Entertainment

Diddy's lawyers focus on Cassie's texts, try to portray her as willing participant in 'freak-offs'

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's behest that she previously testified she "hated doing."

Judge wants defence to finish cross-examination Friday, aims to avoid Cassie returning to court next week

Sean (Diddy) Combs' ex-girlfriend grilled about messages at sex trafficking trial

2 days ago
Duration 2:03
WARNING: Video contains disturbing details | Cassie Ventura, the ex-girlfriend of Sean (Diddy) Combs, faced cross-examination Thursday at his sex-trafficking and racketeering trial, as the defence pointed to messages they say show consent. She alleges that Combs directed her to perform degrading sex acts — claims central to the case that could carry a life sentence.

WARNING: This story may affect those who have experienced​ ​​​sexual violence or know someone affected by it.

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's behest that she previously testified she "hated doing."

It was the third day on the stand for the 38-year-old Cassie, whose legal name is Casandra Ventura, after two days of questioning by prosecutors in a New York courtroom.

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.

A courtroom sketch of a man in a yellow suit sitting at a desk with his back slightly turned. A man in a dark suit stands to the right of him and a woman in a blue suit stands in front of him, with her back turned.
In this courtroom sketch, Sean (Diddy) Combs takes notes during the morning arguments in his sex trafficking trial in New York City on Thursday, as his lawyers begin cross-examining his ex-girlfriend, the R&B singer Cassie. (Jane Rosenberg/Reuters)

Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women to take part in these drug-fuelled 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, a key element of the federal charges.

Cassie forced to read text messages in cross-examination

Messages between Combs and Cassie — both romantic and lurid — were the focus of the fourth day of testimony in front of a Manhattan courtroom.

Defence attorney Anna Estevao read what Combs wrote, while Cassie recited her own messages.

Cassie read messages to Combs containing graphic details about what she wanted to do during the freak-offs.

A court sketch of a woman with her hair in a bun stands turned toward a court witness stand where a woman is sitting.
Lawyer Anna Estevao cross-examines Cassie, whose legal name is Casandra Ventura, on the fourth day of Combs's sex trafficking trial on Thursday. (Jane Rosenberg/Reuters)

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's 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.

WATCH | Cassie testifes about years of alleged rape, blackmail and physical abuse:

Cassie details sexual violence, blackmail at Sean ‘Diddy’ Combs trial

3 days ago
Duration 2:11
WARNING: Video contains disturbing details | Singer Cassie Ventura gave her second day of testimony as the prosecution’s key witness in the sex-trafficking trial of Sean 'Diddy' Combs — detailing years of rape, blackmail and physical abuse.
 

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.

Cassie, however, did complain once that jurors weren't hearing the full context of the messages the defence was highlighting, saying, "There's a lot we skipped over."

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's 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 only wanted her to do drugs with him, not friends.

WATCH | Cassie's tells court graphic details of being coerced into 'freak-off' sex parties:

Cassie Ventura details alleged abuse, ‘freak-off’ sex parties at Combs trial

4 days ago
Duration 2:03
WARNING: Video contains disturbing details | Cassie Ventura, Sean 'Diddy' Combs's ex-girlfriend, testified at length at the music mogul’s sex-trafficking trial in New York about the alleged abuse she suffered, including graphic details of being coerced into ‘freak-off’ sex parties.

Judge wants cross-examination finished on Friday

Subramanian sent the jury home Thursday afternoon, telling them he plans to resume Cassie's testimony promptly at 9:30 a.m. Friday.

After the jury had left the room, the judge told defence lawyers they would have up to five hours to question Cassie on Friday.

Prosecutors said they expected to have no more than a half hour of questions for Cassie once the defence is finished.

Combs attorney Marc Agnifilo said he'll let the court know in the morning whether the defence can finish so that Cassie doesn't have to testify on Monday.

Subramanian noted earlier the sides had previously agreed that she would be done by week's end, since she's pregnant and due to give birth soon to her third child.

Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted. The trial is expected to last about two months.

Support is available for anyone who has been sexually assaulted. You can access crisis lines and local support services through this Government of Canada website or the Ending Violence Association of Canada database. ​​If you're in immediate danger or fear for your safety or that of others around you, please call 911.