Investigating the system that protected Sean “Diddy” Combs

SPEAKER_1 (0:00)

This is Fresh Air.

Tonya Mosley (0:00)

I'm Tonya Mosley. For 30 years, Sean Combs was one of America's most visible men. He helped shaped Mary J. Blige's early sound, signed the notorious BIG., and built Bad Boy Records into a hip-hop powerhouse. Then he turned himself into a brand, rapper, clothing mogul, actor, celebrity host. He even got the world to call him by a new name every few years. My guest today, Rolling Stone investigative reporter Cheyenne Roundtree, examines whether those reinventions also gave Combs a way to outrun the scandals that came before. A note to listeners, this conversation includes descriptions of sexual violence, drug use, and other adult subject matter.

Combs is now serving a four-year federal prison sentence after being convicted on two counts of transporting people for prostitution.

Jurors acquitted him of the more serious charges of sex trafficking and racketeering conspiracy. The case followed a 2023 lawsuit by his former girlfriend, Cassie Ventura, who accused him of years of physical and sexual abuse. One assault she described was later captured in hotel surveillance footage aired by CNN.

In 2024, Roundtree and her colleagues published a six-month investigation into Combs' history of violence. Her new book expands that reporting, drawing on more than 100 sources, along with police and FBI records, court documents, messages, and emails. Her book is called Bad Boy for Life, The Rise and Fall of Sean Combs. Cheyenne Roundtree, welcome to Fresh Air.

Cheyenne Roundtree (1:42)

Thanks for having me.

Tonya Mosley (1:44)

Cheyenne, so much of what you found, it's so interesting, it was in plain sight. And yet, many people still would not talk to you.

For the people who were afraid to talk, what were they afraid of? What did they tell you?

Cheyenne Roundtree (2:00)

There was a portion of people that did feel fear of retribution, that he wouldn't be able to influence their careers or life.

After the criminal trial, a lot of people also felt that all of this effort had been put into this investigation, into this criminal trial. And at that point, they just didn't see the point of speaking further on it. So it was a mixed bag of different reasons for not wanting to talk about what they knew or what they saw.

Tonya Mosley (2:30)

Two ideas about Sean Combs continually showed up in pop culture pretty early on. Number one, that he was a tyrant, and also that questionable things happened at his parties. And I want to play two examples. The first is from Scary Movie, which came out in 2000 So this is 26 years ago.

And in this clip, Regina Hall plays a high school student named Brenda, and she's talking with her friend Cindy, played by Anna Faris. Let's listen.

SPEAKER_1 (3:03)

My friend Sean had a pool party this summer.

Tonya Mosley (3:05)

Sean.

SPEAKER_1 (3:06)

You know, Puff Daddy.

Anyway, everybody was drinking Christelle champagne, and then it started to get wild, and people was getting freaky in the pool and stuff. I look over and there was your girl getting bucked wild in the jacuzzi.

Tonya Mosley (3:19)

Okay, that was from Scary Movie from 2000 And now I want to play a second example. This is from MADtv in 2008, and it's a spoof of Hannah Montana. Let's listen.

SPEAKER_4 (3:32)

Anyway, we get to P. Diddy's mansion, and Lance Armstrong and Matthew McConaughey are smoking a joint with Amy Whitehouse. Oh my gosh! Anyway, Diddy says, Hey Hannah, why don't you make out with Amy? God, gross! I know!

But P. Diddy told me to, and he's P. Diddy. The next thing I know, Matthew McConaughey brought in a stripper, I get a lap dance from her, P. Diddy caught it all on his camera phone, and now it's on the Internet.

Tonya Mosley (4:07)

That last clip was from Mad TV back in 2008

Even by 2000, when that earlier scary movie joke appeared, there were already warning signs. A record studio manager had banned Combs after complaints about his behavior toward women, and people at Howard said they had saw him beat up a girlfriend with a belt outside of her dorm. There are also other instances of reports out there around stolen handguns left behind by his entourage during tours. How much of Combs' behavior was kind of like an open secret within the industry?

Cheyenne Roundtree (4:47)

It seemed to be this just kind of background music to whatever he was doing. I think the spectacle of P. Diddy, Puff Daddy was bigger than these incidents that were popping up along the timeline with him. And he was able to overshadow any of these accusations, any of these lawsuits that came up or police reports of minor infractions. And it just kind of kept getting bigger and bigger. And it was one of the things that really surprised me throughout my reporting was the amount of 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 put on it.