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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.
1. 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 would find the escorts through classifieds such as Craigslist or Backpage and, later, a service called Cowboys 4 Angels. The escorts were paid in cash, typically $1,500 to $6,000, and Combs provided drugs to those involved including ecstasy, cocaine, marijuana, ketamine and mushrooms.
She noted that her first “freak-off” occurred in Combs’s Los Angeles home when she was 22, around 2008, and that they became an almost weekly occurrence. Her final one occurred in either 2017 or 2018.
The “freak-offs” would take place in various places including New York City, Miami, Los Angeles, Atlanta, Las Vegas, Ibiza, and Turks and Caicos, Ventura said, adding that either she or Toni Fletcher, a Bad Boy employee, would book the rooms. They would do so under pseudonyms such as Frank Black and Frank White.
2. The ‘freak-offs’ were so intense that it would take days to recover from them
Over time, Ventura said, “freak-offs” were not something she wanted to do as they made her feel “horrible” and “worthless”, and could last two to four days sometimes – with no sleep. 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,” she told the court, adding that the freak-0ffs would sometimes last for days and take her days to recover.
Ventura noted that Combs would use the videos he took of her during these “freak-offs” 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.”
As Ventura was expected to take part in the “freak-offs” even while menstruating and Combs would sometimes direct someone to urinate on her, bedsheets during these encounters could be covered in 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.
3. 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.”
4. Ventura’s music career and entire life was in Combs’s hands
Ventura said Combs “controlled a lot of my life” including her career, how she dressed and who she spoke to. She described Combs to the court as a “polarizing person”.
Over time, 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: he wanted her nails painted white or with French tips, 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 impacted her confidence.
Combs and his team would also periodically take away her laptop or phone: “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”.
5. 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.”
