Introduction

As the music industry grapples with the legacy of Sean ‘Diddy’ Combs, a new chapter of his life is unfolding—one filled with accusations of power abuse, manipulation, and violence. In the wake of Diddy's recent arrest on September 16th for charges of racketeering and sex trafficking, the charges echo the allegations made by his ex-girlfriend, Cassie Ventura, who filed a lawsuit last year accusing him of years of abuse.

Since then, more lawsuits have followed, shedding light on a much darker side of Diddy’s life behind the fame.

Part one of the series focuses on the beginning of Diddy's rise to power and the first major blow to his public image: Cassie Ventura’s lawsuit.

A History of Control and Abuse

For decades, Sean 'Diddy' Combs wielded his power to manipulate, control, and abuse those around him. Whether it was through his business dealings or his personal relationships, a pattern of coercion, intimidation, and violence started to take shape. Behind the public persona of a music mogul who helped launch the careers of some of the biggest names in the industry lay a man determined to maintain control at any cost.

Born in Harlem in 1969, Sean John Combs was raised by his mother, Janice, in Mount Vernon, New York, after his father, Melvin, was murdered in a drug-related incident. This event, happening when Diddy was only two years old, is said to have deeply shaped his life and his drive for success.

Diddy attended Mount Saint Michael Academy and later Howard University, where he quickly became known for his outsized personality and ambition. While still at Howard, he snagged an internship at Uptown Records, where he worked his way up to becoming a trusted right-hand man to CEO Andre Harrell. His rise at Uptown was fast, but his reputation for clashing with colleagues was already forming.

But the seeds of Diddy’s problematic behavior were sown long before his public success. As early as his time at Howard, reports have surfaced of controlling behavior and violent outbursts. According to multiple sources, including a Rolling Stone investigation, there were incidents of Diddy being abusive towards women even then, including one particularly alarming story of him beating a girlfriend with a belt outside a dorm.

The Rise of Bad Boy and the Cracks in Diddy's Empire

In 1993, Diddy’s trajectory took a sharp turn after he was fired from Uptown Records following a tragedy at a charity basketball game he helped organize, which resulted in the deaths of nine people. Diddy’s reputation took a hit, but it also marked the moment he would truly come into his own as a mogul.

Later that year, after securing a $10 million deal with Arista Records, Diddy launched Bad Boy Records. It wasn’t long before Bad Boy became synonymous with the sound of the ‘90s, thanks to breakout artists like Craig Mack and The Notorious B.I.G. Yet, as Diddy’s star rose, so did the whispers of his violent and controlling behavior behind the scenes.

Kirk Burrowes, a former business partner of Diddy’s, recalled witnessing an incident in 1994 where Diddy physically assaulted a woman in the Bad Boy offices. While this incident didn’t make headlines at the time, it was emblematic of a pattern that would soon become impossible to ignore.

The East Coast vs. West Coast Feud: Tupac, Biggie, and Diddy's Role

By the mid-90s, Diddy’s influence extended beyond music, feeding into the infamous East Coast vs. West Coast rap feud. While Diddy admired Tupac Shakur, their relationship quickly soured after Tupac was shot in New York and publicly accused Diddy and Bad Boy of setting him up. Tensions escalated after the release of Biggie Smalls’ track “Who Shot Ya?” in 1995, which Tupac took as a direct taunt.

Tupac responded with the venomous “Hit ‘Em Up,” and the feud spiraled out of control, with both Diddy and Suge Knight stoking the fires. The feud ended in tragedy with the murders of Tupac in 1996 and Biggie in 1997, but it solidified Diddy’s role in one of the darkest chapters in hip-hop history.

Capitalizing on Biggie’s Death

In the wake of Biggie’s murder, Diddy was publicly devastated. However, behind the scenes, the death of his closest collaborator became a business opportunity. Just two weeks after Biggie’s death, Diddy was already pushing for his posthumous album Life After Death to be a commercial success. The album debuted at number one, selling 700,000 copies in its first week.

Diddy’s focus on capitalizing off Biggie’s legacy didn’t stop there. When Rolling Stone offered a cover story to Bad Boy after Biggie’s death, Diddy made it clear that he wanted to be the one on the cover—not Biggie. This move, while shrewd from a business perspective, left a bad taste for many who expected Diddy to take a backseat in the wake of his friend’s death.

The Relationship Between Cassie and Diddy: Control, Manipulation, and Abuse

Cassie Ventura and Diddy met in the mid-2000s when she was just 19 and signed a ten-album deal with Bad Boy Records. At the time, Cassie was a rising star, with her hit single “Me & U” climbing the charts.

Diddy, then in his late 30s, was not only Cassie’s boss but also a figure of overwhelming power in the music industry. According to Cassie’s lawsuit, he used this power to manipulate and control her from the beginning. Diddy’s pursuit of Cassie wasn’t about romance—it was about domination. He quickly pushed her into a romantic relationship, despite both being involved with other people at the time. Their relationship, which would span over a decade, was riddled with manipulation, coercion, and violence.

Cassie’s Lawsuit: The Dark Side of the Glamour

In November 2023, Cassie filed a bombshell lawsuit under the Adult Survivors Act in New York. Here are some key allegations from the lawsuit:

• Forced Drug Use and Sexual Assault: Diddy allegedly forced Cassie to take drugs, including ecstasy, to control her. According to her, these instances often led to sexual encounters where she was too incapacitated to consent.

• Physical Abuse and Isolation: The lawsuit outlined several incidents of physical abuse. In one shocking example, Diddy allegedly stomped on Cassie’s face in a car after a party in 2009, then continued to assault her when they arrived at his home. Cassie’s injuries were severe enough that Diddy kept her in a hotel room for a week to prevent anyone from seeing the bruises. This type of isolation was a frequent tactic he used to control her and hide the evidence of his violence.

• Voyeurism and “Freak-Offs”: Perhaps one of the most disturbing allegations was Diddy’s practice of what he called “freak-offs”—drug-fueled orgies where he forced Cassie to engage in sexual acts with other men while he watched. He not only pressured her into these situations but also recorded them without her consent. According to the lawsuit, Diddy would frequently arrange these events in hotels across the country. Cassie was often given drugs and alcohol to the point of incapacitation during these events.

• Sex Trafficking Allegations: Cassie’s lawsuit also included claims of sex trafficking, alleging that Diddy coerced her into recruiting other people for these “freak-offs.” Diddy even involved his staff in arranging these disturbing encounters, turning his employees into complicit enablers of his behavior. Cassie was forced to participate and facilitate these sexual encounters, which is at the heart of the sex trafficking charges.

• Emotional Manipulation and Fear: Beyond the physical and sexual abuse, Cassie described how Diddy emotionally manipulated her throughout their relationship. He controlled every aspect of her life, from her career to her friendships. In the lawsuit, she detailed how he constantly monitored her, controlled her finances, and used intimidation to keep her from leaving.

The Beginning of the End

Cassie Ventura’s lawsuit was the spark that ignited a firestorm of allegations against Diddy. As more victims come forward, it’s clear that the empire he built was founded on control and fear. In the next part of this series, we’ll explore the other lawsuits that have followed and how Diddy’s carefully constructed legacy is now crumbling under the weight of these accusations.

Cassie’s story is just the beginning. What once looked like an unshakeable empire is unraveling piece by piece, revealing a much darker reality behind the man who once seemed to have it all.