Cassie forced to read aloud explicit messages with Sean ‘Diddy’ Combs at his sex trafficking trial

NEW YORK — R&B singer Cassie was forced under cross-examination Thursday to read aloud explicit messages with her former boyfriend Sean “Diddy” Combs, some of which expressed enthusiasm for sex with other men at Combs’ behest that she previously testified she “hated doing.”

Lawyers for Combs are seeking to show the jury that Cassie was a willing participant in his sexual lifestyle and say that, while he could be violent, nothing he did amounted to a criminal enterprise. Combs has pleaded not guilty to federal sex trafficking and racketeering charges.

Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women to take part in these drug-fueled encounters with sex workers, called “freak-offs,” which sometimes lasted days. He’s also accused of using his entourage and employees to facilitate illegal activities, including prostitution-related transportation and coercion, which is a key element of the federal charges.

Messages between Combs and Cassie — both romantic and lurid — were the focus of the fourth day of testimony in a Manhattan courtroom. Defense attorney Anna Estevao read what Combs wrote, while Cassie recited her own messages.

Cassie, whose legal name is Casandra Ventura, read messages to Combs containing graphic details about what she wanted to do during the freak-offs. At one point, she asked for a short break from the readings, which Judge Arun Subramanian granted.

In August 2009, Combs asked when she wanted the next encounter to be, and she replied “I’m always ready to freak off.” Two days later, Cassie sent an explicit message and he replied in eager anticipation. She responded: “Me Too, I just want it to be uncontrollable.” Combs’ lawyers have insisted that all the sex at the freak-offs was consensual.

Later that year, however, she also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.

While reading their more affectionate conversations, Cassie testified that Combs was charismatic, a larger-than-life personality.

“I had fallen in love with him and cared about him very much,” Cassie said. Estevao spoke gently during the cross-examination, which had such a friendly tone at times that the lawyer and witness seemed like two friends chatting.

Cassie, however, did complain once that jurors weren’t hearing the full context of the messages the defense was highlighting, saying, “There’s a lot we skipped over.”

A packed courtroom watches Cassie’s testimony

As the messages were read, Combs appeared relaxed at the defense table, sitting back with his hands folded and his legs crossed. The courtroom was packed with family and friends of Combs, journalists, and a row of spectator seats occupied by Cassie’s supporters including her husband.

The 38-year-old Cassie — who is in the third trimester of pregnancy with her third child — has been composed on the witness stand. She cried several times during the previous two days of questions by the prosecution, but for the most part has remained matter-of-fact as she spoke about the most sensitive subjects.

The Associated Press does not typically name people who say they have been sexually abused unless they come forward publicly, as Cassie has.

During a break, Combs stood at the defense table, huddling with his lawyers, holding a pack of Post-It notes in one hand and a pen in the other. At one point, he turned to the gallery and acknowledged a few reporters who were studying his demeanor. “How you doing?” he asked.

Combs’ daughters were not in the courtroom Thursday as the explicit messages were read and shown to the jury.

Jurors leaned forward in their seats to follow along as the messages were displayed on monitors in front of them in the jury box. One woman shook her head as a particularly explicit message was shown. A man stared intently at the screen, pressing his thumb to his chin. Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes.

Cassie rejects ‘swingers’ label

Cassie’s testimony on cross-examination was in contrast to Wednesday, when she described the violence and shame that accompanied her “hundreds” of encounters with male sex workers during her relationship with Combs, which lasted from 2007 to 2018.

While prosecutors have focused on Combs’ desire to see Cassie having sex with other men, she testified that she sometimes watched Combs have sex with other women. She said Combs described it as part of a “swingers lifestyle.”

Estevao asked Cassie directly whether she thought freak-offs were related to that lifestyle.

“In a sexual way,” Cassie responded, before adding: “They’re very different.”

Cassie said Tuesday that Combs was obsessed with a form of voyeurism where “he was controlling the whole situation.” The freak-offs took place in private, often in dark hotel rooms, unlike Combs’ very public parties that attracted A-list celebrities.

She testified she sometimes took IV fluids to recover from the encounters, and eventually developed an opioid addiction because it made her “feel numb” afterward.

When questioned by Estevao, Cassie agreed that Combs once communicated to drug dealers in Los Angeles to stop delivering drugs to her, and he suggested she get treatment. Cassie said Combs wanted her to do drugs with him only, not friends.

Cassie’s lawsuit sparked case against Combs

Cassie testified Wednesday that Combs raped her when she broke up with him in 2018, and had locked in a life of abuse by threatening to release videos of her during the freak-offs.

She sued Combs in 2023, accusing him of years of physical and sexual abuse. Within hours, the suit was settled for $20 million — a figure Cassie disclosed for the first time Wednesday — but dozens of similar legal claims followed from other women. It also touched off a law enforcement investigation into Combs that has culminated in this trial.

Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted.

Sisak and Neumeister write for the Associated Press. The AP’s Julie Walker in New York and Dave Collins in Hartford, Conn., contributed to this report.