Crime Fix with Angenette Levy - P. Diddy’s Bizarre Sex Life on Full Display in RICO Trial

Episode Date: June 19, 2025

Sean “Diddy” Combs’ sexual proclivities have been discussed at length during his racketeering conspiracy and sex trafficking trial. His attorneys have said he’s a swinger but federal prosecutors say he’s a sex trafficker who preys on women. Law&Crime’s Angenette Levy talks with Dr. Daniel Bober about Combs’ sex life and how his habits may have developed in his childhood in this episode of Crime Fix — a daily show covering the biggest stories in crime.PLEASE SUPPORT THE SHOW: If your child, under 21, has been diagnosed with type 2 diabetes or fatty liver disease, visit https://forthepeople.com/food to start a claim now!Host:Angenette Levy  https://twitter.com/Angenette5Guest: Dr. Daniel Bober https://www.instagram.com/drdanielbober/Producer:Jordan ChaconCRIME FIX PRODUCTION:Head of Social Media, YouTube - Bobby SzokeSocial Media Management - Vanessa BeinVideo Editing - Daniel CamachoGuest Booking - Alyssa Fisher & Diane KayeSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can binge all episodes of this law and crimes series ad free right now. Join Wondery Plus in the Wondery app, Apple podcasts or Spotify. Freak offs, baby oil, voyeurism and urination are just some of the things the jury has heard about in Sean Combs' sex trafficking and racketeering conspiracy trial. I take a look at where Sean Combs may have developed these tastes and these habits, what they say about him, and new information we've learned about his past. I'm Ann Janette Levy and this is Crime Fixed.

So now I'm going to tell you about parts of Sean Combs' sex life, his proclivities, his desire to stage freak-offs, have taken center stage in his sex trafficking and racketeering conspiracy trial. The jury is literally getting a look inside Sean Combs' bedroom, and it's a lot. It's a lot to see. Combs maintains he's committed no crimes, at least not federal ones. His attorneys have said he's engaged in domestic violence, but they say he's not a racketeer and he's not a sex trafficker.

Combs' attorneys also say he's never sexually assaulted anyone. Now, during his trial, jurors have heard testimony from two women who were in relationships with Sean Combs, Cassie Ventura and Jane. Jane testified under a pseudonym were not revealing her real name. Both women told jurors about hotel nights with Sean Combs. Cassie called them freak-offs. Now, both Cassie and Jane said that they had sex

with male sex workers while Sean Combs directed their interactions. There were candles placed around the hotel rooms, and both women talked about going through a lot of baby oil. They described how Sean Combs liked women and the male escorts to wear a lot of baby oil on their bodies. The women wore high heels. Jane called them stripper heels as high as six or seven inches and they both wore lingerie. Jane described Sean Combs giving her drugs during

hotel nights and the frequency of the nights increasing throughout their relationship. She also described how Combs once asked her to have sex with three different escorts on one night on her birthday. Jane cried at different points in her testimony. Assistant U.S. Attorney Maureen Comey asked her a couple of times if she needed a break. Federal prosecutors say Jane is a victim of sex trafficking and they played an audio message Comey sent to her in August of 2023 to try to support that claim. Hey, um, I really don't know what's going on with you, but I just want to just give you a heads up that I'm about to really disappear on you. You feel me? I'm not not gonna be playing these games with you at all,

at all. So I don't know, you think you're silently treating me, and you think I'm gonna be, nah, you'll have a rude awakening, you'll just have silence, and ain't nobody threatening you, and I ain't trying to go back and forth with no woman, you know what I'm saying? I'm telling you, I ain't got no time for no f***ing games.

Where my life is at right now, I don't have no time for no games, baby girl. Me and you can be mad, I can have a spat, we can have whatever. Then after that, you better get on your job. That's really, that's all it is. Because you got me on my job, nah, it ain't never going to work like that over here. You know what I'm saying? I was trying not to leave this message, but you have left me no choice.

So how do you, you go in the direction of like moving on and like that, or you like just like have me just keep moving. Ain't no threat, I'm just being clear. I can't do this every time you get upset. This is a law and Crime Legal Alert. Did you know that children are being diagnosed with serious conditions like type 2 diabetes

and non-alcoholic fatty liver disease? And research is potentially linking ultra processed foods to these outcomes. Morgan & Morgan is stepping in to fight to hold food companies accountable. With decades of experience fighting large corporations, they are ready to stand up for families that deserve justice. So if your child under the age of 21 has been diagnosed with type 2 diabetes or fatty liver

disease, visit www.forthepeople.com slash food or scan the QR code on your screen to learn more. But Sean Combs' attorneys say he just lives a swinger's lifestyle. Jane testified that Sean Combs told her from the beginning that he was seeing other women. But is what Cassie and Jane described swinging? The drugs, the hours-long sex sessions with male sex workers directed by Sean Combs? We're going to talk about it later. But where did Sean Combs develop these tastes?

I wonder, and we've discussed it before, does it go back to his childhood? It's possible. Let's go back to the beginning. Sean John Combs was born on November 4, 1969 in Harlem. His mom was Janice and his dad was Melvin. We'll have more on Melvin and Janice in a bit. Now we know that Janice moved Sean Combs and his sister to Mount Vernon, New York, after Melvin was killed.

Published reports claim Janice worked three jobs to put her kids through private school. In a 2006 documentary, Sean Combs' Portrait in Black and White, Combs revealed a lot about his upbringing. He explained the difference in how his grandmother raised him compared to his mother, telling a story about someone stealing money from him after his grandmother sent him to the store to buy cigarettes. His mom told him to get the money back and not to come home unless he got the money.

He left crying. He found the guy and he got beat up, but he said he got the money back. In the documentary, Combs said, My mother, I guess, was raising me for the real world. She always told me if someone hits me to hit them back harder. Combs' father, Melvin Combs, was raising me for the real world. She always told me if someone hits me to hit them back harder. Combs' father, Melvin Combs, was shot and killed

on Central Park West in 1972. But for years, Combs believed his father died in a car crash because that's what his mother told him. Combs talked about his father in the documentary, saying in his own words that he later found out his father's brains were blown out. And Sean Combs said he learned he was the father of a hustler and a gangster, which he had always suspected. And there has been talk over the years that Melvin Combs worked for Harlem gangster Frank

Lucas, whose story was depicted in the film American Gangster. Combs apparently found out his father was friends with Lucas, a drug dealer, but has said in other interviews that his father was a drug kingpin in his own right, which is something he didn't really want to glorify. Lucas has said that he and Melvin Combs did business together. Now, in the documentary, Combs said his only memory of his father was him tossing him up in the air when he was very, very little. He was a very stylish dresser. The ladies loved him. His whole everything is real meticulous.

He had a lot of drive, a lot of determination. You know, he ain't want to be poor. Here's music journalist, Sean Sotero, talking about Melvin Combs. Melvin Combs' story is very interesting. I found something actually just the other day, you know, it's a daily news story from February 1973, which is a few years, maybe a year and a half or so after he was killed. But it was around the time that this

drug case in which he had been involved in which, you know, finally convictions happened in it. But this article says, well, look, you know, this this case, which was, you know, this case, which was, you know, breaking up a giant heroin ring, started when Melvin Combs' phone was wiretapped, and that that was sort of the break in this case. And the article doesn't out and out say this, but it seems to imply that Melvin Combs' death was somehow connected to that, right? And you hear rumors people associated with Harlem in that time have said, well, look, people mistakenly thought Melvin Combs was an informant, and that's why he was killed, right?

It's sort of something that people who knew him back then or knew the area back then have said. And so it seems to me this article sort of trying to put two and two together and say maybe the reason they thought that was because there was in fact this wiretap on his phone. So that part was true, but obviously wiretaps are not something one does voluntarily, right?

So if this daily news article is to be believed, I think that maybe sort of explains the story behind his death, possibly. But yeah, I think, you know, Diddy definitely had the image of his father was very important to him. There was a speech he gave at Howard, maybe 2005 or so, something like that, where he recalls very vividly, you know, I was in college at Howard and the first thing I did was go to the library

and look at the microfiche and look up the Amsterdam News and see this story about my father. Like, it is something that is very important to him, this image of his father as sort of the drug dealer, but not just the drug dealer, sort of the suave, but not just the drug dealer, sort of the suave, powerful guy who hung out with the biggest of the big gangsters, Frank Lucas, like you mentioned, who of course, his story is now immortalized in movies. He's about as famous as you can get in that sort

of milieu. So I think that Diddy seemed to hold on to that image of his father and it seemed very important to him that his father was someone big and notable and important. Combs also discussed being a somewhat lonely person in his belief that he's not really a good friend. I don't really think I make a good friend. I don't think I'm someone who someone's going to call when they're going through something. I don't think I'm going to have the patience to really slow down to give them the attention they need. Now, there are other things that Combs revealed about his childhood that have always made me wonder, wow, what's going on around him and did it shape how he views sex and how

he treats women? Combs spoke in the documentary about how he lost his virginity when he was just 12. Combs talked about watching shows about sex as a kid. He said, the first time I had sex, I wasn't scared, it felt so good to me. But I just remember how impressed I was because I used to watch Midnight Blue, and how I felt I was just as good as the porno stars like in Midnight Blue. Now, since the last time we talked about Sean Combs' childhood, a documentary came out on Peacock.

It's called Diddy, The Making of a Bad Boy. Combs' childhood friend, Tim Patterson, appeared in the documentary and said, "'Sean Combs was bullied as a kid.'" He also said that when they were kids, Combs' mother had wild parties at her house on the weekends. Patterson and another man told producers that women from Harlem would go to the house

in Mount Vernon and hang out. There were all kinds of people there doing drugs and other things. They were described as pimps and pushers. Patterson said it wasn't unusual for them to walk in on people having sex in a bedroom. It was just another Saturday night. So was Sean Combs exposed to all of this at a young age

thinking this was normal? Or are Sean Combs exposed to all of this at a young age thinking this was normal? Or are Sean Combs' sexual proclivities just that of a billionaire with different tastes? So I want to bring in Dr. Daniel Boeber. He is a forensic psychiatrist, and he and I have talked about Sean Combs before. But Dr. Boeber, we are now learning more information about Sean Combs and his sexual proclivities from the first couple of times you and I talked about this. Since the trial has started, we've learned kind of more intimate details about Sean Combs and the fact that he's like asking and instructing male sex workers or at least one of them to urinate

in Cassie Ventura's mouth. And I don't understand that. I don't know if any of us can understand that except somebody who probably gets some type of gratification out of that. Can you explain to me why someone would be into that? And the only thing that comes to mind to me is being able to actually command somebody to do that and they actually do it. So we know that Diddy was exposed to early sexual trauma when he was a child. He witnessed things that most kids should not be exposed to and that in no way excuses his behavior. But you know with this early sexualization and distortion of boundaries

comes a form of trauma and this really affects your sense of attachment, your sense of intimacy. And for him with all the wealth, all the fame, all the power, it's really about as said, control and dominance. And the reason is, is because there's an element of detachment there, right? It's why he pays someone because it's purely transactional. There is no connection there. He can keep it at a distance. He can observe it and he can control it for his own gratification. I've seen this in a lot of celebrities I've treated and there's historical accounts, for example, of Elvis Presley and some of his sexual proclivities. These are people that have instant gratification 24-7. They have unlimited resources, unlimited

money, unlimited fame. They could do anything they want. And so there's almost an element like, almost like an addict would operate, right? Where they keep upping the ante, they keep getting that dopamine rush, but at some point they become desensitized to it and it's not enough to arouse them anymore. So they keep taking it to the next level and there's this almost this sense that I could have anything I want any time

and this is just not doing it for me anymore. So I need to take it to the next level. And with the example that you pointed out in the beginning of the conversation, I think there's also an element of degradation there, right? I can force someone to do this and they will listen to me. I have so much power, so much control that they literally will do anything I ask

and I think there's a certain rush that they get from that. Okay, so we have a lot to unpack there. Let's go back to, you know, there's the power, the degradation, the rush, the dopamine hit, that makes sense. You mentioned the childhood and you and I have talked about this before and the fact that Sean Combs said in the one documentary that he lost his virginity at a very young age. And he's very descriptive when he talks about this. And he also talked about watching that channel, the Midnight Blue channel.

And then there was like pornography and stuff like that. So he's seeing all of this. But since you and I talked about this the last time, the Peacock documentary also came out and his friend Tim It was featured in this documentary and he talked about how you know he lived on the first floor of this house where they lived in Mount Vernon and On the weekends there were times where they would be hanging out on this You know upper floor of this house where Sean Combs lived with his mother and his sister.

And they'd walk into a room and there would be people having sex in the room. Something was going on in that house, according to Tim Patterson, where people were having sex in this house and it was normal. So that exposure as well, something like that possibly sets the stage for Sean Combs engaging in these other behaviors. Right, so think about it. Intimacy is really about vulnerability. Anytime we fall in love or we're intimate with someone, we're exposing ourselves to something.

We're exposing ourselves to getting hurt. So there's an element of vulnerability. But when you're someone like Sean Combs, who's been exposed to early childhood sex, where the boundaries are so confusing and you don't quite know what to do with it, sometimes it's a much safer place in your head to keep it distant, to keep it objectified, to monetize it, to make it transactional. That way you protect yourself. So it's essentially a protective mechanism. Now, of course, it's deviant, it's degrading, it's humiliating to people, it's domination. But I think in his case, this is where it comes from. What's really disturbing to me and I, what is kind of and I'm kind of piecing this together in my head you are obviously the professional here but I've covered enough of this stuff to kind of

think about these things. He's a child he's remembering these things as a child about watching pornography so he's watching pornography at a young age now he, he's a rich guy. I mean, he's a wealthy guy, he's a billionaire. And he is almost like using women he's supposed to love, that's who he's engaging in these freak-offs. He says they're all consensual, he's being accused of sex trafficking. But he's almost staging his own pornographic films, like right in front of him. And the testimony has been that he directs these.

I mean, there's always white fingernails. The women have to have their fingernails painted white. There's like a set, the candles. They have to go to the store and get the candles. And there's candle wax everywhere. There's baby oil. Like everybody's got to be like having all this baby oil all over themselves. And he is directing it, do this, do that.

It's kind of, it's beyond my comprehension. And then he's masturbating while this is going on. So what is up with that? Because it's voyeuristic to me. Right, well it is voyeuristic, but think about the sense of power and control that gives him. He's essentially directing his own pornographic film, creating his own pornographic set, gratifying himself in full view of everyone.

It's the ultimate rush for him. It's the ultimate fantasy. And the fantasy is a reality. He has so much fame and wealth and celebrity that these people are willing to do this. Now, I question whether they're truly willing participants, where it's truly consensual. I have questions about that and I've discussed this in other segments where when someone has that much of a hold over you, financially a threat of physical or sexual harm, is it really consensual? You might do it, but are you really consenting to it? And

even if you do it once, that doesn't mean that you consent to it every single time. So I think it's complicated and I think that's something that the defense is going to seize upon that these people were there willingly, did whatever he wanted them to do, and they made mature adult decisions to do this, and it was purely consensual. But I would argue that given his enormous power and control over them, that he did have a hold over them, and it may not have truly been consensual. Well, and that's the rub here. That's the argument and the division here.

He's saying it was always consensual. The women are saying and the government is saying, no, it's not. It wasn't. And it's sex trafficking. And these are the reasons why. There was coercion. There was force, things of that nature. And they're going to lay out enclosing arguments why. They're going to try to tie this all together. You and I were talking kind of offline about how sometimes people in positions of power and people of significant wealth and things like that do things like this.

And why is that? I think there's a certain sense of entitlement. You know, I contribute this to society. Everyone on the planet knows who I am. So the rules don't really apply to me. I give something to people that no one else can give them. So this entitles me. This gives me the right to basically do what I want without consequences, with impunity. And I think they really believe that the rules don't apply to them.

So somebody like Sean Combs, you're saying, you know, if he's indeed guilty of these charges, feels the rules don't apply to him. And I guess maybe you could argue that when he's paying 100 grand for a video to some guys in a hotel that shows him beating up a woman, beating up Cassie. Well clearly that was consciousness of guilt and you know he was trying to suppress the release of that video but I also think there's a degree of what we call impression management. He didn't want the public seeing that. He didn't want them forming that opinion of him.

And he denied it and denied it and denied it until the video came out. And then it was time to go into damage control. Yeah, yeah. But back to the sexual proclivities and stuff like that, I just, I don't know if the public can really wrap, and maybe they can, but a lot of people can't wrap their heads around the fact that he was doing this a lot.

These freak-offs were going on for a really long time, sometimes days. There would be obviously breaks. It wasn't constant, but they would be doing drugs and these sex workers are saying, yeah, I've come in. I do what he said and he's directing all of it, and these hotel rooms are just absolutely trashed. So this was obviously something, it's almost like, and I know you haven't evaluated him,

was he addicted to this? Was he almost like a sex addict? It's like going into a swimming pool, right? It feels really cold at first, but after a while you get used to the water. It's the same thing, right? At first, it's very novel, it's very exciting, but then after a while it becomes routine.

And then you say to yourself, well, what can I do to take this to the next level? Can I humiliate someone? Can I do it on film? Can I pay people to do it? Can I get multiple people to do it? And so again, I think you have someone with so much celebrity and power that the gratification, they become desensitized to it

and they have to up the ante. And again, I think of people like Elvis Presley, who I, you know, would hear stories about him watching women have sex through a one-way mirror where he wasn't actually participating in it, but he was watching it because it was something that he orchestrated. So I think this is a, I don't want to say a common thing, but I think when people feel that they are literally invincible and can do anything they want and there's no consequences, I think they are intoxicated with that power and they will do things like this for thrills. Is voyeurism more common than we realize? Yeah, voyeurism is something that happens

in people who aren't wealthy, who aren't celebrities. And I will say this, you know, there are people that can do things that we may think are deviant, but if they are truly consensual, and both parties are involved willingly, and I do are truly consensual and both parties are involved willingly, and I do mean truly consensual, then it's not necessarily a mental illness. It might be just something that you know couples do for sexual gratification. When it starts to become deviant or criminal is when there isn't consent, and I think that as you say is the rub here.

Yeah, and there you know there there have been two victims, basically, where the testimony was, well, yeah, at first I tried it and wanted to make him happy, and I was into it. And then there apparently became a point where it was just not cool anymore, and they didn't want to do it. And there was a switch. Something changed.

So it's very disturbing you know, it's very disturbing, the whole thing. And it'll be interesting to see how this ends. Dr. Daniel Boeber, thank you so much for your time. Thanks, Anjanette. And that's it for this episode of Crime Fix. I'm Anjanette Levy. Thanks so much for being with me.

I'll see you back here next time.