Pattern of Abuse: Inside Sean Combs' Documented History of Violence

Cheyenne Roundtree, an investigative reporter at Rolling Stone, was blindsided like much of the world when Cassie Ventura filed a civil lawsuit against Sean Combs in November 2023. The suit alleged that over a decade, Combs had beaten her, raped her, forced drugs into her system, and coerced her into sexual encounters with male sex workers. Roundtree had grown up watching them as a power couple—Ventura was a style icon, a talented woman living what seemed like an enviable life. Combs was the mogul, the music industry titan she knew from his records and his empire.

Combs and his legal team denied everything. They called the lawsuit baseless, riddled with lies, a blackmail attempt. Then they settled it for twenty million dollars. Within days, more women came forward. Joi Dickerson-Neal filed suit alleging she had been drugged and raped by Combs in 1991 when she was a student, and that he had filmed the assault and shared it. Anna Kane alleged that Combs and two others had gang-raped her in 2003 when she was seventeen. His team kept denying, calling the cases money grabs. But then a security video from a Los Angeles hotel in March 2016 surfaced—footage showing Ventura fleeing a room as Combs, wrapped in a towel, pursued her, beat her, kicked her, and dragged her back inside.

The video forced a shift. Combs's attorneys acknowledged the domestic violence but framed it as something locked in the past, a chapter closed. He had renamed himself Love, they said. He was a new person, a father figure. But the mounting lawsuits told a different story entirely. Over the next three years, Roundtree dug through archives, finding stories and police reports that had been lost to time, often because they existed only in paper form, never digitized. She spoke to people who had known Combs at every stage—as a boy in Harlem, a teenage intern, a producer, the founder of Bad Boy Records, a Grammy winner, a business mogul, and finally as an inmate. The lawsuits triggered a federal investigation. Combs was indicted. Now fifty-six, he is serving a fifty-month sentence for transporting people across state lines for prostitution.

Roundtree's book, Bad Boy for Life, traces the patterns and repeat behaviors, the rumors and run-ins that threaded through every reinvention of his identity. It begins in Harlem, where Combs's father, a gangster, was shot dead when Combs was a toddler. His mother, Janice, moved them to Mount Vernon, a suburb north of New York City. Childhood friends remember her as glamorous and determined, but also as someone whose discipline went beyond tough love, whose parties exposed young Combs to sexual activity at an early age. By the time he reached Howard University, something had manifested. At Howard, Combs was known for his drive, his style, his legendary parties. He later described a Romeo and Juliet romance there—a girlfriend whose parents pulled her from school because her grades had dropped from As to Bs. He spoke of the pain of their separation with romantic language, as if they were destined but kept apart by fate. Former classmates told Roundtree a different version: Combs was jealous and abusive. He had shown up at her dorm, called her outside, whipped her with his belt, and dragged her by her hair while horrified students watched from their windows. Decades later, when his attorney described his relationship with Cassie Ventura at trial, the language echoed—a great modern love story, forces keeping them apart.

The pages of Bad Boy for Life are dense with allegations, many from women who have since filed civil suits. Up to seventy lawsuits are believed to be moving through the system. Common patterns emerge: drinks spiked at one-night encounters, rape, the assault filmed, the footage shared. Other accounts describe Combs singling out a woman and pursuing her relentlessly, using any means necessary. "No is not a stopping point for Combs," Roundtree says. He was known for untamed rage, for assaults on girlfriends and on men he deemed rivals. Ventura had signed to his record label at nineteen, a model turned singer with a hit called Me & U and a ten-album deal. Combs pursued her despite the seventeen-year age gap. One of his assistants recalled him saying she was "very mouldable" and that he had "her right where I want her. She's young." He controlled every aspect of her life—her diary, her clothes, her hair, her nails, even her medical records, which went directly to his email. He tracked her menstrual cycle. Her career stalled. Though she recorded hundreds of tracks, Combs, as her boss, did not release them. Publicly, she was his "wife partner" for ten years. Behind the scenes, she never lived with him, never spent Christmas with him.

The relationship was dominated by what Ventura called "freak-offs"—coerced, multi-day, drug-fueled sexual encounters with male sex workers in hotel rooms. Every detail was micromanaged, choreographed, directed, watched, and filmed by Combs. Ventura was twenty-two when he first proposed the idea. She had no concept of how it could be arousing, but she wanted to please him. After the first one, she felt dirty but relieved that Combs was happy, that she had done something right. Hundreds more followed around the world with men she did not know. She felt disgusting, humiliated. When she tried to leave, Combs threatened to release the videos. In one exchange, she mentioned showing the world photos of her beaten face and body. "Release the videos also," he responded. Her life became a cycle of preparation, endurance, and recovery. In 2017, their final year together, she wrote to him: "That's why nothing gets done. Always healing." She officially separated from Combs in 2018 and filed her lawsuit five years later. When federal investigators approached her to build a criminal case, she handed over phones, iPads, video material, the names of sex workers, and other witnesses.

Combs was charged with racketeering conspiracy, sex trafficking by force, fraud or coercion, and transportation to engage in prostitution—laws developed to dismantle criminal networks like the mafia. The 2025 trial lasted seven weeks. Prosecutors argued that Combs used his business empire as a front for a criminal operation, relying on associates to force and intimidate women into freak-offs and to transport and supply drugs. The defense argued that what occurred did not constitute a formal criminal enterprise. He was acquitted of most charges. He was found guilty only of the clear examples where he paid male escorts to travel across a state line. Had they stayed within their states, he could not have been charged. Roundtree notes that the music industry has yet to have its #MeToo reckoning. Hollywood had one. Music never really did. R. Kelly is the only other high-profile musician now in prison because of abuse uncovered in that movement. Others have remained untouched by rumors and accusations. "Maybe it's because an artist is so singular," Roundtree says. "Those songs are our fondest memories. It's hard to give that up, to separate the art from the artist." Combs is set to be released in early 2028. He faces multiple pending civil cases, though his attorneys recently stopped representing him over unpaid legal bills. Roundtree believes he will want to tell his story and attempt a comeback. "He has had a microphone in his hand since he was in his early twenties," she says. "I don't think that desire to be loved and validated has gone away. There'll be a next chapter for Sean Combs."