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Sexually explicit messages between RnB singer Cassie and her former boyfriend Sean “Diddy” Combs have been read in court, with some showing her expressing apparent enthusiasm about the “freak off” sex sessions with escorts she alleges she was forced into.

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

Sean "Diddy" Combs listens as lawyer Anna Estevao (not seen) cross-examines Casandra "Cassie" Ventura (not seen) during Combs' sex trafficking trial in New York City, New York, U.S., May 15, 2025, in this courtroom sketch. REUTERS/Jane Rosenberg
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Messages sent by Cassie to Diddy were read in court. Pic: Reuters/ Jane Rosenberg

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.

Janice Combs arrives at Federal court during the Sean "Diddy" Combs' sex trafficking and racketeering conspiracy trial at U.S. court in Manhattan, in New York City, U.S., May 15, 2025.   REUTERS/David 'Dee' Delgado
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Janice Combs was in court to support her son once again. Pic: Reuters/ David ‘Dee’ Delgado

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.”

Brian Steel arrives at Federal court during the Sean "Diddy" Combs' sex trafficking and racketeering conspiracy trial at U.S. court in Manhattan, in New York City, U.S., May 15, 2025.   REUTERS/David 'Dee' Delgado
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Brian Steel is one of the defence laywers on Combs’s team. Pic: Reuters/ David ‘Dee’ Delgado

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.

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Cassie breaks down in tears during previous day’s evidence

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.

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Legendary playwright Sir Tom Stoppard dies aged 88

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Legendary playwright Sir Tom Stoppard dies aged 88

Playwright Sir Tom Stoppard, who won an Oscar and a Golden Globe for Shakespeare In Love, has died at the age of 88.

A statement from United Agents said: “We are deeply saddened to announce that our beloved client and friend, Tom Stoppard, has died peacefully at home in Dorset, surrounded by his family.

“He will be remembered for his works, for their brilliance and humanity, and for his wit, his irreverence, his generosity of spirit and his profound love of the English language.

“It was an honour to work with Tom and to know him.”

King Charles said in a tribute: “My wife and I are deeply saddened to learn of the death of one of our greatest writers, Sir Tom Stoppard. A dear friend who wore his genius lightly, he could, and did, turn his pen to any subject, challenging, moving and inspiring his audiences, borne from his own personal history.

“We send our most heartfelt sympathy to his beloved family. Let us all take comfort in his immortal line: ‘Look on every exit as being an entrance somewhere else’.”

Sir Tom’s entertainment career spanned more than six decades, in which he won a host of Tony and Olivier awards, as well as the Golden Globe and Academy Award with Marc Norman for their 1998 screenplay Shakespeare In Love – starring fellow Oscar-winner Gwyneth Paltrow.

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Sir Tom Stoppard in 1999. Pic: PA
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Sir Tom Stoppard in 1999. Pic: PA

His work, known to blend intellect, emotion and humour, often explored philosophical and political themes, challenging societal norms to remind audiences of the power of thought.

His other award-winning plays included Rosencrantz And Guildenstern Are Dead, The Real Thing and Travesties.

The playwright also wrote prolifically for TV, radio and film, including adapting Leo Tolstoy’s novel Anna Karenina for the 2012 film starring Keira Knightley and Jude Law, and TV series Parade’s End with Benedict Cumberbatch and Rebecca Hall – adapted from novels by Ford Madox Ford.

He received countless accolades and honours during his career, including being knighted by the late Queen for his services to literature in 1997.

Queen Elizabeth II shakes Sir Tom's hand before presenting him with the insignia of a Member of the Order of Merit in 2000. File pic: PA
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Queen Elizabeth II shakes Sir Tom’s hand before presenting him with the insignia of a Member of the Order of Merit in 2000. File pic: PA

Sir Tom meets then Prince Charles in 2009. File pic: PA
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Sir Tom meets then Prince Charles in 2009. File pic: PA

He won the David Cohen Prize For Literature in 2017, following in the footsteps of laureates Harold Pinter, Hilary Mantel and Seamus Heaney.

Sir Tom released his semi-autobiographical work titled Leopoldstadt in 2020 – set in the Jewish quarter of early 20th century Vienna – which later won him an Olivier award for best new play and also scooped four Tony awards.

The West End play, which featured his son Ed Stoppard, also saw him honoured by PEN America, the literary and human rights organisation, which handed him the Mike Nichols Writing for Performance Award.

Pic: Matt Humphrey/PA
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Pic: Matt Humphrey/PA

From refugee to playwrighting sensation

Sir Tom was born Tomas Straussler in Czechoslovakia, but fled and changed his name amid the Nazi occupation, finding refuge in Britain in 1946.

He became a journalist in Bristol in 1954 before becoming a theatre critic and writing plays for radio and TV, including The Stand-Ins, later revised as The Real Inspector Hound, and Albert’s Bridge first broadcast by BBC Radio.

His career took off with hit play Rosencrantz And Guildenstern Are Dead, which premiered at the Edinburgh Fringe Festival in 1966, before it was produced for the National Theatre and on Broadway, winning four Tony awards in 1968 including best play.

Sir Tom Stoppard and Dame Judi Dench at a photocall in London in 1999. File pic: PA
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Sir Tom Stoppard and Dame Judi Dench at a photocall in London in 1999. File pic: PA

Sir Tom began advocating on behalf of Soviet and Eastern Bloc dissidents after writing Every Good Boy Deserves Favour, a play inspired by his friendship with Viktor Fainberg, who had been imprisoned in Czechoslovakia by the Soviets.

Much later, in 2002, his trilogy of plays set in 19th century Russia, The Coast Of Utopia, were staged at the National Theatre.

His most recent plays include Heroes, Rock ‘n’ Roll and The Hard Problem.

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PM’s rap battle with Sky’s Beth Rigby goes viral – and one of the AI satirists behind it explains why

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PM's rap battle with Sky's Beth Rigby goes viral - and one of the AI satirists behind it explains why

Satire has long been an occupational hazard for politicians – and while it has long been cartoons or shows like Spitting Image, content created by artificial intelligence (AI) is increasingly becoming the norm.

A new page called the Crewkerne Gazette has been going viral in recent days for their videos using the new technology to satirise Rachel Reeves and other politicians around the budget.

On Sky’s Politics Hub, our presenter Darren McCaffrey spoke to one of the people behind the viral sensations, who is trying to remain anonymous.

He said: “A lot of people are drawing comparisons between us and Spitting Image, actually, and Spitting Image was great back in the day, but I kind of feel like recently they’ve not really covered a lot of what’s happening.

“So we are the new and improved Spitting Image, the much better Have I Got News For You?”

He added that those kinds of satire shows don’t seem to be engaging with younger people – but claimed his own output is “incredibly good at doing” just that.

Examples of videos from the Crewkerne Gazette includes a rapping Kemi Badenoch and Rachel Reeves advertising leaky storage containers.

More on Beth Rigby Interviews

They even satirised our political editor Beth Rigby’s interview with the prime minister on Thursday, when he defended measures in the budget and insisted they did not break their manifesto pledge by raising taxes.

“Crewkerne Man” says providing satire for younger people is important as Labour is lowering the voting age.

Asked why he is trying to be anonymous, the man said the project is not about one person – or even the whole group – but rather their output.

He also claimed the UK is “increasingly seeing arrests – especially with comedians”, pointing to the Graham Linehan case.

“So we just never know where the Labour Party is going to drive the policy next, in regards to free speech,” he said.

“So for me, certainly it’s a matter of safety.”

Watch Beth Rigby’s actual interview with Sir Keir Starmer below.

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The prime minister defends the budget

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Tilly Norwood: Creator of AI actress insists she’s not designed to steal jobs

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Tilly Norwood: Creator of AI actress insists she's not designed to steal jobs

The creator of an AI actress has told Sky News that synthetic performers will get more actors working, rather than steal jobs.

AI production studio Particle6 has ruffled feathers in Hollywood by unveiling Tilly Norwood – a 20-something actress created by artificial intelligence.

Speaking to Sky News’ Dominic Waghorn, actor and comedian Eline Van der Velden – who founded Particle6 – insisted Norwood is “not meant to take jobs in the traditional film”.

AI entertainment is “developing as a completely separate genre”, she said, adding: “And that’s where Tilly is meant to stay. She’s meant to stay in the AI genre and be a star in that.”

“I don’t want her to take real actors’ jobs,” she continued. “I wanted to have her own creative path.”

Norwood has been labelled “really, really scary” by Mary Poppins Returns star Emily Blunt, while the US actors’ union SAG-AFTRA said in a statement: “Tilly Norwood is not an actor, it’s a character generated by a computer program that was trained on the work of countless professional performers – without permission or compensation.”

Responding to the criticism, Ms Van der Velden argued that Hollywood is “going to have to learn how to work with [AI] going forward”.

“We can’t stop it,” she said. “If we put our head in the sand, then our jobs will be gone. However, instead, if we learn how to use these tools, if we use it going forward, especially in Britain, we can be that creative powerhouse.”

Eline Van der Velden said she wanted the character to 'have her own creative path'
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Eline Van der Velden said she wanted the character to ‘have her own creative path’

Read more:
How AI music is fooling most of us
Tom Hollander ‘not scared’ of AI star

Ms Van der Velden said her studio has already helped a number of projects that were struggling due to budget constraints.

“Some productions get stuck, not able to find the last 30% of their budget, and so they don’t go into production,” she said. “Now with AI, by replacing some of the shots […] we can actually get that production going and working. So as a result, we get more jobs, we get more actors working, so that’s all really, really positive news.”

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