Crime Fix with Angenette Levy - P. Diddy Preparing For Possible Comeback After Trial

Episode Date: June 13, 2025

Sean “Diddy” Combs rose to the top of the music and fashion industry because he worked hard but he also knew how important marketing and good PR was in reaching his goals. Now Combs is on trial for racketeering and sex trafficking and is conducting a different type of PR campaign and it’s not he first time he’s been on trial. Law&CrIme’s Angenette Levy talks with Combs’ former publicist in this episode of Crime Fix — a daily show covering the biggest stories in crime.PLEASE SUPPORT THE SHOW:Take your personal data back with Incogni! Use code CRIMEFIX at the link below and get 60% off an annual plan: https://incogni.com/crimefix Host:Angenette Levy  https://twitter.com/Angenette5Guest:Rob Shuter https://www.instagram.com/thenaughtygossip/?hl=enProducer:Jordan ChaconCRIME FIX PRODUCTION:Head of Social Media, YouTube - Bobby SzokeSocial Media Management - Vanessa BeinVideo Editing - Daniel CamachoGuest Booking - Alyssa Fisher & Diane KayeSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can binge all episodes of this law and crimes series ad free right now. Join Wondery Plus in the Wondery app, Apple podcasts or Spotify. Sean Combs rose to the top of the music and fashion industry from humble beginnings only to see it come crashing down as the feds launched a sex trafficking investigation. But it's not his first brush with the law. I look at how Sean Combs came back from another court battle with his former publicist and whether history

could repeat itself. ["The Last Supper"] Welcome to Crime Fix. I'm Anjana Levy. Sean Combs rose to the top of the music industry because he worked hard, but he also knew how to promote himself. He knew how important it was to project an image.

Good PR was priceless, and he knew that, and he still knows how important it is to project an image and to tell the public a story. Now, as he's standing trial on sex trafficking and racketeering conspiracy charges in the Southern District of New York, Sean Combs knows how important it is to project an image, one that will be received positively by the public.

He even told a court sketch artist to soften how he looks so he wouldn't look like a koala. Seriously, a koala. But that shows you right there that he's watching and he's seeing how he's being portrayed in the media. And as he fights these charges, he's waging a PR campaign, even though he's in jail. And there are no cameras in the courtroom. Now just look at the sketches, the hearts he sends to family and friends in court. Yes, it's for them, but it also looks pretty good on TV and on social media. Now one of Sean Combs' former publicists, Rob Shooter, is going to join me here to

discuss all of this. And you're going to love it. Rob's great and he has a lot of insight and he's going to tell us what he's hearing about whether Sean Combs will be convicted or whether he could possibly walk away from all of this. But first, just a quick recap on how we got here. In November of 2023, Sean Combs' ex-girlfriend Cassie Ventura filed an explosive civil lawsuit claiming years of physical, emotional and sexual abuse by Sean Combs. This is where we first heard the term freak-offs,

and we heard about the baby oil and the rest of it. The couple dated for 11 years, finally breaking up in 2018. Combs settled that suit within one day of it being The couple dated for 11 years, finally breaking up in 2018. Combs settled that suit within one day of it being filed and denied the allegations Cassie made. It's now come out during the trial that Cassie got 20 million dollars from Shawn Combs and 10 million dollars from the hotel where Combs beat her. So the settlement total was 30 million dollars. Months after they settled, the video from the Intercontinental Hotel aired on CNN confirming that Combs had beaten Cassie. This was after Homeland Security agents raided Combs'

homes in Miami and Los Angeles. Sean Combs was arrested in September of 2024 and charged with racketeering conspiracy, sex trafficking, and transportation to engage in prostitution. The government is essentially accusing Sean Combs of being a gangster, running an enterprise, the Combs Enterprise, and using his business and his employees to cover up and commit crimes including bribery, extortion, kidnapping, arson, sex trafficking, drug trafficking, forced labor, and obstruction of justice. For his part, Sean Combs has pleaded not guilty to all of the charges, and he maintains

he has never sexually assaulted or sex trafficked anyone. So the trial is now well underway, and we've learned through this trial that Cassie's lawsuit basically started this entire federal investigation into Shawn Combs. But this isn't Shawn Combs' first brush with the law, and it's not his first trial. The first one happened more than 20 years ago.

But this time around, things are much, much different. Social media is a way to reach millions of people and shape public opinion. While he was doing this, he asked her, do you know what the F you did? She showed jurors bruises and cuts on her legs and bandages on her neck and back. There was another incident on the beach where Diddy got in her face and said, I'm the devil and I could kill you. That was our friend, former federal prosecutor, Nima Romani, he's on TikTok.

In New York, content creators and social media influencers have converged on the courthouse and they are busy, busy, busy churning out content about the trial. He allowed her to threaten somebody's job, didn't he? Allegedly. From there, the questions transitioned to what happened before Mia left the trial. He led a threat in somebody's job, didn't he? Allegedly. From there the questions transition to what happened before Mia left the company. Some say things are going well for Combs,

others say not so fast. There was a surprise, okay? The feds have flipped a second witness. Mr. Garcia, it was a shock. Nobody expected that. It's very exciting. I'm really enjoying myself meeting so many people from around the world that have come to really find out what's happening with Sean Combs. People are from China, we have people coming in from New Zealand, all over the place, as well as in the country we have from Texas, California, lots of people want to know what's happening. Do you feel like there are people, I mean it seems like there are people who think that Sean Combs is guilty who are content creators.

Are there people down there who are content creators who see more of his point of view? Have you seen any of that? Yeah, there's a lot of people that are on Sean Combs' side. They feel like the government has charged him wrong or either they overcharge him. Our content shows just how important personal safety is and that's especially true when it comes to protecting your privacy online. You would be absolutely shocked at how much of your personal information is out there, like your address and phone number. Ever

wonder why you get so many spam calls and emails? That's because this information, it's all public. That's where our sponsor, Incogni, comes in. It's a service that helps you take control of your online privacy by removing your personal data from data brokers, huge companies that sell and trade your info without your permission. Incogni actually found more than 50 brokers

with my information, and here's the kicker. These data brokers, they have to remove you from their database if you ask them to. Now you're thinking, Anjanette, who in the heck has time to contact a data broker? Well, that again is where Incogni comes in. They contact those companies for you to get your online safety back. You don't have to do a thing and then they alert you after the request has been completed. After signing up, I get virtually no spam, so I highly recommend giving Incogni a try. Right now, anyone who uses code CRIMEFIX at incogni.com slash crime fix gets 60% off. That's code CRIMEFIX at incogni.com slash crime fix for 60% off an annual incognito plan.

If there's one thing Sean Combs knows how to do, he knows how to put out music and he knows how to market and spin. And from what we've heard in this trial, he knows how to bury a bad story. Security guard Eddie Garcia used to work at the Intercontinental Hotel in Los Angeles, and he worked there in 2016

when Combs attacked Cassie Ventura in the hallway and surveillance cameras were recording. Well, according to Eddie Garcia, Combs' assistant Christina Coram called him and she wanted to see the tape and Combs wanted to get the copies of the tape. Long story short, Eddie went to his boss Bill Medrano and Eddie said Bill said he'd give up the tape for $50,000. Eddie said Combs was willing to pay and thanked him and called him Eddie my angel. Eddie said he went to Combs's office. He had a brown paper bag and a money counter and gave

him a hundred thousand dollars. Fifty thousand for Bill, fifty thousand for Eddie and another hotel employee. The feds say that was bribery and it was a predicate act under the racketeering conspiracy. So how damaging is that testimony? I asked attorney Philip DuBey. Remember the crux of RICO is that you are operating an enterprise, in this case they're alleging he's the mob boss to a criminal enterprise, and that predicate offenses are being committed during the course and scope of this enterprise. And I'll give you that, it

sounds like a bribery, but if you think about it, it looks like he's just trying to protect his reputation, but it's not necessarily in the name of the enterprise. It is individual capacity as Sean Diddy Combs. So I think it falls short of what the federal RICO statute calls for. Now does it mean that the prosecution can't make that out? Not at all. They have the goods, they've got the video, they've got the witness saying that he offered me this money. It's now for the jury to decide if they feel it is a bribery within the meaning of RICO or if it was a bribery

within the meaning of the California Penal Code where the DA's office never filed. If they would have been presented with a report from the LAPD that this employee had been bribed, they could have filed charges. This was years ago. So what does that mean? It means that the statute of limitations is long past. And when you cannot get these defendants stateside, you try to go after them federally. And they use the RICO and the human trafficking and the transportation statutes as creative

ways to get around the lapped statutes of limitation. And for now, we have to wait and see what a jury is going to do with it. The jury has also heard from two other women testifying under pseudonyms, one a former assistant and another going by the name Jane. Jane says Combs forced her to take part in hotel nights where she had sex with male sex workers. So that's how the trial is going so far. But as I mentioned earlier, this is not the first time that Sean Combs has been on trial

for a crime, although this time is much, much different. I'd argue the stakes are even higher this time. Remember, Shawn Combs was charged in the shooting at Club New York in Manhattan. Combs was at the club with his then-girlfriend Jennifer Lopez, his bodyguard Wolf Jones, and rapper Shine Barrow. A woman named Natanya Rubin was shot in the face but survived. Natanya Rubin swears to this day that Shawn Combs is the person who shot her, but a jury acquitted Combs at the trial and found Shine guilty. Shine was sentenced to 10 years in prison and now says he was the fall guy. After Combs' acquittal at that trial in 2001, he rebranded. Two weeks

after the verdict, Combs announced he wanted to be called P. Diddy. No more Puff Daddy. He started a show on MTV, making the band. His Sean John clothing line expanded and there were other business ventures. Martha Stewart even wrote about attending Combs' 40th birthday party on her blog and how nice it was. Yes, Martha Stewart.

Sean Combs totally rebranded himself into a businessman after that nightclub shooting. And now here we are. So I want to bring in somebody who knows a lot about doing publicity for Sean Combs. He's his former publicist, Rob Shooter. He is the host of the Naughty But Nice podcast. You can also check out Rob Shooter's Naughty But Nice on Substack. Check it out. It's great. Rob, first of all, how do you think this trial is going so far from a PR perspective for Sean Coase? Yeah, I've been following it really, really closely. I'm on a text exchange with several people who used to work for Puff,

and we have a really different opinion. Some of us think that Puff is going to walk away from this, and some of us think he is not, but I think that's what makes this so interesting. There's no clear outcome. We have covered, we have seen celebrity trials before, and we think we know what's gonna happen. I'm not sure here.

I'm not sure what's gonna happen some days. I think Puff does really well. Other days, I think the evidence is just damning. And so I don't know what these 12 jurors are ultimately gonna decide. That's interesting that you say that because I've talked to people who basically say they do think he's going to walk away from this, that he will not be convicted of racketeering

and things like that. And then, you know, it's weird though, because he'll have a good day in court. You hear that the jurors, at least maybe five or six of them look like they're, from what I'm hearing, almost cheering on Brian Steele as he's cross-examining Mia. This is what I'm getting from people I trust in the courtroom. And then I hear after they're listening to the testimony from Eddie the Angel, the guy that picked up the money and the cash in the bag for the hotel video, that the jurors looked more solemn and more serious and like, whoa, they were really hearing something

that sounds kind of mobish. So it vacillates. So you're saying it's a mixed bag among people who used to work for Sean Combs about how this is going. Yeah, we're not sure how this is gonna go, but I've done publicity media for a really long time. You don't have to work in the media or be a celebrity or a publicist to understand this.

When you're with a friend and they tell you one story, you generally believe them. And then you go and talk to another friend and they tell you the different story and then you believe them. So in the moment, the reaction from the jury, I don't think we should be focusing on that. It's big picture. What's the big takeaway? And I think it's emotional too. When they go home and I know they're not meant

to speak about this, but they do and they think about it, what is the big picture here? So the individual evidence is either damning or actually quite helpful. But what is the big picture? And I don't have the answer for that. You know, that's very interesting you bring that up as well because the jurors are not supposed to watch the news.

However, and we don't have cameras in this courtroom, but that almost makes the news more important because I'm sure that Sean Combs, I mean, Sean Combs is a guy who's very in tune with how important public perception is and how important image is. So how important is public perception and shaping it when it comes to a high profile criminal trial like this? I mean, this guy, if he's convicted, he's going away likely for the rest of his life.

So even though you've got the 12 people in the box and their opinion is what matters, how important is that public perception part of this? Puffy is running two trials at the moment, one in the public arena, what we think about him, and also two for those 12 members of the jury. We know now just from evidence that just three, four weeks after Puffy was arrested and jailed, he was thinking about a PR campaign around his birthday. That's who he is.

I was a young guy when I started to work with Puffy. It was over 20 years ago. He was my first major client. I went on to represent Alicia Keys, Jennifer Lopez, Jessica Simpson, tons of big celebrities, but Puffy was the first. And the reason I was so good at it is because Puffy trained me. Even though I was his publicist, I really wasn't. He was his own publicist, and I was implementing his plan. So I believe that his fingerprints are going to be all over this trial. He's going to direct what he wants, not just in PR, but also to his lawyers.

And it's difficult to argue with that. Somebody who's made almost a billion dollars, very confident about their own voice. Big celebrities that I've worked for, or very wealthy people, have a lot of confidence, and they should, because they have proved to everybody, they have proven to everybody, that they know what they're doing. And so for Puffy to give up control is almost impossible.

He's gonna be running the show, and it's two campaigns. One campaign to the 12 members of the jury and another campaign to the rest of the world. You know, looking back on this, and you talked about how you learned at his feet essentially, and he was good at it. I feel like, you know, I remember back when that trial happened for the nightclub shooting,

and he walked away from that with an acquittal. And Shine ended up going to prison for a number of years. And when that whole thing happened, I felt like Sean Combs, his image, I mean, he was involved in something really awful. Somebody was shooting at a nightclub. It was horrendous. And so he really had this image of somebody who

was trying to look good, but almost had still like a gangster kind of image, like a veneer on him. And then it seemed like after that trial, he tried to rewrite his story. And he did largely. He stopped going by puffy, starts calling himself Diddy or whatever. And then that's when it's like, I'm the businessman. And he really cultivated that image of I'm a businessman. I'm not just a guy who does records, but I do clothes. I'm a fashion designer, Sean John. I got this thing going on with Macy's, hanging out with Martha Stewart, for goodness sakes. I mean, like, do you, did you kind of see that evolution with him? Yeah, I'm ashamed to admit that I was part of that. I was part of that campaign to cover up

the truth. Puffy really had to walk a tightrope, tightrope here. He didn't want to alienate the people that bought his music. And so he had to have a swagger about him, but he also, too, did not want to alienate Anna Wintour, Clive Davis at the record label, these big wigs who wanted somebody quite respectable, and so Puffy knew how to do both really very well. I think it's important to remember, too, he was the first one to do this.

Today, every celebrity has a fragrance, a clothing line. They all have these side hustles. Puffy was the first, he was the first successful, really successful celebrity to branch out and that's what made him so, so wealthy, so, so powerful and so, so famous. Right. And that's what stuns me is because beneath all of that, you know, under that veneer, under the public campaign, the public face, the magazine covers, the cologne campaigns, the Sean John, you know, the whatever, and the white parties, you know, where some of

this stuff would go to charity and things like that. You have a guy who's addicted to drugs, who's hiding it from the public, who's going on Ellen and you go back and look at that stuff now and you're kind of like, oh, some of it's very cringe. And then he's doing freak offs in hotels and kicking his girlfriend and doing horrific things, and it all comes crashing down. So if he does walk away from this, Rob, is there a road back for him? There is, there is. I'm ashamed, I'm horrified to admit it. In Hollywood, I now am a celebrity reporter, a columnist,

so now I'm no longer a publicist, now I follow the industry from a different angle. There is a way back, and I think of lots of different disgraced celebrities that have made somewhat of a comeback. Do I ever think he will be invited to the Met Ball ever again? No. Do I ever think he'll be invited to the Met Ball ever again? No. Do I ever think he'll be invited to the Oscars to present a game? No. But he will have a career after this. We've seen it with people like Michael Jackson.

We've seen it with other celebrities, with directors who have been accused of terrible things. This is the dirty secret about the celebrity business. It's about money. And if you make money, there is a way for you to come back. So after this, after this, he could be potentially more successful in certain areas of his business.

We've seen his music skyrocket. Since he went on trial, he's getting more downloads, more streams than he did for the last 10 years. People were not listening to Puffy's music anymore. Now they are. And so it's a perverse thing about the celebrity culture is that often crime pays.

Yeah, and there's a documentary crew traveling around with his family, with his children. And that to me is these days, everybody's got a documentary. Let's say he walks away from this, if he's acquitted, he's going to do a documentary. Somebody will buy it. Maybe he goes to rehab for sex addiction and drug addiction and what have you, who knows? I'm just thinking in my head, that's what celebrities do. They get into trouble and they go to rehab. I mean, it's just kind of like, this is my thought process on what could be cooking behind

the scenes. You're not wrong. Yeah, you're not wrong. And as long as the public forgive, and you don't need the entire public to forgive to be successful, you need a very small percentage to support you. I was down at the courthouse and I was surprised to see so many bloggers, so many influencers outside the courthouse, more influencers than actually traditional press who were there too. I saw CNN and the big crews from the networks.

But there was a lot of bloggers there. These folks were getting millions of followers. They potentially were getting more hits than the traditional media. And Puffy knows that. Puffy's talking to them. He's not talking to Wolf Blitzer or Lester Holt or people like you and me. He's talking to his fans. He's cutting us out of the conversation. And if he can reach those people and convince them that he was targeted as a very powerful black man,

people in the world did not like this. This is the argument. I know him. This is the argument he I know him. This is the argument he's gonna present. And I gotta tell ya, it's a pretty convincing argument for a section of the population. That's all he needs if he gets off. I'm told, my sources tell me, there's already discussions within Team Puffy about a comeback, new music, a documentary, a tour. He's been talking to Kanye West.

We know that because the tapes were leaked from inside jail. Kanye West, after confessing to being a Nazi, is still selling tickets. And so we can, like, nod and it's not good. I'm not endorsing this. But it's naive to think he couldn't have a comeback. AMT – No, I'm not saying it couldn't happen, but you're right. I mean, with the age of social media and influencers, TikTok, Instagram, the whole thing, there's a whole segment of the population.

So he's running a social media campaign from the defendant's chair and from his jail cell. And we will see what happens as this whole thing unfolds. Rob Schueter, thank you so much. Hey, it's great to talk to you. I love your show. I'm a fan of it. Thank you for having me on. Thank you so much.

And that's it for this episode of Crime Fix. I'm Ann Jeanette Levy. Thanks so much for being with me. I'll see you back here next time.