Delve into the disturbing revelations from the criminal investigation of Sean "Diddy" Combs' notorious private parties. From shocking testimonies to disturbing evidence, we examine the darkest details that have emerged from court documents, witness statements, and federal investigations.
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00:00High heels, a lot of them.
00:02Also bottles and bottles of Astroglide and baby oil and lubricant.
00:08Welcome to WatchMojo.
00:09And today we're breaking down the darkest, most disturbing details about freak-offs
00:13that have emerged in the criminal trial of Sean Diddy Combs.
00:16He was asked, was Cassie Ventura on drugs when she was taking part in these freak-offs?
00:21He said she didn't appear to be on drugs.
00:25Combs' favorite place to hold freak-offs.
00:28It might not seem like it when it's all said and done,
00:31but I don't think he has nothing to worry about.
00:32I don't think he's worried because he's going to be federal.
00:36And if he gets convicted, Trump's going to pardon him.
00:38So, what's the worry?
00:40You think the President of the United States would pardon Sean Combs for sex trafficking?
00:46On the heels of the news that Diddy's defense team is reportedly seeking a pardon
00:50from President Donald Trump comes another bombshell.
00:53David James, a former assistant to Sean Combs,
00:55testified that the disgraced mogul's preferred location to set his freak-offs
00:59was at the Trump International Hotel in New York City.
01:02And at one point, he was even asked himself about hiring a prostitute
01:07and bringing it back to Combs' home without his knowledge,
01:10buying cocaine without Combs' knowledge.
01:13So again, it's what did Combs know?
01:15What did he not know?
01:16What were these employees doing on their own accord?
01:19Or were they really carrying out this RICO conspiracy?
01:23James revealed that the hotel personnel knew him, quote,
01:26very well and even gave him a key to the building
01:28as he coordinated the transportation of supplies to the various freak-offs.
01:33In a resurfaced 2012 clip from The Celebrity Apprentice,
01:36future President Trump said that he, quote,
01:38loved Combs and referred to him as a, quote, good guy.
01:42I am a very strict and focused businesswoman
01:45because working for Diddy for six years trained me to have to be perfect.
01:50Working for Diddy?
01:51Absolutely.
01:51I love Diddy.
01:52You know he's a good friend of mine.
01:53He's a good guy.
01:54Is he a good guy?
01:56I don't want to answer that question.
01:57Oh, well, I think he's a good guy.
01:58I'm going to stick up for him.
02:00Cassie's refusal to participate in a freak-off resulted in that hotel footage.
02:04She claimed in her lawsuit that she was physically assaulted by Diddy.
02:08Now our team in the L.A. Bureau, we have got our hands on that surveillance footage
02:12and it appears to corroborate Cassie's claims identically.
02:18Really, Jake, the lawsuit lines up with exactly what we are seeing.
02:21If you've been following the turbulent Combs case,
02:24then you'll likely remember the disturbing security camera footage published by CNN
02:28that depicted the rapper violently attacking Cassie Ventura.
02:31Ventura, the federal government's key witness in the trial,
02:34was Combs' on-again, off-again partner for over a decade.
02:37Diddy is one of the most powerful people in music history.
02:41He is a mogul.
02:42We have not seen any support in Hollywood.
02:44All of his famous friends, since these allegations came forward,
02:48we have not seen anyone come to his defense.
02:50And that silence is very loud, Jake.
02:52As Ventura testified in May 2025,
02:55that 2016 footage was the result of her trying to leave one of the freak-offs,
02:59said Rachel Maiman, a former federal prosecutor for the Southern District of New York.
03:04Quote,
03:04It sets the stage for the rest of the case,
03:07where the prosecution is going to have to back up her testimony with all of their evidence.
03:11Pretty quickly over time, I knew the freak-offs weren't something I wanted to be doing, she said.
03:16Especially how frequently.
03:17I didn't feel like I had much choice.
03:21I didn't know if he would be upset enough to be violent,
03:23or if he would write me off and just not want to be with me at all.
03:27Combs had employees on payroll to operate freak-offs.
03:31Now, the last witness to take the stand was George Kaplan,
03:34a former assistant to Sean Combs,
03:35who says one of his responsibilities was to set up Diddy's hotel rooms.
03:40The first time he unpacked his bag, he said he found baby oil, Astroglide, candles, and liquor.
03:45The other times, he'd have to buy the items on his corporate card.
03:48He also had to make sure the rooms were in polished shape before checkout to protect Diddy's image.
03:53While the man formerly known as Puff Daddy is currently the only defendant facing criminal charges,
03:58it is abundantly clear that he couldn't have gotten away with it all by himself.
04:02To that end, the federal indictment against Combs alleges that he, quote,
04:06used the Combs business, including certain employees,
04:09to carry out, facilitate, and cover up his abuse and commercial sex.
04:13And that, quote,
04:14those employees, including security staff, household staff, personal assistants,
04:19and high-ranking supervisors, and other close associates, acted as Combs' intermediaries.
04:24There was an incident he talked about where he felt he could not follow Combs' orders.
04:28It involved a personal chef, Chef Jordan,
04:32where supposedly there was an altercation between her and Combs.
04:36Combs asked James to go to the police and file a report
04:39claiming that the chef had been the aggressor.
04:42These employees were responsible for, among other responsibilities,
04:46procuring baby oil, as well as booking and cleaning hotel rooms.
04:49In addition, they were expected to deliver both commercial sex workers
04:53and large amounts of cash to pay them with.
04:56And he said he was instructed by Diddy to pick up drugs two times.
04:59Both times he testified, Diddy gave him cash to pay for it
05:02and gave him a number to call someone to pick it up.
05:05Now, tomorrow we'll continue with his testimony, with George Kaplan's testimony,
05:09but after Kaplan, we expect to see rapper Kid Cudi on the stand.
05:13Meet the Punisher.
05:14As I described in the text, they were very subtle.
05:16So, um, Mr. Combs was always basically across the room
05:21and it would be in a low tone and it would just be suggestive.
05:25It was anything, nothing aggressive, nothing that, uh,
05:29would create some sort of, uh, scenario that this was, like, unnatural between them.
05:35Just so it's clear, we're not talking about Frank Castle.
05:38No, in this case, the Punisher is the stage name of exotic dancer Sheree Hayes,
05:43whose testimony revealed several bizarre, previously unknown aspects of the freak-offs.
05:48Said the BBC, Hayes, quote,
05:50was hired to create sexy, erotic scenes with Combs' then-girlfriend Cassie
05:54while a naked man watched from the corner.
05:56If there was no accusations, uh, like, in hindsight, all this stuff is in hindsight,
06:02like, in the moment, I, I didn't see it as anything but, uh, but, uh, a couple doing
06:08something, uh, risque and, and Cassie as a partner trying to create a fantasy for who I
06:14believed was her husband and, and for the majority of this.
06:17Perhaps strangest of all were the conditions under which Hayes was expected to work.
06:22Not only was he instructed to completely ignore the aforementioned naked man,
06:26but did he wore a veil to cover his face?
06:29Hayes testified that over 8 to 12 encounters with the two, quote,
06:33Combs watched and gave directions.
06:35The directions included adjusting candles and instructing the two to have sex.
06:39The scion and the wincing, um, was associated with some of the direction was very specific
06:44and it could be one after the other in terms of, um, move the candle to the left,
06:50move it a little more, move it a little more, now move your body a little more, stuff like that,
06:55and it, it was kind of unnatural for a scenario where you're trying to create a, a sexual situation.
07:01Meet Jonathan Odie.
07:02New at noon, the man accused of opening fire inside the Trump National Doral Resort
07:07made his first appearance in court.
07:08Jonathan Odie is facing several charges.
07:11Among them, he's being held without bond on two charges on a $4 million bond on a second-degree murder charge.
07:17The South African-born Odie first rose to notoriety in 2018
07:20after storming the Trump National Doral, Miami, and engaging in a firefight and chase with police.
07:26A particularly confusing detail was Odie's reported references to Diddy at the time,
07:31which were explained somewhat by the ongoing trial.
07:34I had, like, 15 encounters, and I heard lots of business,
07:38because what they would do is, Sean talks a lot on the, on the phone and on the TV,
07:44with speakers and stuff, and I would be in the, I was like a sex slave, okay?
07:48Cassie Ventura identified him as one of the escorts that Combs had hired for the Freak-Offs,
07:52and that his 2018 claims of being a, quote,
07:55sex slave actually bore some merit.
07:57Odie elaborated in a Miami Herald interview from prison,
08:00stating that he'd sometimes been requested to wear a police officer uniform,
08:05and that he made $800 per, quote, unquote, performance.
08:08I decided to record that, so in the event anything worse happened,
08:16like if she died, or anybody died,
08:22they would be on camera, they would be on video, whatever.
08:27So I would be responsible for any of that.
08:29How Combs guaranteed Freak-Off participation.
08:32And then she was asked, after the defense had suggested
08:35she might have been motivated by money here,
08:38would she give back the $20 million
08:41that Sean Combs gave her as part of a civil settlement?
08:45She said, I would give the money back because I would have agency and autonomy,
08:50and I wouldn't have to work so hard to get those things back.
08:54During her often disturbing testimony,
08:56Cassie frequently spoke of the ways that Combs would attempt to control her
09:00and ensure her submission.
09:01In one such case, Diddy allegedly forced her to carry one of his many firearms.
09:06She has retroactively described it as a scare tactic.
09:09It reminds me of R. Kelly's case.
09:12This is about money, power, and sex.
09:16Not unlike what he did with Cassie,
09:18Combs is described in the indictment as using his considerable power and influence
09:22to rope unwilling victims into participating.
09:24As the document describes,
09:26The culture of silence was colossal.
09:40You know, it really protected Sean for a number of years.
09:44These people think that they're so powerful,
09:46that it was never going to catch up with them.
09:48Combs prepped a freak-off while waiting to be arrested.
09:50Now the Sean Diddy Combs investigation,
09:53new surveillance video shows Combs being taken into custody.
09:57The mogul's long career in music came to a decisive end
10:00following his September 2024 arrest at the Park Hyatt Hotel in Midtown Manhattan.
10:06You might have heard that part.
10:07The part you might not have known about would be the fact that,
10:10despite the knowledge that he would have to surrender to authorities,
10:13he was undergoing prep to hold yet another freak-off.
10:16The publicly released images of Combs' hotel room
10:19were what gave rise to the now infamous baby oil memes,
10:22and a grim insight into how he worked and operated.
10:25According to Special Agent Yasin Binda,
10:28some of the mysterious powders and substances found in the room
10:31were determined to be the narcotics, ketamine, and MDMA.
10:34This has to be a 100% culture shock.
10:36I can't imagine living a lifestyle of the incredibly rich and famous,
10:41and then going into this very dark, impersonal, cold, austere facility.
10:48Combs carefully planned out the freak-offs.
10:51On the stand, we did hear from a male escort
10:53who was testifying about his interactions with Cassie Ventura during those freak-offs.
10:59He described in graphic detail how they would begin with massages and baby oil,
11:04as Sean Diddy Combs would be in the corner,
11:06and he would be taking care of himself at those times.
11:10Like a supervillain orchestrating his master plan,
11:12Diddy was allegedly tightly in control of all aspects of the freak-offs.
11:16And we mean all aspects.
11:19Per Cassie's testimony, and as described by the New York Times,
11:22quote,
11:23Also some exhibits of a hotel room where some of the freak-offs
11:32would end up being happening, taking place, rather.
11:36You can see that picture that was right there that we were just showing.
11:39That's showing some of the Astro Glide as well as that baby oil.
11:43This is inside one of those hotel rooms where all that damage took place.
11:47Cassie also testified that Combs, quote,
11:49asked that the baby oil be heated and that he wanted her glistening with it,
11:53requiring that she apply it in frequent intervals.
11:56Ventura even went so far as to describe the freak-offs as, quote,
11:59very choreographed and explicitly tailored to realize his voyeuristic personal fantasies.
12:05He was testifying that he was responsible for stocking the hotel room.
12:09Let's take a look at some of his testimony.
12:11He was saying the items that he was required to get included 25 to 30 pill bottles,
12:15which included ecstasy as well as Percocet, food, drinks,
12:19personal items such as baby oil, lubricant, as well as condoms.
12:23Combs and his participants needed IV replenishment afterwards.
12:27The freak-offs have been reported to last for days at a time,
12:31becoming a physically and emotionally exhausting experience
12:34for those strong-armed into participating.
12:36Part of Combs' employees' responsibilities, as noted in the federal indictment,
12:41was securing large quantities of IV fluids to help with his recovery afterwards.
12:46Cassie testified that alongside the IV fluids,
12:48Combs would provide massages and professionally cooked meals.
12:52Even those supposed kindnesses came with a dark side,
12:55given the frequency of the freak-offs,
12:57Cassie noted that her reliance on the fluids left her with an opioid addiction.
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13:15The freak-offs were filmed, and Combs held on to the footage.
13:21She also testified that Combs first proposed the freak-offs after he began physically abusing her.
13:27After the first time, she said,
13:28Perhaps most disturbingly of all, it's now public knowledge that Diddy allegedly conspired
13:48to have the freak-offs filmed and used as blackmail and extortion material.
13:52In one hard-to-stomach incident,
13:54Cassie recalled Combs playing a video of a sexual encounter in public.
13:58They never seemed to make eye contact with one another,
14:01not even after she was crying about having loved him once
14:04and planning and participating in these freak-off sex parties
14:08because she feared him and she wanted to make him happy,
14:12but feeling worthless, feeling disgusting, because she didn't want to do it.
14:17In a 2013 recording played by Diddy's lawyers,
14:21Cassie is heard threatening a man who claims to have such footage.
14:24David James, Diddy's ex-assistant, also testified that Combs claimed to have kept a video
14:29of James dancing while on drugs, implying that he would hold on to it,
14:32quote,
14:33Protecting him and protecting his public image was very important,
14:39and that was something I was very keen on doing.
14:42Now, Cassie testified that Kaplan quit after seeing Diddy abuse her.
14:48Now, we haven't heard that from him yet,
14:49but he is back on the stand in the morning.
14:52Which freak-off revelation shocked you the most?
14:54Be sure to let us know in the comments.
14:56We'll see you next time.