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All the new details of Cassie's 'toxic' relationship with Diddy as she continues testimony in sex trafficking trial

Home> Celebrity> News

Updated 10:39 16 May 2025 GMT+1Published 10:00 16 May 2025 GMT+1

All the new details of Cassie's 'toxic' relationship with Diddy as she continues testimony in sex trafficking trial

Cassie faced Diddy's legal team on Thursday

Ellie Kemp

Ellie Kemp

As the trial of Diddy continues, we've heard his ex-girlfriend, Cassie, testify for around two days.

On Thursday (May 15), it was her turn to be cross-examined by Diddy's lawyers.

Sean ‘Diddy’ Combs’ trial officially began on Monday (May 12) and his former partner Casandra Ventura, known professionally as Cassie, has been questioned extensively about the rapper-producer.

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Combs was arrested last September while he was in New York and was hit with a slew of charges, including racketeering and sex trafficking by force, fraud or coercion.

Combs has repeatedly denied all the charges against him and has pleaded not guilty.

Cassie and Diddy dated on-and-off for around 11 years (Getty Images)
Cassie and Diddy dated on-and-off for around 11 years (Getty Images)

Here's what Cassie answered during her first day of cross-examination, as more questioning is expected to take place as the trial continues today (Friday May 16).

Cassie's 'freak-off' text messages

Defence lawyer Anna Estevao examined numerous text messages exchanged over Diddy and Cassie's 11-year relationship.

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In messages from 2009, Combs affectionately called Cassie 'babygirl' and said: “I love you so much it makes me cry.”

Diddy has denied all the charges (Hollywood To You/Star Max/GC Images)
Diddy has denied all the charges (Hollywood To You/Star Max/GC Images)

Cassie responded similarly, writing, “I love you so much I can’t wait till we don’t care anymore.”

Other text messages showed Cassie expressing both enthusiasm and reluctance about the alleged 'freak-offs'. In one message she wrote, “Can’t wait,” while in another exchange, she and Combs both expressed being 'horny'.

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However, Cassie later described a freak off as making her feel 'grimy' and 'dirty.'

Combs’s legal team have maintained these acts as part of a consensual 'swingers' lifestyle, emphasizing that controversial sexual preferences do not equate to sex trafficking.

Diddy's alleged drug use

Cassie alleged that Combs was addicted to opiates and regularly used ecstasy, MDMA, and cocaine. She recalled an incident at the Playboy Mansion in 2012 where Combs allegedly overdosed on opiates.

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Cassie has alleged years of abuse during her and Diddy's relationship (Thaddaeus McAdams/Getty Images)
Cassie has alleged years of abuse during her and Diddy's relationship (Thaddaeus McAdams/Getty Images)

Though publicly reported at the time as an 'extreme migraine,' she claimed in court that it was a drug overdose.

She also testified that while Combs was accused of spiking baby oil with GHB during freak offs in a prior lawsuit, she never saw drugs in the lubricant.

Cassie also told the court that Combs sometimes expressed concern for her own mental health and once suggested she see a doctor after noticing side effects from drug use.

Romantic jealousy

Cassie admitted feeling jealous of Kim Porter, the late mother of four of Combs’s children, as well as another woman he later began seeing.

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Combs with Kim Porter (Johnny Nunez/WireImage)
Combs with Kim Porter (Johnny Nunez/WireImage)

"I had some jealousy of Ms Porter," the singer said in court.

Estevao then said that Ventura was 'upset' that she didn't get to have a relationship with Combs' children, four of which he shared with Porter, which the dancer admitted was true.

When discussing the other woman Combs was seeing, Estevao says Ventura was 'insanely jealous', to which she responded: "I did say that, I expressed my feelings. That was who I was then, I was definitely jealous."

Her own relationship with Kid Cudi was also discussed during the trial, where she claims she used a 'burner phone' to contact the rapper as she said it would have been 'way too dangerous' if Combs found out.

The InterContinental Hotel incident

Cassie spoke about Diddy's alleged addiction to drugs in court (Mike Coppola/Getty Images for People.com)
Cassie spoke about Diddy's alleged addiction to drugs in court (Mike Coppola/Getty Images for People.com)

As questioning continued, the court reviewed messages sent before a stay at the InterContinental Hotel on March 5, 2016.

This is when Combs allegedly attacked Cassie. In one message, Combs told Cassie: “You look so sexy today.”

Estevao asked if this was in the lead-up to the alleged assault, to which Cassie confirmed.

She also testified that she felt pressured to participate in a freak off. “Baby I want to FO so bad but I don’t want to f*** myself up,” she messaged.

She eventually gave in 'after he asked me over and over again'.

Cassie stated she tried to appease Combs to protect her career, particularly with a movie premiere approaching.

Estevao pointed out that Combs had supported her publicly, 'attending a promotional luncheon' and sending 'loving messages'.

Cassie agreed but indicated she felt coerced nonetheless.

What Combs' attorney has said

If convicted, Combs faces up to life in prison (Samir Hussein/Getty Images for Sean Diddy Combs)
If convicted, Combs faces up to life in prison (Samir Hussein/Getty Images for Sean Diddy Combs)

In response to the news of Combs' arrest last year, his attorney Marc Agnifilo told UNILAD at the time: "We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office.

"Sean 'Diddy' Combs is a music icon, self-made entrepreneur, loving family man, and proven philanthropist who has spent the last 30 years building an empire, adoring his children, and working to uplift the Black community. He is an imperfect person, but he is not a criminal.

"To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court."

The trial is expected to last around eight weeks. If convicted, Combs faces up to life in prison.

UNILAD has previously contacted representatives for Combs and Ventura for comment.

The trial continues.

If you've been affected by any of the issues in this article, you can contact The National Sexual Assault Hotline on 800.656.HOPE (4673), available 24/7. Or you can chat online via online.rainn.org.

Featured Image Credit: Jason LaVeris/FilmMagic

Topics: Diddy, Sex Trafficking, Crime

Ellie Kemp
Ellie Kemp

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