The 38-year-old, whose full name is Casandra Ventura, faced a full day of cross-examination from the hip-hop mogul’s defence lawyers, who are attempting to convince the jury she consented to a “swingers lifestyle”.
Combs, 55, has pleaded not guilty to charges of sex trafficking, racketeering conspiracy and transportation to engage in prostitution, in relation to Ms Ventura and other women. His lawyers have conceded he could be violent, but say nothing he did amounted to crimes of this nature.
Ms Ventura alleges she was physically abused and degraded for years by the powerful hip-hop star and music executive, accusing him of violence, coercion, blackmail and rape.
Prosecutors say he exploited and used his network of employees to facilitate illegal activities, which is a key part of the racketeering charge.
Sean ‘Diddy’ Combs trial: Day 4 – As it happened
But during the fourth day of the trial in Manhattan, New York, defence lawyers pushed back, focusing on texts and emails that were both romantic and sexually explicit.
“I’m always ready to freak off,” the court heard Ms Ventura wrote in one message in August 2009. In another she told him, about a freak off: “Can’t wait.” And in another, jurors were told, she described a video of one sex session with an escort as “dope”.
The pair were together, on and off, for about 11 years from 2007 to 2018.
Combs, whose mother Janice has been in court all week to support him, along with some of his children, appeared relaxed as the messages were read aloud for jurors.
Messages from 4 March 2016 – the day before an incident at the InterContinental Hotel in Century City, Los Angeles, in which Combs was filmed on CCTV seeming to attack Ms Ventura in a hallway, as he was wearing just a towel and socks – were also read in court.
Footage from this incident, which was first made public in May 2024, has been a key piece of evidence during the trial. Ms Ventura has told the court it happened as she tried to leave a freak off session after being hit by Combs.
Freak off ‘felt dirty, grimy’
During cross-examination, the court heard Ms Ventura sent a sexually explicit message the day before this.
She also sent him a message saying, “Baby I want to FO so bad but I dont want to f*** myself up”.
Ms Ventura has told the court this was damage limitation and that she wanted to keep him happy, as she had a film premiere coming up a few days later.
Jurors also heard details of an email she sent in 2009, in which she expressed conflicting feelings about taking part in these sex sessions with escorts.
In the email, she told Combs she needed to trust him “beyond it just being sexual” – that in order to be more open sexually, “I need to feel safe, like home”.
She told him “the last time was a mistake but since has made me feel a little dirty, and grimy as opposed to sexual and spontaneous”.
This was the reason she was going “back and forth in my mind with wanting and not wanting to do it”, she wrote. At first, when they were “so in love… there were no questions asked, it felt right”.
She told him: “I get nervous that I’m just becoming the girlfriend that you get your fantasies off with.”
Ms Ventura has told the court that she fell in love with Combs very quickly when they got together, when she was 21 and he was 37. She has said she wanted to please him, but became fearful of him.
At one point during cross-examination, she raised that she felt jurors were not hearing the full context of some of the messages being highlighted, saying: “There’s a lot we skipped over.”
Combs’s lawyers are painting his sexual preferences as part of a “swingers” lifestyle that has been mentioned previously at trial, saying people might not agree with it but it does not make him guilty of sex trafficking.
Questioned on this, Ms Ventura said they were “very different”.
She was also asked about drug use, her own and Combs’s, and at one point told the court she believed he was addicted to opiates when they were together.
She also said he was taken to hospital after overdosing on opiates at the Playboy Mansion in 2012 – something which was reported on by outlets including TMZ at the time, when it was said he had suffered a migraine.
Judge frustrated with Diddy’s lawyers
Away from the questioning, a notable moment in court came when Judge Arun Subramanian became frustrated with Diddy’s lawyers over how long they will spend cross-examining Ms Ventura.
He told them they should get a day and a half – the same time the prosecution had. “In what universe did you not understand this is what was going to happen?” he told them.
The judge is keen to keep the trial on time and particularly Ms Ventura’s evidence, as she is eight months pregnant with her third child with husband Alex Fine, who has been supporting her in court.
Read more:
The rise and fall of Diddy
Diddy – a timeline of allegations
Everything you need to know about the trial
She has now spent almost three days on the witness stand – tomorrow will be her fourth – and became emotional towards the end of her testimony on her second day.
The criminal case against Combs comes after Ms Ventura sued him in 2023, accusing him of years of physical and sexual abuse. The suit was settled in 24 hours, for a figure that was undisclosed at the time.
Ms Ventura has confirmed during the trial that this was $20m (about £15m).
Combs, 55, has been jailed since September, and faces at least 15 years or possibly life in prison if convicted.
