Cheyenne Roundtree

As always, I hope that you're well and I really hope that you're enjoying your week.

Joining me for a coffee break today is award-winning investigative journalist Cheyenne Roundtree, whose book, Bad Boy for Life, is out now.

In 2025, Cheyenne covered Sean Coombe's criminal trial in real time for Rolling Stone, which included courtroom testimony from Cassie Ventura and a July 2025 verdict.

bad boy for life is a deeply reported account of sean coombs rise from bad boy records mogul to convicted defendant and draws on interviews with more than 100 sources many of whom are speaking for the very first time now i would usually say now sit back or go for a walk but instead grab a cup of coffee or tea and enjoy the conversation shine round tree welcome to the conversation coffee break

Oh, There's a bit of gameplay there, Cheyenne.

I can hear it from you.

Well, that just leaves me to say, Cheyenne Roundtree, thank you so much for joining me for this very long.

And I need to stick to the 30 minutes coffee break, but I keep going over.

... as far, as far as I can tell.

Also, Rolling Stone investigative reporter Cheyenne Roundtree talks about her new book, Bad Boy For Life, which tells the story of Sean Combs across the names he gave himself: Puffy, Puff Daddy, P. Diddy, and Love.

Plus, Justin Chang reviews the new film Your Mother, Your Mother, Your Mother, starring Mahershala Ali.

That's coming up on Fresh Air Weekend.

Justin Chang is a film critic for The New Yorker.

He reviewed Your Mother, Your Mother, Your Mother.

Coming up, investigative journalist Cheyenne Roundtree talks about her new book, Bad Boy for Life: The Rise and Fall of Sean Combs.

I'm Tonya Mosley, and this is Fresh Air Weekend.

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.

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.

Thanks for having me.