20/20 - Bad Rap: Invincible

Episode Date: April 2, 2025

Today, we're bringing you episode two of the latest podcast from 20/20 and ABC Audio, "Bad Rap: The Case Against Diddy." This week, we chart Diddy’s rise from musician to mogul, from the center of hip-hop to the center of American culture. But that rise wasn’t always a smooth ascent. Along the way, he had moments of alleged violence and brushes with the law. Were these lapses in judgment or serious red flags that signaled a darker side to his success?  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

Hi there 2020 listeners, it's Deborah Roberts here. We're going to bring you the next installment of our six-part series on Sean Diddy Combs. Here's Bad Rap, The Case Against Diddy, episode two, Invincible. On an August night in 1995, the four corners of the hip hop world gathered at the Paramount Theater in Midtown Manhattan. Artists from the South, the Midwest, and from the East and West Coast were all under the same roof. They were all there for the second annual Source Awards. It was a celebration of hip hop,

a music genre that was rapidly moving from underground to mainstream. The event felt like a pretty standard award show. An eager crowd filled the auditorium, waiting to hear the results. And the winner is... West Coast rapper Snoop Doggy Dog, also known as Snoop Dog, won Artist of the Year.

East Coast rapper The Notorious B.I.G. won Album of the Year for Ready to Die. And Outkast, a duo from Atlanta, won Best New Artist of the Year. The night was filled with performances and acceptance speeches. And one of those speeches turned the 1995 Source Awards into one of hip-hop's most infamous nights. Yeah, yeah.

Record executive Suge Knight and rapper Danny Boy won the award for best motion picture soundtrack for their work on the movie Above the Rim. Suge climbed on stage in a bright red button down shirt. First of all, I'd like to thank God. Suge is not a small guy by any stretch of the imagination. He stands at maybe 6'2", and is definitely over 260 pounds. Before he got into the music business, he spent a year in the NFL as a defensive end

for the Los Angeles Rams. In 1995, he was running one of hip-hop's two big record labels, Death Row Records out of LA. Now, after thanking God, Shug didn't go on to give a standard acceptance speech. Any artist out there want to be an artist and want to stay a star, don't want to have to worry about the executive producer trying to be all in the video, all on the record, dancing. Come to Death Row." The crowd had an immediate reaction. Some applauded, but lots of people booed when

Shug said that any artist who didn't want their producer in their videos and songs should work with his company, Death Row. Everyone knew who he was talking about. Sean Diddy Combs. Or, as he was known back then, Puff, Puffy, or Puff Daddy, the head of the other big hip-hop label, Bad Boy Records, based in New York City. Unlike most producers and record execs, Diddy wasn't happy just sitting in the crowd or getting on stage to accept an award. He was an aspiring rapper himself and craved the spotlight. In fact, when artists from his label went up to perform a medley that night, he joined them. Well, he actually started the whole thing. And if I should die before I wake, I pray to God I die, bad boy, bad boy. Suge Knight and Diddy were already rivals, businessmen vying for their record label to

be king. But Justin Tinsley, a reporter at ESPN's Sports, Race and Culture outlet Anscape, says Suge's speech at the Source Awards was a turning point. Their rivalry became much darker. About a month after the awards, they were both in Atlanta for the birthday party of a rapper and producer Jermaine Dupree. Tinsley says tensions between Shug and Diddy and their entourages were high. Sides get the barking with each other, things spill out in the parking lot, and one of Shug's closest friends is murdered in the parking lot.

Atlanta police said Diddy's bodyguard, Anthony Wolf Jones, was their prime suspect. Jones' attorney said he had absolutely nothing to do with the shooting, and no one was ever charged. But the shooting made the friction between Diddy and Shug worse. And that's partly because their beef was part of something much bigger. The East Coast West Coast rap rivalry, which people have obsessed over for decades and we could probably write a whole other podcast about. But here's what you need to know to understand what happened next.

Diddy represented one of the East Coast's biggest rap stars, the Notorious B.I.G., or Biggie Smalls. Suge Knight represented one of the biggest West Coast rappers with his own unique approach to music, Tupac Shakur or Tupac. And both rappers and their styles were vying to be the biggest in the country. So the beef between Diddy and Suge was also connected to a rivalry between Biggie and Tupac. And I'm not just talking about a couple of diss tracks like

Kendrick and Drake today. Tupac was shot and killed in 1996. Biggie was shot and killed in 1997. The two stars, only in their 20s and at the start of promising careers, were suddenly dead. Their murders captured international attention and really marked this era of hip hop music. Their deaths also generated tons of unsubstantiated theories. In particular, there were theories that each rapper was killed

by someone tied to their rival's label. No one has been convicted for either Tupac or Biggie's deaths. But this is the bottom line. A feud heated up after Suge Knight publicly called out Diddy's need for attention. The only two people left were the label heads. Suge's career was never truly the same after Tupac's murder. Def Ro pretty much crumbled in the months after that. But Diddy?

Diddy became an even bigger star. Just like at the Source Awards, Diddy took center stage. He put out his first album as Puff Daddy in 1997, the same year Biggie died. It was called No Way Out and included the hit song, I'll Be Missing You, a tribute to Biggie featuring his widow, Faith Evans, who was also an artist on the Bad Boy label. I'm feeling good, man. Give me anything to hit half your breath.

I know you're still living your life after death. That's how I take it. That song was the first hip-hop song ever to debut at the top of the Billboard 100. And that year, Diddy received seven Grammy nominations, including for Best New Artist. And now Diddy is an established artist on top of an already established executive.

So his star power really began to rise. Suge had made fun of him for wanting to be in the spotlight. But lo and behold, there he was, basking in it. In an interview later that year, Diddy was asked about the perception that he was exploiting Biggie's death. It wasn't just that one of his album singles was a tribute to the late rapper.

He also used some of Biggie's lyrics for the album. Because you know how people think. They'll say, well, you know, you took some. I can't move on how people think. You know what I'm saying? I can't only be judged by God. You know what I'm saying? And I gotta constantly be living with myself.

I gotta live with myself at the end of the day. I gotta close my eyes and know what's right. You said that after Biggie's death, you took some time off to reflect? Yeah. I mean, after Biggie's death, I was like, that was my heart. So my heart wasn't beating. So I was dead too. And it was just a situation where I didn't want to. 1997, the year Biggie died, was a wildly successful year for Diddy. Vibe magazine reported that his Bad Boy label sold $200 million worth of records and had the number one spot on the Billboard Hot 100 for 22 straight weeks. Rolling Stone approached Bad Boy Records about putting someone associated

with the label on the magazine cover. Kirk Burroughs was the president of Bad Boy at the time. In 2024, he told Rolling Stone that he urged Ditty to put Biggie on the cover. His posthumous album, Life After Death, had been at the top of the charts all year, and he was still on people's minds. So Burroughs is allegedly telling Diddy, you'll have your chance to get another cover, but Biggie will never come out with another album. Give him that moment. And according to Burroughs, Diddy basically says, no, he's dead. This is my time now. In response to the Rolling Stone piece that included this story from Burroughs, He's dead. This is my time now." In response to the Rolling Stone piece that included this story from Burroughs, one of

Diddy's attorneys said he cannot address every allegation picked up by the press. Diddy ended up on that 1997 Rolling Stone cover, and Kurt Burroughs lost his job later that year. He unsuccessfully sued Diddy in 2003, alleging he was wrongfully fired. In the cover shot, Diddy is shirtless, with B.I.G. written on his chest. He's wearing white Versace shorts and an oversized brown overcoat. There's water dripping down him, and he has black paint under his eyes like a football player. The title of the story? The New King of Hip Hop. Puff Daddy. I'm Brian Buckmeyer. From ABC Audio, this is Bad Rap, the case against Diddy.

Episode 2. Invincible. The Case Against Diddy. Episode 2, Invincible. Sean Diddy Combs knew how to put himself at the center of things. That started with music and lavish A-list parties, but eventually it became much bigger. He ventured into fashion, alcohol, and TV. The whole time he proved himself to be an expert at branding and reinvention, cultivating this cool guy image and protecting it fiercely. In this episode, we'll trace Diddy's rise from musician to mogul, from the center of hip-hop to the center of American culture.

But that rise wasn't always a smooth ascent. Long before he was charged with sex trafficking and racketeering conspiracy, he was associated with moments of violence and brushes with the law. Were they just lapses in judgment, or warnings that signaled a much darker side to his success? That's after the break. On April 11th, the amateur arrives in IMAX. I want to find and kill the people who murdered my wife. Critics rave the amateur is a tense, unpredictable ride. You're just not a killer, Charlie.

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Only in theaters at IMAX April 11th. Get tickets now. Hey, I'm Brad Milky. You may know me as the host of ABC Audio's Daily News podcast, Start Here, but I'd like to add aspiring true 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. On April 8th, the final season of the Handmaid's Tale arrives. This is the beginning of the end. And the revolution... What's happening? Rebellion begins. How many bodies are you gonna throw in the fire? When is enough enough? When there's no one left to fight. Where is June Osborn?

Rise up and fight for your freedom! The Hulu Original Series, The Handmaid's Tale. Final season premieres April 8th, streaming on Hulu. Final season premieres April 8th, streaming on Hulu. Before Sean Dinney Combs was crowned the new king of hip hop by Rolling Stone, he was a kid with a temper. In fact, that's why he says he got the name Puffy. He'd huff and puff whenever he got angry. Combs was born in Harlem, but grew up about 10 miles north in Mount Vernon, New York. Writer and music journalist Torre interviewed Diddy many times.

His father was from the streets of Harlem and he was very proud of the heights that his father rose to in that culture, but he's really a suburban guy. Diddy's father, Melvin Combs, was believed to be part of a heroin selling operation, and he was killed in what some think was a drug deal gone bad. His father died when he was three, and so his mother, Janice, became the center of his world. She clearly, or at least she from the stories was like, you know, whatever you want, you know, worship the ground you walk on and would take on a second job to be able to get him

something expensive that he wanted. And so the idea that Sean should have is starting to be inculcated there. His single mom sent him to private Catholic high school. He then went on to attend the prestigious historically black college, Howard University in Washington, D.C. in 1987. But he knew he wanted to be in the music industry. So he started working on convincing André Hirel, who at least I considered to be a godfather of hip-hop and R&B, to hire him as an intern.

Hirel was a former rapper but is better known for founding and running Uptown Records in New York City. In a 2017 Van Lee Fair interview, Diddy talked about why working with Horel was so important to him. I said I would clean your car, I would wash whatever, I'll do whatever. Because where he's at, that was the pulse of the music. Diddy wanted to be at the pulse of music too, and his determination to get the internship paid off.

He dropped out of Howard his sophomore year and started promoting rappers in New York City, really starting to build his music network while interning at Uptown Records. In 1991, he and rapper Heavy D organized a charity basketball game at the City College of New York. It was advertised as a chance to see New York City rap stars like Run DMC and Boyz II Men compete on the court. And people flocked to the game. It was clear, even then, that Diddy understood how to create and market an event everyone

wanted to go to. But he was young and inexperienced. The gym had a 2,700-person capacity, but almost 5,000 people showed up. As the crowd rushed to get in, 29 people were injured and nine died in a stampede. One headline from that day read, The Carnage at City College. Days later, a 22-year-old Diddy gave a press conference at the Plaza Hotel in Manhattan. He looked so young, so defeated. At one point, he put his hand over his eyes and nose as if he were overwhelmed and exhausted.

I would like to let the families of the victims know how deeply hurt we all are. That incident followed Diddy for years. In that same 1997 interview when Diddy was asked about capitalizing on Biggie's death, he was also asked to reflect on this City College stampede. I've gone through a lot. I've seen a lot of tragedies. I've seen a lot of death, you know, in my short time. And I don't know why.

Believe me, I ask myself the same question. Like, you know, why have I been chosen to see all of this, you know, death at such a young age? At the end of the day, I have to also live with the fact that, you know, I was throwing an event, trying to do something good and something bad happen. No criminal charges were ever filed for the stampede, fact that I was throwing an event trying to do something good and something bad happened. No criminal charges were ever filed for the stampede, but civil lawsuits from victims

and their families went on for years, directed at Diddy, Heavy D, and the City College of New York. A judge in one lawsuit filed by four victims found that Diddy, Heavy D, and the college were equally responsible for the injuries and deaths. Here's what really stands out to me about the City College Stampede. When it happened in 1991, Diddy was, as the New York Times put it, a largely unknown rap promoter. Writer and music journalist Dore says Diddy was buried in bad press.

Writer and music journalist Dore says Diddy was buried in bad press. It seemed that this young guy had been too reckless and building whatever promotion career that he was trying to build. And surely this would be the end of his career. But by 1999, some eight years later, when many of the lawsuits from the stampede were coming to an end, Diddy was a millionaire with a couple of Grammys. His career hadn't been stunted at all. This is the beginning of this sense of invincibility that he seems to take on. Some of that perceived invincibility came from his earlier success at Uptown Records.

He moved up pretty quickly from intern to executive. Torre says Diddy thrived because he was tapped into hip-hop at the street level. At the time, there was this thing going on in Harlem that we called Blend-a-Tapes. And if you were into hip hop, listening to R&B could be a bit of a stretch, right? It didn't really hit the same, but you love those singers. And so DJs started making tapes where they took the vocals from the singers we liked and putting them over hip hop beats.

He takes this idea that's already going on in the street and cleans it up and puts it with Mary J. Blige. And it is a revolutionary moment. -♪ You remind me of a love that I want to do. Is it a dream or is it stage double? Did he help turn Mary J. Blige and R&B group Jodeci into stars? But that success led to a power struggle

between him and his boss, Andre Harrell. So in 1993, Harrell fired his eager young protege. Andre says to him, you know, there can only be one lion in the jungle, and he fires him. But he let him take two rappers that Andre didn't know what to do with. Those rappers were Craig Mack and Biggie Smalls, and Diddy knew what to do with their talent. Justin Tinsley, the reporter from ESPN's Anscape,

says in particular, Diddy had a strong vision for Biggie. Diddy and Biggie were one of the biggest tag teams. Biggie came roaring out the gates with a single called Juicy, which, if you know Biggie. Diddy and Biggie were one of the biggest tag teams. Biggie came roaring out the gates with a single called Juicy, which if you know Biggie's story, he didn't necessarily want to record that song at first. And it was Diddy's insistence that basically forced him to record that song. And obviously the song became a hip-hop classic. It was all a dream. I used to read Word Up magazine. Salt and pepper and heavy D up in the limousine. As Biggie became one of the most famous rappers in the world, Diddy signed more artists to Bad Boy.

By 1997, the year Biggie died, Bad Boy had an impressive roster of talent, including The Locks, Mace, Faith Evans, and 112. There was a time when it was ubiquitous, his records. I remember multiple nights of being in a club, they're playing a string of bad boy records. You get in a cab to go to another club, the radio is playing bad boy records in the cab,

you get in the next club and they're playing bad boy as soon as you walk in. It was just everywhere. And it wasn't just about the music. Bad Boy's artists had an era-defining style, a look, baggy, bold, flashy clothes. They were really smart in that they followed the Motown playbook. There's a charismatic CEO who creates the brand and creates the image.

There's a brand image that links them all together and they're part of the culture. But after an incredible rapid rise to the top of the charts and cultural power, Bad Boy hit somewhat of a sophomore slump. There really wasn't much of an ability to create or recruit new superstars after that. In 1998 and 99, Bad Boy put out new albums by Faith Evans, Total, and 112. But initially, only 112's album was meeting

the high expectations for the Bad Boy label. What were those high expectations? The albums going platinum, selling more than 1 million copies quickly. Diddy's second album, Forever, was also not as successful as his first. Forever debuted at number 2 on the charts in 1999, but fell to number 13 within three weeks. He was nominated for a Grammy for the single Satisfy You featuring R. Kelly, but they lost to The Roots and Erika Badu's You Got Me. The label's revenue dropped significantly. Bad Boy Records was mostly riding on the

cloud and running off the royalties of its legendary earlier albums. Still very well known and cool, but kinda stalled. A cover story in the December 1999 edition of Vibe Magazine wrote that Sean Combs was fighting to prove he still got it. This was just two years after Rolling Stone had called him the new king of hip hop. And in 1999, Diddy faced setbacks beyond Bad Boys dropping sales. He got into more legal trouble. And I can kinda see Shug Knight's comments about Diddy wanting to be in music videos hanging over him. Because this legal trouble started with Diddy trying to control his image in a music video.

Diddy was featured on the rapper Nas's song, Hate Me Now. Which was so the puff vibe, you can hate me, but I'm gonna make you love me, and I'm never gonna stop. They were producing a music video to air on MTV, just as more people than ever were watching the network. So a lot of time and money was put into music videos. And the expectation was that millions of people would end up watching them. Nas and Diddy's music video was meant to be flashy, edgy and attention grabbing.

It depicted both rappers being crucified like Jesus Christ. But after filming, Diddy had second thoughts. And he called Nas and was like, can you kill the video? Let's have a whole new concept. And Nas was like, we could just snip you out of the part of the desert. Like, let's just do that.

And he called his manager, Steve Stout, who was like, no, we spent a million that. And he calls his manager, Steve Stout, who was like, no, we spent a million dollars on the video, we're not changing it. And also it's already at MTV, they're about to play it. They played the video, the original cut of the video with Puff in the desert as Jesus. He sees it in his office at Bad Boy.

He freaks out. He and some number of bodyguards, goons, went to Steve's office. Steve's in the middle of a meeting. They barge in and they start beating him up. Steve Stout alleges that Diddy punched him in the face and bashed his head with a phone. Diddy was charged with a crime of assault, but he ended up pleading guilty to a lesser non-criminal charge of harassment, a violation,

and was sentenced to a one-day anger management course. He and Stout reached a separate civil settlement out of court. It was all bad press for Diddy, but culture critic Jamila Lamuze says besides his reputation as a hitmaker, he had another source of perceived invincibility. He knew how to redirect attention and put his cool guy image back in the spotlight. In 1999, when Diddy was turning 30,

that meant getting headlines for a new relationship with It Girl actor and singer Jennifer Lopez. She had recently had her breakout role as a star of the Selena movie, played a glamorous queen in the music video for Diddy's song, Been Around the World, and now she was making her connection to Diddy and his music world official. It gave her some street credibility.

She's doing, you know, records with rappers after this relationship. They definitely heightened each other's celebrity quite a bit. They were a big couple. They were a very influential couple. The cover of Jet magazine read, Puffy Combs and Jennifer Lopez. Shope is his most talked about couple. Other headlines said, call it chemistry,

Jennifer Lopez and Puff Daddy. And Bright and Hot, superstar couple riding roller coaster romance. A couple days before New Year's Eve in 1999, the influential couple went to a club near Times Square. While they're in the club, there was a dispute with a guy named Scar, who's deceased now. Derek Parker is a retired NYPD detective who responded to the scene at the club.

I think money was thrown in his face, or money was thrown at Diddy or something like that. A shooting broke out, and three people were injured. Diddy and Jennifer Lopez fled the scene and got into a car. When they were pulled over, police say they found a gun in the front seat. It was a lot of chaos back then. When we went to the precinct, there were over 300 reporters outside. Two of entertainment's biggest stars spent much of this Monday after Christmas in a New York City police station. Jennifer Lopez and the rap mogul Sean Puffy Combs were held for

possessing a stolen gun. Prosecutors ultimately dropped the charges against Jennifer Lopez, but Diddy and his bodyguard were charged. Today's indictment on two counts of criminal possession of a weapon carry a possible 15-year prison sentence if Combs is found guilty. As the criminal case moved forward, news reports pointed back to the City College stampede of 91 and the attack on Steve Stout earlier in 99. And they began to ask whether Diddy had a pattern of causing violence.

Many are asking, does trouble find him or does he go looking for it? You can't be the great Gatsby in the Hamptons and John Gotti in Manhattan. Columnist Jack Newfield writes for the New York Post. He says the latest incident is merely the most recent event in a string of brushes with the law. There are those who say he's a target, he's a rich black man, he's an easy prey. I think it's the opposite. I think he's gotten away with almost murder. I think it's the officer. I think he's gotten away with almost murder.

Diddy and his bodyguard pleaded not guilty to the weapons charges and were ultimately acquitted at trial. But someone was convicted for the shooting. A young rapper from Belize named Shine, who Diddy had signed to his bad boy label. Shine had run out of the club that night with a gun in his waistband.

And some officers caught him, while others chased after Diddy and Jennifer Lopez. Shine was convicted of multiple assault charges, gun possession, and reckless endangerment. He went to prison for nearly nine years and was deported back to Belize after his release. He spoke to ABC News about the shooting and his relationship with Diddy last year.

Was Diddy a good coach? He was an extraordinary coach. He was able to bring the best out of me. Shine admits he had a gun and used it as the fight broke out, but he says that he shot it into the air, not at anyone. He thinks that Diddy should have stood up for him in court. Even now, he calls himself the Fall Guy. Taking the fall means not snitching, not getting your friends in trouble.

Even today, I wouldn't want to do anything to get anyone in trouble. So did anyone come to you and say, hey man, we need you to take this hit for Diddy? No, I did that out of honor and integrity. Do you regret that night? I am always remorseful that anyone got hurt, even if it wasn't for my gun, because according to the victims, it was Diddy that shot them.

But I don't regret defending myself because I wouldn't be here. Did you see any behavior then that indicated some of the allegations we hear about now? I never saw anything that's being alleged. I was incarcerated, so I don't know what this gentleman was doing. I don't know his lifestyle, But I could say someone that was prepared

to sacrifice his friend, his brother, his protege, someone that was prepared to have me sit in jail to totally destroy my career, destroy my life, rob me of my freedom, to be a participant in that. Of course, it doesn't surprise me that he would be accused of the atrocious things that he is, because what he did to me and my family was to me demonic.

Diddy's representatives told ABC News he categorically denies Shine's allegations, including any suggestion that he orchestrated Shine taking the fall for him. Shine became a politician in Belize, but his music career, well, that ended that night in 1999. But once again, Diddy's did not. Jamila Lemieux, the culture critic,

says the assault on Steve Stout and the shooting just didn't stick in most people's minds. He did a really good job of branding himself to middle America as the cool hip hop guy. His relationship with Jennifer Lopez was much more compelling, more tantalizing. The couple was a mainstay on red carpets and eventually Jennifer Lopez's fashion headlines drowned out the more negative press. There were two outfits in particular that really defied her tying with Diddy. One where she wears this all white outfit with this rhinestone bandana.

You know, she's supposed to look like a hood girl and he's by her side in a coordinating outfit. And then there was, of course, the famous Versace dress. That's a green and blue sheer dress she wore to the Grammys in 2000. It was so low cut, you could see her belly button. Diddy was by her side when she wore that, you know? So he was really there for the moment in which JLo becomes JLo. This is when she becomes JLo as opposed to Jennifer Lopez.

And this is when Sean, Puff Daddy Combs became Diddy. Something Diddy's really good at doing is rebranding himself, right? So those name changes often came on the heels of a scandal or something unscrupulous about him being reported. Then he comes back, new name, new album, new era, new image. After the break, his new image was all about being more than a rapper and record executive.

It was focused on being an all-around mogul, so an even more powerful and unavoidable, even more invincible. Hello, it's Robin Roberts here. Hey guys, it's George Stephanopoulos here. Hey everybody, it's Michael Strahan here. Wake up with good morning America. Robin, George, Michael, GMA, 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. By 2010, when Diddy was in his 40s, it was hard to believe he had ever floundered as a businessman.

Sure, his Bad Boy record label wasn't as hot as it was when it first started. But he still had a popular catalog of artists he helped make famous. And in the 2000s, Bad Boy put out new music by Boyz n the Hood, Mace, and Young Jock. Diddy also released an album of remixes of Bad Boy's songs that showed his deep connections in the music world. It included hit artists like Usher, Ludacris, and Missy Elliott. But Diddy knew the way to get really, really rich and stay powerful was to diversify his brand. It's what other rappers like Jay-Z were doing too. So by 2010, he wasn't just a music guy anymore. He had influence and

money in fashion, TV and alcohol. His wealth skyrocketed. His bad boy business empire, with Diddy at the center, is now worth an estimated $345 million. He seemed to encapsulate the word mogul. And that's why in 2010, ABC's Nightline profiled him for a segment called Modern Mogul. I was going to make the clothes that you would get dressed in, the fragrance you would put on, listen to the music that I produced, to buy the vodka that was in the club. Some people might think that's a form of megalomania.

That you would think that. A form of megalomania. That you would think that. A form of megalomania. Well, it could be. Is there anything you would not promote? I mean, how about diddy dog food? No, I wouldn't do diddy dog food. I don't know, make your dog yap to a rap or something. I wouldn't do diddy dog food.

You wouldn't do dog food. I mean, I would do what's organic for me. Like a rap or something. I wouldn't do Diddy dog food. You wouldn't do dog food. I mean, I would do what's organic for me. Like I love candles. I would do candles. I love jewelry. I would do jewelry that fits. I would do hotels. Whatever was in the realm of entertainment or lifestyle, a curator of cool, that's what

I'd do. Diddy was an early adopter of the idea that a celebrity should extend their reach beyond just one industry. And he proved to be really good at building a sprawling business empire. One of his first steps in becoming the curator of cool was launching his Sean John clothing line. The idea behind the brand was to introduce hip hop fashion

to a global audience. Music writer, Torre says Sean John was really successful. Did he even won the Council of Fashion Designers of America menswear designer of the year award in 2004? And it was a really interesting way to put him in Macy's, later Walmart with a t-shirt, but also in a boutique on Fifth Avenue, right?

So that he's able to sort of mass market and look upscale at the same time. Diddy got into another popular celebrity investment, the alcohol business, by partnering with Serac. He showed up in many of their ads. The newest addition to the Serak family, Summer Kalani. Limited edition. Jamila Lemieux, the culture critic, says Sirak was huge in building his wealth.

That relationship made him more money than he made in the music industry. As reality TV became more popular, diddy realized he could jump on the trend early and use it as an opportunity to reach an even wider audience. From 2002 to 2009, he produced and starred in the MTV show Making the Band. This was when MTV had a huge cultural influence, especially among young people. And at the time, MTV was starting to make the move from music videos to reality TV shows.

In Making the Band, he was looking for the next big hip hop group. And artists competed to be selected. Once they were selected, they'd get contracts to work with Diddy and release their music exclusively under the Bad Boy label. He'd only control their music and an exchange that'd get his mentorship and his connections. On the show, Diddy presented himself as a tough boss with high standards. He famously made competitors walk from Manhattan to Brooklyn to get him cheesecake from juniors. Singer and producer Donnie Klang was on Making the Band. Making the Band was Diddy would show up unannounced. It could be 3 o'clock in the morning,

which happened a couple of times. Wake us up out of our beds. We'd have to sing. And somebody was getting cut. Right then and there, in that moment, you're going back up, packing your suitcase, and you're walking out after being in a deep sleep in the middle of the night.

That sounds like the kind of stuff you'd expect from 2000s reality TV. On reality TV, people put on a persona. They played a character. He seemed to be playing the cutthroat boss, can't stop, won't stop, bad boy for life, to quote some of his music, who seemed to be insisting on high standards. But all these years later, with so many allegations against Diddy, you look back at that persona

and you think, was that TV? Or something darker? Singer and actress Dee Woods competed on Making the band 3 in 2005, and she was ultimately selected to be part of the winning group, Danny D.K. The day we were chosen, it actually fell on my sister's birthday. And so I immediately called her. And the first thing I said when she answered the phone, I was like, it's bad boy for life, baby. But in a 2025 interview with ABC News, Wood says Diddy was more than another reality TV

tough boss. She says he was a bully. There's a clip where he starts critiquing her body and asking if she's feeling thick. He goes on to warn her, you're like a burger away. Presumably what he's saying is, you're like a burger away from weighing too much. Although they weren't shown on air, Wood says that he kept going and going with the insults.

And I just had to bite my tongue and let somebody disrespect me in ways that I'd never imagined. Like, totally disgusting, totally just grotesque, like about the different parts of my body, you know, telling me to turn around. It was even to the point where one of the female camera operators told her crew to stand down, to power down, because she didn't feel comfortable airing

or filming that to be aired. Woods and four other women made up Danny King. She says they all were treated like pieces of meat by Diddy. Only seeing, only valuing you for your sex appeal. And in some of the environments, you know, it was even scary to be by yourself. You know, we'd walk with each other to the bathroom, stand in front of the door for each other. Did you ever see or hear of Diddy doing anything sexually inappropriate?

The inappropriate things that I witnessed were that of the messages that my group member received from him. And it was things that no figure of authority or employer or a man of his age should be saying to a young woman who also works for him. Did she turn down his advances? Yeah. Dee Wood says her bandmate, Aubrey O'Day, is the one who got those messages. Wood says it felt like Diddy had too much power for them to complain. He threatened us all the time about holding us in our contracts.

He threatened us all the time about shelving us. Shelving them meant not releasing their music, but also not letting them release it elsewhere. The music could just die on a shelf somewhere. meant not releasing their music, but also not letting them release it elsewhere. The music could just die on a shelf somewhere. She says Diddy also had the power to fire them. One day, Diddy called Dee Woods and Aubrey O'Day into a meeting. Dee Woods says he fired Aubrey and then turned to her. And it's like, and you, I heard you're not happy here either.

I don't want you here that you can get out. Knowing his power in the industry, she tried to be polite and leave on good terms. A lot of people were living in fear, living with scarcity mentality, and just trying to survive in their own way. Dawn Richard, another member of Danny Kane, filed a civil lawsuit against Diddy in 2024 and amended it in March of 2025. The lawsuit alleges that he withheld over a million dollars of her rightful wages and

royalties, made threatening statements, threw objects at her, and spoke to female contestants on making the band in a hostile manner, calling them bitches and hoes. She alleges that she witnessed Diddy arranging for dozens of young women and girls to be transported to his parties, where they were sexually violated by him and his guests. She also alleges witnessing his physical abuse against his then-girlfriend Cassie Ventura. In a letter to the court, Diddy's attorneys said they will move to dismiss this suit, calling it full of outrageous accusations. They're also arguing that Don Richard's claims are invalid because the statute of limitations on most of them has expired and she already released her claims against Sean Combs through a waiver she signed

in 2021. For Diddy, making the band served a couple of purposes. It gave him more artists to sign to his label, and it introduced him to a wider mainstream audience. Dave Chappelle even made fun of Diddy's MTV persona. And in my opinion, when Chappelle turns you into a skit, it's a sign you've become famous beyond your world. First y'all gotta walk to Queens and get me a sugar cookie. When Diddy was making all of his big business plays in the 2000s, he saw a chance to use his showmanship and MTV fame to break into politics, too. Just as rapper Andre 3000 and record executive Russell Simmons started Get Out the Vote

initiatives, in 2004 he started his own, Vote or Die. God has blessed me with a talent to be able to communicate to young people, young people and minorities. By the way, this was the same year he took a helicopter to his white party holding an original copy of the Declaration of Independence. His branding was in full force. To promote voter die, Diddy interviewed Barack Obama on MTV when he was running for the U.S. Senate.

Obama seemed to recognize that Diddy had real influence. Absolutely. Listen, you're a motivating force for young people all across the country. Your music moves people. You are your trendsetter. But part of what we wanna do is to make sure that we're setting a trend in terms of political participation.

When you wanna be the president of the United States, you call your man, call MTV. Even when it came to politics, did he seem to see where things were going? It's like he was always one step ahead, always able to outmaneuver a scandal, always able to find the next thing to keep him and his brand relevant. And culture critic Jamila Lemieux says

Diddy managed to create the perception that he was still a kingmaker in music. He always made a point of connecting with new, young talent. Diddy was an early mentor of Usher's. Usher lived with him when he was a young teenager, which people have a lot of questions about now, and he's talked openly about being exposed to too much. In 2016, Usher talked to Howard Stern

about living with Diddy. There were very curious things taking place. Uh-huh. And I didn't necessarily understand it. Uh-huh. You're a dad now. Would you ever send your kid to Puffy Camp? Hell no. See?

Usher ended up mentoring another young artist, Justin Bieber. And in 2009, Bieber also hung out with Diddy. Bieber shared a video of it on his YouTube channel. You know, where we hanging out and what we doing, we can't really disclose, but it's definitely a 15-year-old's dream. Today, those clips might make you ask, what were the curious things that Usher saw?

And what did Diddy think was a 15-year-old's dream? But back then, most people weren't asking whether there was a darkness to Diddy's mentorship of young artists. Diddy was just wealthy, fashionable Mr. Cool. Being connected to him, someone who seemed so central to music and culture, had to be a helpful thing. People are really overly impressed by men. We do not hold men to rigorous standards of behavior, particularly famous men, right? We don't take into consideration their relationship to women when we're judging their character. We don't take into consideration acts of violence

that they may have committed. You know, we look past those things when we like someone, when we like a man. Diddy had also spent years cultivating the idea that he was a representation of Black excellence. Here's the writer, Torrey, on what that meant. Black excellence was about pride, was about being extraordinary,

was about standing on the shoulders of the civil rights movement and the stuff our parents talked about, like, let's be even better. You know, it's like saying I'm rooting for everybody black, you know, and, you know, I mean, he was at least as far as the marketing, Puff was very much like, let's dress up, let's be stylish, let's be our best selves, let's be excellent. That idea of black excellence, of class, of prominence, was part of his brand. It's what made his success something to aspire to. He wasn't just a person, he was the idea of success itself.

I mean, he was interviewing Barack Obama just four years before he would be elected as the nation's first black president. Jamila Lamuse says that black excellence, that reputation, gave Diddy some real protection. There are a lot of black people who are resentful of years of discrimination and stereotyping and mythology that suggests that all black men are predators and all black men are violent and they're wanting to go against those stereotypes and go against those images, so much so that they're willing to sacrifice actual people, actual

victims and their experiences to protect these men and to protect the image of Black excellence that they may represent. -♪ Na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na na And this meant that anyone who crossed his path knew his power. Especially a young singer hoping to make it in a cutthroat world. Like Cassie Ventura. We began to see her more in the public as Diddy's girlfriend and less as the artist, Cassie. And yeah, he was just like yelling at us, cussing us out because she didn't want to have sex with him. And then he whisked her away again. [♪ MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFFECTS, MUSIC PLAYING, WHOOSHING SOUND EFF was written and produced by Camille Peterson, Vika Aronson, and Nancy Rosenbaum. Tracy Samuelson is our story editor. Associate producer, Amira Williams.

Production help from Shane McKeon. Fact checker, Audrey Mostek. Story consultant, Sweeney St. Phil. Supervising producer, Sasha Aslanian. Original music by Evan 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 Cohan is ABC Audio's director of podcast programming. Lor Mayer is our executive producer. Hello, it's Robin Roberts here. Hey guys, it's George Cephonopoulos here. Hey everybody, it's Robin Roberts here. Hey guys, it's George Stephanopoulos here. Hey everybody, it's Michael Strahan here. Wake up with Good Morning America.

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