Day 4 of Diddy Trial: Cassie Cross Examination Puts Intimate Relationship Under Legal Microscope

The fourth day of the criminal trial of Sean “Diddy” Combs featured the third consecutive day of testimony from key witness and former partner, Cassie Ventura. With the defense now in control of the narrative through a strategic Cassie cross examination, lawyers for Combs focused heavily on reframing the couple’s long-term relationship, emphasizing mutual affection, emotional connection, and shared intimacy, while attempting to undermine Ventura’s allegations of abuse, coercion, and exploitation.

A Relationship Revisited

Early in the day, Combs’ attorneys pressed Ventura to confirm that she once knew and loved “the real Sean.” a side of the music mogul she described as “sweet” and “attentive.” These descriptions, paired with a stream of loving emails and texts from the couple’s early years, were used by the defense to establish that their 11-year relationship had genuine emotional depth. Messages from 2009 and 2010 showed Combs declaring his love for Ventura, calling her “Babygirl” and writing that their relationship consumed his life. Ventura responded in similar fashion, expressing confusion over how deeply she had fallen for him.

When asked why she spent so much time with Combs, Ventura simply responded, “Because I fell in love with him.”

Yet as the Cassie cross examination progressed, it became clear that love and manipulation often coexisted. Ventura testified that the relationship began intensely and quickly became more controlling. She confirmed that early reluctance to go public with their relationship later gave way to increased surveillance, with Combs requiring constant updates about her whereabouts. She also admitted he became angry and suspicious, especially when he believed she was unfaithful.

“Freak Offs” and Consent Under Scrutiny

A significant portion of Thursday’s testimony centered around the controversial “freak offs,” drug-fueled sexual encounters involving multiple partners. Ventura testified that she initially agreed to participate to please Combs, but later felt coerced and emotionally cornered. While the defense introduced emails and texts in which Ventura appeared to speak positively or jokingly about the encounters, including one where she wrote, “I am always ready to freak off lol,” she clarified on the stand that it was far more complicated than simply wanting to please her partner.

In a particularly revealing moment, Ventura acknowledged that these encounters became “a job,” especially after she began secretly dating rapper Kid Cudi.   She testified that she used a burner phone to communicate with Cudi to try to keep Combs from finding out.  She testified that she feared that someone would get hurt if Combs discovered the affair, which he eventually did, leading to an alleged physical assault in 2011. According to Ventura, Combs kicked her in the back after learning of the relationship. The defense asked whether the Cudi relationship made Combs mad, to which she replied, “It wasn’t good.”

The court also heard that Ventura and Combs exchanged emails about drug use and explicit video recordings, including one instance where Ventura confirmed deleting a sexual video from her camera and asking Combs if he had pills. These exchanges were presented to cast doubt on Ventura’s claims that she never consented freely to the sexual experiences she now alleges were exploitative.

Jealousy, Fame, Surveillance, and Addiction

Further complicating the image of their relationship, Ventura admitted under cross-examination to feelings of jealousy toward Kim Porter, Combs’ ex and the mother of his first few children. Despite a long-term relationship with Combs, Ventura testified that she was never given the opportunity to bond with his children — something she found deeply upsetting.

Combs’ defense also highlighted Ventura’s alleged relationships with Michael B. Jordan and her secret use of a burner phone to contact Cudi. She acknowledged that Combs would often bombard her with phone calls when he believed she was being unfaithful, adding that his suspicions could be triggered by almost anything.

When asked whether she believed Combs was a drug addict, Ventura replied, “I would say he was an addict.” She described his erratic behavior, especially during withdrawal periods, and confirmed that he once overdosed on painkillers. Combs, she claimed, used cocaine and ecstasy regularly throughout their relationship.

Tension in the Courtroom

Tensions rose during the afternoon session when prosecutors objected to the introduction of explicit emails and texts. The objection was sustained by Judge Arun Subramanian, who then called for an abrupt 10-minute recess as Ventura whispered something to the bench. The judge later expressed frustration over the trial’s pacing and the extended duration of the Cassie cross examination, particularly given the late stage of Ventura’s pregnancy. He reminded both legal teams that she was supposed to finish testifying by the end of this week and that he didn’t want he to have to return to the stand on Monday.

Toward the close of the day, Ventura discussed a 2016 incident where Combs allegedly assaulted her at the InterContinental Hotel in Los Angeles. She said she had initially resisted his requests for a “freak off” during a press tour for her film The Perfect Match, but eventually agreed. According to Ventura, Combs feared entering “the matrix,” their shared term for becoming too intoxicated for intimacy, and she tried to keep the encounter short.  She could not recall exactly what drugs she took that day, only that she felt pressured.

Weakness in Sean Combs’ Legal Team

As proceedings concluded, Judge Subramanian again urged Combs’ legal team to quicken their pace. Defense attorney Marc Agnifilo responded that they were dealing with a “critical witness” and would continue Friday morning with an estimate for completion.

Those inside the courtroom noted that defense lawyer Anna Estevao, who led the cross-examination seemed to be a bit out of her realm with this.  Lead attorneys and Sean Combs passed her several notes throughout the Cassie cross examination, so much so that they ran out of pink notes and had to start passing yellow notes from another note pad.  As much talk as there has been around the great legal team Sean was able to put together, it is interesting that they may have put one of the least savvy attorneys on the team, on this “star witness.”  There is some thinking that her trying to find her footing is in part why the cross examination has taken so long.

Cross-Examination Continues

This stage of the Cassie cross examination has revealed the deep contradictions and emotional complexity of Ventura’s long-term relationship with Combs. What emerges is not a simple story of love or abuse, but an intricate and often troubling dynamic shaped by fame, power, control, and vulnerability. As the trial progresses, the court will continue to examine these contradictions in search of clarity and justice.

What’s Next?

The Defense seemed to hint that former Bad Boy artist, as a member of Danity Kane and Diddy’s Dirty Money, Dawn Richard would be the next prosecution witness to take the stand.  Dawn filed her own lawsuit against Diddy last year despite appearing on his most recent album, The Love Album, in 2023.  The Dirty Money album came out in 2010 during the height of Diddy’s relationship with Cassie, so it is likely that Dawn can testify to things she saw in the Diddy and Cassie relationship, which might be able to show more of the prosecution’s RICO claims.