Diddy Trial Focused On More Criminal Allegations

The federal sex trafficking and racketeering trial of Sean "Diddy" Combs in New York City continued Wednesday with significant testimony from Casandra "Cassie" Ventura, his former girlfriend and a key prosecution witness. 

R&B singer Ventura pocketed a whopping $20 million settlement in her bombshell 2023 lawsuit against Sean “Diddy” Combs — which opened the floodgates of claims against the hip-hop mogul, it was revealed in court Wednesday.

The trial Wednesday focused on allegations that Combs ran a criminal enterprise involving coercion, drug-fueled sexual performances called "Freak Offs," and violence against women over two decades. 

Key Testimony: 

Casandra Ventura, an R&B singer known as Cassie, dated Combs on and off from 2007 to 2018, starting when she was 19 and he was 36. She signed to his Bad Boy Records label in 2006. Her testimony is central to the prosecution’s case, which alleges Combs coerced her and others into sexual acts, used drugs and violence to control them, and blackmailed them with recorded videos.

Rape Allegation: Ventura testified that Combs raped her in 2018, after their relationship ended. She described the incident in her living room, saying, “I just remember crying and saying no but it was very fast,” as she fought back tears. This followed her claim that he beat her during "Freak Offs," leaving her with injuries like a gash on her eyebrow in 2013 from being thrown against a bed frame.

2016 Hotel Assault: Ventura revisited the March 2016 incident at the InterContinental Hotel in Century City, Los Angeles, captured on surveillance video shown to jurors. She testified that Combs threw a vase at her in the elevator lobby, yelling that she “wasn’t going to leave him there.” She showed jurors photos she took afterward, revealing a swollen lip from the assault.

Freak Offs and Coercion: Ventura detailed participating in “hundreds” of Freak Offs, which she said became “a job” expected of her. She testified that Combs forced her to hire escorts for these marathon sessions, which could last 1.5 to four days, using his money. 

She preferred ketamine during these events for its dissociative effects, as they were “humiliating” and “disgusting.” If she refused, she risked violence, stating, “It would be a problem, we’d end up fighting.” A 2016 text message shown in court revealed Combs insisting on a “proper” Freak Off without ketamine, claiming a “successful” one was when “we remember.”

Power Dynamics and Control: Ventura described Combs’ control over her life, including paying her rent and having keys to her apartments, which he used “whenever he wanted.” She moved to Los Angeles to be near him, saying, “I was in love and I wanted to be near him.” She testified that she felt she had “no choice” in participating in Freak Offs due to the power dynamic, stating, “I didn’t really know what ‘no’ could be or what ‘no’ could turn into.”

Ventura testified that she saw Combs assault one of his employees and recounted his dismissive attitude toward her injuries, such as ignoring a photo of her eyebrow gash. She also described a meeting at SoHo House with Combs and Kid Cudi, where Cudi’s car was later set on fire, though she did not directly link Combs to the arson in her testimony.

Ventura broke down in tears when asked what, if anything, she enjoyed about the Freak Offs, saying it was the only time she could spend with Combs, despite feeling “disgusting” and “humiliated.” She underwent rehabilitation and trauma therapy in 2023 due to “horrible flashbacks” and suicidal thoughts, which prompted her lawsuit.

WARNING: GRAPHIC CONTENT While testifying in the Sean ‘Diddy’ Combs trial, his ex-girlfriend Casandra Ventura told the Court that the hip-hop mogul had raped her in 2018 after their decade-long relationship had ended https://t.co/XNnpI0A62z pic.twitter.com/8S1UoyiWp4

— Reuters (@Reuters) May 15, 2025

Ventura, eight and a half months pregnant, wore a turtleneck dress and dark jacket. Combs listened intently, often with his chin on his hand. His mother and at least two children were present, though some family members left during graphic testimony, as they had on May 12.

Outlets like Reuters, The Daily Mail US, and ABC News described Ventura’s testimony as “dramatic” and “graphic,” emphasizing her emotional delivery and the severity of her allegations.

The trial is expected to last eight weeks, with Ventura’s cross-examination and testimony from other accusers, like “Jane” and the former employee, likely to dominate upcoming sessions.