20/20 - Bad Rap: USA v. Sean Combs

Episode Date: April 30, 2025

Today, we're bringing you episode six of the latest podcast from 20/20 and ABC Audio, "Bad Rap: The Case Against Diddy." Sean Combs now awaits trial in Brooklyn's infamous Metropolitan Detention Center. In May, his highly publicized case is scheduled to go to trial. What do we know about the charges Diddy faces, the case prosecutors plan to present, and how his legal team might try to get him acquitted? Host and attorney Brian Buckmire breaks down the legal issues of Diddy's upcoming trial with Aaron Katersky, Sean Combs now awaits trial in Brooklyn's infamous Metropolitan Detention Center. In May, his highly publicized case is scheduled to go to trial. What do we know about the charges Diddy faces, the case prosecutors plan to present, and how his legal team might try to get him acquitted? Host and attorney Brian Buckmire breaks down the legal issues of Diddy's upcoming trial with Aaron Katersky, Chief Investigative Correspondent for ABC News. Remember, you can catch new episodes of "Bad Rap: The Case Against Diddy" early by following the show on ⁠Apple Podcasts⁠, ⁠Spotify⁠, ⁠Amazon Music⁠, or wherever you listen to podcasts. Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's Deborah Roberts here to bring you another weekly episode of Bad Rap, the case against Diddy. Remember, you can catch new episodes a day early if you follow Bad Rap, the case against Diddy on Apple podcasts, Spotify, Amazon Music, or wherever you listen to podcasts. And now, here's our next episode. From early morning workouts that need a boost to late night drives that need vibes, a good playlist can help you make the most out of your everyday. And when it comes to everyday spending, you can count on the PC Insider's World Elite

MasterCard to help you earn the most PC optimum points everywhere you shop. With the best playlists, you never miss a good song. With this card, you never miss out on getting the most points on everyday purchases. The PC Insider's World Elite MasterCard. The card for living unlimited. Conditions apply to all benefits. Visit pcfinancial.ca for details. The first time I saw Sean Combs enter court after he was charged, I remember doing a little bit of a double take. Sean Combs sitting right there. I mean, he looked right at me.

That's ABC News chief investigative correspondent Aaron Kutursky. Aaron's been covering the courts in New York and other places for more than 25 years. He's reported on the trials of lots of high profile people, including defendants like Diddy, who were charged with sex crimes, people like Harvey Weinstein and Ghislaine Maxwell. We have some access in some of the hearings of sitting in the jury box. So you're really just a railing away from the defendant in some cases. And right after his arrest, I didn't think he looked great. Aaron says Diddy looked stunned,

like he was a little surprised at where he found himself. Cameras aren't typically allowed inside federal courtrooms, so the only way to see what's gone on at Diddy's hearings has been to go in person. Aaron's gone to nearly every hearing in Diddy's federal criminal case so far. I was there in the courtroom today. David Eshaun Combs entered in a black t-shirt, gray sweatpants and sneakers.

Several of his children and his sister were there watching as he pleaded not guilty. And then they saw him led out by the marshals. And I remember a different hearing. He walked in, he looked like he had lost weight. He looked like he was in a jovial mood, smiling at people in the courtroom. He clearly enjoys when his family comes to court. It is noticeable. For a while, his attorneys were pointing out

who was who in the courtroom, so the judge had a sense of who was in the room, and the judge actually welcomed his family to court, which I had never really heard before. How he's going to be when he's on trial, there's no telling because what's coming is going to be fairly graphic and potentially damning. And Aaron says there's something else that struck him in these early hearings. There is one other optic and that's who's at the other table. The prosecutor's table is all women who are

bringing a case against an accused sexual abuser. And I think that's another powerful image that the jury may well notice too. The allegations in the criminal case against Sean Diddy Combs span two decades of the mogul's life and career. The indictment lists all of the names he's gone by. It's called USA v. Sean Combs, aka Puff Daddy, aka P. Diddy, aka Diddy, aka P.D., aka Love. The Case is Sprawling aka love. The case is sprawling, both in how much time it covers and the criminal behavior it accuses Combs of. It alleges that through all of those name changes and career moves, Diddy created and

ran a criminal enterprise, whose members and associates engaged in and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice. These charges are serious, and if convicted, Diddy could wind up in prison for the rest of his life. Combs has pled not guilty to all charges. His attorney called the federal case against him an unjust prosecution and said Combs is an imperfect person, but not a criminal. Over the course of this series, we've traced Diddy's rise to fame, power, and wealth, and the allegations that have cast a shadow over that rise.

and the allegations that have cast a shadow over that rise. Diddy's trial is set to start soon, so we're switching gears. This episode is gonna sound a little different. Aaron and I are gonna sit down for a talk and nerd out on the legal issues we think you need to know about before the trial begins. It'll be a conversation between a defense attorney and a long-time legal reporter. We'll cover the charges against defense attorney and a longtime legal reporter.

We'll cover the charges against Diddy and what they really mean. We'll highlight some of the evidence the government says they have and dig into possible strategies for his defense. I'm Brian Buckmeyer. From ABC Audio, this is Bad Rap, the case against Diddy. Episode 6, USA v. Sean Combs. In this series, we've talked about the many civil lawsuits against Diddy. Roughly 60 active cases in total now.

The first one that really set this story in motion was the one brought by Diddy's ex-girlfriend, Cassie Ventura. You'll remember that suit quickly settled with no admission of guilt. The other civil lawsuits are moving at their own pace. But this trial is for the criminal case brought by federal prosecutors from the Southern District of New York. – Criminal cases could put him in jail. Civil cases could cost him money. But there's one that may be more important than any other, and that's the civil case since settled, brought by Cassie Ventura, his former girlfriend,

because that's the one that caught the eye of federal prosecutors. So how do you think that maybe Cassie's and other lawsuits may affect the federal criminal investigation and even the case? Federal prosecutors do what you and I do, right? They read stuff. They read the papers, they watch TV,

and if they look at something and they say, man, what's alleged here? This could be criminal. So the prosecutors are reading these things and it does give them at least at the outset a place to start. And that's when they start to figure out with, in this case, federal agents from Homeland security investigations, where they need to search, what they need to look for,

and where it all might be. I'm curious for this answer especially, because you and I know so much about this case and I don't think it's an easy one to distill into a sentence. But imagine someone is living under a rock and they're kind of just running by and they're like, Aaron, what's this case about?

Like, just give me a sentence. If you were to boil it down to a sentence, a couple of words, what is this whole case against Diddy about? Freak offs? Yeah. I only laugh because we have circled that idea so many times talking about this case.

And yet it does do an injustice because the freak offs, which the defense and prosecutors characterize certainly in different ways are either these orgies that women are forced to participate in or it's a prudish government snooping into somebody's private bedroom activities. I like the larger umbrella and how you kind of pose it, at least from the defense standpoint of Sean Combs

just really liked some freaky stuff. And maybe they do a couple of pills before they have sex. Maybe they drink too much alcohol before sex. And everyone was okay with that kind of lifestyle. And I think you said it well, that the government is just like a prudish prosecution. Yep. And the case in some ways turns on how our sensibilities

about sexual assault have evolved, right? Because we now have a more discerning sense of what it means to consent or not, or to be put in situations where consent is possible or not. And I think we as a society may look differently upon that type of argument than we would have 20 years ago. According to prosecutors, there was no consent. These women had no choice. They were drugged. They were held against their will. There's a kidnapping that's part of this. There's an awful lot of deviant behavior that's described in the indictment.

behavior that's described in the indictment. The freak-offs come up so often when we talk about this case because they bring together the three main charges Diddy is facing. Racketeering conspiracy, two counts of sex trafficking, and two counts of transportation to engage in prostitution. Prosecutors say these alleged crimes involve at least seven victims. Transportation to Engage in Prostitution is pretty self-explanatory, but the other two charges are worth spending some time on. Racketeering Conspiracy. We've talked about it in previous episodes.

It's where two or more people agree to take part in a pattern of criminal behavior. It's sometimes called a RICO charge. And RICO is just an acronym for the name of the federal law originally intended to combat organized crime. Rudy Giuliani famously used it to target the mafia in New York City as a U.S. attorney in the 80s. And just the idea that he's charged with racketeering conspiracy means federal prosecutors are treating him like a mob family. He is an entity, a criminal entity in the eyes of prosecutors unto himself. And the whole purpose of this criminal enterprise that they allege Sean Combs to be is to gather up women and use them, coerce them for combs' own sexual pleasure.

Then there's the sex trafficking charge. It's a term you've probably heard before, but I think it's often misunderstood. So here's an attorney's definition. Sex trafficking is making a person engage in sex acts they don't consent to through force, fraud, or coercion. And it doesn't necessarily have to involve the exchange of money. What kicks this up to a federal charge and not just a state charge is when the victims are made to cross state lines. So you can see how the freak-offs encapsulate all three of these charges.

According to prosecutors, Diddy allegedly ran a criminal network that helped orchestrate sex parties, including transporting sex workers and other alleged victims from one state to another and forcing them to participate. Like we mentioned earlier, prosecutors have also accused Diddy of other

crimes—bribery, forced labor, obstruction of justice, kidnapping, and arson. The kidnapping and arson stood out to me. Prosecutors don't name the victim of the arson. They call this person Individual One. However, the timing and facts described by the government sound a lot like the explosion of rapper Kid Cudi's car. Remember, Cassie describes that incident in her lawsuit. She alleged Diddy was involved in the explosion after he found out Cassie and Kid Cudi briefly dated. Kid Cudi told the New York Times that his car did in fact blow up.

This arson charge by prosecutors allegedly shows the lengths that Combs would go to maintain control over his victims. And it's a pretty powerful example, not only of the control that Diddy could allegedly exert, but also the power that he had to give orders. Local authorities never charged Combs for anything related to Kid Cudi's car explosion, and his lawyer maintains Combs had no involvement in the incident. After the break, we look at the prosecution's case against Diddy, including possible evidence and who their star witness might be. The all-new all-electric Can-Am Origin motorcycle takes you everywhere.

Sleek power for the streets and deep adventure routes for the trails. Discover your origin today. Learn more at CanAmMotorcycles.com. crime expert to my resume, and here's how I'm going to make it happen. Every week, I'm going to unpack the biggest true crime story that everyone is talking about. ABC's got some unique access here, so I'll talk to the reporters and producers who have followed these cases for months, sometimes years. We're bringing the latest developments and the larger context on the true crime stories you've been hearing about. Follow the crime scene for special access to the people who know these stories best. America's favorite number one morning show. The morning's first breaking news, exclusive interviews, what everyone will be talking about that day. Put some good in your morning

and start your day with GMA. Good morning America. Put the good in your morning. GMA 7A on ABC. A couple weeks ago, I was glued to my computer, constantly refreshing the court's filing system for updates on Diddy's case. April 15th was supposed to be the day prosecutors would file a list of witnesses they may call to testify.

But that didn't happen. At least not in a way that was accessible to the public. But here's what we do know. According to recent court filings, prosecutors are planning to call multiple alleged victims. The government refers to them as victim 1, 2, 3, and so on, keeping their identities anonymous. You have to believe Cassie Ventura is the star witness, right?

Because there she is on video video being punched and kicked and dragged in the hallway of a hotel in Los Angeles by Sean Combs. And that to prosecutors is almost where the case starts and ends. But the defense is saying that that video does not depict what we think it does. It depicts the end of an otherwise loving relationship. And they're saying that Cassie Ventura, despite what you see in the video, was actually enjoying herself in the company of Sean Combs and male prostitutes and these sex performances called freak-offs. And that's going to be at least part of their argument.

Cassie alleged in her lawsuit that this incident, seen on hotel surveillance video and released by CNN, happened right after a freak-off. Diddy's team has asked the judge to exclude the video from trial, arguing CNN edited the footage and that it's inaccurate. CNN denies the allegation. The judge has agreed with the prosecution, and the video will be played at trial. This case isn't just based on the evidence or the testimony of prospective witnesses. I mean, they raided two of his homes. And so what kind of stuff can we expect that might come from those homes that I think that the defense is feverishly trying to have suppressed?

Well, it seems as if you're to take some of the allegations and civil complaints at their word that Combs recorded a lot of things that went on at his private parties. And it's possible that prosecutors may have some access to videotapes or audio tapes that could be potentially damning evidence. Undoubtedly they would try to use phone records to make sure that Combs was in the place they

say he was in at the time they say whatever occurred occurred. There'll be some of that, but they have all of that. Electronic devices, iCloud accounts, so whatever photos, videos and documents exist, the government has them. Speaking of the prosecutors in the case, and you're sitting there in court, because we can read the documents. We can read the articles. How powerful is their presentation of the evidence? And do you feel like they have what they need?

Not only to further this prosecution, but potentially to get a conviction. They certainly feel they have what they need, not only to further this prosecution, but potentially to get a conviction? They certainly feel they have what they need. And you well know an office like the Southern District of New York does not bring a case that they don't think they can win. They only shoot for the moon if they can get the moon. And they think the video evidence and some of the other evidence that they've amassed from the home through the searches of his electronic devices through eyewitness interviews

is going to be enough to convict. Their presentation, the defense is always more theatrical. I mean, look at you in this suit and I mean, look at you, maroon with the skinny tie. I mean, you look good. My tailor and I would call it ox blood, but let's not split hairs. No federal prosecutor would be caught in this. They'd look with what I'm wearing. Yes. The dull blue and the- I get a few looks when I'm in the SDNY in this suit. I mean, you look good. And federal prosecutors are much more buttoned up, not only in appearance, but in presentation.

And so they may say the most damning thing in the most mundane way. And that's how they get these defendants. When you've got a client in the SDNY, it's almost not so much as how do I beat this case? It's how do I shave off a couple of years? Can my client proffer? Is there someone else involved? Is there a bigger fish in this case? And so is there a bigger fish? What did he like? I don't know that there is, Brian. I think, look, first the defense has said a plea deal is off the table. He intends to fight this. He intends to win. He denies ever sexually assaulting anyone, man, woman, child, adult, anybody his representatives have said. And he believes that the prosecution is in large part underpinned by race and that he got a raw deal when the magistrate approved the search warrants of his house and his electronics and the like, and that he can beat this. So a plea deal seems to be off the table from the defense point of view,

but there are loads of allegations of who may have known what, when and where. Once you have Sean Combs, who else is there really? That was the case with Jeffrey Epstein. They only went after Ghislain, after Epstein died by suicide and in jail. So I understand why you preface it as, are there other people who are involved? And I've seen this on social media a lot and I hesitate to always respond when I see it by writing a comment. But some of the criticism is, how do you have a RICO with only one defendant? Because by definition to conspire, you have to have two or more. I can't conspire by myself, I can conspire with you,

but I can't conspire by myself. So you have a RICO where only Diddy is named as a defendant, but even the allegations, there has to be a quote unquote criminal enterprise and this can't operate on its own. So are we gonna have a RICO case with only one defendant? Prosecutors were clear in their paperwork that there was this network of individuals that supplied the baby oil and the drugs,

and got all the hotel rooms ready for the freak offs, and arranged travel for the male prostitutes, which the defense says are legal escorts. Now is stacking up boxes of baby oil in a hotel room a charge worthy crime? I don't know. Whether their actions are criminal in and of themselves is an open question. And who's to say who's not talking to the feds behind closed doors? Eventually, we'll see who takes the witness stand,

but we may never know all the names of the people from Diddy's inner circle who cooperated with prosecutors. After the break, should we expect Diddy to testify? And what should his defense be? She has dwarfism. Starring Ellen Pompeo and Mark Duplass. Something is off. She's just a little girl. You think she's a faggot? She has adult teeth? There are signs of puberty? Inspired by the shocking stories that tore a family apart.

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And it's about to be ridiculous, unbelievable, unfair, damn right nasty. Straight up, can't miss, don't blink, grab your popcorn and strap in cinema. This isn't about who's next. This is about who's now. This is about who's now. This time, it's different. The NBA Playoffs presented by Google. Continue on ESPN ABC. A couple weeks ago, Diddy added a new lawyer to his team, according to court filings, Brian Steele.

He's a high-profile Georgia attorney who recently got a lot of attention for representing rapper Young Thug in a racketeering case that lasted almost a year. The artist ultimately pled guilty to some charges and no contest to others. A big win for him, he was released on probation and sentenced to time served. Brian Steele brings the number of attorneys on Diddy's team up to four. Two men, two women. So back to my conversation with Aaron. Let's fast forward.

The government puts on their case defense. I'm anticipating they put on some kind of a case. At some point in time, the judge is going to look to Sean Combs and say, do you want to testify? What's your feeling about his answer on that one? I mean, everyone always asks me and I know it's reading tea leaves, but defense attorneys always tell his client, no, right? Do not testify.

I don't see Sean Combs taking the witness stand to you. So if I was a betting person, I would say no, but as much as we joke that sometimes the defense attorney says don't testify, legally speaking, it is the client's right whether or not they testify. I can only advise someone whether or not it's a smart idea. Sometimes people with large egos make large mistakes.

I also don't think that this is a case where it would make sense for him to testify because it's gonna be a situation of who do you believe more, Sean Combs or these alleged victims? And I don't think you want that to be the argument you have. You want this to be an argument of

the prosecutor didn't meet their burden. They don't have credible witnesses. They haven't proven this case beyond a reasonable doubt. And I think you achieved that a lot easier and a lot smoother without the cross-examination of your own client. And I'll say this, I'm 0 for 12 with clients testifying. Well, the cross-examination would be brutal

because it's in the first question. So when you were hitting Cassie after dragging her through the hallway, were you really mad about something else? And that is you, right? Smacking her, let's play that again jurors. Let's see that a else? And that is you, right? Smacking her. Let's play that again, Jurors. Let's see that a third time. That is you, right? Let's just make sure. This is a case that I would be worried about, but what abouts. What about this time?

What about when you said this? What about, what about, what about? And I think as much as Sean Combs has been in the public eye and as much as we've seen things that were reevaluating 20 years later, like the Conan O'Brien interview when he talks about locking the doors, those things have a very different context now than they did back then. So it would be interesting to see. Like I've said before, I'm not involved in Diddy's case, but as a defense attorney, I've spent some time puzzling over the legal arguments Diddy's defense team could make,

and here's what I've got. The trafficking charges Diddy faces are federal because they involve movement across state lines. So, if you could argue against the things that make them federal crimes while admitting to the elements that would make them state crimes, then they would have no business in federal court and they would get thrown out. Admitting to state crimes would be a problem, except those crimes have a statute of limitations. And for Diddy, the statute of limitations on some of the major allegations against him have expired, including the incident

where he attacked Cassie in a hotel. I want to run this by you real quick because we always like to play a little devil's advocate. Yeah. What if Sean Combs simply comes out and says, I committed all the state crimes. I am a domestic abuser. I hit women, I beat women.

I had a really dark part of my life, but at no point in time was my violence the purpose for them crossing state lines. The same way that you and I may take our lives out to dancing in Brooklyn and then decide to go get dinner in Manhattan. We have the ability to go from one borough to the next. Well, we don't have Sean Combs money because he has the ability to go from one borough to the next. Well, we don't have Sean Combs money because he has the ability to go from LA to Miami to France.

And so he may not use his force to get them to travel state lines. It's just that when he's in LA, there's an argument and there was violence. They made up and they voluntarily decided to go to Florida. And so it's not that he's using the force, fraud or coercion to have them transfer over state lines. It's just that he has bumps in his relationship

of violence in different states. That would knock out the sex trafficking. And if he has a group of people that work for him, because he's not folding his own sheets, he's not cleaning up his own hotel rooms, does that mean it's a criminal enterprise because people help him to do the things that a rich and famous person has the ability to? And I've always been in the business of, you know what, your reputation may take a hit,

but you're not going to go to jail or prison. And I think you could have fallen on that sword and say, I don't traffic, but I am a flawed person. In my mind, and again, I'm putting aside the arson and a lot of other things, that could be the beginning of a potential defense. Because this could all be state charges and you just try to negate the federal aspect of it. Does that pass the Laugh Tasker or work in your mind in any way, shape or form? Sure. We haven't seen his attorneys try to do that yet. So far they've gone for bigger swings. That does not involve him conceding any aspect of bad behavior. Other than maybe at the outset they conceded he had some problems with drugs and alcohol that they didn't specify, but that's what

they made it sound like. But they've gone for the bigger swing of this is a racist prosecution. Cassie was a willing participant. This is a loving relationship. This video isn't what it seems. They haven't done a more nuanced defense, at least yet. And I would look for prosecutors as much as they included to also put some blinders on the jury to say, this isn't about Biggie Smalls, this isn't about a gun case in Manhattan and all the other things that Combs has been associated

with, true or not, this is about whether his life operated as a criminal enterprise for the purpose of coercing women into these sexual acts. I think this is a case from the perspective of prosecutors solely about the victims and how Combs allegedly committed crimes using them. but it is going to be interesting and it's going to be dramatic and it's going to be painful and it's going to be graphic. It will not lack for interesting discourse. Well, Aaron, it's always a pleasure. It's not a see you in court. I hope you were never reporting on any of my cases, but yes, I'll probably see you in court too. We'll probably see each other in court when we're covering this case actually. Look forward to it. It's going to be fascinating.

Jury selection in Diddy's trial is set to start on May 5th. Follow this podcast so you can stay up to date on the case. Twice a week we will bring you the important developments from the courtroom and analysis of what it all means. So follow Bad Rap, the Case Against Diddy in your favorite podcast app. If you like this podcast, please share it and give it a five star rating on Apple podcasts or Spotify. That helps other people find it. Bad Rap, The Case Against Diddy is a production of ABC Audio. I'm Brian Buckmeyer.

This podcast was written and produced by Vika Aronson, Camille Peterson, and Nancy Rosenbaum. Tracy Samuelson is our story editor. Associate producer, Amira Williams. Production help from Shane McKeon. This Original Music by Eben Viola. Mixing by Rick Kwan. Ariel Chester is our social media producer. This podcast was powered by the journalists at Impact by Nightline, 2020, GMA, and the ABC News Investigative Unit. Thanks to those teams. And special thanks to Stephanie Maurice, Liz Alessi, and Katie Dendas.

Josh Cohen is ABC Audio's director of podcast programming. Laura Mayer is our executive producer. Hello, it's Robin Roberts here. Hey, guys. It's George Stephanopoulos here. Hey, everybody. It's Michael Strahan here. Wake up with good news.

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