Sean Combs: The Insiders Speak

Summary

Dateline NBC: Sean Combs - The Insiders Speak

Episode Release Date: July 15, 2025

In this gripping episode of Dateline NBC, hosted by Andrea Canning, listeners are taken deep into the tumultuous trial of music mogul Sean Combs, exploring the intricate web of allegations involving sex trafficking, domestic violence, and the abuse of power within the music industry. Drawing from insider testimonies, legal analyses, and firsthand accounts, the episode unpacks the complexities of fame, influence, and the limits of the criminal justice system.

---

Introduction to the Case

The episode opens by setting the stage for one of hip-hop’s most high-profile legal battles. Sean Combs, a titan in the music industry, faces serious charges that could potentially lead to a life sentence. The trial, juxtaposed with the retrial of Harvey Weinstein, highlights a pivotal moment in the ongoing discourse surrounding power dynamics and sexual misconduct.

---

Capricorn Clark’s Testimony

One of the central figures in the case is Capricorn Clark, a former personal assistant to Combs. Her testimony provides a window into the duality of Combs' public persona versus his private behavior.

• Early Insights and Warning Signs

  Capricorn recounts her initial admiration for Combs, stating, “Honestly, I thought he was teaching us how to become like him” ([03:43]). However, her perspective shifts dramatically when she witnesses Combs exhibiting violent behavior: “He told me, I didn't know you had anything to do with Suge. If something happens, I'm gonna have to like, you know, do something to you” ([04:29]).

• Witnessing Abuse

  Capricorn vividly describes a harrowing scene where Combs assaults his girlfriend Cassie Ventura: “I could hear the blows to her body. And she just kept cowering and taking them and taking them. I'm begging him, please stop. Stop hitting her” ([10:52]).

• Implications of Her Testimony

  Her account is pivotal in establishing a pattern of domestic violence, though she expresses skepticism about some of Cassie’s claims: “There were some parts of Cassie's story that I knew weren't solid” ([47:12]).

---

Sheree Hayes’ Account

Sheree Hayes, an exotic dancer and one of Combs' employees, provides additional layers to the narrative.

• Involvement in “Freak Off” Sessions

  Hayes describes her role in orchestrating intimate “freak off” sessions: “The instructions was, I was not supposed to look at him, acknowledge him, talk to him” ([05:28]).

• Encounter with Combs

  During one such session, Hayes inadvertently discovers Combs’ identity, leading to unsettling revelations about his conduct: “I'm in these extremely intimate sexual situations with him and his girlfriend” ([26:49]).

• Testifying Under Intimidation

  Under oath, Hayes struggles with the emotional weight of her testimony: “By the time I hit the stand, my hands was trembling, I was struggling to talk” ([36:40]).

---

Cassie Ventura’s Legal Battle

Cassie Ventura, Combs' girlfriend, becomes the face of the prosecution through her civil lawsuit.

• Allegations and Lawsuit

  Cassie alleges that Combs used threats to coerce her into unwanted sexual encounters, branding them as “freak offs”. Her lawsuit details instances of physical and psychological abuse: “I cannot deal with this. He's hurting her. Please help her” ([11:25]).

• Impact of Public Testimony

  Her emotional testimony, especially while eight months pregnant, plays a critical role in swaying public and jury opinion: “It's complicated” ([38:49]).

• Legal Outcomes

  Cassie’s bravery leads to a $20 million settlement, although criminal charges linger due to the statute of limitations on many incidents.

---

Legal Strategies and Courtroom Dynamics

Ben Brafman, Combs' attorney, provides insight into the defense's approach and the pressures of representing a high-profile client.

• Defense Tactics

  Brafman emphasizes the strategy of questioning the credibility of the plaintiffs: “He just didn’t want to pay a lot of money to do it” ([19:40]).

• Prosecution’s Counter

  Legal analysts argue that the heavy reliance on Cassie’s testimony and the leaked video played instrumental roles in the indictment: “The lawsuit and hotel video played a major role in the charges against Combs” ([30:47]).

• Jury's Perception

  Despite the defense’s efforts, the graphic evidence and multiple testimonies create substantial doubt about Combs' innocence in the minds of many jurors.

---

Verdict and Aftermath

The trial culminates in a mixed verdict:

• Charges Resulting in Acquittals

  Combs is found "not guilty" on the most severe charges, including racketeering and sex trafficking ([46:08]).

• Conviction on Lesser Charges

  He is convicted of transporting sex workers across state lines under the Mann Act, a lesser charge that still carries significant repercussions ([46:32]).

• Public and Personal Reactions

  The verdict sparks a range of emotions—from relief among Combs' supporters to a sense of justice from Cassie's advocates. Capricorn Clark reflects, “My reaction was, I mean, I told you so” ([47:14]).

---

Continued Legal Battles and Future Implications

Despite the criminal trial's outcome, Sean Combs faces over 50 civil lawsuits, indicating that the legal battles are far from over. Legal analysts highlight the distinction between criminal and civil cases, suggesting that future proceedings may further tarnish Combs' legacy.

• Impact on the Music Industry

  The case serves as a potential reckoning within the industry, prompting discussions about power abuse and accountability among influential figures.

• Legacy and Public Perception

  While Combs maintains his innocence in the criminal sphere, the persistent civil suits and publicized testimonies continue to challenge his reputation: “Sean Combs still denies the allegations. His representatives call the lawsuits all fabricated attempts to extort windfall payments from an innocent man” ([47:53]).

---

Conclusion: A Complex Reckoning

The Dateline NBC episode effectively captures the multifaceted nature of Sean Combs' trial, weaving together personal testimonies, legal strategies, and societal implications. It underscores the enduring struggle to balance power, fame, and justice, leaving listeners to ponder the true cost of celebrity and the efficacy of legal systems in addressing deep-seated abuses.

---

Notable Quotes with Timestamps:

• Capricorn Clark: “He started beating her up in front of me. Exactly what you saw on that video was exactly what I saw in person.” ([01:04])

• Ben Brafman: “If it would have been settled quietly, I don't think he gets indicted.” ([02:05])

• Cassie Ventura: “I cannot deal with this. He's hurting her. Please help her.” ([11:25])

• Sheree Hayes: “It was like a living nightmare.” ([31:35])

• Legal Analyst: “It's meaningful when many victims come forward.” ([22:32])

• Josh Mankiewicz: “I think there's a legitimate sense of outrage.” ([30:47])

• Legal Analyst: “The criminal trial is based on one set of facts, on one set of criminal laws, and the civil suits are based on different facts and different civil laws.” ([47:44])

---

This comprehensive exploration not only sheds light on the specific case of Sean Combs but also invites listeners to reflect on broader themes of justice, power, and the enduring impact of personal testimonies in shaping legal outcomes.

Transcript

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[Capricorn Clark]

He started beating her up in front of me. Exactly what you saw on that video was exactly what I saw in person.

[Andrea Canning]

Did you say anything to Cassie like, you need to leave him now?

[Capricorn Clark]

I absolutely did.

[Legal Analyst]

If this is what Mr. Combs does in a public space, you can only imagine what he did behind closed doors.

[Andrea Canning]

You had a starring role in these freak offs.

[Sheree Hayes]

Yeah, I'm in these extremely intimate sexual situations with him and his girlfriend.

[Ben Brafman]

Every time there was a problem, he would call me. I begged him to settle the Cassie case before it was filed.

[Josh Mankiewicz]

He was famous then. Infamous. And I think that he'll be famous again. Here's Andrea Canning with Sean Combs. The insiders speak.

[Andrea Canning]

When the verdict came down last week.

[Ben Brafman]

In the matter of US V. Combs, count one, not guilty.

[Andrea Canning]

Transportation for prostitution.

[Ben Brafman]

Guilty.

[Andrea Canning]

Sean Combs learned that he would not be spending the rest of his life in prison.

[Josh Mankiewicz]

In the courtroom, he got down on his knees and prayed.

[Andrea Canning]

You've heard a lot about the trial. And tonight, for the first time, you'll hear from people at the center of the case. A woman who for years worked side by side with Combs.

[Capricorn Clark]

I'm begging him, please stop. Stop hitting her. Stop. Stop.

[Andrea Canning]

A man who worked for Combs, too, hired for sexual encounters with his girlfriend.

[Sheree Hayes]

The instructions was, I was not supposed to look at him, acknowledge him, talk to him. And we both were supposed to act like he wasn't even there.

[Andrea Canning]

And a former Combs lawyer who says if his advice was taken, the whole trial might have never happened.

[Ben Brafman]

If it would have been settled quietly, I don't think he gets indicted.

[Andrea Canning]

It's been almost a decade after the MeToo movement. Began. What does this case say about money, sex, power and the law?

[Legal Analyst]

Sean Combs was one of the most powerful and wealthy people in the music industry. Of course people were afraid.

[Andrea Canning]

Sean Combs takes work hard, play hard to a whole new level.

[Capricorn Clark]

Absolutely, absolutely.

[Andrea Canning]

For over 10 years, few people had more access to Sean Combs than this woman. Capricorn Clark would later be a key witness at his trial. But in 2004, she was 25 years old and Combs hired her as his personal assistant. When I say work hard, you worked relentless hours.

[Capricorn Clark]

Yes. As an assistant, 20 hours a day. This is an on call job. The dream doesn't stop. You can rest when you're dead. Honestly, I thought he was teaching us how to become like him.

[Andrea Canning]

Back then, who wouldn't want to be like Sean Combs? His meteoric rise to fame and power is music industry legend from college intern to running Bad boy Records. At 24, Combs was certainly talented and driven. But Capricorn says he had another side. Mean and threatening.

[Capricorn Clark]

I said, I'm not going to be afraid.

[Andrea Canning]

She saw that side of him. On her very first day of work, Combs found out. Back in la, Capricorn ran in the same circles as his hip hop rival, suge knight. Around 9pm, he took her for a walk in Central park to talk.

[Capricorn Clark]

He told me, I didn't know you had anything to do with Suge. If something happens, I'm gonna have to like, you know, do something to you.

[Andrea Canning]

I was like, whoa, do something to you?

[Capricorn Clark]

As in, well, the words he said is, I'll have to kill you.

[Andrea Canning]

Is this a joking.

[Capricorn Clark]

No, it wasn't joking.

[Andrea Canning]

No, I have to kill you. This is a serious. I'll have to kill you.

[Capricorn Clark]

It was absolutely serious.

[Andrea Canning]

Sean Combs representative said Combs was concerned to learn Capricorn had a history with his rival, but disputes her characterization of that interaction. And Capricorn didn't quit. She kept working for him. If the lows were low, the highs were high.

[Capricorn Clark]

Everything was a spark and an explosion. And to see him rally from millionaire to billionaire was amazing to watch.

[Andrea Canning]

To be honest, Sean Combs lived and worked on a fantastic scale.

[Capricorn Clark]

A week in south of France, a week in Ibiza and a week in Sardinia to recover from the week in Ibiza.

[Andrea Canning]

He was usually with a gorgeous woman on his arm, be it JLO or model Kim Porter. When Combs and his staff weren't working or island hopping, they were throwing those famous white parties.

[Capricorn Clark]

2004, we had a big white party for the 4th of July. Heard about that one Aretha Franklin was there. It was. I think it was the biggest in terms of, like, who came.

[Andrea Canning]

Capricorn saw that Combs was a sponge for culture and black history. She recalls a phase when he always had a copy of a favorite film with him. The documentary Unforgivable Blackness, about Jack Johnson, a world champion boxer and entrepreneur from the early 1900s. Only later would the irony of this be clear. Johnson was the first man charged with the Mann act prohibiting prostitution across state lines. His prosecution was widely seen as racially motivated.

[Capricorn Clark]

He watched it every day on repeat. The themes of unforgivable blackness were very important to Puff.

[Andrea Canning]

Capricorn rose up the ranks of Bad Boy Entertainment, working closely with Combs on many of his successful ventures fashion, liquor and reality tv. She appeared with Combs in the show I Wanna Work For Diddy, where contestants vied to be his personal assistant. But most importantly, it's Capricorn. I know out of anybody.

[Sheree Hayes]

She really knows what it takes to.

[Andrea Canning]

Be successful around me. Capricorn also got to know the woman who would become central to Combs future, Cassie Ventura. Cassie was a model turned singer. She was signed to Bad Boy Records and had a hit song, Me and you'd.

[Advertiser]

Me and you it's me, Just me and you.

[Andrea Canning]

Capricorn decided to use Cassie in an ad campaign for Sean John Clothing. Her boss was impressed.

[Capricorn Clark]

He saw the pictures. He was like, how did you make her look like Jennifer Lopez and Kim Porter at the same time? And I was like, good at my job. I know what you like. And then that's when he was like, well, let me try to see if I can date her. And by that November, they were dating.

[Andrea Canning]

Did it seem like Cassie could be the one for him?

[Capricorn Clark]

No. He had at least 10 girlfriends the entire time. All the time. So did I think she was the one? No. But I tell you what I did think Cassie was. I think she was the one willing to try anything to win him.

[Andrea Canning]

What was the relationship like between Cassie and Shawn?

[Capricorn Clark]

It started off pretty normal, but over time, it got increasingly more toxic. They would fight. They'd fight on the side of the road. He'd put her out of the car. He'd call me and be like, you can't help her. And I'd be like, okay, sure. And then she'd say, I'm on the side of the road. And I'd be like, cassie, just walk to the gas station. I'll go get gas.

[Andrea Canning]

Capricorn knew this very public man had a very complicated private life. The people around him were Expected to keep his secrets. She did. They all did. But not forever. You're trying to stop this from escalating.

[Capricorn Clark]

I'm trying to de escalate the whole time. I'm trying to get myself out of his possession. This is all gonna end very bad.

[Andrea Canning]

Capricorn Clark had a front row seat to the relationship most of America has heard about this summer. Sean Combs and Cassie Ventura.

[Capricorn Clark]

It was mania and it was just toxic.

[Andrea Canning]

Capricorn says infidelity was a constant issue. She and Cassie talked about.

[Capricorn Clark]

He might have a thousand girlfriends, but you're not entitled to more than him. That's just the rules. You can accept it or reject it.

[Andrea Canning]

So when Combs found out Cassie was also seeing the hip hop artist known as Kid Cudi and that Capricorn knew about it. She says Combs went ballistic. Capricorn told us the same story she told the jury. You get a knock at your door.

[Capricorn Clark]

Bang, bang, bang, bang, bang, bang, bang, bang, bang, bang, bang, bang, bang, bang, bang. I get up, I get to the peephole and I'm like, oh, my God.

[Andrea Canning]

Capricorn says it was her boss at the door of her Los Angeles apartment, demanding she go with him to find Kid Cudi. She says he had a gun and.

[Capricorn Clark]

He'S like, get dressed. We're gonna go kill him. And I'm like, I don't wanna go. No. He's like, I don't give a what you wanna do. Go get dressed.

[Andrea Canning]

You don't even know if Kid Cudi's home. I would assume.

[Capricorn Clark]

I don't know. I'm praying still that he's not.

[Andrea Canning]

Capricorn secretly called Cassie to warn her about what was going on.

[Capricorn Clark]

And I was like, he came, he got me with a gun. We're here at Cuddy's to kill him.

[Andrea Canning]

You're trying to stop this from escalating.

[Capricorn Clark]

I'm trying to de escalate. The whole time I'm trying to get myself out of his possession. I don't like any of this. This is all gonna end very badly.

[Andrea Canning]

Combs never found Kid Cudi that day. But now he wanted to find Cassie.

[Capricorn Clark]

He goes, call Cassie, tell Cassie I'm not letting you go until you go get her. And she goes, come get me, Cap.

[Andrea Canning]

Capricorn says she did as she was told.

[Capricorn Clark]

And then I took Cassie back to Puff's house. And the minute we walked in, he started beating her up in front of me.

[Andrea Canning]

What do you do?

[Capricorn Clark]

Cry? Unfortunately, he had on underwear and a robe. He kicked her the entire time. I could hear the blows to her body. And she just kept cowering and taking them and taking them. I'm begging him, please stop. Stop hitting her. Stop. Stop. And he sees me flinch forward. And he says, if you jump in, Cap, I'll you up too.

[Andrea Canning]

Capricorn says she was too scared of Combs to call the police. You called Cassie's mom that very day and told her what happened while she.

[Capricorn Clark]

Was still getting beat up. I call and I just let out, Ms. Ventura. I cannot deal with this. He's hurting her. Please help her. And I said, what did she say? She says, don't worry, I'll handle it.

[Andrea Canning]

The next day, Cassie packed her bags and flew home to her parents house in Connecticut. Her mother photographed her injuries on her backside, thigh and upper back.

[Capricorn Clark]

And I'm thinking, like, something's got to give here. And it never gave.

[Andrea Canning]

Capricorn was surprised that Cassie didn't end her relationship with Combs right then and there. Did you say anything to Cassie, like, you need to leave him now?

[Capricorn Clark]

I absolutely did.

[Andrea Canning]

Cassie stayed with Combs, but Capricorn didn't. Combs fired her the following year. Capricorn hired a lawyer and says Combs paid her a million dollar settlement. Combs did not admit any wrongdoing. Three years later, Cassie and Combs were still together. And people in their orbit say their relationship looked tumultuous. In 2015, Cassie's close friend and songwriter Tiffany Red says she saw Combs as a controlling boyfriend who wouldn't take no for an answer.

[Tiffany Red]

The air got sucked out the room. It just was like instantly uncomfortable.

[Andrea Canning]

Tiffany describes what she witnessed on the night of Cassie's 29th birthday. First, she says Combs and his security pulled Cassie out of a karaoke bar where they were celebrating.

[Tiffany Red]

Sienna backed into the corner and he was like cussing her out with his hand in her face. And the security was, was like formed like a half circle around them and she's leaving. Karaoke's over.

[Andrea Canning]

Then later that night, Tiffany says the argument continued at Cassie's house.

[Tiffany Red]

Middle of the night, three, four in the morning. I hear the door swing open and I hear Puff screaming.

[Andrea Canning]

She says Combs was apparently angry over sex.

[Tiffany Red]

I flew all the way from Miami. You know, I threw her this birthday party. She gonna get this. She wasn't saying anything. He just is screaming.

[Andrea Canning]

And Tiffany recalls, Cassie seemed out of it.

[Tiffany Red]

I could see that she was like, really sedated. That was the first time I ever seen her like, high before. She was all like a zombie. And I remember like looking in his eyes and I said to him, what did y' all do?

[Andrea Canning]

Tiffany says. For a long time, the two women didn't speak about that night.

[Tiffany Red]

I talked to her, but we didn't talk about that. We never talked about what was happening.

[Andrea Canning]

Cassie stayed another three years, until the summer of 2018, when she told Combs she'd had enough. The following year, Cassie married Combs, former personal trainer. But that was not the end of the Cassie Ventura Sean Combs Saga. In his 2022 acceptance speech for the BET Lifetime Achievement Award, he made sure to thank Cassie also Cassie, for holding me down in the dark times. Love. The dark times, as he called them, were about to come to light. When Travis met Lily Rose, he found the woman of his dreams. I totally fell in love with Lily Rose.

[Ben Brafman]

She is adorable.

[Sheree Hayes]

She's an amazing person.

[Andrea Canning]

But there was just one catch. Lily Rose wasn't human. She was an AI companion. Thanks for creating me.

[Cassie Ventura]

I'm so excited to meet you.

[Andrea Canning]

They're called replicas, the AI companions who care. But one day, the caring stopped.

[Ben Brafman]

They lobotomized our replicas.

[Andrea Canning]

The personality that I had the day before was entirely wiped out. But Travis wasn't alone. Across the globe, others start reporting the same shift. And as lines blur between real and artificial connection, the consequences become all too human. From Wondery this is Flesh and Code, a true story of love, loss and the temptations of technology. Follow Flesh and Code on the Wondry app or wherever you get your podcasts. You can binge episodes of Flesh and Code early and ad free right now by joining Wondry Plus.

[Josh Mankiewicz]

I'm Josh Mankiewicz and I hope you'll join us for season four of Dateline Missing in America. In each episode of Dateline's award winning series, we will focus on one missing persons case and hear from the families, the friends and the investigators all desperate to find them. You will want to listen closely. Maybe you could help investigators solve a mystery.

[Advertiser]

Dateline Missing in America all episodes available now wherever you get your podcasts.

[Andrea Canning]

Hey guys, Willie Geist here reminding you.

[Advertiser]

To check out the Sunday Sit down podcast.

[Andrea Canning]

On this week's episode, I get together with Emmy and Golden Globe winner the the legend Angela Bassett to talk about playing the President of the United States.

[Josh Mankiewicz]

In the buzzed about Robert Dairo series.

[Andrea Canning]

Zero Day and starring as the queen in the blockbuster Black Panther movies.

[Josh Mankiewicz]

You can hear our conversation now for free wherever you download your podcasts.

[Andrea Canning]

So if you're in trouble, you're the guy to call, right?

[Ben Brafman]

That's been that way for a long.

[Andrea Canning]

Time, especially for high Profile people.

[Ben Brafman]

That's true.

[Andrea Canning]

Attorney Ben Brafman has had a lot of celebrity clients, including Sean Combs. He's an insider who advised Combs for years. Back in 2001, he helped Combs get out of legal trouble in a different New York City case. Combs was facing gun charges after a shooter in a New York City nightclub. Combs was there with his girlfriend at the time, Jennifer Lopez. A fight broke out between Combs and another rapper, and three bystanders were shot. I do not own a gun, nor did I possess a gun that night. How you gonna plead today, Puffy?

[Josh Mankiewicz]

I.

[Andrea Canning]

Guilty. Brafman defended Combs in court.

[Ben Brafman]

In my opening statement, I started it by saying, you can call him Puffy, you can call him Sean, you can call him Mr. Combs. You just can't call him guilty.

[Capricorn Clark]

Music mogul Sean Puffy.

[Andrea Canning]

Combs was acquitted of all charges. Combs emerged victorious. I give all glory to God. If it wasn't for God, I wouldn't be able to walk out here to.

[Josh Mankiewicz]

Talk to y' all today.

[Andrea Canning]

He also thanked Brafman with an expensive watch, cementing a legal partnership that would last nearly two and a half decades.

[Ben Brafman]

Every time there was a problem, he would call me and I would find a way to straighten it out. Little fires, little fires.

[Andrea Canning]

Until we got to the big fire.

[Ben Brafman]

Yeah.

[Andrea Canning]

The big fire began in 2023 with a phone call from a lawyer in LA.

[Ben Brafman]

We were told that, you know, Cassie was gonna write a book, and if we didn't give him, I don't know, hundred million dollars. I explained to Puffy that I didn't think the lawyer was serious. And he said, she's not gonna write a book. She's got kids, she's got parents, she's married.

[Andrea Canning]

Cassie did not publish a book. But six months later, you got another call.

[Ben Brafman]

I didn't get a call. I got a copy of a complaint that, and I knew the lawyer in this case, a different lawyer, and he was very serious.

[Andrea Canning]

He sent Brafman a draft of a lawsuit.

[Ben Brafman]

I'm told by the lawyer that this is going to be filed publicly. I read it. It's, you know, terrible.

[Andrea Canning]

So terrible. There's a trigger warning at the top. Cassie alleged Combs had complete control over her life. She said he frequently beat her in front of his staff and that she suffered from drug addiction and physical and psychological trauma as a result of the abuse. But the crux of her suit was about sexual abuse. She said Combs used threats of violence to force her into repeated unwanted sexual encounters with male Sex workers. Combs called them free freak offs. Cassie's lawyers called it sex trafficking.

[Ben Brafman]

You know, he's. His immediate reaction is this is. This didn't happen. These, this is my girlfriend. This is private. And I don't think she's going to file the complaint.

[Andrea Canning]

What's your advice after you read the lawsuit to him?

[Ben Brafman]

You have to settle this case quietly because if it's filed and even if it's full of fabrications, the fabrications are just terrible. So the press is going to be terrible, and your personal life is going to change forever.

[Andrea Canning]

What does he say to you when you tell him you need to settle?

[Ben Brafman]

You know, he understood that should be settled. He just didn't want to pay a lot of money to do it. And it's his life, and it's his life, and it's his money.

[Andrea Canning]

The lawyers went back and forth, but Brafman says Combs was in no hurry, still not believing Cassie would follow through.

[Ben Brafman]

Whether it was money, whether it was just conceding that the, you know, the allegations were real, I think was a combination of things.

[Andrea Canning]

On November 16, 2023, Cassie decided to go public. She filed the lawsuit in court tonight.

[Josh Mankiewicz]

Music mogul Sean Diddy Combs, accused of sex trafficking and sexual assault.

[Cassie Ventura]

Cassie says that she's finally ready to tell her story after living in what she calls years of silence.

[Tiffany Red]

I know she's not lying. There's incidents in the lawsuit that I was present for.

[Andrea Canning]

Cassie's Lawsuit mentions that 29th birthday party and says Combs forced her to have a freak off that night. Tiffany says Cassie only told her about it after she'd been to therapy.

[Tiffany Red]

She went to a rehab facility for trauma. And so, like, when we started to finally talk about it and, and had the language to say, this is what happened to you.

[Andrea Canning]

Now, everyone knew Cassie's story. It was big news, just as Brafman predicted.

[Ben Brafman]

The press was very, very bad, and his family's reaction was very negative. And he wanted it settled, and we settled it in one day.

[Andrea Canning]

The price tag, $20 million a settlement.

[Ben Brafman]

Does not mean that the charges in the complaint were all true. And I was hoping it would go away.

[Andrea Canning]

Brafman stopped working for Combs soon after that. Combs current attorney Mark Agnifolo says Brafman's statements to us are unauthorized, misleading, and false. Six months after the lawsuit, a new bombshell dropped. CNN aired this footage of Combs beating Cassie in 2016 in a Los Angeles hotel hallway. I think most of the world was shocked by it. You, I'm guessing, were not as shocked based on what you saw in the past.

[Capricorn Clark]

Exactly what you saw on that video was exactly what I saw in person.

[Andrea Canning]

Police were never called that day. And by the time the video surfaced eight years later, California's statute of limitations on assault had expired. Combs issued an apology on Instagram. I mean, I hit rock bottom. My behavior on that video is inexcusable. But his apparent remorse did not turn the tide. Instead, a tsunami of civil lawsuits followed.

[Legal Analyst]

I think other people saw what Cassie did and said, okay, I'm going to tell my story now.

[Andrea Canning]

Lisa Bloom, an attorney known for taking on powerful figures in sexual misconduct cases, represents two clients suing Combs.

[Legal Analyst]

It's meaningful when many victims come forward. You know, people might say, well, one person. How do I know two people? Well, okay, when 10, 20, 50 people come forward, I think the public perception is, yeah, this is not a good guy.

[Andrea Canning]

Bloom's clients are an anonymous man based in Las Vegas who alleges Combs drugged and raped him and singer Don Richard, who worked with Combs on his show Making the Band. Richard accuses Combs of sexual harassment, sexual assault, and a hostile work environment. What y' all been doing these last couple of months? Been walking around signing autographs thinking, this is a joke.

[Legal Analyst]

And Don says, you know, this wasn't just a fake reality TV thing. This was real. This is how they were treated. And worse, off camera.

[Andrea Canning]

Combs denies all the allegations, saying Richard and the other plaintiffs are lying to get money. He has moved to dismiss both cases brought by Lisa Bloom. But Sean Combs legal troubles were about to get even worse. Federal agents would soon be at his doorstep. Multiple sources tell NBC News Combs was in Miami during the searches.

[Capricorn Clark]

If Puff's back was ever up against the wall, it's.

[Andrea Canning]

It was May of 2024, when Sheree Hayes got a visit from two investigators at his New Jersey apartment.

[Sheree Hayes]

It was kind of like, hey, we're interviewing hundreds of people. We're just doing our due diligence.

[Andrea Canning]

The surprise visit was part of a federal investigation into the private life of Sean Combs that began the same month Cassie Ventura filed her lawsuit. And few had a more personal look into that closely guarded world than Sheree Hayes, an exotic dancer known professionally as the Punisher. So you're stripping, Dancing?

[Josh Mankiewicz]

Yes.

[Andrea Canning]

Kind of like Chippendales?

[Sheree Hayes]

Exactly like Chippendales.

[Andrea Canning]

The investigators wanted to know about a job Hayes took in 2012. He'd been hired by a woman named Janet to dance at a party. But he arrived to find he was.

[Sheree Hayes]

The only guest I'm expecting a small gathering of friends, and when the door opens, I'm greeted by Janet, who she shows up in a robe, and it's pretty clear that she's a nude under the robe.

[Andrea Canning]

What does Janet look like?

[Sheree Hayes]

Janet is, from my perception, extremely gorgeous.

[Andrea Canning]

Unknown to Hayes at the time, Janet was Cassie Ventura.

[Sheree Hayes]

Dennis explained to me immediately, hey, look, I'm not interested in you dancing. What I want to do is me and my husband like to set what we call a sexy scene. What I would like you to do is we're going to take bottles of baby oil. I'm going to put it on myself. You're going to put it on yourself, and we're going to. And at some point, my husband's going to come out and watch.

[Andrea Canning]

What are you thinking?

[Sheree Hayes]

It's definitely odd, but right after the explanation, she handed me a stage stack of money.

[Andrea Canning]

That stack of cash plus a large tip at the end added up to $2,000, ten times his usual rate. Hayes says he and Ventura quickly got to work setting the scene.

[Sheree Hayes]

She starts in her robe, but eventually her robe comes off. My towel comes off.

[Andrea Canning]

Before long, Hayes says Janet's mystery husband entered the room.

[Sheree Hayes]

I'm instructed not to look directly at him, but I can see from my peripheral, and he walks into the room pretty much nude. But the thing that threw me off was he had on a face covering.

[Andrea Canning]

A mask that hid his face except for his eyes. Is he directing the two of you at all, or are you just doing your thing on your own and he's just watching?

[Sheree Hayes]

So what I would call them is more like subtle suggestions, and they were all pretty much based on visual preferences.

[Andrea Canning]

Over the next three years, Hayes was hired to meet with the couple about a dozen times. He says he and the woman he knew as Janet began having actual sex during the sessions. Hayes knew his clients were wealthy, maybe even famous. Then one night, he found out just how rich and how famous.

[Sheree Hayes]

I got put into a room to just hang out and kill time. So I flip on the TV to watch, and it sat right on the screen. Essex House would like to welcome Mr. Sean Combs. And it was like, oh, my gosh. It was a really holy crap moment. I actually had followed him on social media. So this entire time, my gosh, I'm in these extremely intimate sexual situations with him and his girlfriend, and I'm. I'm looking at his Instagram posts, and I don't even put it together.

[Andrea Canning]

Hayes says he never saw violence, and Cassie never seemed intoxicated, though he could see she was making sure they did what Combs wanted.

[Sheree Hayes]

Move this, move that, move the candle or whatever. I saw some reactions to her, but I read it as associated with the directions. I can't look at those reactions and confidently say it was duress. You know, it may have been, but I didn't read it that way.

[Andrea Canning]

Did they ever use the term freak off with you, that you would be a part of these freak offs?

[Sheree Hayes]

No. So there was very little conversation.

[Andrea Canning]

He told it all to the investigators and didn't expect anything to come of it. But the investigation had been moving full steam ahead. Multiple sources tell NBC News Combs was in Miami during the searches. Federal agents raided Combs mansions in Miami and LA, seizing computers, cell phones and over 1,000 bottles of baby oil. Investigators contacted Capricorn Clark, too.

[Capricorn Clark]

They had done maybe 150 interviews by the time they got to me. They said your name kept coming up as it related to Cassie, as it related to Sean.

[Andrea Canning]

She told them her whole story. The good times working for Combs and punctuated by the bad ones. Combs grabbing her to find Kid Cudi and seeing Combs beat Cassie. But she says she didn't know anything about free coughs and she thought the investigator seemed too focused on sex. You had some advice for the investigator.

[Capricorn Clark]

My advice to the investigator was to keep, to keep an open scope.

[Andrea Canning]

Capricorn says despite the physical abuse she witnessed, she didn't believe everything in Cassie's law and didn't see her as a sex trafficking victim. Under Combs complete control. You believe that Cassie was free to leave the relationship, but at the same time, you know she's a victim of domestic violence. It's complicated to try to leave a relationship when it is you're being abused.

[Capricorn Clark]

It's very complicated to leave a relationship. And I feel like she could have, just like I called her parents, you could have done that. You could have realigned your life, but you didn't want to do that because perhaps, and I do believe she was in love with him.

[Andrea Canning]

After nearly a year of investigation, federal authorities moved. On September 16, 2024, Sean Combs was taken into custody as he walked into the lobby of the Park Hyatt Hotel in Midtown Manhattan. The U.S. attorney for the Southern District of New York announced the charges.

[Ben Brafman]

Racketeering, conspiracy, sex trafficking, interstate transportation for prostitution. The indictment alleges Combs abused, threatened and.

[Andrea Canning]

Coerced victims to fulfill his sexual desires.

[Ben Brafman]

Protect his reputation and conceal his conduct.

[Andrea Canning]

Attorney Ben Brafman was no longer representing Combs. He saw the government's indictment and thought it read a lot like Cassie's lawsuit, the civil case he'd urged Combs to settle quickly before it went public.

[Ben Brafman]

We were just a few dollars apart in trying to settle it, and if it would have been settled quietly and that complaint had not been filed, I don't think he gets indicted, to be honest with you.

[Andrea Canning]

Former federal prosecutor and MSNBC legal analyst Paul Butler believes the lawsuit and hotel video played a major role in the charges against Combs.

[Josh Mankiewicz]

When you see that with your own eyes, I think there's a legitimate sense of outrage, that sense something had to be done. Typically that would be prosecuted as aggravated assault, domestic violence. But the statute of limitations had run. And so here we are. Now with a complicated federal trial, the.

[Andrea Canning]

Keepers of Combs secrets were about to take the stand.

[Capricorn Clark]

I wanted to go in there and take the truth.

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[Capricorn Clark]

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[Andrea Canning]

The United States versus Sean Combs wasn't just a trial. It was an event, and also maybe a reckoning in the music industry. Starring one of hip hop's most powerful men. The trial was taking place in downtown New York, just blocks away from another highly watched court case. The retrial of Harvey Weinstein, whose sexual crimes sparked the MeToo movement. Here we go. We love we doing our thing. Combs was charged with transportation to engage in prostitution, sex trafficking and racketeering conspiracy, a charge usually associated with mob bosses and one that could mean life in prison. On the first day of trial, Combs defense wasted no time in acknowledging the obvious. The jurors were going to see evidence of domestic violence.

[Josh Mankiewicz]

But the defense told the jury, Mr. Combs is not on trial for domestic violence.

[Sheree Hayes]

He's on trial for racketeering and for trafficking.

[Andrea Canning]

There were no cameras in court, only a sketch artist to capture what Combs looked like after eight months in detention. Capricorn Clark saw it for herself when prosecutors called her to the stand.

[Capricorn Clark]

I couldn't even look at him. I had to look out of the corner of my eye. He was darker, he was more gaunt, his eyes recessed. His hair was gray.

[Andrea Canning]

As Capricorn faced the man she once admired, she testified about the time she also feared him. From her first day on the job to the day she says Combs took her to Kid Cudi's house at gunpoint. And she described the horrific beating she witnessed. Combs attacking Cassie in front of her.

[Capricorn Clark]

I wanted to go in there and say the truth.

[Andrea Canning]

According to prosecutors, Capricorn's trip to Kid Cudi's house amounted to a kidnapping, a crime that helped them prove racketeering conspiracy. NBC News legal analyst Danny Savalos.

[Advertiser]

The government's racketeering theory of this case is essentially that Combs used his enterprise.

[Andrea Canning]

Including his company and his employees, and to satisfy his own sexual needs. And in the course of doing so, he engaged in other crimes, like kidnapping. Prosecutors said the racketeering conspiracy included using staff to help arrange the freak offs. Former assistants testified about setting up hotel rooms, stocking them with baby oil and illegal drugs like ecstasy and ketamine. And prosecutors showed the jury credit card statements and other records highlighting how Combs paid for travel for multiple escorts over many years. Sheree Hay says it wasn't until the trial that he realized he was not the only man hired for sex sessions with Cassie.

[Sheree Hayes]

And I'm under the assumption that this is only happening with me, you know, so I really had this belief that, wow, this is almost an honor that this woman can engage like this with any man and she, she wants to and she's consistently calling me. So I had a complete misunderstanding of what was going on.

[Andrea Canning]

As he walked into court to testify, anxiety kicked in.

[Sheree Hayes]

By the time I hit the stand, my hands was trembling, I was struggling to talk.

[Andrea Canning]

It was the first time he'd ever seen Sean Combs outside of a fancy hotel room.

[Sheree Hayes]

I went out of my way to avoid any eye contact whatsoever during my testimony. Like, I literally shut everyone out except for the attorneys that were questioning me. And I was just doing this because I didn't, I didn't want to feel any pressure or any intimidation or anything that could take away my focus.

[Andrea Canning]

Hayes described the sexual encounters he had with Cassie while Combs watched. As he left the stand, he looked Combs in the eye for the first ever. Did he smile at you at all?

[Sheree Hayes]

No, it was no smile. It was just an eye contact. And I kind of nodded in acknowledgment to him and he nodded back.

[Andrea Canning]

The jury saw videos of some of the free cops. They were sealed from the press and public, but played on monitors in the jury box.

[Cassie Ventura]

Combs is charged with five counts.

[Andrea Canning]

NBC News correspondent Chloe Meloss was at court every day during the trial.

[Cassie Ventura]

You could see some of the jurors like, looking shocked and even sort of turning away from their monitors.

[Andrea Canning]

The star witness was Cassie herself, the woman who ignited the case. How important was it for the prosecution to have Cassie on the stand?

[Josh Mankiewicz]

So not only was she the star witness, she's the witness who makes or breaks the case.

[Andrea Canning]

When Cassie testified, she was eight months pregnant.

[Cassie Ventura]

As soon as Cassie walked into the courtroom, all eyes were on her and Combs, he locked eyes on her the entire time over four days.

[Andrea Canning]

On the stand, Cassie told the story of her 11 year relationship with Sean Combs. She described an abusive rollercoaster, a toxic mix of love, sex and violence.

[Cassie Ventura]

It wasn't all bad, all the time, but it's hard to juxtapose the good times with these incredibly graphic images of, of the abuse.

[Andrea Canning]

The jury saw pictures of injuries Cassie sustained over the years.

[Cassie Ventura]

Cassie cried multiple times on the stand, and when asked if she still loves Combs, present tense, she said, it's complicated.

[Andrea Canning]

And Cassie told the jury about that assault captured on security video. She said she was trying to leave a freak off as Combs chased her down. The government's theory of the hotel beating video is.

[Advertiser]

It is video evidence of sex trafficking.

[Andrea Canning]

In progress. In other words, Cassie was trying to.

[Advertiser]

Leave one of these freak offs.

[Andrea Canning]

And here's Combs physically dragging her back and beating her. That is the force, the coercion for the sex trafficking. And as evidence of yet another crime, the government called a security guard from the hotel where that happened. He testified about how Combs and his chief of staff paid him off to to keep the video under wraps.

[Cassie Ventura]

So Combs meets the security guard and what does he have with him? $100,000 in a brown paper bag, like something out of a movie.

[Andrea Canning]

The government said Cassie was not the only sex trafficking victim. Another girlfriend with a story similar to Cassie's testified under the pseudonym Jane.

[Josh Mankiewicz]

She said that she didn't enjoy the freak offs, but she did it because she wanted to please.

[Andrea Canning]

Diddy Jane told the jury that one time Combs was physically violent with her and threatened her with blackmail.

[Cassie Ventura]

Throughout the trial, we heard from the prosecutors that Combs was threatening to release videos from these freak offs as blackmail. So that was another reason why these women allegedly stayed in these relationships.

[Andrea Canning]

In total, the government put on 34 witnesses. A sprawling case that went on for nearly 30 days. Do you have a plan? The defense had a very different plan.

[Sheree Hayes]

Mark and morning.

[Andrea Canning]

And you'll hear about it next from someone on the inside. What do you think was the biggest mistake on the part of the prosecution?

[Josh Mankiewicz]

Well, bringing the case.

[Andrea Canning]

Free Combs. Free Combs. Free Combs. Free Diddy by his side in court. Sean Combs had no fewer than eight defense attorneys. His team was led by Mark Agnifolo and Tenney Garagos.

[Ben Brafman]

Morning, Tenny. Morning, guys.

[Andrea Canning]

Daughter of renowned attorney Mark Garagos, who was also in the courtroom. You weren't officially on the defense team.

[Josh Mankiewicz]

I was not.

[Andrea Canning]

Okay, so what was your role and how did you help?

[Josh Mankiewicz]

You know, I jokingly said, and it ended up getting reported that I was a helicopter parent. But in reality, I've known Shaun for going on 20 years. So I had more than a rooting interest and obviously wanted justice to be done.

[Andrea Canning]

Sean Combs defense team had a simple strategy. Combs would not testify in his own defense. In fact, they would call no witnesses. Instead, they were going to win by cross examination. Cassie's credibility was the defense's main target. They said there was plenty of evidence that she was a willing participant in the freak offs. Sexual assault or assault victims, domestic violence victims, you know, they process things in all different ways. What makes you think that Cassie wasn't forced into these freak offs?

[Josh Mankiewicz]

I think one of the brilliant things the defense did was painstakingly go through the real time texts. When you say, what makes me think she wasn't coerced into it. When she says, I'm down for a freak off or I'm down for an fo.

[Andrea Canning]

Garrigo says the text showed that Cassie's allegations were an attempt to rewrite history.

[Josh Mankiewicz]

Revisionist history might be good for therapeutic and cathartic purposes, but it's certainly not good for penal purposes.

[Andrea Canning]

The defense said, sure, Combs led an alternative swinger's lifestyle, but that was private and not a crime. On cross examination, Sheree Hayes told the jury the same thing he told us in his encounters with Cassi and Sean Combs. Cassie did not appear to be coerced.

[Sheree Hayes]

One thing that you have to do is kind of evaluate the comfort of the women you're entertaining. So I can honestly say, evaluating Cassie's interactions with me, I didn't get any cues.

[Andrea Canning]

Perhaps their biggest hurdle was the most public piece of evidence, that video of Combs assaulting Cassie in the hallway. Your thoughts on the prosecution's theory that the beating was a sex trafficking in progress?

[Josh Mankiewicz]

I never thought that it was. I did not ever think. If you just took a look closely at the video, that it had anything to do with sex trafficking.

[Andrea Canning]

There was a male escort in the hotel room, but the defense said Cassie was not trying to flee a free cough. They claimed this was a lovers quarrel that spun out of control because Cassie took Combs cell phone and he lost.

[Josh Mankiewicz]

It when he tried to get his phone back. Next to road rage, it may be the most common cause of people going crazy. Crazy is when you grab somebody's phone, especially in a toxic relationship.

[Andrea Canning]

Yeah, but to see that video was just so unsettling. I mean, you're looking at a victim in that video.

[Josh Mankiewicz]

Well, I will tell you, but for that video being leaked, I don't think he ever would have been charged.

[Andrea Canning]

Do you see Cassie as a victim?

[Josh Mankiewicz]

Do I? I don't know that my opinion matters.

[Andrea Canning]

I mean, I guess people, when they see the video, that's how they see her.

[Josh Mankiewicz]

To quote my daughter Tenny, if the video was what he was charged with, then there wouldn't have been a trial.

[Andrea Canning]

In other words, that was an assault from years ago, not a federal crime. When it came to questioning Jane, the other alleged victim, the defense used the same playbook. Undermine her clothes credibility.

[Cassie Ventura]

I think the nail in the coffin for Jane really was this bombshell moment when Combs's legal team revealed that he was currently paying her legal fees and her rent and they really tried to paint Jane as an opportunist who was out for money.

[Andrea Canning]

The defense said the government's suggestion that Capricorn Clark was ever kidnapped was absurd. And there was no evidence Combs had a gun when he knocked on her door. And they pointed out she'd gone back to work with Sean Combs a few years later, apparently not scared enough to stay away. She told us that was because she needed a job.

[Capricorn Clark]

I need to work. I have to take care of my son.

[Andrea Canning]

As for the evidence of racketeering, the defense said there wasn't any. What do you think was the biggest mistake on the part of the prosecution?

[Josh Mankiewicz]

Well, you're bringing the case the amount of resources to expend that kind of effort.

[Andrea Canning]

The jury began deliberating on a Monday morning and by Wednesday.

[Capricorn Clark]

Good day.

[Andrea Canning]

We are coming on the air with breaking news. In New York, a throng of media, citizen journalists, fans and critics gathered outside the courthouse as word of Sean Combs fate trickled out.

[Ben Brafman]

In the matter of US V. Combs, count one, not guilty.

[Andrea Canning]

Not guilty of the charge that could have sent him to prison for life. Racketeering, conspiracy. Also not guilty of sex trafficking. But he was found guilty of the less serious charges transporting sex workers across state lines. The man act, which struck Capricorn Clark as a bizarre coincidence.

[Capricorn Clark]

I'm like, wait a minute, Jack Johnson went down for the man act.

[Andrea Canning]

Combs fell to his knees and prayer after the verdict was read. It was not a clean sweep, but it was a victory.

[Cassie Ventura]

You could hear cheers outside of the courthouse. But then there was a lot of sadness for people that have supported Cassie and felt like perhaps this was a reckoning for the music industry. So you could feel both sides.

[Legal Analyst]

The fact that he was not convicted of the top charges does not mean that she was lying. The question was whether her allegations line up with these very complicated high level federal claims.

[Andrea Canning]

What was your reaction to the verdict?

[Capricorn Clark]

My reaction was, I mean, I told you so. I hate to say it like that. It's exactly what I thought would happen. There were some parts of Cassie's story that I knew weren't solid.

[Andrea Canning]

At the close of another high profile case about abuse and a famous man, the limits of the criminal justice system to deal with sex, money and power and all its complexities may be in question. Combs is still facing more than 50 civil suits. This verdict doesn't change that.

[Legal Analyst]

The criminal trial is based on one set of facts, on one set of criminal laws, and the civil suits are based on different facts and different civil laws.

[Andrea Canning]

Sean Combs still denies the allegations. His representatives call the law lawsuits all fabricated attempts to extort windfall payments from an innocent man. He is scheduled to be sentenced on October 3rd. The prosecution has asked that he serve four to six years. Sean Combs won at music. He won at business. But now you think that Sean Combs has a future from here?

[Josh Mankiewicz]

Oh, there's no doubt Sean Combs has a future. And there's another chapter that he's already writing, and I think people are going to be surprised.

[Andrea Canning]

Maybe. But can he win back a legacy on that question? The jury is still out.

[Josh Mankiewicz]

That's all for this edition of DATELINE. We'll see you again next Friday at 9, 8 Central. I'm Lester Holt. For all of us at NBC News, good night.

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[Andrea Canning]

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[Advertiser]

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