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- [00:01]
Jesse Weber
You're listening to a long crime series available exclusively on Wondery. To listen to the remaining episodes, join wondery and enjoy ad free listening to over 50,000 episodes, including more thrilling long crime series like new episodes of Karen, the Retrial and Sidebar with Jesse Weber. Join Wondery in the Wondery app, Spotify or Apple Podcasts this podcast is a.
- [00:26]
Elizabeth Milner
Law and crime production. The the allegations discussed are based on court documents, public testimony and media reporting.
- [00:32]
Mackenzie Joy Brennan
The content may include graphic descriptions of.
- [00:35]
Elizabeth Milner
Alleged sexual acts, violence, abuse and drug use. These topics may be disturbing or triggering for some listeners. Listener discretion is strongly advised.
- [00:48]
Jesse Weber
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 arranged 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 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 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 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 the that co conspirators do not need to know the full scope of the enterprise or even each other to be criminally liable. Judge Arun Subramanian 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 was rather than their statements could show agreement to join an illegal scheme.
- [03:40]
Elizabeth Milner
The judge says that he will change the sentence in context of conspiracy, actions may speak louder than words. 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.
- [03:56]
Jesse Weber
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.
- [04:29]
Elizabeth Milner
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.
- [04:39]
Jesse Weber
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 Mann 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.
- [05:37]
Elizabeth Milner
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 across state lines, was a sex worker.
- [05:49]
Jesse Weber
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.
- [05:58]
Elizabeth Milner
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.
- [06:06]
Jesse Weber
Throughout the entire back and forth, Judge Subramanian 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.
- [06:20]
Elizabeth Milner
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.
- [06:32]
Jesse Weber
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 Kristi Slavik. Prosecutor Kristi 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.
- [07:19]
Elizabeth Milner
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 uses inner circle and money to cover up his crime and even referred to his assistants as foot soldiers and other things like that. So really pointing out how those who were in Sean Combs inner circle helped build this case of racketeering conspiracy against the defendant.
- [07:41]
Jesse Weber
Then Slavik reminded jurors of the testimony from Cassie Ventura.
- [07:46]
Elizabeth Milner
They talked about 2011, where Sean Combs attacked Cassie after he found out she was sleeping with Kid Cudi. 2013, when Sean Combs attacked Cassie in her apartment when Cassie was with nia and Deontay. 2013 again that same year, Rick Sean Combs assaulted Cassie in Jamaica because she was taking too long in the bathroom. 2015, where Sean Combs beat up Cassie at a Las Vegas party in Drock. Actually ended up crying after seeing Cassie's injuries. And then, of course, the 2016 incident that happened at the Intercontinental Hotel.
- [08:16]
Jesse Weber
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.
- [08:29]
Elizabeth Milner
They were saying that Sean Combs groomed Jane into sex trafficking. So they say that the first stage again being the drugs, the outfits, putting pornography on something that kind of diddy enjoyed, 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.
- [08:55]
Jesse Weber
Slavic told jurors that violence was not an unfortunate side effect. It was part of 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 freak off.
- [09:13]
Elizabeth Milner
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, GHB2C, and mushrooms as well.
- [09:28]
Jesse Weber
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.
- [09:43]
Elizabeth Milner
To kind of help paint the picture a little bit more. In these summations, the question always is, why didn't she leave?
- [09:49]
Jesse Weber
Then she pointed outward to what she said Combs thought he could get away with.
- [09:55]
Elizabeth Milner
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.
- [10:15]
Jesse Weber
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 coordination in terms.
- [10:31]
Elizabeth Milner
Of count, very 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 Ibiza, as an example, or New York City.
- [10:41]
Jesse Weber
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.
- [10:51]
Elizabeth Milner
They brought back that flight summary chart. Again, something that I think works in their favor, because the jury can take this stack when they go to deliberations and really see everything laid out in a way like a roadmap.
- [11:02]
Jesse Weber
One name came up again and again. Jules.
- [11:07]
Elizabeth Milner
They point to one specific instance, starting In August of 2009, August 26th of that year, where Sean Combs coordinated with Jules. Jules being the escort that he and 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 Intercontinental Hotel.
- [11:26]
Jesse Weber
The government said Combs didn't just use Jules. He moved him, booked his flights, paid.
- [11:32]
Elizabeth Milner
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 also paid for by Sean Combs, and that Sean Combs even texted jewels that he'll tip him more if he can make it out to New York City, because, again, he's traveling from la, so there's that 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.
- [12:15]
Jesse Weber
Count five pointed to Jane.
- [12:18]
Elizabeth Milner
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.
- [12:32]
Jesse Weber
More names followed. Jessica, Paul, Reggie, Florida flights to Turks and Caicos, texts to an escort agency rep.
- [12:42]
Elizabeth Milner
They 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 Terps and Caicos. And he was traveling from Los Angeles for these hotel nights or Wild King nights, whatever you want to call them.
- [13:05]
Jesse Weber
The paper trail led to Las Vegas.
- [13:08]
Elizabeth Milner
The government said the defendant directed Jane to have hotel nights with three escorts that Reggie, an escort or entertainer, 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.
- [13:24]
Jesse Weber
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 the jury could trace step by step.
- [13:40]
Elizabeth Milner
I think it's probably one of the strongest charges that the government has in 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.
- [13:53]
Jesse Weber
Christy Slavic ended her closing with a forceful call to action. She said the jury had seen the pattern, the violence, the enterprise. She told them it was time to hold Combs accountable. But the defense still had its say, and When Mark Agnifolo stepped up, he didn't just dispute the government's case, he tried to dismantle it piece by piece.
- [14:17]
Elizabeth Milner
Literally. One of the first lines, he said in his closing argument was this. It's 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?
- [14:51]
Jesse Weber
Agniphilo 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. 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 Agniphiolos said the biggest problem wasn't any one witness. It was the lack of something much larger.
- [15:43]
Elizabeth Milner
There is a gaping lack of evidence. He says that he was trying to do this enterprise. By what? Having sex with his girlfriend?
- [15:51]
Jesse Weber
He told jurors that the so called enterprise was nothing more than a high profile entourage, people doing their jobs, not committing crimes. On the trafficking charges, Agnifolo said what looked extreme from the outside was simply part of a world built on sex, evil ego and blurred lines. He didn't deny it was messy, but he said it wasn't criminal.
- [16:14]
Elizabeth Milner
Mark Agnipolo was like, okay, I suppose you can sex traffic your girlfriend if you sell her into prostitution. There are 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.
- [16:41]
Jesse Weber
As he neared the end, Agniphilo made a sweeping accusation. This wasn't about justice, he said. It was retaliation.
- [16:51]
Elizabeth Milner
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, 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.
- [17:11]
Jesse Weber
Mark Agnifolo 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. No 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 persons 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 Mann 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, 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.
- [20:45]
Elizabeth Milner
All I can see right now is 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 have 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.
- [21:06]
Jesse Weber
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 York prosecutors came at him with all that they had.
- [21:24]
Dan Abrams
They're not stopping.
- [21:25]
Jesse Weber
But one thing stands between all of.
- [21:29]
Dan Abrams
Us and a prison, and that is.
- [21:32]
Jesse Weber
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.
- [21:43]
Mackenzie Joy Brennan
Sean Combs has not sexually assaulted anybody. I've been saying this for months.
- [21:48]
Elizabeth Milner
We've said it with each lawsuit that.
- [21:50]
Mackenzie Joy Brennan
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.
- [22:09]
Jesse Weber
Or not these are actually going to.
- [22:11]
Mackenzie Joy Brennan
Stand up in a court of law. Because today they did not.
- [22:15]
Jesse Weber
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.
- [22:31]
Dan Abrams
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. Cows. 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.
- [22:59]
Jesse Weber
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.
- [23:13]
Dan Abrams
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.
- [23:28]
Jesse Weber
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.
- [23:41]
Elizabeth Milner
I think consent was really a topic 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 freak offs 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 consent being at the heart of the issue.
- [24:05]
Jesse Weber
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 spent considerable time walking jurors through the timeline from the Intercontinental Hotel incident to what prosecutors called the freak offs 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.
- [24:37]
Elizabeth Milner
I was a little surprised, especially to count two, but I think probably and likely a question that went through those jurors minds is probably the relationship and how long the relationship lasted.
- [24:48]
Jesse Weber
Count two was the first major sex trafficking charge. It stemmed 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.
- [25:10]
Elizabeth Milner
The jurors were really paying close attention to both sides closing argument, especially Mark Agniphilo'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 Agnipolo is getting up there in his closing argument and saying, okay, well, they did 75 different creek offs, 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.
- [25:43]
Jesse Weber
That relationship lasted over a decade. For jurors, that longevity may have blurred the lines between coercion and and consent. Milner suggested that Agniphilo's 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.
- [26:07]
Elizabeth Milner
Maybe they were like, okay, well, when the breakup happened, was it because of these freak offs? But whether or not that was the reason that the relationship ended, seem like the relationship ended because of possible jealousy because of another woman. And it didn't seem like their relationship ended necessarily necessarily because of the freakoff.
- [26:23]
Jesse Weber
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 acquit 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 Mann 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.
- [27:24]
Dan Abrams
The man that carries with it sex offender registration.
- [27:28]
Jesse Weber
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.
- [27:57]
Dan Abrams
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 bad things fall into the legal definition of sex trafficking 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.
- [28:27]
Jesse Weber
So what does that mean for sentencing? I think it's possible that he goes to prison.
- [28:31]
Dan Abrams
I don't think he's going to max out. I don't think it's going to be.
- [28:34]
Elizabeth Milner
A 10 year federal prison sentence. But.
- [28:36]
Dan Abrams
But it's possible that the judge decides that not staying at the MDCC is enough and he actually needs to go to a federal facility somewhere else in the country.
- [28:45]
Jesse Weber
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.
- [29:03]
Matt Murphy
Bluntly, we're not looking at double digits. 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.
- [29:25]
Jesse Weber
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.
- [29:51]
Matt Murphy
Can the court aggravate nonviolent offenses that he was convicted of, which are the Mann 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.
- [30:08]
Jesse Weber
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.
- [30:20]
Matt Murphy
So in federal court, they rely very heavily on those presentencing investigations. So essentially what will happen is there'll be a federal probation officer and they talk to family members, they'll talk to employers, they'll talk to neighbors, and 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.
- [31:06]
Jesse Weber
Recommendation to the court how the probation officer interprets the case. Could shape Combs faded sentencing. But beyond time behind bars, there's another risk, one that could hit him where he's arguably most vulnerable. His wealth.
- [31:22]
Matt Murphy
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.
- [31:30]
Jesse Weber
But in this case, Murphy says the feds would be on shaky ground.
- [31:35]
Matt Murphy
He didn't make any money from the freak offs. 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.
- [31:47]
Jesse Weber
And Murphy warns that going after Combs assets could backfire legally and publicly.
- [31:54]
Matt Murphy
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'd be a very poor move if they tried 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.
- [32:21]
Jesse Weber
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 onto 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.
- [32:55]
Matt Murphy
Comes to all those pending civil suits. Because now those same people, in theory, would have to come in and testify.
- [33:01]
Jesse Weber
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 Dawn Richard 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.
- [33:26]
Matt Murphy
There's a lot to be said for this idea that they were all 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 their way through the system. I'm sure some of them will be dismissed on their merits. You know, 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 of these as possible.
- [33:48]
Jesse Weber
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 and 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.
- [34:11]
Matt Murphy
He will have freedom at some point. A lot of people were predicting he was never going to see freedom ever again.
- [34:19]
Jesse Weber
The sentencing hearing is currently scheduled for October 3, 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.
- [34:32]
Matt Murphy
We know that behind the scenes, what they want, of course, is they expect a chance that he's going to be released.
- [34:38]
Jesse Weber
But that road is steep.
- [34:40]
Matt Murphy
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.
- [35:02]
Jesse Weber
That red flag obviously stuck with the judge. Attorney Mackenzie Joy Brennan says what happens next may come down to how that same judge interprets what the jury didn't see.
- [35:14]
Mackenzie Joy Brennan
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.
- [35:41]
Jesse Weber
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. 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 Dominick Strauss Kahn, and yes, Sean Combs.
- [36:21]
Dan Abrams
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.
- [36:37]
Jesse Weber
Jettison's team put together a detailed bail proposal before trial.
- [36:41]
Dan Abrams
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.
- [36:56]
Jesse Weber
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?
- [37:12]
Dan Abrams
The judge denied bail based on the statute, and the statute stated a certain amount of information, part of the man act that, you know, 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 they 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.
- [37:41]
Jesse Weber
A new proposal was submitted July 29, but there's no guarantee the judge will bite, especially when it comes to geography.
- [37:49]
Dan Abrams
I don't think, and this is my opinion, that the judge would let him 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 entrance 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.
- [38:18]
Jesse Weber
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.
- [38:29]
Dan Abrams
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 Agnifolo both stood up and said, hey, Mr. Juddison 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, Conor McGregor, Plaxical Burris, Cat Williams, Lawrence Taylor. So I'm not going to put my reputation or my license in jeopardy for X amount of money.
- [39:21]
Jesse Weber
The idea was house arrest, but strict.
- [39:24]
Dan Abrams
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.
- [39:48]
Jesse Weber
Still, even Juddelson concedes the odds of the plan amounting to anything are slim.
- [39:54]
Dan Abrams
Is there a strong possibility? I would say, at this point, no.
- [40:00]
Jesse Weber
That bail decision denying Combs release pending sentencing may have offered the clearest signal yet.
- [40:06]
Mackenzie Joy Brennan
At the bail hearing, the judge said that the defense failed to show with clear and convincing evidence that Diddy is not a danger to the community.
- [40:15]
Jesse Weber
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 Mackenzie Joy Brennan. We asked Brennan what the split verdict suggests about how the jury interpreted the evidence.
- [40:46]
Mackenzie Joy Brennan
The charges that he was convicted on, they were the smallest deal and they were a slam dunk. The Mann act, that's just transporting people across state lines for purposes of sex work.
- [40:58]
Jesse Weber
The Mann 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.
- [41:07]
Mackenzie Joy Brennan
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.
- [41:39]
Jesse Weber
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.
- [41:48]
Mackenzie Joy Brennan
Was some thought that the jury was not going to be able to reach a consensus. I think we learn a lot about the jury on the fact that neither of those charges succeeded.
- [41:58]
Jesse Weber
And outside the courtroom, Brennan saw another kind of reckoning playing out, one shaped not just by evidence, but by perception.
- [42:07]
Mackenzie Joy Brennan
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, 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.
- [42:43]
Jesse Weber
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.
- [43:01]
Mackenzie Joy Brennan
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 MeToo 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. Where powerful men were being held to account. I think we've backtracked a little bit.
- [43:27]
Jesse Weber
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.
- [43:40]
Mackenzie Joy Brennan
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.
- [43:49]
Jesse Weber
This wasn't just legal theory. It was about language perception and generational blind spots.
- [43:57]
Mackenzie Joy Brennan
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.
- [44:33]
Jesse Weber
One of the prosecution's biggest challenges was showing how powerful figures manipulate not just bodies, but. But entire belief systems, especially when the power imbalance is so steep.
- [44:46]
Mackenzie Joy Brennan
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.
- [45:15]
Jesse Weber
And once that kind of pressure takes hold, Brennan argues, it colors everything that comes after, even the moments that look like consent.
- [45:25]
Mackenzie Joy Brennan
You're going to act your heart out, to act like you like it next time you're at a 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.
- [45:53]
Jesse Weber
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.
- [46:05]
Mackenzie Joy Brennan
Once you bring violence into the picture, every subsequent act is influenced by that.
- [46:11]
Jesse Weber
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 continue. 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 imagined the crime.
- [46:46]
Mackenzie Joy Brennan
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.
- [47:46]
Jesse Weber
The statute was originally crafted to dismantle traditional organized crime families. But in recent years, prosecutors have started using it in a different way.
- [47:55]
Mackenzie Joy Brennan
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.
- [48:11]
Jesse Weber
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.
- [48:33]
Mackenzie Joy Brennan
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.
- [49:00]
Jesse Weber
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.
- [49:25]
Mackenzie Joy Brennan
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.
- [49:54]
Jesse Weber
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.
- [50:08]
Mackenzie Joy Brennan
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?
- [50:18]
Jesse Weber
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.
- [51:00]
Mackenzie Joy Brennan
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.
- [52:21]
Jesse Weber
They gave the jury just enough truth to hold onto and drew a hard line at what they insisted wasn't true. It was a risky but effective sleight of hand.
- [52:33]
Mackenzie Joy Brennan
On the other hand, you have the defense argument than being like, let's not introduce character evidence against Diddy, 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.
- [52:58]
Jesse Weber
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.
- [53:15]
Mackenzie Joy Brennan
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 MeToo movement anymore. I think we've taken some steps back, and we have yet to see where that pendulum's gonna land.
- [53:30]
Jesse Weber
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.
- [53:42]
Mackenzie Joy Brennan
I think one big one would be working on things like NDA permissibility and statute of limitations on sex crimes.
- [53:51]
Jesse Weber
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.
- [54:01]
Mackenzie Joy Brennan
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.
- [54:13]
Jesse Weber
Those time limits fail to account for how long it often takes survivors to come forward.
- [54:19]
Mackenzie Joy Brennan
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.
- [54:26]
Jesse Weber
In this case, as in so many others, they created a silence that even federal subpoenas struggle to break.
- [54:34]
Mackenzie Joy Brennan
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 NDAs and the picture if they say anything to help victims or to help law enforcement. So those are hugely damaging. 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.
- [55:27]
Jesse Weber
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.
- [55:38]
Mackenzie Joy Brennan
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.
- [55:59]
Jesse Weber
With dozens of civil suits still pending, legal pressure on Combs may not be over.
- [56:05]
Mackenzie Joy Brennan
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.
- [56:16]
Jesse Weber
For those who watch the trial closely, the case exposed, 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. Our writer and producer is Cooper Mahl. Our associate producer is Tess Jagger Wells Edit and sound design by Anna Maclean guest booking by Diane Kay and Alyssa Fisher Additional production support from Giuliana Battaglia and Stephanie Doucet Legal review by Elizabeth Voulai key art designed by Shawn Panzera and special thanks to Elizabeth Milner for her in depth reporting on this case. Follow Law on 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. Join Wondery in the Wondery app, Spotify or Apple Podcasts and get ad free access to more thrilling law and crime series like new episodes of the Retrial and Sidebar with Jesse Weber. Start your free trial today.