Sean Combs Trial Day 4: Cassie Ventura’s Cross-Examination Focuses On Relationship, Drug Use, Texts

Day four of Sean “Diddy” Combs’ federal trial in New York saw emotionally charged testimony from singer and former girlfriend, Cassie Ventura. 

Thursday, May 15, marked the beginning of her cross-examination, shifting the courtroom focus from prosecutors’ direct claims of abuse and coercion to defense efforts aimed at reframing the pair’s decade-long relationship as consensual, complex, and mutually destructive.

Combs has pleaded not guilty to five charges, including sex trafficking and racketeering conspiracy, centered around allegations that he exploited women through a network of employees and orchestrated illegal activities. Ventura, pregnant and visibly composed, returned to the witness stand for a third consecutive day, recounting intimate details of their relationship while fending off defense attorneys’ attempts to undermine her credibility.

A Relationship Under the Microscope

The defense began by closely scrutinizing Ventura and Combs’ 11-year on-and-off relationship, presenting a slew of text messages that painted a portrait of intimacy, jealousy, and entanglement. Ventura acknowledged she had once been in love with Combs, describing him as “sweet” and “attentive” in the early stages. But she also emphasized a shift over time. What began as passionate quickly morphed into manipulation and violence.

“You told him you wanted to do ‘freak offs?’” one attorney asked, referencing the group sex encounters that have come to define much of the case’s public narrative. Ventura responded, “No, there’s a lot more to that,” indicating the situation was layered with coercion and not as clear-cut as the defense implied.

Messages presented in court included Ventura helping Combs arrange these encounters. “We can’t judge them for being illegal or criminal if both sides are willing participants,” attorney Donte Mills, a legal analyst not involved in the case, commented. “The defense is trying to build the foundation that this was a relationship she actively participated in.”

Drugs, Control, and Complicity

A significant portion of the cross-examination revolved around drug use—specifically, who initiated it, who supplied it, and who was responsible. Ventura admitted that both she and Combs were addicts at the time, noting that drug use became a shared part of their lifestyle. She testified about using ketamine, MDMA, and opiates—often with Combs, and sometimes without him.

The defense focused on messages where Ventura asked Combs for pills and discussed partying at Burning Man. She acknowledged having friends who also supplied her with drugs, and agreed that Combs grew increasingly angry when she used substances outside of his control. “If the two of us weren’t getting high together, it was a problem,” she said.

The court also heard about an alleged 2016 attempt by Combs to cut Ventura off from drugs, instructing Los Angeles dealers not to sell to her. The defense argued that this was a sign he was trying to help her get clean. Ventura’s response: it happened, but not necessarily out of concern—it was about control.

The Weight of Violence and Public Image

The trial took a darker turn as Ventura faced questions about incidents of physical violence—some of which she witnessed firsthand, and others she heard of or learned about later. She recalled Combs allegedly throwing a hanger at a friend, and another moment where he hurled someone into patio furniture during a balcony altercation. Though she admitted not seeing the hanger incident, she testified to seeing the aftermath—her friend injured and shaken.

The defense brought up the threat of damaging videos—footage from “freak offs”—and Ventura’s fear that they could ruin her career. In turn, they questioned whether her civil lawsuit against Combs was timed for maximum exposure. When asked if she understood his career might also be ruined as a result of her lawsuit, Ventura replied, “I could understand that.”

Jealousy, Secrets, and Emotional Turmoil

Ventura was questioned about the jealousy that plagued their relationship, particularly over Combs’ relationships with other women. At one point, a message from Ventura read: “You’re making me look like a side-piece and that’s not what I thought I was.” She admitted she was often “insanely jealous” when seeing him publicly with others, particularly in 2013 when she believed she was his main partner.

The defense revisited her relationships with Kid Cudi and, later, actor Michael B. Jordan, attempting to establish a pattern of infidelity and retaliation. Ventura testified that her emotional unraveling was exacerbated by deception not only from Combs but from his inner circle, who she believed became complicit in protecting him.

“I sent the video of him with another woman to his staff because I had spent all my time with them. I thought they were my family,” she said. “Everybody was lying.”

Love, Addiction, and Dual Realities

In a surreal twist, the courtroom reviewed pages of affectionate messages between the two. Ventura agreed they had exchanged loving texts and acknowledged that Combs often encouraged her artistry and praised her appearance. At the same time, she said he put her down, emotionally destabilizing her while positioning himself as her savior.

Asked whether Combs was addicted to anything, Ventura didn’t hesitate. “Success,” she said. She then confirmed he had also been addicted to opiates, like her, and suffered visible withdrawals.

Despite the defense’s relentless efforts to reframe the relationship, the courtroom has heard repeated testimony from Ventura about manipulation, trauma, and emotional damage. The prosecution will have a chance to redirect questioning Friday after the judge instructed the defense to wrap cross-examination by noon.

Cassie Ventura remains at the center of this high-profile case—not just as a witness, but as a woman navigating the intersection of power, fame, and survival.

SEE ALSO:

Inside Day 3 Of The Explosive Testimony Against Sean ‘Diddy’ Combs

Sean Combs’ Legal Team Claims ‘Mutual Abuse’ In Relationship With Cassie Ventura