Law&Crime Sidebar - 10 Horrifying P. Diddy and Cassie Details That Kick-Started Rapper’s Legal Trouble

Episode Date: September 26, 2024

Many of the allegations against Sean “Diddy” Combs in his federal criminal indictment have direct correlations with a civil lawsuit filed by his ex, Cassie Ventura. Law&Crime’s Jesse Weber takes a deep dive into the bombshell, multimillion dollar lawsuit that Combs settled within 24 hours.PLEASE SUPPORT THE SHOW: Download the FREE Upside App at https://upside.app.link/sidebar to get an extra 25 cents back for every gallon on your first tank of gas.HOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger and Christina FalconeScript Writing & Producing - Savannah WilliamsonGuest Booking - Alyssa Fisher & Diane KayeSocial Media Management - Vanessa BeinSTAY 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 Wondry Plus in the Wondery app Apple Podcasts or Spotify. Agent Nate Russo returns in Oracle 3, Murder at the Grandview, the latest installment of the gripping Audible Original series. When a reunion at an abandoned island hotel turns deadly, Russo must untangle accident from murder. But beware, something sinister lurks in the grand. View Shadows. Joshua Jackson delivers a bone-chilling performance in this supernatural thriller

that will keep you on the edge of your seat. Don't let your fears take hold of you as you dive into this addictive series. Love thrillers with a paranormal twist? The entire Oracle trilogy is available on Audible. Listen now on Audible. It appears Cassandra Ventura may be a key figure with respect to the criminal charges facing Sean Diddy Combs. So with that, we're going to go back and break down her initial lawsuit against Combs, the lawsuit that started the ball rolling, which eventually led to Combs' arrest. What did she say happened to her? And is this a preview of what she could maybe testify to at a future trial? Welcome to Sidebar. Presented by Law and Crime. I'm Jesse Weber. Now, if you've been following our coverage of Sean Combs' criminal case

here on Sidebar, you know that we have talked a lot about someone who could be a major witness a trial someone who is most likely cooperating with the government someone whose allegations against combs i think it would be fair to say make up a huge part of the current indictment i'm talking about cassandra ventura cassie combs ex-girlfriend and remember she sued him back in november of 2023 for sexual assault battery sex trafficking this was among other claims and that case that case ultimately started the ball rolling with with more lawsuits filed against Combs and ultimately culminated with these criminal charges.

In fact, there is an argument to be made that in Sean Combs indictment for racketeering conspiracy, sex trafficking, transportation to engage in prostitution, she's allegedly victim one, who was allegedly sex trafficked by force, fraud, or coercion. There is an argument to be made that that is her. Actually, one of her main accusations that we're gonna go into is specific,

specifically described in this indictment. Again, it seems to me that her claims are what make up the majority of this indictment. So with that, we thought, let's go back. Let's revisit her lawsuit. Let's see what she claimed can kind of give us a preview of maybe what to expect. And yes, she settled this lawsuit with Combs the day after she filed it. But that doesn't mean that her claims and allegations can't be used by prosecutors, that it can't be used to prosecute Combs. actually, again, in my view, and other analysts believe this too, it seems that they are. So let's do a deep dive into her lawsuit. That may be a preview of what we see at Combs' upcoming trial, whatever that might happen.

Now, before I begin, let's not forget what Sean Combs is currently charged with, what he's accused of. The racketeering charge in the indictment is essentially that Combs led a criminal enterprise, whose goal, other than to operate a global media and entertainment business, was to engage in the abuse of women, sex trafficking, forced labor, prostitution, the distribution of drugs, to use violence and threats, to commit crimes like kidnapping, arson, bribery, obstruction of justice, all to carry out the goals of this enterprise,

all the while making sure to satisfy the sexual desires of Sean Combs. And one of those desires, as alleged by prosecutors, and also alleged by several Combs' accusers in separate civil lawsuits that they filed against him, including Cassandra Ventura, were the commission of freak-offs, these elaborate, coerced sexual performances, sometimes induced by drugs that Combs wanted. Now, he's also charged with sex trafficking with respect to victim one. Again, argument could be made, that's Ventura, that is using force, fraud, or coercion to have this person, engage in commercial sex acts, meaning for money or something of value was given or promised.

There's an element that this has to be enticing, harboring, transporting this person over state or foreign lines. And then we have the final count, which is transporting people over state or foreign lines for the purposes of prostitution. By the way, really, really appreciate you guys following our continued coverage of the Sean Combs case and all the different facets of it. And I have to call out one of our sponsors because it's with their support. that helps us to keep on doing this. And this is called Upside. Now, Upside's awesome.

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how Combs is a rapper, a record executive, how he rose to prominence in the entertainment industry, and then she explains how in 2022, when he won the Lifetime Achievement Award at the BET Awards, he called out Ventura in his speech, and also Cassie for holding me down in the dark times, love. But then the suit says, quote, the truth, however, is that Cassie, Ms. Cassandra Ventura, was held down by Mr. Combs and endured over a decade of his violent behavior and disturbed demands. For Miss Ventura, the dark times were those she spent trapped by Mr. Combs in a cycle of abuse, violence, and sex trafficking. And then lists a number of, quote, violent and unlawful acts, which we're going to get into. But it's important to start from the beginning.

with this. So in the complaint, she explains how she met Combs when she was 19 years old back in 2005. He was apparently 37. He signed her to his record label, Bad Boy Records, as an artist. And from there, she claims that Combs, her boss and who she describes as, quote, one of the most powerful men in the entertainment industry lured her into a fast-paced drug-fueled lifestyle and into a romantic relationship with him, where he, quote, asserted complete control over her personal and professional life, thereby ensuring her inability to escape his hold. She claims that he provided unprecedented avenues for success for the aspiring artist, but in return demanded obedience, loyalty, and silence.

And that is key. That is a common characteristic in sex trafficking claims, the promise of something valuable to force someone to engage in sexual activity. And there are more references to this, where Combs, according to, to Ventura would buy her designer clothing, pay for lavish vacations for them, bought her a car. So I want you to keep that in mind as we talk more about this. Now, the complaint goes on to say, quote, within a year of signing with Bad Boy Records, Mr. Combs became deeply entrenched in Miss Ventura's life, almost immediately asserting

possession and control over her and inserting himself into all aspects of her career and her personal life. and expanding upon that concept of control and ownership, as Ventura defines this. The complaint also states that Combs started renting her an apartment that was within walking distance of his place. And the complaint says, quote, Mr. Combs also became deeply involved in Ms. Ventura's personal life, with his personal staff attending to Ms. Ventura's day-to-day travel and other needs, including medical care. On multiple occasions, Mr. Combs had Ms. Ventura's personal medical record sent directly to his email address. For instance, when Ms. Ventura began experiencing memory loss,

potentially due to excessive drug use and or head injuries caused by Mr. Combs' beatings, her MRI results were provided directly to Mr. Combs. Mr. Combs also repeatedly arranged for his staff to drive Ms. Ventura to certain doctor's appointments. By the way, that is alluded to in Combs' criminal indictment as well, because in the indictment, it states, quote, Combs maintained control over his victims through, among other things, physical violence. promises of career opportunities, granting and threatening to withhold financial support, and by other coercive means, including tracking their whereabouts,

dictating the victim's appearance, monitoring their medical records, controlling their housing, and supplying them with controlled substances. Now, by the way, according to Ventura, Combs pursued her and began this romantic relationship with her, even though he had been dating, Kim Porter, and Ventura apparently had a boyfriend. And she explained that she would acquiesce to his requests and demands, including her taking a copious amount of drugs at his insistence, because she was afraid. She was afraid of the repercussions for her and her career. The complaint says, quote, compounding this all-encompassing intrusion into her life, Mr. Combs secured his control over the young and impressionable Miss Ventura by introducing her to a drug-fueled lifestyle that kept her complacent and compliant. Now I want to get into the physical and sexual abuse allegations.

That's a main component of this case. So the complaint lists out many alleged incidents. For example, it states, quote, Mr. Combs would violently beat Ms. Ventura leaving bruises on her body. After every instance in which he beat Ms. Ventura, Mr. Combs used his money and power to orchestrate extensive efforts to hide the evidence of his abuse, including by hiding Ms. Ventura in hotels for days at a time to let her bruises heal. It goes on that in one such instance, after a party with Jay-Z, Mr. Combs beat Ms. Ventura repeatedly in an escalade, including by kicking and hitting her. There's another instance that says that in January of 2009,

after Mr. Combs learned that Ms. Ventura spoke to another music manager at a party in Los Angeles, he became enraged. It goes on to state that in the car leaving the club, Mr. Combs beat Miss Ventura. her into a corner of the vehicle and stomping on her face. Now, to be clear, we don't know if any of these specific instances of abuse will make their way into this criminal case, whether it's only respect to the freak-offs, because, again, the indictment really focuses on that and not necessarily individual isolated moments of abuse, but we'll wait and see. Now, for anyone following this story, in this complaint, in this lawsuit,

is the first time that we heard about this infamous March 2016 incident at the Intercontinental Hotel in Los Angeles. This is where Ventura claims that a drunk Sean Combs punched her in the face and as she tried to escape the hotel room, he follows her into the hallway, yells at her, grabs her, and throws glass vases. And we all saw this episode with our own eyes when CNN published video of this encounter a few months back, seeing Combs in a towel allegedly beating Ventura in that hallway, kicking her, dragging her, an episode that Combs apologized for on Instagram just two days after that video was released. And this was also referenced in the criminal indictment as well. It's actually one of the more specific instances that is described.

And as Ventura and prosecutors allege, Combs attempted to bribe a security guard to keep all this quiet and that Combs and his team may have purchased that surveillance footage so that no one would see it. Now going back to why this was mentioned in the indictment and what was said in this complaint, according to prosecutors and according to Ventura, at that hotel room, that 2016 incident, she was allegedly escaping a freakoff, which again is at the center of this criminal indictment against Combs. And it's the first time, I will tell you, I ever heard of it. I ever heard of a freakoff was in this lawsuit. These voyeuristic sexual performances where Combs would allegedly force Ventura to engage in sex acts with other men, mostly male sex workers.

As her complaint explains, Combs would allegedly demand these freakoffs or FOs at random times, and she was expected to find the place and hire the men. These would happen, according to Ventura, frequently at all different locations, including prominent hotels. The FOs would get so wild that there's an allegation that there was damage sustained at the hotel rooms? The complaint says, quote, sometimes Mr. Combs would pay to fly male sex workers to his location, including to multiple cities in the United States as well as abroad. He required Ms. Ventura and his staff to help him make these arrangements. Mr. Combs' assistants would help to set up the FOs, including by setting up the hotel suites with baby oil and astroglyde.

Mr. Combs always supplied Ms. Ventura and the sex workers with copious amounts of drugs before and during the FOs. Ms. Ventura was given ecstasy, cocaine, GHB, ketamine, marijuana, and alcohol in excessive amounts during FOs, which allowed her to disassociate during these horrific encounters. It became commonplace to get IV fluids in the days after an FO to recover from the excessive substances pushed upon her. And to be clear, according to Ventura, this is not. not something she wanted to do. In the complaint, it says frequently her anxiety before an FO would become so great that she would become physically ill,

sometimes to the point of vomiting. While kneeling over the toilet, Mr. Combs would shame her into performing for him, eventually forcing her to get up and proceed with the encounter. She knew firsthand that telling Mr. Combs that she did not want to engage in FOs was met with anger and violence. In addition, any suggestion that Ms. Ventura would refuse the F.O. or otherwise report Mr. Combs abuse was met with ultimatums by Mr. Combs, who would say that

Ms. Ventura would not go to the police because she had a lot to lose. Now, not only is that consistent with what is alleged in the criminal indictment, the fact pattern as laid out by prosecutors, but that specifically is what accounts for her sex trafficking claim in this lawsuit and the racketeering, sex trafficking, and transportation to engage in prostitution charges that he faces. Ventura alleges in her complaint that Combs would pleasure himself during these FOs and also film the encounters. And get this, after she claimed she tried to delete photos and videos of these FOs, Combs told her he's got the videos. And in fact, quote, on one occasion, he sat next to her on a flight and made her watch a video she thought she had deleted, reinforcing her inability to escape and the immense power he held over her.

It goes on to state that over the years, she again and again tried to escape his tight hold over her life. Every time she hid, Mr. Combs' vast network of corporations and affiliated entities found her, and those who work for Mr. Combs' companies implored her to return to him. Many went as far as to explicitly state that her failure to return to Mr. Combs would hinder her success in the entertainment. industry. Again, that goes to this racketeering conspiracy. It's not Combs acting alone. There's a team. There's an enterprise. That's what the allegation is put forward by prosecutors. Now, later on in the complaint, she explains how by 2017, 2018, she wanted to leave Sean Combs. And she says how at one point they went to dinner, seemingly to try to talk about ending the

relationship. But at the end of the night, he allegedly forces himself into her apartment and rapes her as she says no. Now, if you didn't think all of these allegations were shocking enough, and by the way, remember, this was the first lawsuit. This started at all. This was the first time we were hearing these shocking allegations for the first time. But there were other parts of this complaint where she mentions other high-profile individuals that is, again, shocking.

For instance, she explains how in 2011 during a rough pack, in her relationship with Sean Combs, she started a relationship with rapper Kid Cuddy. And the following year, she claims, quote, Mr. Combs told Miss Ventura that he was going to blow up Kid Cuddy's car and then he wanted to ensure that Kid Cuddy was home with his friends when it happened. And around that time, Kid Cuddy's car exploded in his driveway. And guess what? This is a part of the criminal indictment as part of the racketeering conspiracy charge. where you're showing this criminal enterprise, prosecutors list out a number of alleged underlying crimes

committed by the enterprise members. Included in there is arson. This seems to be with respect to the Kid Cuddy Car incident, and prosecutors in a following subsequent letter to the court had indicated they have evidence fire reports to back this up. But continuing on with other high-profile people mentioned in Ventura's lawsuit, what about Combs' longtime rival music executive Shug Knight? He's mentioned.

The complaint reads on one occasion when Mr. Combs and Ms. Ventura were using drugs together in his home, one of the security staff barged in and announced that Shug Knight was spotted at Mel's drive-in diner in Los Angeles. Mr. Combs began to get dressed, retrieved multiple guns from a safe, and ran out of his home to where he believed Mr. Knight was dining. Miss Ventura became terrified and began to cry. The complaint goes on to say that on at least two occasions, Mr. Combs demanded that Ms. Ventura hold Mr. Combs' gun in her purse. There was no clear reason why Mr. Combs required her to hold his guns, except to reinforce to his young girlfriend that he was violent, powerful, and dangerous. The idea of brandishing firearms to intimidate and threaten others is also a part of the criminal indictment. And remember, firearms were seized in the raids on Combs' properties back in March, including ARFIF.

with defaced serial numbers. That in and of itself is a federal crime. But now going back to the complaint, let's put a bow on this. It says, Ms. Ventura has now fully escaped Mr. Combs. But the harm that the assaults and sexual abuse he caused her to experience for nearly a decade will forever haunt her. She has required intensive medical and psychological care to recover from the trauma she lived through. And in another point, it says she cannot, however, continue to live in silence about what she endured. Mr. Combs remains immensely powerful and immensely dangerous. And Ms. Ventura therefore seeks justice for the decade of her life that Mr. Combs took away from her with threats of violence, excessive use of drugs, physical and psychological abuse, and sexual slavery. And that indicates to me that she is possibly going to be a government witness who will testify against Sean Combs.

But we'll wait and see. So that is a summary of her allegations, her claims, and perhaps what makes up the criminal charges that Combs currently faces. and moreover what we can expect Cassandra Ventura to testify to should she, in fact, be a cooperating witness for the government. That's all we have for you right now here on Sidebar. Everybody, thank you so much for joining us. And as always, please subscribe on Apple Podcasts, Spotify, YouTube, wherever you get your podcasts. I'm Jesse Weber. I'll speak to you next time. You can binge all episodes of this law and crime series ad free right now on Wondery Plus. Join Wondery Plus in the Wondery app, Apple Podcasts, or Spotify.