The legal team representing Sean “Diddy” Combs has argued that his ex-girlfriend, singer Cassie Ventura, maintained contact with the rapper even after their breakup—challenging her claims of abuse and coercion.
Ventura, the prosecution’s key witness in the ongoing high-profile sex trafficking trial, took the stand earlier this week, offering disturbing testimony about her relationship with Diddy. She alleged that the music mogul forced her into drug-fueled “freak-off” sex parties that left her with recurring urinary tract infections and mouth sores.
However, during Friday’s cross-examination, Diddy’s attorney, Anna Estevao, contested Ventura’s claims, portraying her as a willing participant in the encounters. The defense presented a 2009 text message in which Ventura allegedly told Combs she was “already for a freak off,” suggesting consent and complicity.
The defense further sought to cast doubt on her allegations by highlighting a series of affectionate messages Ventura reportedly exchanged with Diddy after their 2018 split. Cassie previously testified that their last sexual encounter occurred on September 27, 2018, and accused Combs of raping her that night following a breakup dinner.
Despite that, Estevao presented messages suggesting an ongoing emotional connection between the pair—even while Ventura was dating her now-husband, Alex Fine.
In one October 2018 message, Combs reportedly told Ventura he would “fall back” but encouraged her to reach out if she needed him. Ventura allegedly replied, “I’m lost without you.”
Other texts shown in court included affectionate exchanges, with Diddy calling Cassie his “ride or die always” and one of the “greatest women in the world.” Ventura allegedly responded, “That blew my mind a bit,” adding, “I don’t hate you. I never have.”
She also reportedly told Diddy, “I wouldn’t be at the beautiful point in my life if I hadn’t been with you.”
Ventura said the last time she saw Combs was in November 2018 at the memorial service for Kim Porter, Diddy’s ex and the mother of his children, in Georgia.
The cross-examination concluded with a resurfaced text exchange from 2012, in which Combs allegedly asked Ventura if she wanted a “freak off for the last time.” She reportedly responded, “I want a freak off for the first time … for the rest of our lives.”
The trial continues, with both sides fiercely contesting the nature of the past relationship and the consent surrounding the alleged events.