May 24, 2025

Saturday 5/24 Witness Profile: Cassie Ventura — From Pop Star to Star Witness

Show Notes
Transcript

With court on pause for the holiday weekend, Did He Do It? goes deep on Cassie Ventura—the pop sensation turned pivotal witness at the center of the Diddy trial. Nate Oliver traces Cassie’s rise from small-town Connecticut to the top of the charts, her whirlwind romance with Diddy, and the dark spiral into control and abuse that would later rock the music world. Then, relive the week’s most explosive testimony as Cassie faces her past in the courtroom, exposing secrets, scandals, and the true cost of survival.

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Calaruga Shark Media. Court is closed today for the long weekend,

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but with so much swirling around this case, We're taking

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you deeper into the lives of the people at the

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heart of the trial. I'm Nate Oliver, and this is

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Did He Do It? Your daily unfiltered look inside the

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Diddy sex trafficking and racketeering trial. Today we're stepping away

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from the courthouse drama to bring you a full length

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profile of the woman at the center of it all,

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Cassie Ventura. Cassie Ventura's story starts in New London, Connecticut,

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where she was born Cassandra Elizabeth Ventura on August to

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twenty sixth, nineteen eighty six, to Regina and Roderick Ventura.

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Her family background is a tapestry of cultures. Her mother

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is African American, Mexican, and West Indian, while her father

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is Filipino. Cassie describes her childhood as care free, raised

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by parents who were both army brat and navy brat,

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and she tried everything from ballet to karate and piano.

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By age fourteen, she was already modeling for local department stores,

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and by sixteen, appearing in seventeen magazine and Delia's catalogs.

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After graduating from the Williams School in two thousand and four,

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she moved to New York City to chase her dreams

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in modeling and dance, booking gigs with Wilhelmina Models and

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Calvin Klein, and appearing in music videos, including a cameo

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in Mario's Just a Friend two thousand and two. Cassie's

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big break came in two thousand and four when she

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met producer Ryan Leslie. He signed her to Next Selection

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lifestyle group, and her debut single Me and You exploded

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onto the charts in two thousand and six, peaking at

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number one three on the Billboard Hot one hundred. Her

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self titled debut album followed, earning praise for its minimalist

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pop R and B sound and spawning hits like long

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Way to Go. Cassie became a muse for the fashion world,

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modeling for Calvin Klein, Adidas, and Abercrombie and Fitch and

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gracing the pages of GQ and seventeen. She even starred

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in the dance film Step Up to the Streets, showing

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off her acting chops and recording the lead song for

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the soundtrack. But it was her connection to Sean Ditty

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Combs that would shape the next decade of her life

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and ultimately bring her into the national spotlight for reasons

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far darker than music. Cassie met Ditty as a nineteen

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year old rising star, and by twenty one their professional

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relationship had turned romantic. Diddy signed her to bad Boy Records,

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and the pair became a fixture in the music and

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fashion worlds. But as Cassie would later reveal, the glitz

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and glamour massed a much more sinister reality. Cassie's relationship

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with Ditty was marked by control and volatility. She described

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how he dictated her career, her image, and even her

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day to day life, requiring her to send photos of

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her looks for approval before events. Friends and family noticed

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her spark dimming. Cassie's mother, Regina, later testified that her

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daughter confided in her about Ditty's violence as early as

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twenty eleven, and that she once took out a home

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equity loan to pay Ditty twenty thousand dollars after he

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demanded compensation for Cassie's relationship with another man. Cassie's modeling

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and acting career continued but she withdrew from the spotlight

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in the late twenty tens, focusing on her personal life.

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In twenty nineteen, she married personal trainer Alex Fine, and

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the couple now have two daughters, with a third child

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on the way. We'll be back in a moment. When

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the Ditty trial opened in Manhattan this month, Cassie Ventura

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became the prosecution star witness. Over four days and more

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than twenty hours on the stand, Cassie delivered testimony that

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shook the courtroom. She described a relationship defined by violence, humiliation,

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and fear. Cassie recounted how Ditty orchestrated what he called

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freak offs, drug fueled sex parties, where she was coerced

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into participating with escorts and strangers while Ditty watched, directed,

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and sometimes filmed. Eventually, it became a job for me,

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she testified, explaining how these events consumed her life and

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left her exhausted, dehydrated, and emotionally numb. Cassie told a

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jury about the physical abuse, being beaten, choked, and urinated on,

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sometimes for refusing Ditty's demands. She described a brutal twenty

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sixteen beating in a Los Angeles hotel Hallway, an incident

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caught on security camera and later settled for ten million

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dollars with the hotel. She also testified about a twenty

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eighteen rape in her own living room after she tried

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to leave Ditty for good. Cassie said Ditty threatened to

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release explicit sex tapes and to harm her and others,

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including rapper kit Cut, if she ever spoke out or

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tried to escape. Her mother, Regina Ventura, took the stand

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to corroborate Cassie's story, showing the jury photos of bruises

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on Cassie's body and describing the terror of wiring Ditty

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twenty thousand dollars to keep her daughter safe. Cassie's former

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best friend, Carrie Morgan, testified about watching Cassie lose her

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confidence and spark, and about the controlling, belittling dynamic that

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defined her relationship with Ditty. Cassie's testimony was supported by

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a parade of witnesses, former assistants who described Ditty's demands,

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male escorts who were paid to participate in freak offs,

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and hotel managers who detailed the aftermath rooms trashed with

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candlewax oil, and broken glass. Digital evidence including laptops and

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phones registered to alias's like Frank Black, painted a picture

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of surveillance in control throughout it all. Cassie insisted her

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participation was never truly voluntary. Make the wrong face, and

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before I knew it, I was getting hit in the face,

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she told the jury. She explained that she stayed out

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of fear. Fear of violence, fear of blackmail, and fear

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that Diddy's power in the industry would make it impossible

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for her to escape. As the trial heads into its

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third week, Cassie Ventura stands at the center of a

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case that has rocked the music world and exposed the

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dark side of fame and power. Her story is one

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of talent and ambition, but also of survival and resilience

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in the face of unimaginable abuse. That's our deep dive

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for today. When court resumes, We'll be right back with

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every new revelation, every legal twist, and every rumor from

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inside and outside the courthouse. I'm Nate Oliver and this

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is did he do it?