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Welcome to the first edition of Diddy on Trial.

About a month from today, the embattled hip-hop mogul Sean “Diddy” Combs will stand trial on federal charges of racketeering conspiracy, sex trafficking and transportation to engage in prostitution. The sprawling case has all but ended the career of a music industry kingmaker who earned riches and fame as an artist, producer, manager and record executive. He’s pleaded not guilty.

You’ve probably seen a lot of headlines about Diddy over the last few years — a federal investigation, a raid on his homes, a wave of civil suits alleging rape and sexual abuse. Diddy has denied all the allegations. The upcoming criminal trial opens up a dramatic new chapter. We’ll guide you through the proceedings — expected to run about eight weeks — and keep you updated on the most consequential moments, with insights from our team inside the courtroom and the reporters and correspondents who have been following every twist and turn. 

In daily editions starting May 5, when jury selection is set to begin, we’ll highlight the most important narratives, the most compelling testimony and the most significant revelations. You’ll get exclusive access to analysis and insights from senior legal correspondent Laura Jarrett, entertainment correspondent Chloe Melas, national reporter Janelle Griffith and reporter/producer Adam Reiss, who will provide color from inside the courthouse. Plus, every Friday we’ll recap the week’s major moments.

In the lead-up to the trial, you’ll see this newsletter in your inbox at least once a week. We’ll bring you up to speed, dive into each side’s legal strategy and introduce you to the key players, including the attorneys, the judge and the possible witnesses. 

In today’s edition, Janelle and I take a closer look at the lawsuit against Diddy that laid the groundwork for this blockbuster trial.

— Daniel Arkin, national reporter

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How did we get here?

Before the Brooklyn jail cell, before the federal indictment, before the raids, there was a civil lawsuit — disturbing claims brought to federal court by one of Diddy’s ex-girlfriends, the model and R&B singer Casandra Ventura, also known as Cassie.

Cassie’s allegations were explosive. She accused Diddy of repeated physical abuse over more than a decade. She accused him of forcing her to have sex with male sex workers while he masturbated and filmed them. She accused him of raping her in September 2018, near the end of their relationship.

The claims drew wide attention and inspired a larger reckoning with Diddy’s behavior. The suit itself was only the start of a series of pivotal events.

In the last few years, following the November 2023 filing of Cassie’s suit, Diddy has faced a wave of other civil lawsuits accusing him of rape and other sexual abuse. Then came a sweeping federal probe, raids on the hip-hop icon’s homes in Los Angeles and Miami Beach, and the indictment at the center of the upcoming trial.

Cassie is not named in the indictment against Diddy. The initial version referred only to a “Victim-1,” whose accusations closely mirrored those of the model and singer.

Diddy and Cassie settled her lawsuit in one day, without disclosing the terms of the agreement — and with Diddy denying any wrongdoing. He has denied all civil and criminal claims via his attorneys.

Cassie’s suit alleged that not long after she met Diddy in 2005, when she was 19 and he was 37, he signed her to his record label and asserted complete control on her personal and professional life, including by plying her with drugs. Throughout their relationship, Diddy “was prone to uncontrollable rage” and would frequently beat her “savagely,” it said. His staff and the employees of his various businesses witnessed the beatings, but none dared to speak up against him.  

Cassie said in the document that she was a victim of sex trafficking because Diddy forced her to have sex with male sex workers — encounters he called freak offs, she said — in multiple jurisdictions, including at high-end hotels and his homes. Her suit said she was given alcohol in excessive amounts and “copious amounts of drugs” before and during the freak offs, which she took because “they allowed her to disassociate during these horrific encounters.”

It remains to be seen whether Cassie will be called to the witness stand. If she is, her testimony could prove to be the dramatic centerpiece of the entire trial.

This is the first edition of our new Diddy on Trial newsletter. If you’d like to stay informed each week with the latest reporting and analysis from the courtroom, click the button below.