Casandra “Cassie” Ventura, a former girlfriend of Sean “Diddy” Combs, is perhaps the most important witness in Combs’s high-profile federal trial.
Her explosive 2023 lawsuit against Combs, accusing him of physical and sexual abuse, was the catalyst for the charges Combs is currently facing. Despite Combs settling that lawsuit with Ventura for an undisclosed sum, it prompted a federal investigation that culminated with Combs’s arrest in September 2024.
On Tuesday, the eight-and-a-half-month pregnant singer took the stand for the first time in advance of what is expected to be days-long testimony.
Here are the key takeaways from her first day of testimony.
Ventura provided detailed explanations of the ‘freak-offs’, which were almost weekly
Ventura described Combs’s infamous “freak-offs” as “the hiring of an escort and setting up this experience so that I could perform for Sean”, adding that it allowed Combs “to watch me with the other person and actually direct us on what we were doing. Eventually it became a job for me, pretty much.”
She testified that she would be directed by Combs to find the escorts through classifieds ads on platforms such as Craigslist or Backpage and, later, through a service called Cowboys 4 Angels. The escorts, she said, were paid in cash, typically ranging between $1,500 and $6,000. Ventura alleged that Combs not only choreographed the sexual encounters but also provideddrugs to those involved including ecstasy, cocaine, marijuana, ketamine and mushrooms.
Ventura said that she was first introduced to these “freak-offs” during the first year of their relationship. Her first “freak-off” occurred in Combs’s Los Angeles home when she was 22, around 2008, she said. After that, she alleged that they became nearly weekly occurrences. Her final one took place in either 2017 or 2018, she said.
The locations of the freak-offs varied, she said, and would take place in locations such as New York City, Miami, Los Angeles, Atlanta, Las Vegas, Ibiza, and Turks and Caicos.
Ventura stated that either she or Toni Fletcher, a Bad Boy employee, would book the hotel rooms – often using pseudonyms such as Frank Black and Frank White.
The ‘freak-offs’ were so intense that it would take days to recover from them
Over time, Ventura said the “freak-offs” were not something she wanted to participate inas they made her feel “horrible”, “humiliated” and “worthless”. The “freak-offs” could last two to four days sometimes – with no sleep. Drugs would help them stay awake, she said.
Still, she told the court “I was in love and wanted to make him happy” and “I didn’t know what no could turn into.”
“Freak-offs became a job where there was no space to do anything else but recover and just try to feel normal again,” she testified, adding that the freak-0ffs would sometimes last for days and take her days to recover.
Ventura also testified that Combs would take videos of the “freak-offs” and alleged that he use the videos as “blackmail materials”.
“I felt pretty horrible about myself. I felt disgusting. I felt humiliated,” she said. “I didn’t have the words to show how horrible I felt. I couldn’t talk to anyone about it.”
She claimed that she was expected to take part in the “freak-off” sessions even while menstruating, and that Combs would sometimes instruct someone to urinate on her. Bedsheets during these encounters, she said, were often soiled with baby oil, blood and urine. She said she didn’t want that to happen, but “you don’t have a lot of control at that moment.”
“I just felt humiliated, it was disgusting, it was too much,” she said.
Combs’s lawyers have depicted the sexual encounters as consensual. He has pleaded not guilty and denied the allegations against him.
Combs’s violence throughout Ventura’s relationship with him caused constant fear
Ventura depicted Combs’s tempestuous moods and the resulting violence he would inflict on her if she didn’t act a certain way. She said she never knew if he would show up at her home in Los Angeles happy or yelling, prompting her to have constant “stomach-in-knots” moments.
“Make the wrong face and the next thing I knew I would get hit in the face,” she said. “He would say: ‘Watch your mouth.’”
She testified that he would drag, kick and even stomp on her, later noting that she would agree to things she didn’t want to do for fear of how he’d react if she said no.
“I didn’t want him to be upset or not trust me. He was a scary person, he would be violent,” she said.
Upon being asked how many times Combs threw her to the ground during their relationship, as seen in the 2016 hotel video, Ventura said: “Too many to count.”
Ventura’s music career and entire life was in Combs’s hands
Ventura said that Combs “controlled a lot of my life” including her career, how she dressed where she lived and who she spoke to. She described Combs to the court as a “polarizing person”.
“Control was everything,” she testified.
Over time, she said, she began to experience his “abusive side” and “controlling side”, adding that his mood would vary day to day, which affected her “greatly”.
Combs even preferred Ventura to groom herself a specific way for the “freak-offs”: he wanted her nails painted white or with French tips, to wear high heels, have her hair combed a certain way, and even suggested she get breast implants.
“I had to look a certain way during freak-offs,” she said, noting that his remarks on her appearance affected her confidence.
Combs would choreograph and dictate the sexual acts he wanted to see her and the escort perform, frequently instructing them to reapply baby oil, she said. Combs would also have the hotel rooms staged, often with scented candles or colored lights.
Ventura also alleged that Combs and his team would periodically take her laptop or phone away from her: “It depended on how long I was being punished for,” she said.
Decisions about her career also had to go through Combs, which Ventura said left her manager, James Cruz, to manage her “with one hand tied behind his back”.
Combs kept guns in his homes and repeatedly forced Ventura to handle them
Ventura recalled that Combs had guns in safes in his multiple homes, which alarmed her. She cited one particular incident during which Combs made her carry one of the guns, something he did on multiple occasions, which “terrified” her.
That incident involved Combs pursuing his longtime rival Suge Knight.
“We were having a freak-off in one of his homes in LA and he said Suge was at Mel’s Diner and we packed up and drove down there,” Ventura said. “I was screaming and crying: ‘Please don’t do anything stupid.’ I didn’t know what they were going to do.”
• Information and support for anyone affected by rape or sexual abuse issues is available from the following organizations. In the US, Rainn offers support on 800-656-4673. In the UK, Rape Crisis offers support on 0808 500 2222. In Australia, support is available at 1800Respect (1800 737 732). Other international helplines can be found at ibiblio.org/rcip/internl.html
