Sean ‘Diddy’ Combs trial begins Monday over ‘freak offs’, sex trafficking and racketeering charges — What we know

Hip-hop icon and entrepreneur Sean “Diddy” Combs, once a towering figure in entertainment known for lavish Hamptons parties and building the Bad Boy Records empire, is set to stand trial in a federal courtroom this week on a series of serious charges, including sex trafficking, racketeering conspiracy, and coercion.

Prosecutors allege that over the course of two decades, Combs abused his power, wealth, and celebrity to exploit and abuse women in secretive, drug-fueled gatherings referred to as “Freak Offs.” According to the indictment, these were orgies in which women were allegedly drugged and forced to perform sex acts, sometimes on male sex workers, while Combs filmed them.

Allegations of violence and control

The 17-page federal indictment paints a dark picture of a man who used his fame as a weapon. Prosecutors claim that Combs choked, kicked, and dragged individuals—often by their hair—to intimidate or silence them. In one instance, he is alleged to have dangled a victim from a balcony.

Combs is accused of deploying employees from his various businesses—including music, fashion, media, and liquor ventures—to aid in these crimes, which prosecutors say also included bribery, kidnapping, and arson.

Investigation sparked by Cassie’s lawsuit

The investigation gained momentum after singer and former girlfriend Cassie Ventura (legally Casandra Ventura) filed a lawsuit in late 2023 accusing Combs of years of physical and sexual abuse. Her case introduced the public to the term “Freak Offs,” and although the lawsuit was settled within a day, it triggered a wider probe.

Federal agents later raided Combs’ properties in Los Angeles and Miami, seizing nearly 100 electronic devices. They also confiscated three AR-15-style rifles with defaced serial numbers. Combs was indicted in September 2024 and has since been held in federal custody, deemed a risk to witnesses and victims.

Trial to spotlight four accusers

Though dozens of men and women have made allegations, the trial will center around the accounts of four women, including Cassie. Prosecutors plan to support their testimony with video footage, hotel and travel records, text messages, and emails. One piece of damning evidence includes a 2016 security video showing Combs assaulting Cassie in a Los Angeles hotel hallway—footage that Combs later admitted to, calling it “disgusting.”

Defense: Acts were consensual

Combs’ legal team insists the relationships and sexual activities were consensual and have accused prosecutors of trying to criminalize “non-traditional sexual behavior.” His attorney, Marc Agnifilo, argued that Cassie’s lawsuit settlement opened the floodgates for opportunistic, false claims. He acknowledged Combs' past drug use and volatile relationships but said the mogul had been undergoing therapy.

“That was their thing,” Agnifilo said of the so-called Freak Offs. “It was a sought-after, special part of their relationship.”

History of legal trouble

This is not Combs’ first brush with the law. In 2001, he was acquitted of weapons charges related to a nightclub shooting. Rapper Shyne, part of his entourage, was convicted and served nearly nine years.

At a pretrial hearing last week, Combs declined a plea deal. As he exited the courtroom, he reportedly raised a clenched fist—defiant in the face of a trial that could land him in prison for decades.