Dateline NBC - Sean Combs: The Insiders Speak

Episode Date: July 15, 2025

Andrea Canning speaks to insiders and reports on the verdict in the Sean Combs trial.

And he started beating her up in front of me. Exactly what you saw on that video was exactly what I saw in person. Did you say anything to Cassie? Like, you need to leave him now. I absolutely did. If this is what Mr. Combs does in a public space, you can only imagine what he did behind closed doors.

You had a starring role in these freak-offs. Yeah. I'm in these freak-offs. Yeah. I'm in these extremely intimate sexual situations with him and his girlfriend. Every time there was a problem, he would call me. I begged him to settle the Cassie case before it was filed. He was famous, then infamous,

and I think that he'll be famous again. Here's Andrea Canning with Sean Combs, the Insiders Speak. When the verdict came down last week. In the matter of U.S. versus Combs, count one, not guilty. Transportation for prostitution, guilty. Sean Combs learned that he would not be spending the rest of his life in prison. In the courtroom, he got down on his knees and prayed. 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. I'm begging him, please stop. Stop hitting her. Stop, stop. A man who worked for Combs, too, hired for sexual encounters with his girlfriend. 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. And a former Combs lawyer who says if his advice was taken, the whole trial might have never happened. If it would have been settled quietly,

I don't think he gets indicted. It's been almost a decade after the Me Too movement began. What does this case say about money, sex, power, and the law? Sean Combs was one of the most powerful and wealthy people in the music industry. Of course, people were afraid. Sean Combs takes work hard, play hard to a whole new level.

Absolutely. Absolutely. For over 10 years, few people had more access to Shawn 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. 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. 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.

I said, I'm not going to be afraid. 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, Shug Night. Around 9 p.m., he took her for a walk in Central Park to talk. 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. I was like, whoa. Do something to you as in? Well, the words he said is, he's like, I'll have to kill you. Is this a joking? No, it wasn't joking. I have to kill you?

This is a serious I'll have to kill you. It was absolutely serious. 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.

Everything was a spark and an explosion. And to see him rally from millionaire to billionaire, it was amazing to watch, to be honest. Sean Combs lived and worked on a fantastic scale. A week in south of France, a week in Ibiza, and a week in Sardinia to recover from the weekend Ibiza. He was usually with a gorgeous woman on his arm, be it J.Lo or model Kim Porter.

When Combs and his staff weren't working or island hopping, they were throwing those famous white parties. 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. 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. He watched it every day on repeat. The themes of unforgivable blackness were very important to Puff. 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 Want to Work for Diddy, where contestants vied to be his personal assistant. Most importantly is Capricorn. I know out of anybody, she really knows what it takes to 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. Me and you, it's just me and you. Capricorn decided to use Cassie in an ad campaign for Sean John clothing. Her boss was impressed. 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. Did it seem like Cassie could be the one for him? Ah, 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. What was the relationship like between Cassie and Sean? 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 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.

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. Go on, Cassie, Don't let him get you! You're trying to stop this from escalating. I'm trying to de-escalate the whole time. I'm trying to get myself out of his possession.

This is all going to end very badly. Capricorn Clark had a front row seat to the relationship most of America has heard about this summer. Sean Combs and Cassie Ventura. It was mania and it was just toxic. Capricorn says infidelity was a constant issue she and Cassie talked about. 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. 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. 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. 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 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. You don't even know if Kid Cudi's home, I would assume? I don't know, I'm praying still that he's not.

Capricorn secretly called Cassie to warn her about what was going on. And I was like, he came, he got me with a gun. We're here at Cuddy's to kill him. You're trying to stop this from escalating. 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. Combs never found Kid Cudi that day, out of his possession. I don't like any of this. This is all gonna end very badly. Combs never found Kid Cudi that day, but now he wanted to find Cassie. He goes, call Cassie, tell Cassie, I'm not letting you go until you go get her. And she goes, come get me Cap. Capricorn says she did as she was told.

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. What do you do? 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 f*** you up too. 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?

Well, she 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. 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. And I'm thinking like, something's got to give here, and it never gave. 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? I absolutely did.

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 Redd, says she saw Combs as a controlling boyfriend who wouldn't take no for an answer. The air got sucked out the room. Like, it just was, like, instantly uncomfortable. 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. We had her back into the corner, and he was, like, cussing her out with his hand in her face, and the security was like, formed like a half circle around them. And she's leaving karaoke's over. Then later that night, Tiffany says the argument

continued at Cassie's house. Middle of the night, 3, 4 in the morning, I hear the door swing open, and I hear a puff screaming. She says Combs was apparently angry over sex. 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. And Tiffany recalls Cassie seemed out of it. 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 at his eyes and I said to him, what did y'all do? Tiffany says for a long time the two women didn't speak about that night. I talked to her but we didn't talk about that.

We never talked about what was happening. 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. So, if you're in trouble, you're the guy to call. Right. That's been that way for a long time. Especially for high profile people. That's true. 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 shooting 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 are you going to plead today, Puffy?

You're not guilty. Raffman defended Combs in court. In my opening statement, I started 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. Music mogul Sean Puffy 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 talk to you all today.

He also thanked Brafman with an expensive watch, cementing a legal partnership that would last nearly two and a half decades. Every time there was a problem, he would call me in. I would find a way to straighten it out. Little fires. Little fires. Until we got to the big fire. Yeah.

The big fire began in 2023 with a phone call from a lawyer in LA. We were told that, you know, Cassie was going to write a book. And if we didn't give him, I don't know, $100 million, I explained to Puffy that I didn't think the lawyer was serious. And he said, she's not going to write a book. She's got kids, she's got parents, she's married. Cassie did not publish a book, but six months later... You got another call from... I didn't get a call. I got a copy of a complaint that...

And I knew the lawyer in this case was a... A different lawyer. And he was very serious. He sent Brafman a draft of a complaint that, and I knew the lawyer in this case was a— —A different lawyer. —And he was very serious. —He sent Brafman a draft of a lawsuit. —I'm told by the lawyer that this is going to be filed publicly. I read it. It's, you know, terrible. —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 freak-offs. Cassie's lawyers called it sex trafficking. You know, his immediate reaction is, this is bullsh-t. This didn't happen. This is my girlfriend. This is private. And I don't think she's going to file the complaint.

What's your advice after you read the lawsuit to him? 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. What does he say to you when you tell him you need to settle? 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. The lawyers went back and forth, but Brafman says Combs was in no hurry, still not believing Cassie would follow through. Whether it was money, whether it was just conceding that the, you know, the allegations were real, I think was a combination of things.

On November 16th, 2023, Cassie decided to go public. She filed the lawsuit in court. Tonight, music mogul Sean Diddy Combs, accused of sex trafficking and sexual assault. Cassie says that she's finally ready to tell her story after living in what she calls years of silence and darkness. I know she's not lying. There's incidents in the lawsuit that I was present for. 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. She went to a rehab facility for trauma. And so, so like when we started to finally talk about it and had the language to say, this is what happened to you. Now everyone knew Cassie's story. It was big news, just as Brafman predicted. 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. The price tag? $20 million. A settlement does not mean that the charges in the complaint were all true. And I was hoping it would go away. Brafman stopped working for Combs soon after that. Combs' current attorney, Mark Agnifilo, 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. Exactly what you saw on that video

was exactly what I saw in person. 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. I think other people saw what Cassie did and said, okay, I'm gonna tell my story now. Lisa Bloom, an attorney known for taking on powerful figures in sexual misconduct cases, represents two clients suing Combs. 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. Bloom's clients are an anonymous man based in Las Vegas who alleges Combs drugged and raped him, and singer Don Rashard, who worked with Combs on his show, Making the Band.

Rashard accuses Combs of sexual harassment, sexual assault, and a hostile work environment. What's y'all been doing these last couple of months? You're walking around signing m****** autographs, thinking this s**t is a joke? 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. Combs denies all the allegations, saying Rashard 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. If Puff's back was ever up against the wall, it's now. It was May of 2024 when Sheree Hayes got a visit from two investigators at his New Jersey apartment. — It was kind of like, hey, we're interviewing hundreds of people,

we're just doing our due diligence. — The surprise visit was part of a federal investigation into the private life of Shawn 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? Yes. Kind of like Chippendales? Exactly like Chippendales. 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 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. What does Janet look like? Janet is, from my perception, extremely gorgeous. Unknown to Hayes at the time, Janet was Cassie Ventura. Then it's 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. What are you thinking? It's definitely odd, but right after the explanation, she handed me a stack of money.

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. She starts in her robe, but eventually her robe comes off, my towel comes off. Before long, Hayes says, Janet's mystery husband entered the room. 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.

A mask that hit 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? So what I would call them is more like subtle suggestions. And they were all pretty much based on visual preferences. 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. I got put into a room that just hang out and kill time. So I flip on the TV to watch and it said right on the screen, Essex House would like to welcome Mr. Sean Combs. And it was like, Oh my gosh. It was a really 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 looking at his Instagram posts and I don't even put it together. Hayes says he never saw violence and Cassie never seemed intoxicated, though he could see she was making sure

they did what Combs wanted. Moved this, moved that, moved 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. Did they ever use the term freak-off with you?

That you would be a part of these freak-offs? No. So there was very little conversation. 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 a thousand bottles of baby oil. Investigators contacted Capricorn Clark, too.

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 Shawn. She told them her whole story, the good times working for Combs, 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? My advice to the investigator was to keep an open scope.

Capricorn says despite the physical abuse she witnessed, she didn't believe everything in Cassie's lawsuit 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. It's to try to leave a relationship when you're being abused. 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. After nearly a year of investigation, federal authorities moved. On September 16th, 2024, Sean Combs was taken into custody as he walked into the lobby of the Park Hyatt Hotel

in Midtown Manhattan. The US Attorney for the Southern District of New York announced the charges. Racketeering, conspiracy, sex trafficking, interstate transportation for prostitution. The indictment alleges Combs abused, threatened, and coerced victims to fulfill his sexual desires, protect his reputation, and conceal his conduct. 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. 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. Former federal prosecutor and MSNBC legal analyst Paul Butler believes the lawsuit and hotel video

played a major role in the charges against Combs. When you see that with your own eyes, I think there's a legitimate sense of outrage that 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 keepers of Combs' secrets were about to take the stand.

I wanted to go in there and say the truth. 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 Me Too movement. ["Me Too"]

Here we go, we live, we doin' 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's defense wasted no time in acknowledging the obvious. The jurors were going to see evidence of domestic violence.

But… The defense told the jury, Mr. Combs is not on trial for domestic violence. He's on trial for racketeering and for trafficking. 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. 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. 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.

I wanted to go in there and say the truth. 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. The government's racketeering theory of this case is essentially that Combs used his enterprise, including his company and his employees, 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 Hayes says it wasn't until the trial that he realized he was not the only man

hired for sex sessions with Cassie. And I'm under the assumption that this is only happening with me, you know? So I really had this belief that, wow, it's almost an honor that this woman can engage like this with any man that she wants to, and she's consistently calling me. So I had a complete misunderstanding of what was going on. As he walked into court to testify, anxiety kicked in.

By the time I hit the stand, my hands was trembling. I was struggling to talk. It was the first time he'd ever seen Sean Combs outside of a fancy hotel room. 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 want to feel any pressure or any intimidation or anything that could take away my focus. 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 time ever. Did he smile at you at all? No, it was no smile. It was just an eye contact. And I kind of nodded in acknowledgement to him, and he nodded back. The jury saw videos of some of the freak-offs. They were sealed from the press and public, but played on monitors in the jury box. Holmes is charged with five counts.

NBC News correspondent Chloe Maloss was at court every day during the trial. You could see some of the jurors looking shocked and even sort of turning away from their monitors. 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? So not only was she the star witness, she's the witness who makes or breaks the case. When Cassie testified she was eight months pregnant. 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 on the stand, Cassie told the story of her 11-year relationship with Shawn Combs. She described an abusive rollercoaster, a toxic mix of love, sex, and violence. It wasn't all bad all the time, but it's hard to juxtapose the good times

with these incredibly graphic images of the abuse. The jury saw pictures of injuries Cassie sustained over the years. Cassie cried multiple times on the stand, and when asked if she still loves Combs, present tense, she said it's complicated. 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 it is video evidence of sex trafficking in progress. In other words, Cassie was trying to leave one of these freak-offs 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 keep the video under wraps. 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. 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. She said that she didn't enjoy the freak-offs,

but she did it because she wanted to please Diddy. Jane told the jury that one time Combs was physically violent with her and threatened her with blackmail. 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.

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. Mark and Woody. 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? Well, bringing the case.

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 Agnifilo and Tenny Garagos, daughter of renowned attorney Mark Garagos, who was also in the courtroom. You weren't officially on the defense team? I was not. Okay.

So what was your role and how did you help? You know, I jokingly said, and it ended up getting reported that I was a helicopter parent. But in reality, I've known Sean for going on 20 years. So I had more than a rooting interest and obviously wanted justice to be done. 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? I think one of the brilliant things the defense did was painstakingly go through the real-time text. 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. Garrago says the text showed that Cassie's allegations

were an attempt to rewrite history. Revisionist history might be good for therapeutic and cathartic purposes, but it's certainly not good for penal purposes. The defense said, sure, Combs led an alternative swingers 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 Cassie and Sean Combs, Cassie did not appear to be coerced.

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. 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? 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. There was a male escort in the hotel room, but the defense said Cassie was not trying to flee a freak off. They claimed this was a lover's quarrel that spun out of control because Cassie took Combs' cell phone. And he lost it when he tried to get his phone back. Next to road rage, it may be the most common cause of people going crazy is when you grab somebody's phone, especially in a toxic relationship. Yeah, but to see that video was just so unsettling. I mean, you're looking at a victim in that video. Well, I will tell you,

but for that video being leaked, I don't think he ever would have been charged. Do you see Cassie as a victim? Do I? I don't know that my opinion matters. I mean, I guess people, when they see the video, that's how they see her. To quote my daughter, Tenny,

if the video was what he was charged with, then there wouldn't have been a trial. 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 credibility. I think the nail in the coffin for Jane

really was this bombshell moment when Combs' 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. — 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. I need to work. I have to take care of my son. 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? Well, bringing the case, the amount of resources to expend that kind of effort. The jury began deliberating on a Monday morning. And by Wednesday, Good day, 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. In the matter of U.S. vs. Combs, count one, not guilty. 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 Mann Act, which struck Capricorn Clark as a bizarre coincidence. I'm like, wait a minute, Jack Johnson went down for the Mann Act. Combs fell to his knees in prayer after the verdict was read.

It was not a clean sweep, but it was a victory. 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. 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.

What was your reaction to the verdict? 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. 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. The criminal trial is based on one set of facts and one set of criminal laws, and the civil suits are based on different facts and different civil laws.

Sean Combs still denies the allegations. His representatives call the 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? 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. Maybe, but can he win back a legacy? On that question, the jury is still out. 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.