"You have to point out these are the things that people were willing to look past because he was so charismatic, because he gave people great opportunities..."
Cheyenne Roundtree
Investigative journalist Cheyenne Roundtree joins Nadine Matheson to discuss her debut book Bad Boy for Life, a comprehensive look at the rise and fall of Sean "Diddy" Combs. Drawing on three years of reporting, over 100 interviews, and six weeks sitting in the federal courtroom, Cheyenne breaks down what the public saw versus what was happening behind closed doors, from the Cassie Ventura lawsuit to the criminal trial, the emotional complexity of the victims' testimony, and the broader questions about accountability, fandom, and institutional protection.
Cheyenne Roundtree is an investigative reporter at Rolling Stone. She co-authored the magazine's landmark investigation into Sean "Diddy" Combs alongside colleague Nancy Dillon, published shortly after the hotel surveillance video of Combs attacking Cassie Ventura became public. Bad Boy for Life is her first book. Her work focuses on long-form investigative reporting, and she has spent nearly three years covering the Combs story from the initial allegations through the federal criminal trial.