Law&Crime Sidebar - 5 Times P. Diddy Has Faced Off with Police

Episode Date: June 19, 2025

Sean “Diddy” Combs’ federal sex trafficking trial is dominating headlines right now. But this is not the first time that Combs has made the news for major scandals – from a deadly stampede at a concert to a scuffle with a football coach. Law&Crime’s Jesse Weber took a look back at the disgraced music mogul’s prior legal troubles and spoke with Jason Swain, whose brother Dirk was killed during a stampede at a Combs charity event.HOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger, Christina O'Shea & Jay CruzScript Writing & Producing - Savannah Williamson & Juliana BattagliaGuest Booking - Alyssa Fisher & Diane KayeSocial Media Management - Vanessa BeinSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wonderry 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 Diddy Combs' federal sex trafficking and racketeering trial is dominating headlines right now, especially here on Sidebar. We're covering every single angle of this trial. But this is not the first time that Sean Combs has made the news for major scandals, from a deadly stampede at a concert to a scuffle with a foot. football coach, we are taking a look back at the disgrace music mogul's prior legal troubles,

and we are sitting down with the brother of one of the victims of that stampede to get his take on everything that's happened. Welcome to Sidebar, presented by Law and Crime. I'm Jesse Weber. Now, if you've been following us here on Sidebar, you know that Entertainment Titan Sean Diddy Combs is on trial in a New York federal court charged with racketeering conspiracy, sex trafficking by force, fraud, or coercion, transportation to engage in prostitution, but Combs, the original bad boy of bad boy records, is no stranger to law enforcement or a courtroom or scandal. So what we're going to do is we're going to take a closer look at a few other times that Combs found himself in some hot water, and some of them, you might not have even heard of.

So we're going to start off in Los Angeles at UCLA. That is where police had to get involved in a disturbance between Combs and the football. coaching staff at the college. They'll give you a little bit of background for you. So Combs' eldest biological son, Justin Dior Combs, was born in 1993, right around the time that Combs was getting his feet wet in the music business at Uptown Records in New York. His mother is Misa Hilton, by the way, the stylist, the fashion designer, who's actually been seen at Combs' current criminal trial, by the way.

Now, after playing as both a quarterback and quarterback in high school in New York, Justin started college at UCLA in 2012 and joined their football program. Now, according to UCLA's roster, Justin didn't see any playing time his first year, but then took the field in 2013 and the 2014 season. And in June of 2015, Combs apparently took issue with the way that one of his coaches was treating his son. So he ends up taking it up with the coach in person in the sports off season. Now, we got our hands on a report from the University of California Police, which lays out what reportedly happened here. Quote, suspect went to the UCLA weight training facility with his son, a member of the football team, to confront the strength and conditions coach regarding his dismissal of the son from practice that day.

The coach was on the phone and motioned for him to wait. After a short time, the suspect and his son entered the office and words were exchanged. The suspect approached the coach and physically assaulted him, causing some minor scratches and tearing his shirt. Several members of the training staff came to the coach's aide and removed the suspect from the coach's office. The suspect then briefly strangled an intern, causing minor scratches to his neck. Members of the staff were able to move the suspect toward the exit. The suspect briefly put another member of the coach's staff in a headlock type hold. The suspect then obtained a small kettlebell weight and swung it in the direction of the staff members.

The weight did not strike anyone. The suspect then left. The suspect's son claims the suspect's actions were in self-defense. Then there's something that's redacted. the minor nature of the injuries and fleeing use of the weight not resulting in any contact with the victim, the case is referred to the Los Angeles City Attorney's Office for misdemeanor filing consideration. Now, according to UCLA, Combs was arrested in charge with assault with a deadly weapon, and the charges were actually later upgraded to three counts of assault with a deadly weapon,

one count of making terroristic threats, and one count of battery. He was booked into the Los Angeles County inmate reception center. But here's how it all shook out. So ESPN, report, at the time that there was some sort of discrepancy on how much Combs' bail was, so he ends up getting released, and the police department sends over their recommendation to the district attorney's office, and they declined to prosecute. That's according to variety. But that was not the only alleged episode of violence. Many of Combs' legal problems date back to the 90s when he shot to stardom as the founder of Bad Boy Records, which later became Bad Boy Entertainment. him. And he had some pretty serious beef with this fellow record executive over at Interscope

records named Steve Stout. So Stout claimed that Combs and two other men beat him up in 1999. According to the L.A. Times, Combs had a cameo appearance in a music video for the song Hate Me Now by Nas. And his scene was controversial. He was being nailed to a cross, something that he helped conceive and that reportedly cost Interscope an extra $14,000 to make happen. Well, apparently, after talking to his mother and pastor, Combs had a change of heart and decided he didn't want that scene in the video. But when it premiered on TRL, on MTV, who remembers that show, this happened a few days later, the scene was apparently still in there. Within minutes of it reportedly airing, Combs was reportedly on his way to Interscope where he allegedly attacked Steve Stout. And back in 1999, Stout spoke with the L.A. Times about this alleged assault, saying, quote,

one minute I'm in the middle of a meeting and the next minute I'm down on the floor and Puffy and his guys are kicking and pounding me. One of them picks up a chair and throws it at me. Then Puffy throws my desk over and they just walk out like nothing happened. So at least part of the alleged assault was reportedly caught on surveillance video. Combs was, yes, arrested, originally faced felony assault charges, but those charges were later downgraded to a harassment violation. The LA Times indicated that Stout had asked the DA to drop the charges after Combs and apparently apologized to him. And as far as his punishment, a one-day anger management class. Combs was quoted at the time as saying, I'm happy that the court

decided favorably. I am glad to get this whole incident behind me. And now it's time for me to do what I do best, concentrate on my album, and give back to my fans. Well, this alleged assault also led to a lawsuit, which was reportedly settled out of court. This is according to Radar Online. line. Now, just a few months later, Combs was back in the headlines, and this was after a shooting at a New York City nightclub. This is one you might remember. Combs was there with his then girlfriend, Jennifer Lopez, around Christmastime, when there was some sort of argument, weapons were drawn, shots rang out, bullets hit at least three innocent bystanders, including a woman named Natanya Rubin, and she would go on to testify against Combs at his trial in 2001,

saying she saw the rapper fire a gun. Combs' bodyguard, Anthony Jones, and Lopez, they were chased by police when they left the scene and a stolen gun was found in the car when they stopped. Lopez was also detained, which is why we have this kind of rather unflattering mugshot of her, but with respect to Lopez, charges were in pursuit. Jones, Combs, and a former bad boy rapper named Shine Barrow all were charged and went to trial. And prosecutors alleged that Combs was the who opened fire and then tried to bribe the driver of the car to take the fall for having the gun. But here's the thing. Jones and Combs were eventually acquitted of gun possession and bribery charges, but Shine was convicted of assault and reckless endangerment for the shooting and he was

sentenced to 10 years in prison and was released in 2009. Shine was actually deported to his home country of Belize after his release and has since become a successful politician there. But in recent years. Shine has said he was the fall guy for the shooting and that he continues to maintain his innocence in that. He claimed during a news conference in Belize in 2024 that he was defending Combs at the shooting trial, but then Combs brought in witnesses to testify against Shine. And during around the recent interviews, Shine called Combs plan to scapegoat him demonic. Now in response, a representative for Combs released a statement to TMZ saying Mr. Combs categorically denies Mr. Barrow's allegations, including any suggestion that he orchestrated Mr. Barrow to take the

fall or sacrificed him by directing witnesses to testify against him. These claims are unequivocally false. Mr. Combs was acquitted of all charges related to the 1999 Club New York incident and has consistently maintained his innocence. He cannot accept or condone any characterization of his actions as demonic or malicious. Now, I want to quickly mention a battle in civil court that was a loss for Sean Combs. So as we know, Combs is gone by many names over the There's Puff Daddy, P Diddy, just Diddy, but his decision to drop the P and just go by Diddy in 2001 caused some problems across the pond. Because according to reporting from the BBC, a DJ in the UK had already been using the name Diddy for nearly a decade. DJ Richard Diddy Deerlove was best known for his dance remix of the Blondie hit Atomic.

So this case could have gone before the Royal Courts of Justice in London in 2006, but Combs settled with Deerlove out of court for 110,000 pounds. This is what this is based on reporting from the BBC. He was also forbidden from selling things like albums or merchandise under the name Diddy in the UK. But now, we go to one of the earliest and most infamous tragedies involving Sean Combs. On December 28, 1991, Combs and fellow rapper HeavyD hosted a charity basketball game with promises that some of the proceeds would be donated to an AIDS education group. So the game took place at the gymnasium of City College of New York, but the number of people who wanted inside quickly got out of hand. Reporting from the New York Daily News, the Washington Post, and the Associated Press at the time indicates that the gym had a max capacity of fewer than 3,000, but at least 5,000 people showed up wanting to get inside. According to the New York Daily News, before the basketball game started, people who hadn't been let inside broke a window and swarmed toward the entrance of the gym streaming down a staircase.

But the doors at the bottom of those stairs opened towards the staircase, not towards the gym. So once a crowd got down there, they couldn't get the doors open and people started being crushed. There were police officers unseen, but they said they couldn't see what was going on from where they were positioned. And the death toll was initially eight, but that changed to nine when a 20-year-old woman was taken off life support on New Year's Day in 1992. Dozens of other people were injured. And there was a lot of finger-pointing in the aftermath of this tragedy, with many calling it, quote, a preventable disaster. In fact, then mayor, David Dinkins, ordered an investigation which found several key factors. Number one, police didn't intervene quickly enough.

City college officials let student groups plan events without much oversight. Combs delegated planning to assistance with insufficient experience and did not purchase event insurance. People in the crowd rushed in despite being turned away. Why the doors at the bottom of the stairs were even closed in the first place, though, that's still kind of a mystery. But the nine victims, they were all between the ages of 15 and 28. And while no criminal charges were ever filed against anyone for this, multiple families and injured victims filed lawsuits. And Combs always maintained that he wasn't responsible for security. That was up to City College, but others said that Combs had some responsibility too because he was the promoter of the event and that he hadn't adequately prepared for what ended up being a huge turnout.

And in the decades since the tragedy, a brother of one of the victims has pushed to inform more people about what happened and how it impacted families and the community. On that evening, not just my brother Dirk died, but eight other people. And even to this day, it's hard to even understand why it happened. Bronx native Jason Swain produced a documentary series called No Way Out about this stampede, about his brother, 20-year-old Dirk Swain. And we're fortunate enough to have Jason with us right now in studio. Jason, thank you so much for taking the time. Really, really appreciate it, particularly with everything that's going on. Can you just tell us a little bit more about Dirk, what was he like?

Because sometimes that gets lost in the whole story of it all. It's been 33 years, but I still recall Dirk to be just a protector. He's my big brother. It was just, he's my only sibling, three years older. Athlete first, you know, he played basketball. He rapped. He actually did a tape just before he went to the game. And college student, graffiti artist that kind of parlayed his career into architecture in college.

He was a junior in college at the time. he passed away and just quiet unassuming but you know I'm really just a good kind-hearted person hip-pop and basketball is what brought him officially to City College besides other things that happened to him you know it's been so long but I still have to say you know I'm so sorry for your loss you know it's it's never gets easier and he sounded like just such an incredible person he sounded like he was very excited to be going to this event that night right yeah um because unfortunately three months and a week before that he got shot in his head oh my god and lived lost his peripheral vision on the right side it

was a stray bullet or we don't know if it was intended for him but he was on his college campus and this happened and this was his first time going out and he had called all his friends it was Christmas holiday season everyone is home from college he's like meet me at City College And, yeah, you know, they tell me to this day, I'm still really close to his friends. They were like, they're called me. He called everyone to say, listen, I'm coming to City College. My first time going out, he had a soft spot at the back of his head, so he needed oxygen.

But that was his calling. He really wanted to go there. You, were you planning on going there that night? Was there ever any conversation about you coming with him? It was. I had gotten trouble you know we grew up with my dad and on on Christmas Day I came home late I was in high school teenager and I came home late and my father said you in here this weekend and my brother you know he said be home by nine and my brother really wanted to go because

his girlfriend gave him the ticket and it was all on the radio like yeah that was the place to be you know at that time and I told Dirk you know dad told me I got a I said, be here, he said, I forget that. You know, he's not even going to remember that. I want you to go. And I said, well, I don't have money. He pulled out money because he worked in the movie theater while he was from school. While he was recovering, they gave him, like, a real easy job,

because that's where we both worked before he went to college. And he was waiting for me, and I was taking my time. You know, I was ironing my clothes and talking on the phone. And our mutual friends that were going with him said, Dirk said, let's be out you know jay taking too long let's just go and and i was and then when i came downstairs he was gone and um and i actually did a couple of short films just about those those minutes before because it was so um it was so like weird that he would leave me you know because he he we talked about it i actually said i didn't think he should go because i said that because i had gone

gone a week before uh-huh there was another game another similar game with um the show video music box yeah at the time and and we've had been to city college in early days as well but there was never like real true crowd control or organization where there's a ticket hold a line here and then there's line you know they would just open the door and pull a few people in wasn't organized it was, you know, a lot was done by the student government. So when I went the week before, it wasn't organized, and it looked too crowded. You got a sense of what it was like. How did you find out what happened?

I was on the train, and I got off the train. I was downtown. After my brother left, we went to Harlem, a friend of mine, and I went to Harlem. And we came back up and we got off the train and one of Dirk's friends, our mutual friends, but he was Dirk's age, was waiting at the train station in a car. And he said, get in the car. And come to find out, my mother had reached out to everybody, called the movie theater because Dirk's girlfriend saw him die.

She was there. And she called the movie theater where we all were working and they were looking for me. And my mother said, do not look. let Jason find out on the street yeah so they everyone got together to round me up and put me inside an apartment actually the movie theater manager we went to her house and she officially told me that's a she doesn't know but Fatima Dirk's girlfriend said they pulled a sheet over him so I said what you know what does that mean I was already sensing something was

crazy because they wouldn't take me to a hospital and um because uh my friend that was waiting for me at the train station said um something happened to dirk i was like i told him not to go you know i got angry and um then my mother called the house that i was in the apartment um and i spoke to her and she said dirk is gone so we had to go to city college and um they wouldn't let you in to the gym or the um where everyone was seated all the families unless you looked at the Polaroid pictures of the deceased so I went through almost five pictures before I saw a dirk and I saw a dirk had mixed marks on his around like that you could tell they were doing CPR and um and his eyes were open so they showed me that in this crowd and then my

father was like waiting by the door and he grabbed me drop me and we fell to the floor he said they got him jay it's just us man you know because my grew up my father was a single father even though my mother was very much in our lives but they um he he was our primary um you know uh parent and he he was so pissed and we were in front of the gym then we went into the library of it and became official. It's so awful. The way you describe it, like I'm visualizing it happening, and I know it's not easier.

And I'm wondering, you know, in the aftermath of it, trying to make sense of what happened here, you see the response from the city officials, you see the response from the police, you see the response from the mayor when they look into it and they investigate it. What did you think of that response? What did you think of the investigation?

Didn't, at that point, at that time, I didn't understand. I still didn't understand what happened. I couldn't get it. And no one was really, no one was taking accountability for anything that went wrong. It seemed criminal, but it didn't go that route. It was obvious that it was overbooked

because my brother died with his ticket in his pocket and no one even ripped it. They were still selling tickets. Really? Yeah. Yep. He never, they went in. They were waiting at the bottom of the steps.

My brother's friends didn't get a chance to buy a ticket. They just got in. And there were people still outside, and you'll see that in my documentary, people holding up their ticket, and they can't get in. But they were still selling tickets at the door. Like, you know, just didn't make sense. And I don't know officially, like, really. how it was, you know, I guess any evidence to show that it was overbooked. It was just, in my eyes, it seemed overbooked.

But I'm sure the officials figured that out. But the rumor was that it sold out a week before because the radio was really blasting it. You know, if, yeah, like I said earlier, that was the place to be. Yeah, we were talking about it before. Do you have any idea why those doors were closed? the bottom of the stairs someone closed them and I believe certain people said it was Jessica Rosenblum it was who was at the front door Sean potentially but I think they were at risk of thinking people were going to rush the door anyway because they

they said that it's over no one else is getting in and you and people weren't having that especially people who had tickets so someone closed the door and excuse me they closed the door without understanding or I guess helping the people it were about I guess 50 or less people in the staircase waiting to get in yeah celebrities there were hip-hop celebrities there that were with three people who passed away so they should have been in or going through the back LL Cool J should have went through the back it was know you know just imagine a celebrity today walking through the crowd of an event and then they go in now the crowd is really excited even more excited yeah and that's the way it was you know

people will walk right in from the front past the crowd and and then they won't let anyone in and there was lack of security disaster disaster yeah what did what role Do you think Sean Combs plays in this? I think he was like the, I would say, the primary promoter. And, you know, he knows how to get a crowd even then. He knows how to get people to come to a party. And I think he was a party promoter. That was his thing at that time besides the internship label stuff he was doing.

There were 10 defendants, you know. So I can't always, and this is my mother who said this, God bless her, it was, they were 10 defendants, so you can't just point the finger directly at him. But he was the one who paid the money to Cassandra, Kieran on, I think that's her name, and student government, $1,200 to rent the gym, and he just called everybody, you know, or called his friend to call his friend. celebrities and put their names we're going to do a basketball game and it sounds fun I believe if no one passed away it would have been a great event right um for 12 dollars you know in advance $20 at the door you know um but what did you make of his response afterwards um he really didn't say much I've met him a few times but I didn't like he said something in a rap song that my mother and I, my mother was, she's in the

newspaper speaking on it, but it didn't make sense, you know, because we never really heard him say he apologized for being the promoter, just, and being found liable. He was still like, and then he said it wasn't overbooked. He said that in an e-true story thing. And it just didn't make sense. You know, at first I was really pissed off. You know, I was young, I was a teenager trying to find my way. But then, you know, I kind of fell back with, you know, that type of thing.

Just being mad at one person wasn't really the way to go. Well, you've produced this documentary series, as I said, No Way Out. What's the purpose bounding? What do you want people to remember about this? I'll tell you, with so much going on with Sean Combs now, in one hand, you could say things get lost. People don't remember. On the other hand, he's got a spotlight on him.

People now look back a little bit of the things that he was involved in. What are you hoping with this series? What are you hoping through the years to bring more attention to this story? What's the hope? I just want to give a voice to the nine, to the nine people who were killed. They were amazing people. We do a memorial every year at City College, at the staircase. no one's covered it till this year that just passed and so I would I started

doing it and what I wanted was just to give them a voice and just remember remember them you know understand them so I've done a documentary it was kind of a rough draft and you know some schools watch and you know used it to educate you know you on crowd control and stuff like that but we're doing a part two and what I want is to understand like what did you see you know talk to some of the celebrities that were there talk to some of the eyewitnesses because it's just shouldn't never happen again yeah they were crushed in the staircase like and it was it wasn't just Sean's fault it wasn't just the

security's fault it was also the people who were pushing because they didn't know that the doors were pushing this one you know actually open towards them instead of going into the gym so there were a lot of people at the top of the staircase which I did a little investigative reporting and my brother's friend who was there with him told me a lot to took him 10 years though but he finally gave me some insight about it he said there were people at the top of the staircase saying one two three push really and they were trying to push

the doors open when they come this way so it was just is it a sense of also maybe getting justice in some way I don't know if it's identifying the people who were a part of it is it is it trying to get more understanding about what happened I mean what would justice look look like for you at this day and age understanding understanding what happened I think that would be something that um needs to be understood because even myself in the early days I was like how do you go to a basketball game and die like what really happened yeah um I didn't you know I wasn't educated about crowd control anything I think um it helped me and anyone I knew know that pushing is not you know we're not going to do that if it's a crowd we walk away um you know if it's not organized so understanding um I understanding what even law enforcement should do because law enforcement was there and all they were saying was, you know, get on the sidewalk. They're bending a light post, but get on the sidewalk.

Yeah, yeah, yeah. You know, they weren't, and I know there are reasons why they weren't there, but I feel that it'll help even law enforcement and security and other people to understand, let's not let this happen again. Why do you think they weren't there? I know why they weren't there. It was a week that, concert the week before that I mentioned, the police came because it was, the crowd control was bad. So they came and City College reportedly said, we have a private police force, so we don't need your help.

So I think this is in court records. they're they were more so like trying to make an example or something to that extent like oh y'all don't need our help y'all didn't need a help last week because I have the tape where they're driving by in the band and then there's 13 calls trying to get someone that really knows how to do CPR and rescue these people but they did not come inside they were trying to let City College handle it. Wow. Wow. And that's why the city pretty much got sued.

Because, you know, they were supposed to, you know, Sean made a mistake, Heavy D made a mistake. Let's not forget that, but they did call for help. I heard all the 911 tapes. These kids were sounding articulate and begging for help, 13 calls. And that's part of the documentary and understanding how important it is to take this serious. People want to watch it. What's the best way for them to watch the documentary? Oh, right now, the part one is on vimeo.com. Okay. No way out. Vimeo.com. Okay. I got to ask you

while I have you here. I mean, Sean Combs currently on trial, a lot of allegations been thrown against him in the last year and a half in civil suits, also the criminal charges. What's your perspective on seeing him not only on trial, but potentially he could be convicted and sent to prison for the rest of his life? I think if he's guilty of those crimes, he needs to pay. I don't have any experience in his party life. You know, I've seen him in a club, you know, years ago, and he would just, because I always would say, Dirk Swain, like Robert Dirk Swain, but he would say, how's your mother?

You know, because he, my mother and him, you know, spoke many times. But I don't have, I just, I'm actually very disturbed by the video of Cassie. Yep. It really hurts me to watch it. I don't, so if he's convicted of a crime that he's liable for, or he should do his time and just shut up because it's still to this day, you know, yeah, I don't, like I have a daughter, I don't, you know, I know if my daughter called me about,

him doing what was seen in that video, it would really bother me a whole lot. Whereas, you know, I think he needs to pay for anything that he's found liable for. Well, we'll see. I mean, we're still in the middle of it, and I'll tell you this much, just whether he's found guilty or not guilty, there's just been a lot that's come out, and we've learned a whole other side of him. Yeah. than the public knew for the last 20, 30 years.

But listen, Jason, I really appreciate you taking the time. Again, I'm so sorry for your loss on what you and your family have gone through. You're a good man. Thank you so much for taking the time. Nice meeting you. You too. Thank you. And that's all we have for you right now here on Sidebar.

Everybody, thank you so much for joining us. And as always, please subscribe on YouTube, Apple Podcast, Spotify, wherever you should get your podcasts. I'm Jesse Weber. I'll speak to you next time. You can binge all episodes of this law and crime series ad free right now on Wondery Plus. Join Wondery Plus in the Wondery app, Apple Podcasts, or Spotify.