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

Overview

In the premiere episode of The Rise and Fall of Diddy, hosted by Jesse Weber of Law&Crime, listeners are taken on a comprehensive journey through the meteoric ascent and turbulent decline of Sean Combs, famously known as Diddy. This episode delves deep into Combs' early life, his groundbreaking achievements in the music and business worlds, and the series of scandals and legal battles that ultimately tarnished his legacy. Through firsthand accounts, expert insights, and detailed storytelling, Weber paints a vivid portrait of a mogul whose ambition and influence reshaped hip-hop but whose personal life became mired in controversy.

Early Life and Foundations (00:00 - 04:08)

Jesse Weber opens the episode by setting the stage for Sean Combs' rise in the hip-hop industry. Born on November 4, 1969, in Harlem, New York, Combs faced tragedy early on when his father was killed in a drug deal gone wrong at the age of two.

Unnamed Contributor 1 (02:16): "His father was killed in a drug deal gone bad."

This loss left his mother, Janice Combs, to raise him single-handedly, instilling a sense of resilience and determination in young Sean.

Unnamed Contributor 2 (02:27): "His mother was a teacher's assistant. She was also a model. Very, very hardworking."

Despite the challenges, Combs excelled academically and socially. His charisma and hustle became evident during his high school years and further blossomed at Howard University, where he began hosting legendary parties that showcased his innate ability to bring people together.

Building an Empire (04:08 - 07:58)

After an internship at Uptown Records, Combs quickly ascended the corporate ladder, becoming a talent director by 1990. However, an unexpected firing at age 23 spurred him to establish his own label, Bad Boy Records, in 1993.

Unnamed Contributor 2 (04:15): "And then decided to start his own label, Bad Boy, which we know now and the label was widely successful."

One of his first major successes was signing Christopher Wallace, better known as The Notorious B.I.G., whose meteoric rise to fame under Bad Boy Records marked the beginning of Combs' dominance in the music industry.

Unnamed Contributor 3 (04:26): "From there, it just explodes."

Combs' keen eye for talent didn't stop with Biggie. He played a pivotal role in the careers of Mary J. Blige, Faith Evans, and Usher, positioning hip-hop as a mainstream luxury brand.

Unnamed Contributor 3 (05:43): "Sean Combs simply just elevated the culture of hip hop and R&B."

Beyond music, Combs expanded his empire into fashion, liquor, and media, launching ventures like his clothing line and Ciroc vodka, cementing his status as a cultural icon.

The 1999 Nightclub Shooting (07:58 - 12:21)

Despite his immense success, Combs' career was not without controversy. In December 1999, a violent incident at a Times Square nightclub thrust him into the legal spotlight. During a confrontation involving rival Christopher Wallace and Jennifer Lopez, gunshots were fired, injuring three bystanders.

Unnamed Contributor 3 (08:33): "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."

The ensuing trial in 2001 saw Combs acquitted of illegal possession and bribery charges, while his bodyguard was also cleared. However, a protege named Shine was convicted of reckless endangerment and assault.

Unnamed Contributor 3 (11:50): "Two acquittals, one conviction."

This incident exposed a darker side of Combs' empire, suggesting a culture of fear and intimidation.

Continued Reinvention and Early 2000s Success (12:21 - 16:43)

Post-trial, Combs rebranded himself from Puff Daddy to P. Diddy, signaling a new era. He continued to expand his business ventures, launching Revolt Media and signing new artists like Cassie Ventura.

Unnamed Contributor 2 (15:59): "Cassie was 19 years old when she met him."

Combs maintained his position at the pinnacle of the industry, seamlessly blending music with pop culture and ensuring his influence remained unchallenged.

Relationship with Cassie Ventura (16:43 - 21:41)

Combs' personal life, particularly his relationship with Cassie Ventura, became a focal point of his public image. Their relationship, marked by glamour and turbulence, showcased the complexities of balancing personal and professional lives in the limelight.

Unnamed Contributor 2 (17:56): "It became a pattern. The two would be spotted together, then rumors would surface of a split, only for them to reunite once again."

Their decade-long on-and-off relationship culminated in an amicable split in October 2018, followed by Cassie's marriage to Alex Fine in September 2019.

The Cassie Lawsuit and Unfolding Scandal (21:41 - 25:28)

The facade began to crack in November 2023 when Cassie Ventura filed a lawsuit alleging years of abuse, manipulation, and intimidation by Combs. This lawsuit not only revealed the tumultuous nature of their relationship but also ignited a series of similar allegations from other individuals.

Unnamed Contributor 1 (19:45): "I truly believe the downfall of Sean Combs is. And where it began was the Cassie Ventura lawsuit."

The lawsuit brought to light disturbing claims of physical, mental, and emotional abuse, as well as coercion tied to Combs' control over her career.

Unnamed Contributor 2 (20:34): "We had no idea at the time [of the lawsuit] the tumultuous nature of their relationship and how she was being abused physically, mentally, emotionally."

The public response was intense, with widespread support for Cassie and increased scrutiny of Combs' past actions. The settlement, achieved swiftly after the lawsuit was filed, remained undisclosed, further fueling speculation and outrage.

Unnamed Contributor 1 (23:51): "The lawsuit was filed on a Friday, and you heard by Saturday, the next day that the case had been settled."

Implications and Future Developments (25:28 - End)

The revelations from Cassie's lawsuit not only shattered Combs' pristine public image but also opened the door for federal investigations into his activities. The episode concludes with a preview of upcoming revelations, including an indictment charging Combs with racketeering, conspiracy, sex trafficking, and other serious offenses.

Jesse Weber (26:17): "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."

Notable Quotes

• Unnamed Contributor 2 (05:24): "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."

• Unnamed Contributor 3 (07:09): "He's known for being hands on with his artists and being active in their careers and also in their lives."

• Unnamed Contributor 1 (19:54): "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."

Conclusion

Episode 1 of The Rise and Fall of Diddy masterfully chronicles the duality of Sean Combs' life—his unparalleled success in the music and business arenas juxtaposed with the personal demons and legal challenges that ultimately led to his downfall. Through meticulous research and compelling narrative, Jesse Weber offers listeners a nuanced understanding of how power and fame can obscure darker truths, leaving a lasting impact on both the individual and the industry he once dominated.

Listen to More

To dive deeper into Sean Combs' complex journey, continue listening to The Rise and Fall of Diddy exclusively on Wondery+. Available on the Wondery App, Apple Podcasts, or Spotify. Start your free trial today by visiting Wondery.