Diddy and Cassie relationship timeline based on testimony
Sean 'Diddy' Combs trial: 'Freak off' testimony
On Day 2 of the Diddy trial, ex-girlfriend Cassie Ventura testified about the alleged abuse and "freak offs."
NEW YORK (WNYW) - Key prosecution witness Cassandra "Cassie" Ventura, took the stand for the first time in the sex trafficking trial against Sean "Diddy" Combs on Tuesday.
"He would mash me in the head, knock me over, drag me, kick me. Stomp me in the head if I was down," Cassie explained.
In her testimony, she detailed how Diddy controlled her from the start of her career, allegedly pulling her into a drug-fueled, controlling relationship after signing her to his label at age 19, while he was 37.
"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.
Now pregnant with her third child with husband Alex Fine, Cassie described how Diddy exerted power over her during their years together.
A key piece of evidence shown to jurors was a 2016 surveillance video appearing to show Diddy kicking and dragging Cassie in a hotel hallway in Los Angeles.
RELATED: Diddy trial day 2: Cassie Ventura testifies about abuse and ‘freak offs’
Her testimony followed accounts from hotel security guard Israel Florez, who told jurors he saw Diddy with a "devilish stare" after allegedly attacking Cassie, and Daniel Phillips, who testified he was paid in 2013 to have sex with Cassie—expecting a bachelorette party gig but instead finding her in red lingerie as Diddy watched and masturbated.
Diddy, now 55, has pleaded not guilty, and his attorneys argue that while he may have been violent, the relationship was consensual and not criminal.
RELATED: Diddy trial: Male escort testifies he was paid to have sex with Cassie as music mogul watched
Here's a detailed timeline of Diddy and Cassie's relationship based on her testimony.
Diddy's ex Cassie appears in court
Cassie Ventura, Diddy's ex-girlfriend, appeared in court to testify on the disgraced mogul's alleged abuse and "freak-off" parties.
Who is Cassie Ventura?
The backstory:
Cassie is an R&B singer, model, dancer, and actress who broke into the industry in 2005.
Cassie is of Black and Filipino descent. Her mother is African-American, Mexican, and West Indian, while her father is Filipino.
She began modeling at 14, and by 16, she was working with local department stores, Delia's fashion catalog, and Seventeen magazine. Cassie also made a brief appearance in R&B singer Mario's "Just a Friend 2002" music video.
Music producer Ryan Leslie is said to have discovered her while working alongside industry executive Tommy Mottola.
Cassie rose to fame with her debut single "Me & U," which Ryan Leslie wrote and produced. The song became a club hit and remains one of her best-known tracks, along with "Long Way 2 Go."
Cassie signs to Bad Boy
Cassie was first signed to Bad Boy Records in early 2006 and was in an on-and-off relationship with Diddy from 2007 to 2018.
How old was Cassie when she dated Diddy?
Timeline:
Cassie, now 38, testified that she first signed with Bad Boy Records in early 2006 at age 19.
At the time, she described her relationship with Diddy, the label’s founder, as platonic.
But during a trip to Las Vegas for her 21st birthday, Cassie said things changed after he kissed her in the bathroom of his hotel suite.
"I was just really confused at the time," she said. "And young."
Following that encounter, according to Cassie, Diddy began inviting her to hotels in New York under the guise of discussing music projects.
Cassie testified that it was there she was introduced to the "idea of oral sex."
Cassie says things changed after sex with Diddy
She also recalled being "sexually inexperienced" when the relationship began.
Eventually, she said, the two had sex during a trip to Miami after she’d had wine and Diddy gave her ecstasy for the first time.
Cassie said she soon felt consumed by Diddy’s influence.
"Sean controlled a lot of my life, whether it was career, the way I dressed, everything, everything. I just didn’t have much say in it at the time," Cassie testified.
Cassie describes 'Freak Offs' that went on for days
She described how Diddy introduced her to what he called "Freak Offs," orchestrated sexual encounters involving escorts.
Cassie testified that her first "freak off" happened in Diddy's Los Angeles home when she was 22, around 2008. She said a male Las Vegas stripper came to the home, just months after Diddy told her about his interest in voyeurism.
Cassie testified that the Freak Offs involved her being directed to perform sex acts for Diddy, often while he watched.
She said she didn’t feel like she could say no, fearing violence and blackmail.
"I didn’t know what ‘no’ could be, or what ‘no’ could turn into." She added, "Sean is a really polarizing person, also really charming," Cassie said. "It’s hard to really be able to decide in that moment what you need when he’s telling you what he wants. I just didn’t know. I didn’t know what would happen."
When shown still images from the 2016 security footage that appears to show Diddy beating her in a Los Angeles hotel hallway, Cassie said the violence occurred after she was trying to leave a Freak Off. "We were having an encounter called a ‘freak off’ and I was leaving there."
Reflecting on the years-long relationship, Cassie testified that the physical abuse was frequent.
"If they were violent arguments, it would usually result in some sort of physical abuse and dragging, just different things," she said.
She testified that Diddy would mash her head, drag her, kick her and stomp her in the head when she was down.
When asked how frequently Diddy got violent with her, Cassie responded: "Too frequently."
Cassie says she saw Diddy, bodyguards grabbed guns to confront Suge Knight
In her testimony, Cassie says during one "freak off," Diddy and his bodyguard grabbed guns from a safe, loaded them into an SUV to confront rival record executive Suge Knight at Mel’s Drive-In, a landmark diner nearby.
"I was crying. I was screaming, like ‘Please don’t do anything stupid,’" Cassie testified. "I was really nervous for them. I didn’t know what they were going to do."
Cassie lawsuit
Big picture view:
On Nov. 16, 2023, she filed a lawsuit against Diddy, accusing him of years of abuse, violence, and sex trafficking. The suit was filed in Manhattan federal court under New York’s Adult Survivors Act, which allows survivors of sexual abuse to sue even after the statute of limitations has passed. Cassie alleged the abuse began when the relationship started and included a 2018 rape and repeated incidents of domestic violence.
Diddy’s lawyer denied the claims, but just a day after the lawsuit was filed, both sides said they had reached a settlement, though the terms were not made public.
In May 2024, CNN released hotel surveillance video from 2016 showing Diddy attacking Cassie — grabbing, punching, and kicking her in a hallway. After the video surfaced, Diddy issued a public apology, admitting to the incident.
The Source: This report is based on information from the Associated Press.