Diddy: Did He Do It? The Sex Crimes Trial of Sean "Diddy" Combs

With the Diddy trial on pause for Juneteenth, Nate Oliver dives deep into the powerful RICO law at the heart of the government’s case. What does racketeering really mean, and how has it toppled mobsters, cult leaders, and celebrities before? Nate unpacks the history, the stakes, and the prosecution’s strategy—connecting the dots from John Gotti to R. Kelly to Diddy’s own courtroom drama. As the city buzzes and the world watches, this special episode explores how prosecutors build a criminal enterprise case, what the defense is fighting to prove, and why RICO could decide Diddy’s fate. To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus [http://caloroga.supportingcast.fm/].   For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus [http://caloroga.supportingcast.fm/]. You also get 25+ other shows on the network ad-free!

Courts are closed for Juneteenth and yesterday court was adjourned as a juror called in sick. With no news to report we bring you this special edition of another case capruring the country's attention. Garrett Fisher brings you another special edition as Karen Read walks free after being acquitted of murdering her Boston police officer boyfriend. From a snowy January night in 2022 to Wednesday's dramatic courthouse celebration, we unpack three years of conspiracy theories, alleged police corruption, and social media hysteria. Did a biased investigation target an innocent woman, or did a flawed case let a killer escape justice? With a fired state trooper, "Free Karen Read" crowds, and unanswered questions about John O'Keefe's death, this case exposes the messy intersection of power, public opinion, and the pursuit of truth in modern America. To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus [http://caloroga.supportingcast.fm/].   For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus [http://caloroga.supportingcast.fm/]. You also get 25+ other shows on the network ad-free!

As the prosecution nears its dramatic close, jurors witness the most explicit “freak-off” videos yet—footage that matches weeks of harrowing testimony from Jane, Cassie Ventura, and others. With digital trails, encrypted messages, and financial records tying Diddy and his staff to a web of abuse, the courtroom is gripped by tension and emotional testimony. Outside, the media circus and dueling crowds underscore the trial’s cultural weight. Nate Oliver unpacks every revelation, every strategy, and every moment that could decide Diddy’s fate as the defense prepares to take the stage in America’s most-watched trial. To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus [http://caloroga.supportingcast.fm/].   For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus [http://caloroga.supportingcast.fm/]. You also get 25+ other shows on the network ad-free!

Day 32 delivers the most explicit evidence yet as the jury watches graphic “freak-off” videos pulled from Diddy’s own devices—bringing weeks of testimony to life in the courtroom. Prosecutors connect the dots with texts, emails, and financial records showing a web of payments, drug deals, and meticulous logistics behind the scenes. Former assistant Jonathan Perez details cash drops, the infamous Gucci pouch, and the pressure to keep secrets, while new evidence reveals efforts to bribe and intimidate witnesses. As the defense insists it’s all a consensual “swinger lifestyle,” Nate Oliver breaks down every jaw-dropping moment from a day that could define the entire case. To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus [http://caloroga.supportingcast.fm/].   For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus [http://caloroga.supportingcast.fm/]. You also get 25+ other shows on the network ad-free!

As week seven dawns, Nate Oliver recaps five days of bombshell testimony and spectacle. Jane’s harrowing account of coercion, violence, and survival reaches its breaking point under fierce cross-examination, while Diddy’s former assistant and a federal agent reveal the secret logistics and staggering evidence behind the “king nights.” Outside, Kanye West’s surprise visit and a juror’s dismissal turn the courthouse into a media circus. With new witnesses on deck and the stakes higher than ever, Did He Do It? sets the stage for another pivotal week in America’s most-watched trial. To become a premium subscriber (no ads and no feed drops) visit caloroga.com/plus [http://caloroga.supportingcast.fm/].   For Apple users, hit the banner on your Apple podcasts app which seays UNINTERRUPTED LISTENING. For Spotify or other players, visit caloroga.com/plus [http://caloroga.supportingcast.fm/]. You also get 25+ other shows on the network ad-free!