The Rise and Fall of Diddy - The Crown and The Consequences: 1

Episode Date: December 4, 2024

Sean Combs: an unstoppable mogul with a talent for spotting stars and a history punctuated by allegations and legal battles. We unpack his transformation from a record label visionary to a cultural icon, and the whispers that began to tarnish his legacy. How did the golden boy of hip-hop become synonymous with scandal? Listen to The Rise & Fall of Diddy exclusively on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts, or Spotify. Start your free trial today by visiting www.wondery.com/shows/the-rise-and-fall-of-diddy--NEW EPISODES JANUARY 2025 - Sean Combs’ trial is currently slated for May 2025 and wherever this story goes, Law&Crime will be there. Follow The Rise & Fall of Diddy page and stay subscribed to be the first to know when new episodes drop.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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He was hip-hop's reigning mogul, the mastermind who redefined what it meant to have fame, The mastermind who redefined what it meant to have fame, fortune, and dominion over the music industry. From discovering legendary talent to dominating the charts, P. Diddy built an empire that not only shaped the sound of a generation, but also set the standard for success. He lived a life that many could only fantasize about. Luxury, influence, and power at his fingertips. But with the crown came the weight of its burdens. Behind the glitz and glamour, whispers of scandal began to swirl, stories that followed him for years unchallenged, until they could no longer be ignored. How did the man who revolutionized hip-hop and culture also become the focal point of so many allegations? Diddy's life is a paradox. To the public, he's the doting father,

proudly by his children's side as they carve their own paths. Yet behind closed doors, the lawsuits and accusations paint a darker portrait of a man who allegedly wielded his power with intimidation and control. So, how did we get here? I'm Jesse Weber, and this is the Rise and Fall of Diddy. Sean Combs, now known to the world as Diddy, was born on November 4, 1969, to Melvin and Janice Combs in Harlem, New York City, a neighborhood buzzing with life, culture, and resilience. But by the age of two, his life had been marked by an indelible tragedy. His father was killed in a drug deal going bad. The loss left his mother, Janice, to raise him alone. With his father gone, The loss left his mother Janice to raise him alone.

With his father gone, she became his guiding light. His mother was a teacher's assistant. She was also a model. Very, very hardworking. Against the backdrop of Melvin's tragic and senseless killing in the tough streets of Harlem, they relocated to Mount Vernon, a quieter suburb of New York, in search of respite from the challenges Harlem

presented. He went to an all-boys Catholic school. He worked really hard at a young age. He worked as a newspaper boy. He had various jobs. Very hardworking young man since the beginning. In high school, Sean stood out for his charisma and hustle. But it was in college where he began to shine in a different light. At Howard University is when he started throwing these parties. And Diddy was always the life of the party. From what we hear, he would dance. People knew who he was. He was a popular guy. So he became really famous on campus as well from throwing these parties. Combs parlayed his knack for bringing people together and creating memorable experiences into what soon became the hallmark of his career. So eventually he obtained an internship at Uptown Records.

At Uptown, he quickly rose in the ranks. By 1990, he's working as a talent director for Uptown Studios. And that's where he really gets to kind of like his first dive into the music industry. And from the start, he was a wunderkind. He saw the way the music industry operated and how to be successful in the industry. But when the 23-year-old was unexpectedly fired from Uptown, he got a new idea. He decided that instead of following someone around, he would make his own way. And then decided to start his own label, Bad Boy, which we know now. And the label was widely successful.

In 1993, Bad Boy Records was born with a bang. He signs this Brooklyn kid that I think at the time not a lot of people knew about, but we all know to be the Notorious B.I.G. Christopher Wallace, a.k.a. Biggie. From there, it just explodes. This partnership was electric. Biggie became a superstar almost overnight, and Bad Boy was soon releasing chart-topping hits. He just knew how to spot talent, and that's how his own bad boy business begun.

Diddy was a marketing genius. He knew how to sell people, how to sell the music. And that really helped him. It really helped him learn how to package an artist, know what looks right, what doesn't look right, how to sell the music, and how to put the music together. It's funny, there's this famous Diddy lyric, I don't write rhymes, I write checks. And that was Diddy. You know, he wasn't back there producing and making beats. He didn't even, you know,

write some of his rhymes that he was on. But he had this eye for knowing what worked and putting it together. Artists like Mary J. Blige, Faith Evans, and Usher would all pass through his orbit. Through Bad Boy, Diddy was shaping not just music, but an entire cultural moment. He took hip-hop from the underground to the suburbs and turned it into a genre that redefined mainstream appeal. If you're thinking big picture, previous to Sean Combs, rap, R&B, hip-hop was always kind of gritty. It wasn't mainstream. It wasn't considered like a luxury brand. But Sean Combs' kind of rise to fame is that he made this all mainstream. He made this

into a luxury brand, the music, the culture, the genre. Sean Combs simply just elevated the culture of hip-hop and R&B. But Combs' vision didn't stop at music. It started off as a record label and obviously expanded to him having a clothing line, a recording studio. He got into the liquor business. You know, everybody knew Diddy wanted you to drink Ciro rock. That's where he was making more of his money, actually, was off of his material empire. For Combs, each new business was more than a profit opportunity. It was a way to extend his influence. And as it turns out, his luck in the music business struck in every direction he took. He was literally the top of the world when it came to music, entertainment, alcohol, anything that he touched. He had the Midas touch.

By the mid-90s, the kid from Harlem had become the unmistakable king of culture, and he had a new name to mark this shift, Puff Daddy. In an industry where image often matters just as much as talent, Sean Combs' ability to blend artistry with a carefully crafted persona was paramount to his success. He's known for being hands-on with his artists and being active in their careers and also in their lives. He also believes that the industry itself is not just about whether or not you can sing or you can rap, you can dance, or you can act.

It's a persona that you must have. He recognized early on that if you make yourself someone that people want to be, then they'll support you and they'll buy your music and they'll buy your clothing line. And he's realized that if he makes himself out to be someone that people think they want to be, if he lives the life that people think they want to live, where it's glamorous, you're flying around, you're on yachts, you dress nice. He has exquisite taste, and he created this culture of success,

and that really furthered his success in the music industry. He had built an empire, one that tapped into the aspirations of millions and reshaped the very definition of success in the entertainment world. But it didn't come without a price. The problem is when you have that culture and you don't have people telling you no, or you have people kind of chasing you around, you don't have parameters and guidance. And it just seems to get more and more extreme.

The rumblings became more than just hearsay when in the winter of 1999, gunshots rang out from a nightclub in Times Square. So December of 1999, Sean Combs, his then girlfriend J-Lo or Jennifer Lopez, their bodyguard and a young and up and coming rapper by the name of Shine, who is also a protege of Sean Combs, all go to a nightclub. The way this story goes, and according to some of the victims who were shot, there was a dispute that occurred between these people. The altercation began when a patron, Matthew Scar Allen, allegedly threw money at Combs, leading to a confrontation. Combs leading to a confrontation. During the ensuing chaos, shots were fired, resulting in injuries to three bystanders, including Natanya Rubin, who was shot in the face. Now, this is all conjecture, but the story is always that Jennifer Lopez is the individual who had a gun in her purse that brought it into the nightclub and handed it to Sean Combs. And according to at least one of the three victims that were shot,

Sean Combs is the one that shot that person and caused all of this to happen. Now, they leave the nightclub. There's a bit of a chase. Police stop the vehicle where Sean Combs and J-Lo and the bodyguard are all in, as well as Sean, and a gun is found in the vehicle. But who did the gun belong to? J-Lo was quickly not prosecuted.

They're DP, declined to prosecute. So she's out of it. The others weren't as lucky. Sean Combs, the bodyguard, and Shine all go to trial. But this wouldn't be the last time he would find himself in legal trouble. The 1999 shooting was the first big legal battle that we saw Diddy go through. At the turn of the millennium, Sean Puffy Combs found himself in the spotlight, but not for his music or business ventures. This time, it was for a high-profile trial

that would test his public image and shake the hip-hop world. The discovery of the gun in the vehicle after the nightclub shooting led to serious allegations against Combs, including illegal possession of a firearm and bribery. I came here today just to tell the truth, so hopefully we can get down to the bottom of this. The charges against me are 100% false, and hopefully due to time, we'll start to see that. Despite his claims of innocence, prosecutors all alleged that Combs had tried to persuade his driver to claim ownership of the gun, a charge he firmly denied. Jennifer Lopez, though initially taken in for questioning, was released without charges, and a relationship with Combs would end shortly after the incident. The trial began in early 2001 and was closely followed by the media, with cameras flashing outside the courthouse each day as Combs arrived in sharp suits, his every move scrutinized, often appearing alongside his infamous legal representation, Johnny Cochran.

How y'all doing this morning? doing this morning. We're going to win this trial. The facts are going to set Mr. Combs free because he's not guilty here. And that's all that matters is the facts. In court, Combs maintained his innocence, insisting he had nothing to do with the weapon or the violence that night. Shine, however, was not so fortunate. He admitted to firing shots in self-defense, a claim that didn't save him from a conviction. The bodyguard and Sean Combs acquitted. Shine convicted of reckless endangerment, assault on the first degree, possession of a weapon, but acquitted of an attempted murder. Shine ends up doing just shy of a decade. Two acquittals, one conviction. That's the thing about Diddy. There's a lot of speculation. The urban legend is that Diddy was the one who shot

her in the face, but Shine ended up going to jail for it. There's a culture of silence, and it's starting to become apparent. It may have been a victory for Combs legally, but the trial left its mark. The events of that night and the scrutiny that followed showed the world a different side of the hip-hop mogul. His reputation as a successful, untouchable businessman had taken a hit. But the blow didn't sting for long. The 99 club shooting was one of those things where it's like as quickly as it came up, it went away. Yes, there was a trial that lasted for a week. I think it was sometime

in 2000 or 2001. But what was going on with Sean Combs musically, I think really ate up most of the headlines. Just a few months prior to the shooting in August of 99, Sean Combs had come out with his second album. In 2001, he came out with his third album. He started picking up artists that he wasn't really associated with in kind of like the early 90s and the 90s. He went more into like pop culture. Like you started seeing a lot of the ushers and the Justin Bieber-esque type singers collaborating with Sean Combs. And so as he started to become more and more mainstream, it seemed like that 99 shooting really fell by the wayside. So I think just by the amount of news and positive news that was out there, that kind of rebranded him more so than the

allegations in the 99 shooting that he was ultimately acquitted of. After the trial, Combs changed his name yet again. He went from Puff Daddy to P. Diddy, so a bit of rebranding there as well. Into the 2000s, Diddy continued to reinvent himself, launching the Revolt Media Network and expanding his business empire. Yet the controversies persisted. Prior to Diddy's legal drama, it seemed on the surface that he was pretty squeaky clean, a hard worker, a businessman, a mogul. But there were rumblings of certain elements of how he deals with conflict. But for the most part, there were no severe legal actions against Diddy or any severe allegations against Diddy up until the early 2000s.

against Diddy up until the early 2000s. While he continued to build his empire, his name became entangled with allegations that hinted at a volatile and sometimes aggressive side. Stories emerged about altercations and lawsuits involving disputes with individuals both inside and outside the music industry. Then, in 2007, another public incident put Diddy back in the headlines. He was accused of assaulting a man during a scuffle outside a Hollywood nightclub. While he denied the allegations and the case didn't lead to formal charges, the event was a reminder of the bad energy that seemed to follow him.

Diddy's pattern of disputes and altercations raised questions about his temperament and his entourage, with some arguing that his relentless pursuit of success left little room for boundaries. The legal battles and allegations of the 2000s illustrated the tension between the carefully crafted image Diddy projected and the reality of a life often steeped in conflict. Diddy projected and the reality of a life often steeped in conflict. A harsh reminder that his rise to the top wasn't always as smooth or glamorous as it appeared. Diddy was an icon who seemed larger than life, but he was not immune to the consequences of fame and power. Following this turbulent time, in 2006 he pivoted back to growing his ever-expanding empire, time. In 2006, he pivoted back to growing his ever-expanding empire, including signing new artists like Cassandra Ventura, more popularly known as Cassie. Sean Diddy Combs and Cassie

Ventura had first crossed paths in 2005. Cassie was 19 years old when she met him. 19 years old when she met him. Diddy instantly saw in her star power and raw talent. So Cassie was signed to his label, Bad Boy Records, and released her debut album under the label. Me and You was a huge song for Cassie. Long Way to Go, another huge song for Cassie. So she's in this world, you know, as a teenager, essentially, trying to navigate putting out music.

The young artist was undeniably talented and beautiful. And as the public would later learn, she caught Diddy's attention in more than just the business sense. As her notoriety grew, so did her relationship with the then 36-year-old Diddy. Initially, it just looked like a business relationship. Later on, there were rumblings that there was a romantic relationship going on. By the late 2000s, rumors of a romantic relationship between Diddy and Cassie were widespread. Though they kept things low-key at first, their chemistry was hard to ignore. Cassie, nearly 20 years Diddy's junior,

seemed inseparable from him, joining him on glamorous vacations and at high-profile events. What's up, man? Tell me about what you're wearing. This is Nora Tooboo, and it's French designer. And I'm wearing Rick Owens and some Louboutin shoes. Yet the relationship was never simple. Despite their many public appearances together, the two were rarely forthright about their bond, keeping the public guessing about their status.

But they did not, in fact, become public until some years after they met. Now you're in a relationship with a man with a lot of power and money. Soon, though, trouble became a mainstay in their paradise. Throughout the 2010s, Diddy and Cassie became known for their tumultuous relationship. There were rumblings during the time when they were together that the relationship was not that solid because Diddy would be seen out with other women. And they were on and off. Diddy's lavish lifestyle and public persona as a bachelor clashed with Cassie's desire for commitment. After a decade, there's no ring, there's no children.

So you're starting to wonder what is going on with that relationship. And that was kind of the sentiment from the public. During their time together, Cassie would sometimes retreat from the spotlight, leading fans to speculate that they had broken up. It became a pattern. The two would be spotted together, then rumors would surface of a split, only for them to reunite once again. Cassie, who remained signed to Bad Boy for much of this time,

often seemed caught between her career and the relationship, with Diddy's power and influence looming large over both. Cassie and P. Diddy officially broke up in October 2018. After a decade of an on-and-off relationship, they finally parted ways, with reports indicating that the split was amicable. Shortly thereafter, Cassie began dating Alex Fine, a personal trainer whom Diddy had previously hired for her. Cassie and Fine quickly became serious, getting married in September 2019, but they kept most of their major milestones under the radar. but they kept most of their major milestones under the radar. She had a baby with her personal trainer,

and the public knew nothing of their relationship. It appeared Cassie had finally found the man of her dreams. She blissfully faded into obscurity and out of the limelight, refraining from any public discussion of Diddy. That was until November 2023. I truly believe the downfall of Sean Combs is and where it began was the Cassie Ventura lawsuit. The lawsuit filed in New York hours before a bill called the New York Survivors Act was set to expire, alleged years of abuse, manipulation, and intimidation during her relationship with Diddy. But it didn't have to go this far.

She came to him before she filed that lawsuit and said, I believe I was wronged by you. And she gave him an opportunity to settle the case before she brought the lawsuit. And I know that both Sean Combs' attorneys and Cassie's attorneys were in conversation and talks to see if they can resolve the lawsuit, but they were not able to. The details in the November filing were horrifying. We had no idea at the time the tumultuous nature of their relationship and how she was being abused physically, mentally, emotionally, how she did allegedly suffer at very high lengths his abuse and was forced to have sex with male sex workers and tapes. We didn't know that she was being humiliated sexually in the way that she was. We didn't know what she was going through until the lawsuit.

It also revealed unsettling behavior in the acute aftermath of their breakup. She did try to date other people, but this air of intimidation was there that we didn't know of at the time, but we learned from Cassie's lawsuit that she did try to date rapper Kid Cudi and that Diddy blew up his car and told her that he was going to blow up his car.

Things were starting to add up, demystifying what ultimately led to the couple's final split. So it's this intimidation that she was suffering for years, which would explain the back and forth. All the while, this person has the power to continue your career or take your career to the next level. So that's the coercion part, right? That's the manipulation part. I have this power. I have this money. You're signed to my label. You've released music under me and you have to do certain things in order to continue to get those privileges. The lawsuit sent shockwaves through the media and fans alike. For years, Cassie had been known as Diddy's quiet, loyal partner, and many saw her as a poised, reserved figure in the background of his

glittering life. But the lawsuit painted a vastly different picture of their relationship, one filled with allegations of abuse, manipulation, and control. Almost overnight, headlines plastered Cassie's claims across major news outlets, sparking a media frenzy that only intensified with every new revelation. It also deepened the public's curiosity about what had really gone on behind closed doors. Social media platforms were flooded with comments, debates, and messages of support for Cassie. Many people expressed anger, disbelief, and sadness, while some even questioned the authenticity of the allegations,

While some even questioned the authenticity of the allegations, highlighting the complex and controversial nature of Diddy's longstanding public image. As the story developed, media outlets brought in experts and former industry insiders to discuss Diddy's influences, personality, behavior. Conversations began to emerge about power dynamics in the music industry and how fame can sometimes mask darker personal truths. Cassie's story sparked broader discussions on celebrity relationships, with many pointing to the pressures and potential abuses that can go unseen in high-profile partnerships. So what did Diddy have to say in response? Well, initially, Diddy denied it. But faced with the possibility of a trial, Diddy made a quick counter.

The lawsuit was filed on a Friday, and you heard by Saturday, the next day, that the case had been settled. The terms of the settlement were not publicly disclosed. He did pay her. And there's speculation about what the number was. I also heard there was an NDA that was signed. But I think for Cassie, that was sort of a vindication because she could have had a successful music career. We don't know that. But she got in a relationship with her boss, essentially. And then based off the allegations in her lawsuit, that didn't end well. And she was abused instead and forced into things that she never dreamed she would do. The settling of the lawsuit is vindication for her to know, OK, you've acknowledged you heard my story.

And now you've decided to, you know, come to terms with it on my terms. And with the settlement, Cassie again retreated to heal and resume life with her family, putting the nightmare behind her. She did release a statement, but we have not heard from her. And I don't think that was her intent. She didn't want to tell us or broadcast what happened to her. She wanted to be properly acknowledged and she wanted closure for what she experienced in her life. Her final exit from the spotlight may have been silent, but the revelations that followed sparked a much louder conversation. One that would reverberate around the world.

That opened up Pandora's box because then everyone saw what she alleged he did to her and had similar stories. And that's when I think people started to realize this is a pattern. And those lawsuits were saying I was a part of this process where he recruited people to come to parties. And at those parties, there were illicit things happening and things that I did not want to happen to me happened. I was drugged and I would wake up in the morning and things would be done to me or I would be naked in a bed with other people. And I never gave consent because I was drugged and wasn't aware. And once all of

those lawsuits started happening after the Cassie lawsuit, it was only a matter of time before the federal investigators got involved because it was just too much activity around Sean Combs. On the next episode of The Rise and Fall of Diddy, he's hit with more lawsuits, and this time he won't walk away unscathed. My name is Damian Williams, and I'm the U.S. attorney here in the Southern District of New York. Today, I'm announcing the unsealing of a three-count indictment charging Sean Combs with racketeering conspiracy, sex trafficking, interstate transportation for prostitution. This has been a Law & Crime production. I'm your host, Jesse Weber. Our executive producer is Jessica Lowther.

Our writer and producer is Cooper Maul. Our editor is Anna McClain. Additional writing and guest booking by Lisa Fite and Julie Wheeler. Legal review and fact-checking by Elizabeth Voulay. Key art design by Sean Panzera. And special thanks to our contributors, Dave Arenberg, Brian Buckmeyer, Mina Lona, Dante Mills, Tracy Walder, and Bernarda Villalona. Follow Law and Crime's The Rise and Fall of Diddy on the Wondery app. You can listen to more episodes exclusively and ad-free right now on Wondery+. Join Wondery in the Wondery app,

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