Diddy's defense challenges Cassie's claims in tense cross-examination: What we know

Cassandra Ventura, who is known professionally as Cassie, faced cross-examination from Sean “Diddy” Combs’ attorneys when she appeared at the Manhattan courthouse on May 15, 2025, to testify for a third day.

Anna Estevao, one of the rapper’s lawyers, portrayed Ventura as a willing participant in his “freak-offs,” challenging the singer’s alleged claims that she was coerced into s*xual encounters, physically assaulted, blackmailed, and emotionally manipulated by Combs.

According to a report in NBC News, she presented evidence in the court, which included text messages and emails suggesting Ventura not only consented to these encounters but also expressed excitement about them.

She suggested that it was Cassie who ended Combs’ career by making his s*xual behavior public through a lawsuit and not the other way round. They also alleged that her actions were driven by financial motives and a desire for revenge against him, per USA Today.

Combs has pleaded not guilty to charges related to racketeering, s*x trafficking, fraud or coercion, and transportation to engage in prostitution.

Reportedly, the eight-month pregnant Ventura has accused Diddy of physical, s*xual and psychological abuse. During her testimony in Diddy's federal criminal trial in Manhattan, Ventura provided graphic details about the alleged abuse she endured during their decade-long relationship. She gave her first testimony on May 13, 2025.

Here is what we know about the recent cross-examination conducted by Diddy’s defense attorneys.

How did the defense challenge the claims made by Cassie Ventura against Diddy?

According to a report in USA Today, the defense presented text messages and emails suggesting that Cassie Ventura was a willing and sometimes enthusiastic participant in the drug-fueled group s*xual encounters, known as “freak offs.”

Diddy’s lawyers read texts exchanged between the former couple in 2009 during the start of their relationship, which also defined her willingness to participate in the sessions. The report stated that she texted Combs about how she anticipated being positioned during s*x.

These claims were based on their discussion about “freak-offs”. In one of the conversations, Combs said:

"When do you want to freak off?"

To which Ventura replied:

“I'm always ready to freak off. Lolol.”

He added,

“You tell me the day, you choose."

Diddy’s attorneys then painted Ventura as a jealous ex-partner. She accepted that she had “some jealousy” toward the late Kim Porter, Diddy’s former partner and the mother of three of his kids, per a report in USA Today.

His lawyers noted that although Diddy lied and cheated on Ventura and let her down, she “kept coming back to him for 11 years," the report added.

Ventura allegedly said that she was in love with Diddy and saw him as a sweet” and “caring” gentleman. She testified that she worried that she would lose him if she didn’t follow his orders to engage in s*xual encounters.

Comb’s lawyers have reportedly argued that while he has made mistakes, like engaging in domestic violence and abusing drugs, but he never s*xually assaulted anyone.

According to a report in the Washington Post, Ventura’s testimony will reportedly continue on May 16, 2025, along with Dawn Richard, the former Danity Kane singer, who is also expected to testify in the court in Sean "Diddy" Combs’ ongoing federal trial.

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