Sean “Diddy” Combs is facing heightened scrutiny as his civil lawsuit with ex-girlfriend Cassie Ventura unfolds. During the latest court session, the jury was presented with text message exchanges from April 2010 that revealed intimate and controlling undertones in their relationship. The messages referenced “freak-offs,” a term reportedly used to describe coerced sexual encounters involving third parties. Cassie expressed hesitation in one message, saying she wanted to discuss something the next day, to which Diddy replied with suspicion, implying she was becoming “predictable” and trying to back out.
The texts, which were described as emotionally manipulative, highlighted a dynamic in which Cassie often tried to assert boundaries while Diddy responded with dismissive or confrontational language. When Cassie clarified she wasn’t rejecting him, Diddy still accused her of “playing games.” This exchange, according to prosecutors, exemplifies the psychological control Diddy allegedly exercised throughout their relationship.
Additionally, the jury reviewed messages from the weekend of the alleged assault at the InterContinental Hotel in Los Angeles in March 2016. The messages followed an incident caught on surveillance camera showing a violent altercation between the two in a hallway. In the texts, Diddy referred to the weekend’s events with regret, saying, “F*** Friday lol. I don’t even want to do that again,” to which Cassie responded, “Lol true.” These messages, prosecutors argue, were thinly veiled references to the abusive incident.
Testimony has revealed that some of the so-called “freak-offs” lasted up to 12 hours, painting a harrowing picture of what Cassie endured. While the exact content of the messages may be open to interpretation, the prosecution is using them to establish a pattern of coercion, abuse, and manipulation. The text exchanges are being framed as evidence of Diddy’s alleged psychological and physical dominance.
The defense, however, argues that the messages show a consensual but turbulent relationship between two adults and not criminal conduct. They claim Cassie’s texts demonstrate affection and voluntary participation in the relationship’s dynamics. However, legal analysts say that the cumulative weight of testimony, surveillance footage, and now these texts may undermine that argument significantly.
This latest development in the case comes amid broader allegations against Combs involving other women, which have surfaced over the past year. With the jury now privy to both private communications and visual evidence of violence, the stakes for Diddy continue to rise. Legal experts suggest that while no criminal charges have yet been filed in connection to the 2016 incident, the mounting civil case could significantly damage his public and professional image.