Sean Combs, the music mogul known as P. Diddy or Puff Daddy, is currently in federal prison, serving a 50-month federal sentence on two counts of transporting people for prostitution. Combs' 2025 trial centered in part on so-called "freak-offs," with witnesses testifying to days-long, drug-fueled sexual encounters involving his girlfriends and male escorts that Combs directed and often filmed. (Combs and his lawyers deny the civil and criminal allegations. They are appealing his convictions.)
Rolling Stone investigative reporter Cheyenne Roundtree says that while the trial created a media frenzy at the time, rumors had swirled for years about Combs' abusive behavior.
"It seemed to be this background music to whatever he was doing," Roundtree says. "One of the things that really surprised me throughout my reporting was the amount of little things that were well documented, either in the press, newspapers or little police reports, that just disappeared, went away, and there wasn't really much mainstream attention."
Over his career, Combs shaped the sound of many artists, including Mary J. Blige and the Notorious B.I.G., and he built Bad Boy Records into the label that carried hip-hop into the American mainstream. Roundtree's new book, Bad Boy for Life: The Rise and Fall of Sean Combs, examines how the mogul remained so powerful, despite decades of warning signs and allegations. She theorizes that Combs' adaptation of different nicknames provided him with a fresh start, a way to leave the scandals that came before behind.
"The biggest shift we saw was when he went from Puff Daddy, Puffy to Diddy, which came after the criminal trial in 2001, when he was accused of carrying a firearm into a crowded nightclub where people were injured," Roundtree says. "That was a turning point for him, kind of being this mogul business-type figure versus then just this hip-hop music executive."
Roundtree describes Combs as a "gatekeeper" to culture in New York City in the late 1990s and early 2000s. His annual Labor Day party in the Hamptons, in which guests were instructed to wear white, became one of the hottest social events of the era. Ultimately, Roundtree says, Combs' power and success insulated him from consequences and allowed him to mistreat his own employees.
There just seemed to be these consequences for trying to do what was right, for trying to exit, and it just enabled a culture of silence.Cheryenne Roundtree
"His employees were being subjected to witnessing domestic violence, they themselves were being threatened or felt like they were being threatened, that they would be blackballed if they spoke out about what they were witnessing," she says. "There just seemed to be these consequences for trying to do what was right, for trying to exit, and it just enabled a culture of silence."
Roundtree believes that Combs remains focused on controlling his own image, even while in prison: "He is planning a doc of his own and his own comeback story. ... I have no doubt that eventually, whenever he is released, that he will come forward and he will say everything he has to say over these past few years."
Bad Boy for Life is based on interviews Roundtree conducted with more than 100 sources, along with police and FBI records, court documents, text messages and emails.
Interview highlights
On how Combs allegedly leveraged power — and created a culture of silence
He was able to kind of leverage these connections of going to a cool party, controlling this guest list, that it's not just music people that wanted to be invited to, it was power brokers, it was models, it [was] actors. ... He was able to leverage [those connections] into business deals later on, and to be this guy that everyone wanted to be in his good graces so they can have fun.
And I think one of the big things about these "white parties," obviously in hindsight, they've become really questioned and scrutinized, but the people I spoke to, at least for those first early years, it was this fun-time place. And yes, people were drinking and things might've gotten a little bit crazy, but it was all done at first under the guise of just having a good time and letting your hair down with people in your social circle. And later on, that became more called into question and there [were] civil lawsuits filed that claimed that that's where [people] were sexually assaulted. But in the beginning, it was just this idea of people coming together to have a time.
On Combs' relationship with Cassie Ventura
Before she got into a relationship with Combs, [Cassie] was a successful model. I think her friends said that she was making about a quarter of a million dollars a year, which was back in 2008, 2007. So for a 19-year-old girl, that is plenty of cash at the time. And after that she gets involved with Combs, [and] there seems to be a lot more of a financial dependency, or at least Combs inserting himself into her finances. He got her an apartment that was closer to where he lived and closer to the Bad Boy offices. He began paying for more things and treating her to trips. And eventually it seemed that she became totally dependent on his financial giving and also her career was tied to what Bad Boy was allowing her to release. ...
From afar, people thought of them as a power couple, and behind the scenes, Cassie alleged that she was trapped in a cycle of domestic violence and sexual abuse and that she had tried to leave this relationship multiple times, but she kept physically sometimes being dragged back into it. ... Cassie testified at the criminal trial last summer, and she said it was impossible to count the number of times that she was physically abused. She just said it was too often, and it happened frequently enough that other people around her could also kind of allude to different times that they witnessed over a 10, 11-year period.
On how Combs allegedly controlled Ventura's music career
Sources told me that she was constantly working on music, that she was trying to get an album release to follow up and she always had aspirations of continuing her music career. But her relationship with Combs resulted in the deliberate stalling of singles [and] of albums, that he would weaponize his power over her career to stop those albums coming out. I have a source that told me, essentially, [if] they were in a fight, "OK, your show's off. You're not getting your album. This isn't going to come out." And it speaks to why the public never saw it again.
On the abuse Combs' employees witnessed or experienced
People were stepping in ... to facilitate their boss' sexual life. They had to clean up towels with blood, sometimes different bodily discharges and baby oil. And I think that's not a very great workplace to be in, but that was their job. And I know the lines blur [with] personal assistants to high-powered people, but still this was all supposed to be a job in their career, and they had aspirations to work on music, or to get to know more ins and outs of the industry. And their life was revolving around supplying him drugs, or helping him clean off disgusting hotel rooms, or keeping their boss' domestic violence of his girlfriend a secret.
On whether or not Combs has expressed remorse
There was an admission of remorse. Specifically, whenever the video came out of him attacking Cassie in the hallway of a hotel, he posted on Instagram an apology and said that he was so sorry that he sought therapy and that he has worked to be a better man since that moment in 2016. The only other time was when he was found guilty of those two counts [of] transportation to engage in prostitution. And he spoke to the judge directly, and he said he is sorry for everything. Specifically, said an apology to Cassie and to Jane [another accuser] for what he had put them through, for not knowing the harm that he was causing them emotionally. But I should add on the other fronts, he has denied almost every other accusation against him, and he has not expressed remorse for any of the larger elements of artists that have come forward that said they felt that their careers were put by the wayside. He has not apologized on those kind of personal affronts to people.
Anna Bauman and Susan Nyakundi produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Jacob Ganz adapted it for the web.
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