Diddy trial: Defense highlights alleged text messages between rapper and Cassie where the two plan logistics for a “freak-off”

Special agent DeLeassa Penland took the stand at Diddy’s federal trial on June 17, 2025, and defense attorney Teny Geragos conducted her cross-examination. Penland is a special agent with the US Attorney’s Office for the Southern District of New York.

According to CNN, during Penland’s cross-examination, the text messages reportedly exchanged between Sean “Diddy” Combs and his ex-girlfriend, Cassie Ventura, that were presented to the jury via summary charts, were reviewed by Teny Geragos.

Notably, Geragos pointed out a few texts where Ventura and Combs allegedly planned the logistics to organize a “freak-off.” Ventura had seemingly agreed to one in 2013 after Combs reportedly told her in a message:

“Maybe one of those nights”

As per the outlet, another text sent to Combs by Ventura also seemed to address a “freak-off” that happened in October 2012. In the text, she reportedly said that she kept having “sexy flashbacks” of the day in question.

Ventura additionally expressed her love for Diddy in a message on Father’s Day of 2013, as per CNN, where she expressed that she couldn’t “wait until [they had] a baby of [their] own to celebrate Father’s Day.” The text reportedly also featured Ventura saying:

“Thank you for always showing me love and happiness the way it’s supposed to be.”

The outlet reported that other messages related to the “freak-offs,” where Ventura allegedly planned them while speaking to Diddy and the escorts, were also reviewed by the defense. Ventura reportedly told Combs in one of these messages that she was “always ready” to have a “freak-off.”

As per the outlet, Penland was asked by Geragos to confirm that messages relating to a July 2012 meeting were not included in the government’s summary chart. Penland confirmed that she had not seen texts exchanged between Ventura and Diddy linked to that particular meeting. However, she clarified that she had seen the texts exchanged between Ventura and another individual, referred to as “Islander LA.”

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Diddy apologized to Cassie Ventura in one of the messages

As per CNN, on June 17, 2025, after DeLeassa Penland’s cross-examination, some of the texts shared between Diddy and Cassie Ventura were reviewed by Assistant US Attorney Emily Johnson during a redirect.

One of the messages reportedly featured Diddy apologizing to Ventura a few days after the latter was allegedly assaulted by Combs at the Los Angeles-based InterContinental Hotel in 2016, as per CNN. Ventura reportedly told Combs in a text that she had a bruise and added:

“I would be a dummy to subject myself to that possibly happening again. When you get f*cked up the wrong way, you always want to show me that you have the power and you knock me around. I’m not a rag doll, I’m someone’s child.”

As per CNN, the jury members also saw a video that was allegedly recorded during a “freak-off” in October 2012. In addition, they saw another clip with a duration of about four minutes that was recorded around December 2014. A woman’s voice was reportedly heard from a clip that was played inside the court.

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According to USA Today, the next person to testify in the case will be Brendan Paul, another former assistant of Diddy. Paul has been involved in some legal issues in the past, including once when he was taken into custody in March 2024 at the Miami-Opa Locka Executive Airport after authorities discovered cocaine and edibles in his bag. Paul pleaded not guilty to a charge related to drug possession and was instead charged with felony cocaine possession.

Edited by Ankita Barat