised to pull back the curtain on a world of power, violence, and control. Judge Arun-subramanian gave them their final instructions. He reminded them that Sean Combs was presumed innocent, that the government had the burden to prove each charge beyond a reasonable doubt, that sympathy or disgust could not guide their decision. Only the law.

The courtroom waited, and so did the world. Deliberations began the next morning. questions, no notes, just long hours behind closed doors. Over the course of three days, the jury deliberated for roughly 13 hours. And then, on the morning of July 2, 2025, they sent a message to the court. They had reached a verdict. The gallery filled quickly. Reporters, spectators, family members, attorneys on both sides. The jury filed in. The four person stood, and the clerk began to read. Sean Diddy Combs was convicted on two counts of transportation to engage in prostitution.

Charges brought under the Federal Man Act, stemming from allegations that he arranged for individuals, including ex-girlfriends and male sex workers, to cross state lines for illicit sexual events. But, on the most serious charges, racketeering conspiracy and sex trafficking by force-frafficking, by force, fraud, or coercion, Combs was acquitted. Charges that could have carried life sentences dismissed. The verdict was in, but the questions that followed were only just beginning. And outside the courthouse, the crowd began to gather.

Elizabeth Milner was in the thick of the pandemonium. As I can see right now, it's just a crowd of people, both press and the public, just crowding around. Their cell phones are out. Their cameras are out. Some people are standing on what looks to be ladders or at least kind of those metal barricades. I'm even standing in the roadway. I hope they're not necessarily blocking any traffic. But I did hear an audible kind of exclaim when the family did come out. Combs attorneys emerged to declare victory, not just for their client. Today's a great victory. It's a great victory for Sean Combs. It's a great victory for the jury system. You saw that the

Southern District of New York prosecutors came at him with all that they had. They're not stopping, but one thing stands between all of us and a prison, and that is a jury of 12 citizens. They argued that not only had the government overreached, but that the media had fueled a false public narrative from the start. Sean Combs has not sexually assaulted anybody. I've been saying this for months. We've said it with each lawsuit that came out, and today that was proven true.

The media got it wrong about Sean Combs every single day for nearly two years. I ask that for every time you guys see a civil lawsuit, criminal complaints or criminal indictments, you actually take a look and analyze these and see whether or not these are actually going to stand up in a court of law, because today they did not. A case that had rocked the music industry, dominated headlines, and pulled back the curtain on the world of Sean Combs, had taken its final turn. But what it all meant, that was just beginning to unfold. Look, this is a win for Sean Combs. This is a big victory. No matter how you look at this case, there was almost no chance he was going to be acquitted of the transportation for the purposes of prostitution counts.

when you looked at all the evidence, all the records, all the documents with regard to those counts, it was hard to imagine how he would have been acquitted of those charges. The fact that he was acquitted of all of the most serious charges is a big win. That's Long Crime's very own CEO, Dan Abrams. He noted the government's case on transportation was strong, built on receipts and records. But when it came to the more serious charges, the legal standard was different. You needed coercion and force, right? And I think that there was enough consensual activity, consensual relationships between Jane and Cassie,

such that the jurors didn't feel that there was proof beyond a reasonable doubt. In other words, the presence of consensual sex, even in the context of disturbing or exploitative behavior, may have been enough to create doubt. Milner made a similar observation. I think consent was really a top. of discussion as far as, you know, she kept on the relationship. Yes, while it was on and off for an 11-year period, but she kept on the relationship even after these instances of violence, even after doing these freakoffs that she says she didn't want to be doing. And so maybe they

were like, okay, well, maybe at the end of the day, their huge takeaway from it was possibly consents being about the heart of the issue. If there was one count that seemed like a lock for the prosecution, it was the sex trafficking charge tied to Cassie Ventura fine. They saw, spent considerable time walking jurors through the timeline from the intercontinental hotel incident to what prosecutors called the freakoffs to the years of surveillance and isolation. They argued it was all part of a long-term pattern of control, but the jury didn't agree. Combs was acquitted on that charge. It was a decision that stumped even the reporters who followed the case from start to finish.

I was a little surprised, especially to count too, but I think probably and likely a question that went through those jurors' minds is probably the relationship and how long the relationship lasted. Count two was the first major sex trafficking charge. It stem from the same incident that had anchored much of the prosecution's narrative, that viral hotel video, the alleged assault, and the days that followed. But Milner noted that even with graphic evidence and emotional testimony, something about the government's case on that count didn't land.

the jurors were really paying close attention to both sides' closing argument, especially Mark Agnifalo's closing argument, where I think that they really listened to what he had said in terms of just by the government's definition, by the federal law's definition of sex trafficking, it only has to be one instance. And so when Mark Agnifalo is getting up there in his closing argument and saying, okay, well, they did 75 different creakoffs and then it's just that one instance that makes it number 76. And then that all of a sudden becomes sex trafficking, maybe the jury really listened to that and really took note of that. That relationship lasted over a decade. For jurors, that longevity may have blurred the lines between coercion and consent. Milner suggested that Agnifilis framing, minimizing one incident among many, may have resonated. And when the defense shifted focus to the nature of Cassie and Combs' relationship, the jurors may have followed. Maybe they were like, okay, well, when the breakup happened,

and was it because of these freakoffs, but whether or not that was the reason that the relationship ended, it seemed like the relationship ended because of possible jealousy, because of another woman, and it didn't seem like their relationship ended necessarily because of the freakoff. The other complication?

Cassie's lawsuit. Though it was settled before trial, her civil case loomed large in the background. The defense had alluded to it as a motive. The jury may have remembered it. So while Combs was found guilty on the Man Act charges involving Jane, The count tied to Cassie was different.

It rested on a relationship that defied easy legal categories. That murkiness made its mark. It helped to quit Combs on what many saw as the prosecution's centerpiece count. But even without convictions on the sex trafficking or racketeering charges, the two guilty verdicts still carry weight. They are both federal felonies under the Man Act. Each one could come with years behind bars. And depending on how the judge rules,

Combs could face prison, probation, or something in between. But attorney Will Corman points out, there's something else hanging over him now, a label. Violation that man not carries with it, sex offender registration. Registration is not automatic in federal cases, but the court has discretion and prosecutors can argue that the conduct qualifies. Even if Combs avoids prison, Corman noted that the stigma of a potential sex offender designation could follow him long

after sentencing. And that may be the real cost, publicly, professionally, and personally. Because as Dan Abrams points out, this wasn't a case of mistaken identity or false accusation. This isn't one of these cases where it's a question of did he do it or didn't he do it? We know he did it. We know he did really bad things here. The question is, did those really really bad things fall into the legal definition of sex traffic or racketeering. And the jury believes the answer is no. But that doesn't mean that he's going to get the kind of groundswell of support that someone who people believe is literally innocent, falsely accused might get in a different kind of case. So what does that mean for sentencing? I think it's possible that he goes to prison.

I don't think he's going to mix out. I don't think it's going to be a 10-year federal prison sentence. but it's possible that the judge decides that not saying that the MDCC is enough, and he actually needs to go to a federal facility somewhere else in the country. Sean Combs may have dodged the most serious federal charges, but he's still facing prison time. Each count under the Mann Act carries a maximum of 10 years. But what that actually translates to in sentencing is still an open question. Former prosecutor Matt Murphy puts things into perspective, bluntly.

We're not looking at double-distance. I cannot imagine the court imposing that. And remember, because this law is so old and we're in an age of Uber, so literally somebody in New York City, a man or a woman who engages the services of a sex worker who lives in New Jersey, and if they pay for their Uber, that technically is a Man Act violation. It's a morality crime. In a recent filing, prosecutors indicated a sentencing guideline range of 51 to 63 months. The defense is hoping for much less, just 21 months.

And at the time the verdict was read, Combs had already served nearly 10. Still, the government may argue for aggravating circumstances that Combs didn't just commit a technical violation. He used power and violence to exert control. Can the court aggravate nonviolent offenses that he was convicted of, which are the Man Act violations? Can he aggravate those when he was acquitted of the more serious charges, essentially acquitted of everything that involved violence, threats, all of that sort of thing. Federal sentencing also isn't just about courtroom theatrics. A key factor will be the pre-sentencing report written by a probation officer who

investigates everything from a defendant's family life to community ties. So in federal court, they rely very heavily on those pre-sentencing investigations. So essentially what will happen is there will be a federal probation officer and they talk to family members, they'll talk to employers, they'll talk to neighbors. they will make a recommendation to the court as to suitability for release, suitability for time. And that's something that federal judges traditionally really adhere to. They really put a lot of weight on those. So that's something that I think is going to be very interesting. And a lot of that will come down to what the individuals involved in that investigation were going to see

what they thought of the case, even though it shouldn't impact their professional recommendation. Did they think he got away with something horrific here? Did they think that he was getting railroaded from the beginning, I think that may reflect in the recommendation of the court. How the probation officer interprets the case could shape Combs' fate at sentencing. But beyond time behind bars, there's another risk, one that could hit him where he's arguably most vulnerable, his wealth. This is a very, very wealthy man who made that money legitimately in the bad boy records in the music industry and in the film industry. That's how he made his money. But in this case, Murphy says the feds would be on.

shaky ground. He didn't make any money from the freakoffs. He didn't make any money from all of the alleged things he did. He didn't make any money from that horrible video that we saw where he's beating Cassie in that hotel. That's not the source of his income. And Murphy warns that going after Combs' assets could backfire legally and publicly. There's an old adage in the law that bad facts make bad law. And if they run around and try to seize a bunch of stuff based on this, they're literally taking assets from a citizen that earned them legally. He may be a villain. He may be a bully. He may be a horrible person, but he made that money legally. He was not charged here with tax fraud, which means he paid taxes on it. I think it would be a very poor move if they try to take

a bunch of his stuff. They still have to create a nexus between the Man Act and his property, and I just don't see it. Murphy says pushing for forfeiture could set a dangerous precedent, confiscating lawfully earned wealth with little connection to the crimes. But even if Combs holds on to his assets in criminal court, that doesn't mean they're safe. He's still facing a legal onslaught on another front. Civilly, he's facing an avalanche, more than 60 lawsuits. Claims include sexual assault, trafficking, harassment, and emotional abuse. And while the verdict in this federal case gives him room to breathe, it doesn't make those lawsuits disappear. When it comes to all those pending civil suits, because now those same people, in theory, would have to

come in and testify. That's because the burden of proof in civil court is lower, but without a conviction to point to, each plaintiff now has to prove their case from scratch. That doesn't mean they'll all vanish. Some, like Don Rashard and Cassie Ventura, already testified under oath in the criminal trial. Others have legal teams gearing up for scorched earth litigation. But many cases could fizzle. These people, there's a lot to be said for this idea that they were all jumping jumping on the bandwagon trying to get money. Most judges are going to allow the defense to make that argument. At the end of the day, these lawsuits will work the way through the system. I'm sure some of them will be dismissed on their merits. I wouldn't be surprised if some of them

proceeded to trial, but I bet we're going to see his legal team trying to settle and get rid of as many as possible. Either way, it will be costly. Whatever the outcome, this sentencing is not just a legal endpoint. It may determine how much freedom Combs has. how much money he keeps. But as Matt Murphy points out, even with everything hanging in the balance, Combs is still in a far better position than many. He will have freedom at some point.

A lot of people were predicting he was never going to see freedom ever again. The sentencing hearing is currently scheduled for October 3rd, 2025. But Combs' team has filed a motion to expedite. Their reasoning? With the racketeering and sex trafficking charges off the table, They're hoping the court might reconsider bail. We know that behind the scenes, what they want, of course, is they expect a chance that he's going to be released. But that road is steep.

We have to remember that one of the things that Diddy got in trouble for in jail was using other inmates' calling number. So he was calling witnesses in the case from jail using other inmates. That was a direct affront to that judge. Remember, we had all those attempts at bail that were denied at the very beginning of the case, one after another after another. This judge, and it's the same judge who's going to send some, denied that over and over again. That red flag obviously stuck with the judge. Attorney McKenzie Joy Brennan says what happens next may come down to how that same judge interprets what the jury didn't see. The bottom line is nobody knows what's going on in the judge's head.

And I think the only glimpse that I got of which direction he might be leaning is his decision on bail. The bail assessment is very similar. to the sentencing assessment, and the fact that he did not let Diddy out on bail pending sentencing could mean that he's not feeling that this is somebody who won't be a danger to the community. But outside the courtroom, that decision triggered a different kind of scramble, one that played out behind the scenes as Combs' team weighed what it would actually take to get him out. Can he walk out before sentencing? That question has hovered since the moment the verdict was read, and it's not just a legal

one. It is logistical, procedural, and deeply personal. To understand how it might play out, we turn to someone who would know. Ira Juddelson is one of the most well-known bail bondsmen in the country. He's worked on high-profile releases from Bernie Madoff to Dominic Strauss-Kahn, and yes, Sean Combs. In this case, with Puffy, I got brought in, and we talked about possibly renting out his plane and keeping it in Honolulu. We talked about surrendering his passport, his family's passports. We talked about putting up his house. We talked about private security 24-7.

Jettelson's team put together a detailed bail proposal before trial. We gave him the idea of there would be no Wi-Fi in the building that we were looking at and that he would not be able to really be able to connect with anybody but his legal team and his family. We thought at that point that maybe we had a chance. But at the end, the judge denied it. That denial came when the top charges still carried the possibility of life in prison. In the eyes of the judge, Combs had the resources to flee and too much at stake not to. But with the most serious charges now behind him, could the calculus change?

The judge denied bail based on the statute. And the statute stated a certain amount of information part of the Mann Act that was not eligible for bail. There are certain circumstances that can be done. We're going to regroup again. I know that they were going to go talk to Mr. Combs again and see what happens there. We have the October 3rd date, and I don't know where he stood. As of the other day, he wanted to get out. I don't think anybody wants to be at MDC where he is.

We could go back with another package. A new proposal was submitted July 29th, but there's no guarantee the judge will bite, especially when it comes to geography. I don't think, and this is my opinion, that the judge would let us. out of the jurisdiction. When we first put the first package together, we did have an apartment here in the city that I did scout out a brownstone in New York that was sufficient enough. We thought, which was one interest in, one entrance out for our security to be there, and no rooftop couldn't get out from any of the windows. I can't determine what a judge is going

to think. I don't think he would let that happen if he decided to make bail, but you never know. Juddelson says any release plan would rely entirely on independent oversight. No Combs insiders, no bodyguards from the inner circle, just his own vetted team. My team is ex-law enforcement, all gentlemen that have been involved either in the Marshal Service, FBI, police, even some CIA. My people would not risk their lives on something or risk their reputation or even possibly a criminal charge on something like this. So my guys are vetted.

They've been doing this a very long time. They wouldn't jeopardize anything like that. Now, when we first talked about private security, Puffy wanted some of his people. We denied that right away. It's our guys. It's my reputation on the line here. And that's when I went to court. And Tony Rico and Mark Ignifalo both stood up and said,

hey, Mr. Jettleston is, you know, his reputation's on the line here. You know, he's been doing this a long time. I've bailed out Harvey Weinstein, Connor McGregor, Plachsville, Kat Williams, Lawrence Taylor. So I'm not going to put my reputation or my license in jeopardy for X amount of money. The idea was house arrest, but strict. We were going to have a call lock.

So you could see who his calls were going to. We were going to try to take away his Wi-Fi in the building, which would have been a lot easy. We would have limit the people that would come see him. So at the end of the day, we had cameras inside the apartment that we were going to do, which our people were going to put up. And we were going to all let the government be able to get into that system to see who was coming in and out.

Still, Eve and Juddelson concedes the odds of the plan amounting to anything are slim. Is there a strong possibility? I would say at this point, no. That bail decision denying Combs' release pending sentencing may have offered the clearest signal yet. At the bail hearing, the judge said that the defense failed to show, with clear and convincing evidence, that Diddy is not a a danger to the community. So for now, Combs remains in federal custody. His legal team is weighing options. Prosecutors are preparing for sentencing.

And the fate of the man who once called himself untouchable is now entirely in the court's hands. To help make sense of what this outcome really means, we turn to someone who's been following the case closely from a legal standpoint, attorney and legal analyst, McKenzie Joy Brennan. We asked Brennan what the split verdict suggests about. how the jury interpreted the evidence. The charges that he was convicted on, they were the smallest deal and they were a slam dunk.

The Man Act, that's just transporting people across state lines for purposes of sex work. The Man Act has been used in some recent high-profile federal cases, but Brennan emphasized that Combs stood apart from most defendants charged under that law. He's obviously not the traditional Man Act defendant, but I think most of the things that you hear about him being not the traditional defendant, it's because he's not the traditional anything. This is somebody

who has tremendous power is in the 1% of the 1% of famous people with resources, etc. So it's really hard to make an accurate comparison between him and any other defendants on any of these charges because that's kind of the point is he is a huge celebrity and has accrued a lot of power in addition to wealth. She pointed out the broader implications of the jury's decision to acquit on the sex trafficking and racketeering charges, especially after a moment of uncertainty. There was some thought that the jury was not going to be able to reach a consensus. I think we learned a lot about the jury on the fact that neither of those charges succeeded. And outside the courtroom, Brennan saw another kind of reckoning playing out, one shaped not just by

evidence, but by perception. It has been so bizarre, especially in the aftermath, because, you know, Monday morning quarterback sort of idea. but it's been crazy to watch so many online commenters and whatnot say, like, yeah, he's a bad guy, essentially take the defense's whole argument and parrot it. Like, yeah, he's clearly a bad guy. He's a domestic abuser. But this was a bogus RICO charge. And I'm sitting here and I'm thinking, well, from a legal perspective, like, you are absolutely right. And I think that they're going on this mafia picture that they have in their head. But from my perspective, I'm like, he absolutely got employees to do his dirty work. For Brennan, the acquittals on the sex trafficking counts weren't just about the strength of the evidence. They reflected something deeper, something cultural, a shift in how people understand power, coercion, and consent, or maybe a refusal to understand it at all. The sex trafficking conversation is potentially a long one. I think that it really reflects a reckoning that we have still going on societally. We saw the start of it with the Me Too movement, and I think we've taken some steps in the opposite direction in recent years about what consent is and what constitutes coercion.

Obviously, there was a moment where powerful men were being held to account. I think we've backtracked a little bit. She pointed to the defense strategy, which leaned heavily on reframing coercive relationships as consensual ones. That argument, she says, landed especially with this particular jury. They really focused on the idea that this is a private kink and that something can be called a kink, even if other people are saying that they're not consenting to it. This wasn't just legal theory. It was about language, perception, and generational blind spots. The largest demographic on the jury, five out of the 12, were men over 50 years old. And I think that made a huge difference on the sex trafficking because the defense in their case against the sex trafficking,

really went after the concept of coercion and whether or not consent was freely given by the victims. Imagine being one of these men on the jury and thinking, you know, my wife always looks like she likes it, and I don't really think any further than that. So to pull that thread, I would really have to look at a lot of things. One of the prosecution's biggest challenges was showing how powerful figures manipulate not just bodies, but entire belief systems, especially when the power imbalance is so steep. Cassie was 19 when she met Diddy and he was pushing 40, and the power dynamic of her being a young person starting out in the industry

with no background in it and him already being a mogul of sorts, that's a really common dynamic that they actively seek out people who comparatively have less power, have a need for professional development, in addition to the romantic relationship, so that there are kind of multiple fronts of dependence and pressure that the perpetrator can work on. And once that kind of pressure takes hold, Brendan argues, it colors everything that comes after,

even the moments that look like consent. You're going to act your heart out to act like you like it next time you're out of freak off because you remember what happened when you tried to leave last time. And then the defense comes in and tries to show texts that we're loving after that and explicit videos of Cassie appearing to enjoy things after that. Whereas to me, it's like, well, yeah, if you know that you get beaten when you try to leave

or express that you don't want to do this, you're going to try your darndest to look like you're enjoying it. But that really did not seem to be understood here. To the defense, a video of Cassie smiling or a text message saying, I love you, meant everything. To Brennan, it meant something very different. It meant survival. Once you bring violence into the picture, every subsequent act is influenced by that specter. That gap in understanding between what the law allows and what a jury believes is what Brennan says continues to undermine the prosecution of coercive abuse.

That same disconnect, the space between legal definitions and cultural assumptions also shaped the outcome on the racketeering charge. The government tried to use RICO to tell a bigger story. one that could account for the years of alleged abuse, cover-ups, and enablers. But Brennan says that, too, may have been a mismatch with how jurors imagine the crime. Racketeering in and of itself is something that I don't even think a lot of law students understand because it's such an amorphous concept. Even when it was used for more organized crime purposes, it was something that was designed to sweep up all of these crimes that maybe the statute of limitations had expired,

and you have all sorts of different states going on, and maybe you're not confident that you can prove each one of these crimes beyond a reasonable doubt if you focused on them, but when you pull together all this evidence of bad acts, surrounding a person who you know is doing all of this, but you can't put their fingerprints on whatever proverbial crime scene, there needed to be a cause of action

that went after the heads of these organizations. Everybody is most familiar with it in the purpose of organized crime. But that does not mean that it can only be applied to circumstances where there is a very clear organization and very clear pinch people under a mob boss. The statute was originally crafted to dismantle traditional organized crime families. But in recent years, prosecutors have started using it in a different way. What we're seeing nowadays, and it has been done successfully in similar cases, is the RICO statute being applied to employers, who are powerful entertainers, either cults of personality or actual cults.

In the Combs case, prosecutors introduced a broad range of evidence, allegations of arson, financial threats, and abuse spanning more than a decade. The goal was to show a pattern of criminal activity, one directed from the top. But according to Brennan, the biggest weakness in the government's case wasn't the pattern. It was the silence. You didn't have enough employees straight up saying I was being commissioned to commit crimes, and I now regret that. I think the stakes were too high for employees to do that. They either faced prosecution or potential witness intimidation, and for the jury, they really wanted to see employees say those words out loud. I would not ever hang my hat on employees needing to testify for there to be a RICO case.

But juries seem to. If the prosecution struggled to connect the dots without a clear insider, the defense leaned into that absence. In fact, they created one of their strongest advantages by choosing not to call a single witness of their own. No former employees defending combs, no character witnesses softening the image. Instead, they relied entirely on cross-examination. Not calling any witnesses means that you don't have anyone strong enough. to speak to this guy's character or to deny what had happened

that it overcomes the risk of what they might be asked on cross. And that's huge. Think about that. That there is nobody who has more positive than potential negative to say that can be called here. And that it is so risky to open the door to any sort of character evidence

that really any facts that they could have brought in are more likely to be damaging than positive. From a legal strategy standpoint, Brennan says the choice speaks for itself. They didn't risk opening the door to more damaging testimony, and they gave the jury nothing to focus on except the weaknesses in the government's case. They got to basically end with the impression left on cross,

which is we've eviscerated these victims' character, and doesn't that make you think they're probably lying? Cross examinations are always a gamble, but in this case, the defense used them to build their narrative that the women who testified were flawed, inconsistent, and possibly after a payout. Brennan says that story, combined with a tightly controlled presentation, may have been more persuasive than anything a defense witness could have added.

One of the defense's most effective tactics may have been admitting to some wrongdoing. They told the jury that Combs had a dark side, but argued that didn't make him guilty of sex trafficking or racketeering. Brennan saw that as both clever and contradictory. In a case like this, I think a lot of us either in the legal field or more cynical see the fact that they likely had to convince Diddy to let them give an inch here because before the video of Cassie was leaked and before they were aware that there was still a copy out there to leak, they denied that happened.

You know, lest we forget, they did not want to own a lot of those bad facts until they couldn't deny it anymore, and then they were pushed to accept it. But here, yeah, I think it was an extremely powerful strategy, even though I felt that it made for a logically incoherent argument, because on the other hand, you have the defense saying that he's a domestic abuser, not a sex trafficker, and that goes a long way to proving sex trafficking. Those are, like, far from being mutually exclusive, admitting the one brings you much closer to proving the other. But I think in the jury's mind, more than anything, it looks like this is somebody who knows he's done something wrong, knows his problems, and is honest, mea culpa. I have a lot of flaws, but I didn't do that.

That kind of aw shucks, I ain't perfect, but I'm sure not a sex trafficker. Juries tend to really like that. It looks sincere. It looks honest. They don't see it necessarily as being as strategic as it is. the jury just enough truth to hold on to and drew a hard line at what they insisted wasn't true. It was a risky but effective sleight of hand. On the other hand, you have the defense argument then being, like, let's not introduce

character evidence against ditty, but then attacking the character of the victims. I think it made for a very incoherent legal strategy, but it really does show that these kind of esoteric first impressions are more powerful than just about anything else with a jury. To Brennan, the defense's approach may have lacked consistency, but it didn't lack impact. In the end, perception carried more weight than principle. And no matter what sentence the judge hands down, she says the larger takeaway is already taking shape. It sends a really unfortunate message to future victims and future prosecutors about where

we are socially right now. We're not in the thick of the Me Too movement anymore. I think we've taken some steps back and we have yet to see where that pendulum's going to land. In Brennan's view, the Combs case revealed just how many barriers still exist for survivors of sexual violence, not just in the courtroom, but in the laws themselves. I think one big one would be working on things like NDA permissibility and statute of limitations on sex crimes. The prosecution relied on federal statutes, sex trafficking, and the Mann Act, not because they were a perfect fit, but because they were still viable. The reason that they had to use RICO and sex trafficking is that these federal crimes were the only crimes big enough and federal, such that they had a longer statute of limitations. Those time limits failed to account for how long it often takes survivors to come forward.

And then the other thing that is so toxic, we see it across the board in these sexual assault cases, is the use of NDAs. In this case, as in so many others, they created a silence that even federal subpoenas struggled to break. It's super, super common in Hollywood settings, business settings, and there really is virtually no benefit to victims. The only argued benefit is that, like, well, sometimes it's the only recompense they get. their abuser won't admit to anything unless there's an NDA to sign, so we should leave NDAs there because it allows you to have some imperfect solution. I don't know that that gives people enough justice at the end of the day to be worth the harm that NDAs do.

Because you see it, it's not just the victims, it's people who see these crimes happen. It's those employees who just have everything to lose, now that NDA is in the picture, if they say anything to help victims or to help law enforcement. So those are hugely damaged. and we've seen the use of them go up in recent years, and it also makes it really hard for us to know

how many sex crimes are being committed. That silence doesn't just delay justice. It distorts it, and it leaves the most vulnerable people exposed, especially now that the spotlight has moved on. He's emboldened now that not only has he gotten away with this for 55 years, but now he's faced one of the hardest prosecuting teams that exists in this country and gotten off scot-free. And I think we've all seen enough powerful men not stop doing what they're doing

to fully trust that will happen and protect the victims. With dozens of civil suits still pending, legal pressure on combs may not be over. I can only hope that those things keep him afraid enough of repercussions that he will be more careful than he has in the past because now he's known to be accused of these things. For those who watch the trial closely, the case expose the limits of what a courtroom can do, what it can't fix, and what it might take to make that different the next time. What remains to be seen is what kind of life that freedom leads to, whether the courts give Combs a reduced sentence or throw the book at him.

Whether President Trump pardons him or declines to step in, whether his brand survives or burns. and whether the story of Sean Combs ends in redemption or reckoning. This has been a long crime production. I'm your host, Jesse Weber. Our executive producer is Jessica Lowther. A writer and producer is Cooper Mall. Our associate producer is Test Jagger Wells. Edit and sound design by Anna McLean.

Guest booking by Diane Kay and Alyssa Fisher. Additional production support from Juliana Bataglia and Stephanie Doucette. Legal review by Elizabeth Vula. key art designed by Sean Panzera and special thanks to Elizabeth Milner for her in-depth reporting on this case. Follow Long Crimes, The Rise and Fall of Diddy,

the Federal Trial, on the Wondery app. You can listen to more episodes exclusively and ad-free right now on Wondery Plus. Join Wondery Plus in the Wondery app, Spotify, or Apple Podcasts, and get ad-free access to more thrilling long crime series like new episodes of Karen the retrial and sidebar with Jesse Weber. Start your free trial today.