Takeaways from Cassie Ventura’s testimony in Sean ‘Diddy’ Combs’ racketeering trial

Cassie Ventura began crying while discussing the 'Freak Offs' in court on Tuesday. (Jane Rosenberg/Reuters via CNN Newsource)

Warning: Disturbing content.

“The government calls Casandra Ventura.”

With those five words, the prosecution dove into the heart of the racketeering and sex trafficking case against Sean “Diddy” Combs – the testimony of his former longtime girlfriend.

Known as “Victim 1” in the indictment and “Cassie” in the music world, Ventura – who is pregnant and in her third trimester – took the stand Tuesday in what is likely to be several days of intense testimony. She was on the stand for about 4.5 hours Tuesday and is set to return Wednesday for further questioning.

Prosecutors have said Combs and his inner circle used threats, violence, drugs, bribery, arson, kidnapping and lies to coerce Ventura and another woman into extended sexual performances known as “Freak Offs” and to protect the music mogul’s reputation.

The defence acknowledged Combs has been violent with romantic partners and has a “different” sex life. However, they argued the women consented to these sexual arrangements and evidence of domestic violence does not mean he committed racketeering or sex trafficking.

Combs has pleaded not guilty to five counts including racketeering conspiracy, sex trafficking and transportation to engage in prostitution. If convicted, he could face a sentence of up to life in prison.

First meeting since 2018

Tuesday’s highly anticipated testimony represented the first in-person meeting between Ventura and Combs in over six years.

The pair first began dating around 2007 and went public with their relationship in 2012. They split in 2018.

Ventura and Combs last saw each other in November 2018 at the funeral of Kim Porter, the actress who had three children with Combs, defence attorney Teny Geragos said in opening statements Monday.

When Ventura entered the courtroom, she walked down the center aisle with her eyes facing forward. Wearing a brown dress, Ventura passed by the jury box to the witness stand. Combs turned around in his chair and watched her walk to her seat.

She did not appear to make eye contact with him.

The start of Ventura’s relationship with ‘Sean’

Ventura, now 38, detailed how she and the now 55-year-old Combs – who she called “Sean” – began dating nearly two decades ago.

Ventura first met Combs when she was about 19 years old. She signed a contract with his company, Bad Boy Records, in early 2006, and they struck up a platonic relationship.

After a boat party in Miami, their relationship became more intimate and sexual.

“I wanted to be around Sean for the same reasons as everyone else at the time – just this exciting, entertaining, fun guy that also happened to have my career in his hands,” Ventura said. “It felt special because not a lot of people got that time with him.”

She said she soon fell in love with him and “traveled with him everywhere…like (his) little shadow.”

Combs was controlling and abusive, she says

Over time, Ventura said she began to see Combs’ more controlling and abusive qualities.

“Control was everything, from the way that I looked, to what I was working on that day, who I was speaking to,” she said.

He had mood swings that led to physical abuse, she said.

“You make the wrong face and the next thing I knew, I was getting hit in the face,” she said. “If I was a brat or something, he would let me know I needed to ‘fix my face’ or ‘watch my mouth.’”

If he disapproved of something she did, he directed his staff to take her belongings away, she said. He’d also kick her out of the house or her apartment that he was paying for, she testified.

‘Bruises all over my body’

Ventura said some of her arguments with Combs became violent.

“He would smash me in my head, knock me over, drag me, kick me, stomp me in the head if I was down,” she said.

She added she suffered injuries from the abuse, including knots on her forehead, busted lips, and “bruises all over my body.” Asked how frequently he was physical with her, she responded, “Too frequently.”

How the ‘Freak Offs’ turned into a ‘job’

Early in their relationship, Combs proposed the provocatively named “Freak Offs” in which he would watch her have sex with another man while he pleasured himself, a form of sexual voyeurism, Ventura testified.

Each “Freak Off” would usually consist of two to three sexual sessions – each session lasting an hour to three hours – and could involve three or four different men, she explained.

“It’s his fantasy. He was controlling the whole situation, he was directing it,” she said.

The “Freak Offs” became almost weekly, she testified, and stretched until 2017 or 2018. When Ventura “gently” brought up not wanting to do them anymore, Combs was dismissive, she said.

“It got to a point where I just didn’t feel like I had much of a choice, didn’t really know what ‘no’ could be or what ‘no’ could turn into,” she testified.

“Sean controlled a lot of my life, whether it was (my) career, the way I dressed, like everything, everything. And I just didn’t feel like I had much say in it at that time, being really super young, naive, total people pleaser,” she said. “I didn’t know if he would be upset enough to be violent or if he would write me off and just not want to be with me at all.”

She testified she took “all kinds” of drugs provided by Combs or his staff at the “Freak Offs” as a way of dissociating and numbing herself. At a certain point, a “big chunk of her life” was spent recovering from taking drugs and dehydration stemming from the “Freak Offs,” she said.

“The ‘Freak Offs’ became a job, where there was no space to do anything else but to recover and just try to feel normal again,” she said.

Ventura breaks down in tears

Ventura stoically described the sexual acts that occurred during “Freak Offs” but eventually broke down when she was asked how she felt about them.

“I felt disgusting, I was humiliated,” Ventura said. “I didn’t have the words to put together at the time how horrible I really felt, and I couldn’t talk to anybody about it.”

When asked what she enjoyed, if anything, about the “Freak Offs,” Ventura broke down into tears.

“The time spent with him,” she said. “As sad as it was, I thought that like it was (the) only time I could get.”

Hotel assault came after she tried to leave a ‘Freak Off,’ she says

The central evidence in the trial so far has been surveillance video showing Combs beating and kicking Ventura in a Los Angeles hotel in 2016, and in court she offered more details on what led to that incident.

At some point the “Freak Off” turned violent, Ventura said.

“I’m not sure what happened, but I got hit by Sean and I had a black eye, and at that point all I could think about was getting out of there safely,” she said.

The attack came after she attempted to leave a “Freak Off” before it was “over,” she testified.

“It got violent and I chose to leave,” Ventura said. “Sean followed me into the hallway by the elevators, he grabbed me, threw me on the ground, kicked me, tried to drag me back to the room, took my stuff.”

Ventura said she grabbed her belongings and “ran out as fast as I could,” without putting her shoes on, while Combs was in the shower.

She said he had beat her in that same way seen on the surveillance video “too many (times) to count.”

“Are there occasions when you tried to fight back when Sean hit you?” the prosecutor asked.

“No,” Ventura said.

Video of the attack was first published by CNN last year. The jury has viewed surveillance footage of the attack at least five times in the trial so far.

Some ‘Freak Offs’ were arranged across state lines, Ventura says

Some of Ventura’s testimony touched on the role that Combs’ employees and staff played in the “Freak Offs” – a key part of the prosecution’s allegation that he and his inner circle constituted a criminal enterprise.

She testified Combs’ staff would sometimes book the hotel rooms for the “Freak Offs,” and that Combs told her which escorts to hire. Ventura said he paid them in cash and facilitated the escorts’ travel to wherever the couple was at the time.

Ventura said she found the escorts online and then would show them to Combs for him to approve. Escorts were paid between US$1,500 and $6,000 after the “Freak Offs” in cash that was provided by Combs, she said.

Some of the escorts participated in “Freak Offs” in multiple states, according to Ventura. When she needed to fly in an escort for a “Freak Off,” Ventura would tell Combs’ travel agent to arrange travel for a new staff member, she testified. At Combs’ direction, she purposely concealed the true reason for the travel request, Ventura said. “It was important to Sean not to have (the escorts’) identity known,” she said.

A blow-up pool of baby oil

She also said that Combs’ staff would provide materials such as baby oil, Astroglide and condoms for the “Freak Offs,” and when they ran out of lubricant, they’d call someone on Combs’ staff or the hotel desk to bring more.

Law enforcement discovered more than 1,000 bottles of baby oil in searches of Combs’ homes last year, and Ventura explained the product’s role in the “Freak Offs.”

“If he felt like you were too dry, he’d let you know,” she said. “He would say ‘you were too dry you need to put more oil on,’ or ‘you need to be glistening.’”

They used about 10 large bottles of baby oil each time. At one “Freak Off” there was even an inflatable pool filled with baby oil, she testified, and Combs told her to get into the pool to cover herself in oil.

Hotel rooms would typically be trashed after “Freak Offs,” and many times one of Combs’ staff members would go in and clean up, she said. The hotels often charged Combs for the damage, and she recalled hearing staff members take calls from hotels about it.

Ventura says she was ‘insanely jealous’ of his girlfriends

The defence has said the case is really about jealousy, and Ventura admitted in her testimony she was “insanely jealous” of Combs’ other girlfriends.

“I didn’t get that he was him – he was Puff Daddy, and Puff Daddy has many women,” Ventura said. “He likes the company of women, and I had to just really learn that over time, despite what he would tell me just between us.”

She continued, “He made me feel like we were in a monogamous relationship more often than not. It was really me figuring out that we were not.”

Ventura appeared sober all but once during sexual encounters, witness says

Ventura was not the only person to take the stand Tuesday.

The day began with the continued cross-examination of Daniel Phillip, the 41-year-old who testified a day earlier that he was paid thousands of dollars on multiple occasions between 2012 and 2014 to have sex with Ventura while Combs watched and pleasured himself.

Ventura appeared to be sober during these sexual encounters, except on one occasion when she was “slumped over” on a couch, Phillip testified. In that instance, Combs stepped in and said they could not have sex, he said.

Ventura testified later Tuesday that she usually took narcotics with Combs before an escort would join them. Phillip first took the stand Monday afternoon as the second witness in the government’s case.

By Lauren del Valle, Nicki Brown, Eric Levenson, Kara Scannell, CNN

Resources for sexual assault survivors in Canada

If you or someone you know is struggling with sexual assault or trauma, the following resources are available to support people in crisis:

• Call 911 if you are in immediate danger or fear for your safety.
• The Canadian Association of Sexual Assault Centres' website has a comprehensive list of sexual assault centres in Canada that offer information, advocacy and counselling. 
• The Ending Violence Association of Canada‘s website has links to helplines, support services and locations across Canada that offer sexual assault kits.
• Indian Residential School Survivors Society crisis lines: [phone] or [phone] (24/7)
• Toronto Rape Crisis Centre crisis line: [phone] (24/7)
• Canadian Human Trafficking Hotline: [phone] (24/7)
• Trans Lifeline: [phone]
• Suicide Crisis Helpline: call or text 988 (24/7)
• Sexual Misconduct Support and Resource Centre for current and former Canadian Armed Forces members: [phone]
• Read about your rights as a victim on the Canadian Resource Centre for Victims of Crime website.