Skip to main content

Sean ‘Diddy’ Combs is currently sitting in a jail cell in Brooklyn awaiting trial on various charges. His criminal case isn’t the only thing he must worry about now. It seems a new lawsuit is filed against Diddy nearly every week. Along with his criminal charges, he has over two dozen lawsuits to attend to, but do you know which one started it all? The first lawsuit in the recent deluge was filed in November 2023, long before he was taken into custody.

Cassie Ventura was the first accuser to step forward

Cassie Ventura, whom Diddy dated for several years, was the first woman to step forward and accuse him of physical abuse, rape and sex trafficking. In her November 2023 lawsuit, Ventura accused Combs of physically and sexually abusing her over the course of a decade. The lawsuit also claimed he forced Ventura into sexual situations with other men, including at Diddy’s infamous “freak off” parties.

Casandra 'Cassie' Ventura and Sean 'P. Diddy' Combs in 2015 in a crowd bathed in pink light
Casandra ‘Cassie’ Ventura and Sean ‘Diddy’ Combs | Ethan Miller/Getty Images for Showtime

According to NPR, Diddy settled the lawsuit quickly, although his legal team had previously accused Ventura of trying to “blackmail” the music mogul. Her lawyer insisted that Ventura had previously turned down a large cash offer to prevent her from filing the lawsuit. The details of the settlement remain unknown. It is the only lawsuit against the rapper that has been officially settled thus far.

Diddy dated Ventura on and off for around a decade. The pair first met in 2005, but dating rumors didn’t swirl until around 2008. Their romance was always tumultuous. They broke up multiple times over the years. They were last spotted together at the Met Gala in 2018. Both moved on, with Ventura starting a family with her personal trainer husband, Alex Fine.

Her lawsuit inspired others to speak out about Sean ‘Diddy’ Combs

While Cassie Ventura was the first to come forward, she certainly wasn’t the last person in Diddy’s circle to accuse him of wrongdoing. In fact, several of Diddy’s more recent accusers say Ventura’s decision to speak out helped them find their own voices. After Diddy’s September 2024 arrest, the number of lawsuits increased and there doesn’t appear to be an end in sight.

Cassie and Sean 'Diddy' Combs attend "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Costume Institute Gala at The Metropolitan Museum of Art on May 1, 2017 in New York City.
=Cassie and Sean ‘Diddy’ Combs attend “Rei Kawakubo/Comme des Garcons: Art Of The In-Between” Costume Institute Gala at The Metropolitan Museum of Art on May 1, 2017 in New York City | John Lamparski/Getty Images
Related

Ashley Parham Says Sean ‘Diddy’ Combs Targeted Her After She Suggested He Was Involved in Tupac Shakur’s Death

While Diddy settled the lawsuit with Ventura, he doesn’t seem interested in entertaining the others, at least based on what his legal representation has said. His legal team regularly claims the allegations are outright false and baseless. Several times over the last few months, his team, has accused Diddy’s accusers of seeking fame and fortune. The process of wading through the dozens of lawsuits is just beginning.

Diddy’s criminal trial is set to begin in May 2025. He is currently housed at the Metropolitan Detention Center in Brooklyn. Several other famous and infamous prisoners have been housed at the same controversial facility.