Listen Now: Law & Crime’s The Rise & Fall of Diddy
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For decades, Sean Combs was hip-hop's reigning mogul, the mastermind who redefined what it meant to have fame, fortune, and dominion over the music industry. But as Combs reached new heights in music, fashion, and business, allegations of misconduct and abuse began to surface, casting a dark shadow over his legacy.

I'm host Jesse Weber, and in The Rise and Fall of Diddy, we'll uncover how Combs built an empire that shaped a generation while navigating a trail of scandals, lawsuits, and criminal allegations. We'll explore the intersection of power, fame, and accountability in the life of a man who once called himself a bad boy for life.

Will his empire survive or is this truly the end of an era? I'm about to play you a clip from the first episode of The Rise and Fall of Diddy, which is available exclusively on Wondery Plus. Join Wondery Plus in the Wondery app, Apple Podcasts or Spotify. Sean Diddy Combs and Cassie Ventura had first crossed paths in 2005. Cassie was 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.

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 relationships.

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. 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.

Sean Combs trial is currently slated for May 2025. And wherever this story goes, law and crime will be there. So make sure to follow the Rise and Fall of Diddy show page and come back in January 2025 for all new weekly episodes covering every twist and turn of the case available exclusively for Wondery Plus subscribers.