Takeaways from Cassie Ventura’s cross-examination in Sean ‘Diddy’ Combs’ trial

By Lauren del Valle, Nicki Brown, Kara Scannell, and Eric Levenson, CNN

(CNN) — After two days of the prosecution’s questioning, Cassie Ventura faced a tougher interrogation Thursday under cross-examination from Sean “Diddy” Combs’ legal team.

Ventura testified for about five and a half hours Thursday and answered questions about her sexts with Combs, whether anyone else knew about their drug-fueled sex parties known as “Freak Offs” and Combs’ own problems with opiates.

Ventura is the prosecution’s star witness, and her testimony Tuesday and Wednesday alleging her ex-boyfriend Combs physically and sexually abused her is key to the charges against the hip-hop mogul. He has pleaded not guilty to racketeering conspiracy, sex trafficking and transportation to engage in prostitution and could face up to life in prison.

Prosecutors have said Combs and his inner circle used threats, violence, drugs, bribery, arson, kidnapping and lies to coerce Ventura and another woman into participating in “Freak Offs” and to protect the music mogul’s reputation.

The defense acknowledged Combs has been violent with former girlfriends and has a “different” sex life but said those do not equate to racketeering or sex trafficking. They also said the women consented to these sexual arrangements and said they were truly motivated by money and jealousy.

Combs’ trial is not being televised, per the rules of federal court. CNN has reporting from journalists inside and outside the court.

Here are the key takeaways from Thursday’s testimony.

Defense reads aloud Ventura’s sexts

The defense’s cross-examination began with defense attorney Anna Estevao reading aloud affectionate messages Ventura sent Combs over the years.

“I’m a very lucky woman,” Ventura wrote to Combs in a January 2008 text message. “I miss you so much I’d fly wherever you needed me whenever. I love you.”

Many other messages were sexually explicit.

“I’m always ready to Freak Off lolol,” she said in an August 2009 message.

The jury was shown sexts from 2012 reminiscing on past “Freak Offs” and how they enjoyed when they “made love” after one of them. Ventura also confirmed she and Combs had conversations about the “swingers’ lifestyle,” noting it was “very different” from the “Freak Offs.”

In a March 2017 text message, Ventura wrote that she enjoyed “Freak Offs” “when we both want it.”

“I would say that loving ‘Freak Offs’ were just words at that point,” she testified Thursday.

Other messages show Ventura’s frustrations

In other messages, Ventura expressed her hesitancy with the “Freak Offs.”

“The last time was a mistake but since has made me feel a little dirty and grimy as opposed to sexual and spontaneous. That’s the only reason why I go back and forth in my mind with wanting and not wanting to do it,” Ventura wrote him in December 2009. “I got nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it.”

Some messages also showed her frustrations with her relationship with Combs.

“I never seem to make the right decisions to you,” she wrote in October 2007, a few weeks after her 21st birthday party. Ventura testified Combs kissed her for the first time at that party.

“I am really hurt by the way you deal with me,” she wrote him in April 2010. “I don’t need your money, I need some attention. I am thankful, but I can pay for these things myself.”

Ventura agreed that they had open communication, although she testified it was “usually a go one-way street.” She would send messages being open about her feelings more often than he would, she explained.

Ventura didn’t tell employees or friends about ‘Freak Offs’

Ventura acknowledged she never told her friends or any of Combs’ staff members about the “Freak Offs.”

Ventura said she “definitely didn’t” want his staff to know about them. Assistants would often set up the hotel rooms beforehand, she said, but she didn’t recall a staff member walking in during a “Freak Off” session.

Still, she said her friends knew Combs physically abused her, sometimes because they witnessed it themselves. She also told her parents and brother about the abuse at different points, she testified.

Combs overdosed on painkillers in 2012, Ventura testifies

Combs overdosed on painkillers in February 2012 and for a time had an addiction to opiates, Ventura testified.

He and Ventura had a “Freak Off” and went to a sex club before Combs went without her to a party at the Playboy Mansion, she testified. Later that night, she took him to the hospital, where they learned he’d experienced an overdose, she testified.

“From what he told me, he took a very strong opiate that night, but we didn’t know what was happening so we took him to the hospital,” she testified.

Estevao, the defense attorney, asked a series of questions regarding Combs’ use of opiates and his mood when he was not using them.

“He was extremely dependent on his opiates, right?” Estevao asked.

“For a time,” Ventura said.

“He was very upset if his opiates were taken away from him?” Estevao asked.

“I guess so,” Ventura said.

Combs often said he didn’t remember physically abusing her because he was inebriated when he did, Ventura confirmed when asked. She acknowledged getting high on drugs was at times part of the appeal of “Freak Offs,” and they called each other “Get High Partners.”

Ventura said Combs was “explosive” at times when he’d find out that she was doing drugs with her friends or took his drugs without him knowing.

“If we weren’t getting high or if I wasn’t doing it with him, it was a problem,” she said.

Estevao reviewed text messages that she said suggest Combs was going through withdrawal in the days before the March 2016 assault at the InterContinental Hotel. Ventura testified that she does not remember him going through withdrawal at that time, but she acknowledged the texts appear to suggest he was sick at the time.

Multiple arguments over jealousy

The defense has said the case is really about jealousy, and on Thursday sought to show that Combs and Ventura’s arguments usually came when he suspected her of cheating.

Ventura testified that she “had some jealousy” of Kim Porter, the late model and actress who shared three children with Combs. Ventura also said she “was really upset” when she learned Combs was spending time with a woman referred to as “Gina” in April 2014.

Ventura said they argued multiple times about Combs getting back together with Gina and argued about other women.

Combs was often suspicious that she was romantically involved with other men, Ventura said, testifying he expected her to exclusively date him despite his own entanglements with many women over the years.

Ventura added that his jealousy triggered his temper. “It was a little scary,” she said.

Ventura testified that Combs was “irate” when he learned she was briefly dating the rapper Kid Cudi in 2011. Ventura said she broke it off with Kid Cudi after Combs assaulted her and threatened more violence on her and the rapper.

Women on social media would often claim to have a relationship with Combs, Ventura testified. “It happened often enough that I don’t know that I would remember every single one,” she said.

Court pushing to finish Ventura’s testimony before baby arrives

The court has taken a number of steps to ensure Ventura’s testimony is completed by Friday – hoping to wrap up before the pregnant pop singer gives birth.

Ventura is due to deliver her third child next month.

In a discussion late Wednesday about whether to end Ventura’s testimony 45 minutes early, prosecutor Maurene Comey laid out her concern.

“This witness is very, very pregnant. We are afraid she could have the baby over the weekend,” Comey said, according to a court-provided transcript of the exchange. “We want her off the stand before the weekend and we believe 45 minutes could make a difference.”

The court previously issued guidance that proceedings will stretch until 5 p.m. for the first week of testimony, but the following weeks will only last until 3 p.m. Lunch breaks, generally an hour long, have been condensed to about 30 minutes this week. On Thursday, the defense gave Ventura an iPad with exhibits to review during the lunch break in an effort to speed things up.

The judge told the defense team they need to complete their cross-examination of Ventura around lunch Friday, but he left open the possibility of granting them additional time if needed. He said he wants to have Ventura off the stand Friday.

“The direct took a day and a half so the defense will have a day and a half. So you have today, you have the morning tomorrow,” Judge Arun Subramanian told the defense.

Combs closely engaged with defense

Combs has appeared engaged with his attorneys and the testimony in court.

During the questioning of Ventura about text messages, Combs wrote notes on orange sticky notes and passed one after another to his attorney sitting beside him. He also spoke during the break briefly with Estevao, the attorney handling the cross-examination.

His attorneys have indicated they value speaking to him. In a sidebar conversation on Wednesday afternoon recorded in a court transcript, defense attorney Marc Agnifilo asked the court to push the start of cross-examination to Thursday morning so that he could have time to speak with Combs.

“We need to talk to him,” Agnifilo said. “It’s not nothing, but 45 minutes with him, our time is very limited because he’s incarcerated. So we would cherish having an additional 45 minutes to speak to him and get prepared for a very long cross.”

Correction: An earlier version of this story misstated the timeline of Ventura and Combs’ relationship. Ventura testified Combs kissed her for the first time at her 21st birthday party.

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