How Cheyenne Roundtree Became An Essential Voice In The Sean Combs Case

If you’re Black and part of any group chat or text chain with a friend, you were likely sent a link to the Rolling Stone article ”Bad Boy for Life: Sean Combs’ History of Violence,” as soon as it ran on May 24, along with a series of exclamation points or some version of “holy shit,” or “finally.”
It’s not that reporting on Combs’ long, violent past is shocking. The Rolling Stone story was published days after CNN released a video from 2016 of Combs physically assaulting singer and then-girlfriend Cassie Ventura, and months after his properties were raided in connection to a federal investigation into allegations that include sex trafficking and sexual assault. That investigation also contained Ventura’s own lawsuit, first reported in The New York Times, from November last year, in which she accused Combs, A.K.A. “Diddy,” of rape and abuse — the first OMG moment in the Diddy/Black group chat journey.
Cheyenne Roundtree, who wrote the Rolling Stone piece with senior reporter Nancy Dillon, remembers the moment she heard about Ventura’s lawsuit all too well. It was right around her birthday and her impending nuptials, and she was in full festivities mode. But, as has often been the case when she’s had to step out of a party or other personal event to whip out her laptop, take a phone call for 10 minutes or return a text to a source, the news had stolen her attention.
“I think it was just like that breath — I think everyone probably had it — like, oh my God,” Roundtree remembered on a video call from her home in Brooklyn in August.
Ventura “has been a celebrity, but she’s kind of been on the periphery,” she said. “We don’t know so much about Cassie, but we knew that she was Diddy’s partner. She just kind of has always been that; almost like a wife, a partner that stays in her own lane.”
Ventura and Combs broke up in 2018, and in 2019 she married personal trainer Alex Fine, with whom she now has two children.
“So then when the truth came out — this is what this woman says [she was] experiencing for, like, a decade, and she was 19 years old,” Roundtree said of the lawsuit, which detailed Ventura’s relationship with Combs. “She still couldn’t get away from it. I was just like, there’s so much material here.”
Ventura and Combs settled the lawsuit almost as quickly as it was reported, within 24 hours. To Roundtree, that “was unprecedented, crazy.” It also motivated her to jump on the phone to start getting people to talk.
Roundtree’s fearless reporting on film, television, music and pop culture, often focusing on some of the ugliest sides of the entertainment industry, has made her an essential voice in journalism.
She investigated the decades of alleged misconduct and abuse leading up to the headlines about Combs over the last year, doing interviews with Combs’ past colleagues, friends and former classmates at Howard University, among others.
A nuanced case like Combs’ demanded that level of effort. But it was also key that Roundtree take the story because most of the women Combs allegedly victimized are Black women —and that a Black journalist like Roundtree report on them with complexity and sensitivity.
Part of why Black folks’ text chains were blowing up last May, after the Rolling Stone story was published, was because social media users had been lamenting the way many Black media sites had been covering Combs’ case following the raids in March.
“Diddy really had Black media outlets in the pocket the way they refuse to report on his alleged crimes,” one X user commented on March 27 above a link to a story from Black Enterprise headlined, “Diddy May Be Down Bad, But He Did Secure His Bag.”
That same month, The Root shared a since-deleted social media post that likened the harassment allegations against Megan Thee Stallion to the accusations against Diddy. Britni Danielle, senior editor at Andscape, was among many that spoke out against that framing: “I’m sorry. Who even works at @TheRoot these days? This is an unacceptable tweet.”
Still about midway through her own investigative piece at the time, Roundtree remembered seeing some of this sentiment online. To her, the comments pointed to a larger truth about the dismal state of journalism, and particularly Black media, today.
“We keep seeing sites like the Root getting snapped up and devalued,” Roundtree said. “And unfortunately, some of these publications sometimes don’t have the funding” to allow a journalist the time: “I needed six months to even come close to getting to where we were.”
Born in Chicago and raised in Dallas as the oldest of six children (“Lots of noise,” she told me, describing her childhood home with a laugh), Roundtree has been inspired by the “dogged determination” of other investigative reporters.
That wasn’t always the case, though. She once had dreams of being a fashion editor at a women’s magazine a la “Sex and the City” or “Gossip Girl,” following internships in the fashion closet.
“I was untangling jewelry,” she recalled. “And I was like, ‘I think I want to write. I don’t think I want to play with accessories anymore.’”
Years later, as an entertainment reporter at The Daily Beast, she worked on stories that would have three or four sources. But immersing herself in other journalists’ investigations compelled her to do her own.
“We just read a lot of deeply reported pieces with court documents and multiple sources,” she said. “And it’s just reporting that shows [the course of] time and how the truth comes to light. And it’s not easy. It’s not overnight.”
So as Roundtree saw the discussion around the coverage of Combs in Black media continue to swirl online in March, she, too, was “disappointed” that Black legacy media, including one magazine she repeatedly referenced for her own piece, fell short.
“I was sitting there kind of like — Vibe has 20 years of coverage of Bad Boy,” Roundtree said, referencing the magazine’s plethora of articles on Combs’ record label and its artists.
“That was such a good resource for me,” the journalist continued. “And I was like, this should be there. The Source, all those magazines that put [Bad Boy] there — they should be leading coverage on this. But if they aren’t, I will take it on at least at Rolling Stone.”
It wasn’t an easy task. Combs was, as he boasted for years, one of few young Black entrepreneurs in the music industry, and he helped catapult the careers of some of the hottest Black artists of the ’90s and early ’00s, from Mary J. Blige to Jodeci to Biggie Smalls. As Roundtree’s piece details, he was also one of the most influential Black celebrities, helping to shift mainstream culture to the point where people across the racial spectrum were interested in his music, style, merchandise and everything else he attached himself to.
“He was the first OG celebrity influencer that has all these products,” Roundtree added. “And I really wanted to get at that — [Combs] is important. He has shaped so much of our culture — our music, our fashion senses, even what we were drinking back in 2000.”
CÎROC, Combs’ branded vodka, sold for a pretty penny at the club in 2003, even among broke college students. Because it was Combs’, and so it was cool.
Many of those within Combs’ orbit were afraid to come forward about things he’d done to them or to those they knew because they didn’t “want to contribute to this icon’s downfall,” Roundtree said.
That was even despite their understanding of how their stories fit into a larger portrait of Combs. Roundtree’s piece delicately yet steadfastly unravels the layers of power, importance, humanity, abuse and “hustler mentality” inherited from his late father.
Anyone who’s been paying even a little attention to Black stan and online celebrity culture knows that negative stories about powerful Black people, even well-reported pieces like Roundtree’s, can come with repercussions.
Journalists can experience some of that resentment from their own readers. But that sense of being targeted can feel exponentially worse for people who have already survived abuse. It makes sources, including some of those featured in Roundtree’s piece, hesitant to come forward at all.
Particularly since Combs had not been indicted on any charges while Roundtree was reporting her piece, the sources she spoke to “were really scared of that backlash within the community, of just not waiting until the evidence all comes out,” she said. “But they knew their piece of the story and they saw how it fit into the bigger picture.”
That meant that Roundtree had to build trust with her sources, just as she’d done for other articles she’s worked on, like stories about the history of abuse allegations against Jonathan Majors and the allegedly toxic set of “The Idol.”
Some of the sources for the Combs report, she told me, went back and forth on whether or not to participate several times, even up until the release of the CNN video. She had to prove that, as a Black woman and a fan, this role also wasn’t comfortable for her.
“My approach was just talking that through with them and coming from that same background of like, ‘Look, I don’t want to be here either,’” Roundtree said. “‘We both are put in these positions and you have something to say and I’m here to hear it.’”
And that communication became a two-way street, Roundtree said: They developed “trust in me to help tell that story in a delicate way without it seeming like a pile-on, and to tell that story with nuance.” The journalist is also writing a book “about the Bad Boy founder’s rise and fall, the power of celebrity and unpacking how we arrived at this unprecedented moment.”
I asked Roundtree how she feels about the idea that fans sometimes consider journalists’ reporting on their faves to be an attempt to take them down.
After graduating from the University of Missouri in 2016, the same year former President Donald Trump took office, Roundtree was thrown into an already chaotic digital media space. She pointed to his election as one reason why journalists are targeted online for reporting on the news.
“We have grown up in the past eight years since Trump came in [to the White House] that the media is out to shape a perception of someone that’s not fair,” she explained. “And if you’re being targeted, then it’s a conspiracy.”
Social media has only further divided people, Roundtree said. “It becomes easy to buy into that narrative of when something comes out against someone, [saying,] ‘It is a conspiracy’ or ‘Why did it take so long?’”
In this era of online misinformation, though, she puts a ton of work, research and effort into providing the truth to her readers.
“We’re in a time where people are forgetting the role that journalists play,” she said. “We’re not out for getchas and gotchas. But I feel people have now lost or misunderstand the vetting process and the time and effort and trust that goes into doing investigations like this, and how much work goes on behind the scenes.
“It’s months of reporting, dozens of people with documents and the whole shebang to bring this to fruition,” she said. “It’s just an easy thing to say, ‘Oh, this is just a takedown, this is a conspiracy.’”
Or imply that the journalist behind that piece is a Black person acting alongside the establishment to bring a Black man down. That’s a kind of response Roundtree has received for her investigations of people like Combs, Majors and Kanye West.
“There’s been a lot of discussion of like, ‘Oh, did they get the DEI hire to cover this?’” she said. “And I just felt like these are very important men of our culture, of the bigger music industry society — and especially [in the] Black community.”
While Roundtree said that she is “very conscious” about the stories she chooses to cover, she also holds herself to the same journalistic standards each time ― even if not everyone online respects that. She said “maybe 10-15%” of the reaction she gets is trolling, depending on the story.
“It was very kind of, ‘Well, why is she covering this? She’s Black,’” she recalled of another response to her work. “Wouldn’t you want a member of the community that understands the struggles and the sensitivity with that to be someone that is investigating — that is, talking to the sources, who predominantly are Black, about a Black figure and icon?”
How Roundtree deals with trolls also speaks to how she navigates being a journalist who uses social media for her work: “I have all my blockers on — all that stuff,” she told me.
Roundtree said she received some pretty crucial advice from her editor at Rolling Stone that’s helped mitigate trolling.
“I love to do what my editor calls ‘show your work,’ and lay out exactly how many people I’ve spoken with — who they are, their level of seniority, how long I’ve spent on this,” she said, referring to how she often introduces her work on social media and in the articles themselves. “To preemptively show like, this isn’t something that came together quickly in the past week.”
Another thing she said it’s important for readers to understand is how many people it takes to produce an investigative piece like the one on Combs.
“This is a dozen people across different departments, all contributing to this larger picture,” she added.
Combs has now been indicted on sex-trafficking and racketeering charges and was taken into custody on Sept. 16. He pleaded not guilty. On Sept. 24, Roundtree reported that a woman claimed the media mogul and his former bodyguard raped her in 2001, the 11th person to accuse Combs of sexual assault.
The Diddy discourse has fueled a bevy of new theories spreading online about how many people knew about Combs’ misconduct and for how long.
“There’s so many things that we don’t know that I was just like, let’s just use everything that we do know now as kind of like a prelude for what’s to come,” Roundtree said of her May story. “How do we kind of now make sense of this person who we thought we knew?”
That’s really what Roundtree’s piece gets to: It doesn’t tell the reader what to think. It supplies them with information that they need to develop an informed perception about Combs on their own.
Her Combs story, she said, is “recontextualizing the past and helping define who he actually is,” Roundtree added. “That’s what I came away with — I think I know him better now, or his true self.”
But in the age of cancel culture, when unsavory details about a celebrity often turn fans away from their work, the fact that Roundtree has uncovered new, inflammatory information about figures like Combs, West or Majors doesn’t mean that she no longer consumes their art.
“Obviously the music industry has its faults and it has a lot of misogyny, especially with hip-hop and from its infancy,” Roundtree said. “I feel like we have so many more female rappers in the game. And I still love hip-hop.”
In fact, she listened to Bad Boy Records hits all throughout the process of writing the Combs story in order to further immerse herself into his art. But that wasn’t the only reason why.
“It’s good music,” Roundtree said. “And it’s a reason why it’s a leading genre today and why so many people love it. So, that just doesn’t go away because of one person.”
Still, it’s important to know more about the people behind the music, she said.
She felt the same way going into her investigation of alleged toxicity on the “Queer Eye” set following interior designer Bobby Berk’s departure, as a fan of the show and of reality TV.
“This is such a feel-good show on Netflix that has brought many people to tears,” she said. “What’s happened?”
While Roundtree doesn’t claim to be trying to examine how to make Hollywood safer, she said that accountability is her mantra. She also seeks to expand the definition of abuse, so that her readers are better informed.
“It isn’t just confined to sexual abuse,” she said. “There’s harassment, toxic work environments, retaliation and blackballing. It’s about kind of widening the scope of what we think of as abuse and applying it through different sectors and different portions of it.”
Her work also provides a deeper understanding of what internal investigations inside the workplace even look like. “How can we be more transparent?” she asked. “Who is HR serving? There’s just a lot of ways for us to be better.”
Since her pieces have brought several allegations of misconduct and misogyny and other toxicity in Hollywood to the forefront, I asked what stays with her after writing those kinds of articles. For Roundtree, finishing a piece often comes with a better understanding of humanity, flaws and all.
“It’s that kind of duality of — there are really awful things that people do, but the strength that people [have who] come forward, and the empathy and sympathy that they have for, sometimes, their own abusers, really sits with me,” Roundtree continued.
“Talking with people about how they came out the other side” gives her hope, she said, in a job that can be very bleak at times. “A lot of people are doing work in their own lives and communities to prevent that [misconduct] from happening again.”
And in the months following Roundtree’s reporting, Black media has been amplifying the pivotal question: Will this usher in a Black #MeToo movement? They’re asking in no small part due to Roundtree’s influence.
Consider supporting HuffPost starting at $2 to help us provide free, quality journalism that puts people first.
Can’t afford to contribute? Support HuffPost by creating a free account and log in while you read.
Thank you for your past contribution to HuffPost. We are sincerely grateful for readers like you who help us ensure that we can keep our journalism free for everyone.
The stakes are high this year, and our 2024 coverage could use continued support. Would you consider becoming a regular HuffPost contributor?
Thank you for your past contribution to HuffPost. We are sincerely grateful for readers like you who help us ensure that we can keep our journalism free for everyone.
The stakes are high this year, and our 2024 coverage could use continued support. We hope you’ll consider contributing to HuffPost once more.
Already contributed? Log in to hide these messages.
Need help? Visit RAINN’s National Sexual Assault Online Hotline or the National Sexual Violence Resource Center’s website.