The Rise and Fall of Diddy - What They Found and What They Couldn’t: 6

Episode Date: October 21, 2025

A federal raid, an arsenal of weapons, and a mountain of data prosecutors said mapped a criminal empire. This episode, we lay out the physical evidence against Sean Combs, and the testimonies of the agents who tried to connect the dots between drugs, guns, sex, and power. But in a case built on patterns, could prosecutors ever prove who was really in control?Featuring interviews with: Former FBI Agent Colin Schmitt and Cellebrite Examiner Heather Barnhart—-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.

You're listening to a long crime series available exclusively on Wondery Plus. To listen to the remaining episodes, join Wondery Plus 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 Wondry Plus in the Wondery app, Spotify, or Apple Podcasts. This podcast is a long crime production. The content may include graphic descriptions of alleged sexual acts, violence, abuse, and drug use. These topics may be disturbing or triggering for some listeners. Listener discretion is strongly advised. The allegations discussed are based on court documents, public testimony, and media reporting. While normally we wouldn't spoil the ending of a story, the headlines were nearly impossible to ignore. On July 2, 2025, a jury convicted Sean

Combs of two counts of transportation to engage in prostitution, but acquitted him of the racketeering and sex trafficking charges. In the spring of 2024, federal agents raided Sean Combs' homes in Los Angeles and Miami. What they found made headlines, an arsenal of illegal weapons, piles of drugs,

and suitcases stuffed with bottles of baby oil. But the headlines weren't the point. The evidence was. And when the case finally went to trial, two men took center stage, to explain what those raids uncovered. Homeland Security agent Gerard Gannon, who sees the evidence, and Joseph Circello, the agent tasked with turning that evidence into a story the jury could follow.

Because finding guns and drugs was one thing, proving how and by whom they were used, that was something else entirely. I'm Jesse Weber, and this is the rise and fall of Diddy, the federal trial. Homeland Security Agent Gerard Gannon wasn't there to explain theories or argue what the evidence meant. His role was simpler and in some ways more powerful. He was the one who opened the doors to Combs' palatial estate, the one who could tell the jury exactly where each piece of evidence came from, how it was collected, and what condition it was in once it left Diddy's Miami home on March 24, 2024. When Gannon took the stand, he walked the jury. through it all, room by room. First, the drugs. In a Gucci bag, agents found cocaine,

ketamine, MDMA, Xanax, and methamphetamine. In the bathroom, a box engraved with the word puffy held MDMA capsules and hallucinogenic mushrooms. Then came the weapons, a loaded 45-caliber handgun inside what Gannon called, the guard shack, a guest house on the property. And upstairs in the master closet, two dismantled AR-15 rifles with their serial numbers removed. The rest of the hall blurred the line between bizarre and incriminating, 18 pairs of platform heels, a sex toy, 25 bottles of baby oil, 31 bottles of lubricant, and tucked inside a pair of Balenciaga boots, hidden cell phones. To understand how that kind of discovery plays out inside a federal case, we turn to Colin Schmidt,

a former FBI agent whose experience in criminal investigations runs the gamut. The first step would be to determine if they're legally there, so somebody has a gun collection, so to speak. So this certainly wasn't the case. And the second step is you have weapons with shaved off serial numbers, and then you have weaponry that is, frankly, weapons of war. This wasn't just one gun stashed in a drawer. It was an arsenal, and it was discovered in the same homes where witnesses said Combs hosted some of his so-called freak-offs. The prosecution wanted the jury to see a connection.

What they wanted to do is present all these firearms and all these drugs to set the setting, from their perspective, or their hypothesis was that he was using all these freak-offs or whatever as a way to extort or intimidate. people to participate. And it wasn't just the weapons themselves. It was who had access to them. Combs wasn't known for surrounding himself with professional security teams. Instead, Gannon testified, the people inside those homes were friends, employees, and hangers on. Whoever was in there had access to so many weapons that were unnecessary.

He didn't need any of that. And he had the money to hire his own armed professional security, which appears that wasn't the case. he had his friends and his entourage doing his security. The government alleges that the arsenal wasn't just dangerous. It was a potential tool of control, a backdrop to the claims of coercion, intimidation, and trafficking. What the weapons do is it gives them context for when they're questioning the witnesses. Because the bottom line is, in a case like this, you have to have eyewitnesses or his own statements, whether it be through recorded statements on a telephone call or recorded, you know,

video like they found at the hotel, something along those lines. But those weapons are basically what would prompt investigators to ask questions about the weapons. So these witnesses would give greater context and then perhaps weave those weapons, possession of weapons, into the RICO charges. But Gannon could only show what was found, not who held the guns or why. That question would haunt the prosecution's case from start to finish. The weapon only told part of the story. For the prosecution, the copious amount of illegal drugs and controlled substances wasn't a case of a party simply getting out of hand. They said this was about control itself. Those are all party drugs. So the drugs were all indicative of what

their hypothesis or their narrative was. It was just a gigantic orgy of craziness. And these drugs were there to fuel that behavior. Gannon's inventory filled out the world, witnesses had described. One were sex, drugs, and power mixed in ways that blurred the line between consent and coercion. But proving those drugs were tools of exploitation and not just a billionaire's indulgence would take more than a list of items seized in a raid. The law possession for intent to distribute, they have to tie them directly to him. And with so many people coming and going, the question looming over Gannon's testimony wasn't just what they found. It was who it all belonged to.

That was the big problem, as he had literally hundreds of people streaming through these properties at all times. Inside the courtroom, the government argued these supplies weren't random. They fit a pattern described by witnesses, a pattern of highly orchestrated sexual encounters fueled by drugs and intimidation. The government needed to show that this wasn't just a permissive atmosphere, that the drugs in the baby oil weren't props at a party. They were part of a system designed to exploit. But proving that is a high bar.

Under the law, it isn't enough to suggest the environment allowed for abuse. You still have to show that person had care and control over that contraband. And in the world, Sean Combs built, with an entourage, staff, and guests coming and going by the hundreds, That was the prosecution's most difficult hurdle. Because the defense didn't have to deny the evidence was there. They only had to suggest that Combs wasn't the one controlling it. And when the evidence gets messy, so does the case. They had to have identified more people that were involved in this conspiracy.

And frankly, they had just him on trial. Nobody else has been charged under this case. So I think the jury was a little bit overwhelmed with all of this salacious evidence. and they just got back down to really the charging documents and what he was clearly guilty of beyond a reasonable doubt. The weapons and drugs set the stage, but as the trial wore on, it became clear. Physical evidence alone wouldn't be enough.

They couldn't show Diddy was the one who controlled all this contraband. That challenge would define the trial, and it's what made the next phase of the government's case critical, because after Gannon came the witness who tried to do what Gannon couldn't, pull it all together. By the time Homeland Security Agent Joseph Circello took the stand, the jury already knew about the raids. But Circello wasn't there to talk about what Gannon and his team seized. He was there to talk about what they saw. Circello's job was the sift through the data recovered from phones, computers, hard drives,

Piecing together a timeline, prosecutors claim confirmed there was nothing random about how these encounters happened and nothing accidental about who was involved. To prove it, Circello presented a chart, 44 entries spanning from May 2021 to August 2024, mapping out each encounter, payment, and travel record. One pattern jumped out almost immediately. After the Cassie Ventura lawsuit went public, the nature of these encounters. encounters shifted from hotel suites to private residences. But the encounters in the hotels left damage in their wake. Circello found in January 2023, a Los Angeles hotel billed nearly

$4,000 for bodily fluid damage. Then in April, another mess. $1,800 for carpets and linen soaked in baby oil, the same kind, Gannon found in the Miami home. This was just the beginning. beginning of Circello's cryptic discoveries dealing with cash. In financial records, he found a $5,000 withdrawal labeled PD Personal London, and another for 3,500 marked his guest. This one was dated just days after an assault Jane had testified to. Then came the text messages, some dating back as far as 2017. The prosecution zeroed in on an exchange between Diddy and Cassie that year. Cassie wrote You beat my head in, treat me like a hooker. Diddy replied, any other woman would have been happy. Beyond the individual pieces, Sir Cielo's role was about patterns, a pattern of apparent drug use,

a range supplied and widely used at Diddy's properties, patterns of payments, cash often withdrawn around the same time alleged assaults took place, patterns of behavior, like how the freakoff venue shifted after public fall. out from Cassie's lawsuit, and ultimately a pattern of stories. Witness testimony that prosecutors argued matched the digital evidence Circello polled from seized devices. Finding the data was only the start. Interpreting it, making sense of years' worth of digital noise, took time. And no one understands that better than Heather Barnhart, the senior director of forensic research at Celebrate, who's worked on some of the most complex digital investigations in the country.

Acquisition by itself, depending on how big a phone is, could take hours or even a day. We have something called the U-FED is the universal forensic extraction device. So it's exactly what it sounds like. If you have four U-Feds, you could do four phones at the same time. But if you're an organization that only has one, you're doing a lineup of these devices. And then typically, as they're finished, you would feed it into the examiner who would triage it and get something immediately to the investigator. But all of this takes time to extract, to process, to then triage, and press on.

So you could say one device could easily take three days from beginning to, all right, I'm sitting and I'm looking at something and trying to make sense of data. The process is painstaking and critical. If you get proper collection, you can do amazing analysis. And it just requires lawful access. And since this is the feds, we're talking. talking about? They had exactly what was needed. Once they had the data, the real work began. I always tell people in forensic investigations, we're just looking for a thread, a loose thread,

and once you find that thread, you can unravel everything. Finding the thread is one thing. Pulling it all the way through, that's something else. Because the case wasn't just about isolated messages or random videos. The government's theory was bigger, behind the chaotic world of parties and freakoffs, there was a coordinated system, and it was Circello's job to map it. Imagine a web of communication, so a spider web-looking thing that would pinpoint how people even communicate with arrows on who the link in between each individual is. You can also look at a timeline that shows locations where people were at the same time, chat messages where it even detects the tone in these messages just to like help you get

a clue. Circello took every text, call log, flight record, and payment receipt and plotted them on a timeline date by date hour by hour. It wasn't just data. It was a roadmap. The level of effort that goes in to presenting that type of evidence is astounding. Fantastic forensics there. But even the best forensic map doesn't tell you everything, especially in a case where who was there and who was in charge were two very different questions. The jury wouldn't only have to rely on black and white data to evaluate the case. Remember, the feds also found videos, lots of them. Woveen through the text and payment records were graphic recordings of the so-called freak-offs.

But if prosecutors wanted the jury to see the videos as more than just a collection of salacious encounters, They need to show exactly where, when, and how they happened. And that meant digging into the data hidden inside every recording. If it came from a cell phone and it's recorded, there are so many stamps in the metadata of the file saying if it was recorded with three cameras on the back of the phone or front-facing camera, if Flash was used, the location on where it was recorded, the iOS version. version or Android version. So all that detail is so helpful to forensics. But if we're looking at CCTV or any kind of recorded video like that, that is where other pieces of the puzzle have to come into play. Verifying when and where the videos were recorded was only the starting point. The real focus was on how they revealed a broader pattern. One prosecutor's

claimed was anything but isolated. And that meant connecting footage captured from different devices and perspectives, piecing together overlapping clips of the same scene. The level of effort is huge to do an investigation like this, and it's a lot of time sitting behind a keyboard. So if you have forensic software that can help you pinpoint a specific face, so say you're looking for a person or a victim or someone that's involved, and it could just get you to that point in the video, that's really helpful. And there's a lot of investigative software out there that will do that. But without that, if you wanted to prove different angles or different personas that were

in a room or different devices to put a person at the event or the freakoff, it's a lot of work and it's a lot of manual review by the investigator and an examiner. And once the forensic analysis was complete, Sir Cielo's findings were turned over to the investigators leading the case. Typically, the examiner, which is the role I have always identified as, is the person that digs deeply and presents you data, if you're the investigator, and says, here you go, this is what the data shows. And then it's your job as the investigator to tap into the mindset of the victims, of the perpetrators, and then go back to the examiner and say, I think that this person is a

victim. Could you look for these things? Because even the clearest video, even data that checked every forensic box, still required context. And that's where the financial records came in. The texts, the travel logs, the footage, all key components showcasing how these events unfolded. But the money? The money could potentially show how they were orchestrated. Wire transfers, cash app payments,

Venmo receipts, hotel charges, and flight bookings. Making sense of that web of payments isn't simple, especially when you're trying to prove the difference between personal vice and an alleged criminal enterprise, If you think back to that web of communications, if it's a simple transaction, it's going to go from one person to the next and maybe you're using cash app or Venmo or something small or saying I'll pay you some cash. But when it's a major enterprise, you are going to see keywords that are being used. You're going to see major transactions. You will see really detailed communications

because there's so many moving parts. Sir Ciello didn't show the jury a simple spreadsheet of numbers. He mapped the payments against texts, travel records, and event timelines. And when those payments lined up with the videos and the messages, prosecutors argued it wasn't a coincidence. But turning a trail of transactions into proof of organized crime requires more than raw data. You go back to the examiner and say, this is the stuff I found, go validate it. Because obviously software is doing its best job, but you need a really smart transaction. person behind a keyboard to say, this is definitely where this was, what occurred, so nothing's misconstrued. That's how Circello tried to thread it altogether, showing how money moved alongside

people, how bookings lined up with flights, and how payments linked back to the names and devices already appearing in his investigation. But just like the arsenal, the drugs, and the videos, the money raised the same question. Who was actually behind them? What ends up happening is this agent, he ends up having to become a storyteller by piecing this whole thing together bit by bit and trying to weave a narrative that is prosecutable for them. And it's amazing how much he did and it's amazingly hard to do. Sersello traced the paths of money messages and people. He laid out the pattern of who showed up, who got paid, and when and where it all happened. If you do this properly, you should be able to see a link to one person or certain key people that are involved in this type of crime.

But was the pattern enough? That's exactly where the defense pressed. They didn't have to explain away the evidence. They only had to argue that Sir Ciello's web of data, even if accurate, didn't tie directly back to Sean Combs. I think the Diddy case is a good lesson that, It's simple as better. That's the bottom line. Because in a case this sprawling with this many players, complexity may have been the prosecution's greatest weakness. On the next episode of the rise and fall of Diddy, the federal trial, he was the hotel security guard unwittingly pulled into Combs' orbit.

He told the jury that Sean Combs said that this video could ruin his career. She was the one making sure it never came to light. She always helped clean up his mess. And at the center of it all, a man who wasn't taking any chances. Sean Combs did a lot to make sure that this was untraceable back to him. The testimony of Eddie Garcia and an alleged cover-up hiding in plain sight. 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 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 Ducet, legal review by Elizabeth Vuli, key art designed by Sean Panzera, and special thanks to Elizabeth Milner for her in-depth reporting on this case.

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