Cassie bursts into tears as she recalls ‘escort’s vile act’ & Diddy’s final texts as she’s pressed on $20m payout
SEAN "Diddy" Combs' ex-girlfriend Cassie Ventura burst into tears moments before concluding her disturbing testimony on day five of Combs' federal sex trafficking trial.
In a heartbreaking moment on the stand, Cassie said she would trade her $20 million settlement from Combs if it meant she never had to endure his drug-fueled sex parties through their 10-year relationship.
A very pregnant Cassie underwent her final day of grueling cross-examination on Friday as the defense tried to prove she willingly engaged in Combs' sick orgies called "freak-offs."
She burst into tears as she recalled a male escort urinating on her and Combs allegedly beating her during the twisted parties where he forced her to have sex with other men while he watched.
When pressed on the stand about the money she received from her lawsuit against Combs, Cassie wiped away tears as she said, "I’d give that money back if I never had to have freak-offs.
"If I never had to have freak-offs, I would have agency and autonomy. I wouldn’t have had to work so hard to get it back.”
Cassie testified that she ended her relationship with Combs in 2018, but that the two stayed in touch even after he allegedly raped her while she was dating her now-husband Alex Fine.
Combs reached out to congratulate on her pregnancy in 2019 and told her that she was one of the "greatest women in the world."
The court saw one of his final texts to Cassie from March 2020, which read, "One day I hope you forgive me.
"We’re honestly lucky to be alive. We went hard. Please know I send this message with all respect to your marriage. Love.”
Cassie testified that she never participated in another "freak-off," which had occurred weekly for years, after they split.
After Cassie left the stand, Dawn Richard swore in to testify about when she saw Combs allegedly beat Cassie with a skillet in 2009. Her testimony will continue on Monday.
It comes as…
- Cassie Ventura testified that Sean Combs became jealous and took her phone when he heard she was dating an NFL player
- He also took her phone after he heard she danced with Chris Brown, which Cassie denied on the stand
- An audio recording of Cassie threatening a man who secretly recorded a "freak-off" was played for the jury on Friday
- The judge became furious at lawyers when he found out Cassie, who is 8 months pregnant, might have to return to the stand next week
- Cassie revealed she was paid $20 million to settle her lawsuit against Combs
- Ex-hotel security guard Israel Florez testified on Monday about being offered cash after Combs attacked Cassie in 2016
- Male escort Daniel Phillip took the stand to speak about how he was paid to have sex with Cassie in front of Combs
- Combs turned down a plea deal days before jury selection got underway
CASSIE'S TESTIMONY
Over her first two days of questioning by prosecutors, Cassie recounted details of multiple "freak-offs" and violent episodes.
Cassie told the court Combs made incessant demands for orgies, which would last for up to four days as she took drugs including cocaine, ecstasy, and mushrooms to stay awake.
She said she was terrified to refuse Combs' orders out of fear he would hurt her and share videos of the "freak-offs."
An audio recording of Cassie threatening a man she suspected of having a "freak-off" video was played for the jury on Friday, where Cassie said, "I’m going to kill you, and then he’s gonna kill you again."
Combs faces five criminal counts, including racketeering conspiracy, sex trafficking by force, and transportation to engage in prostitution.
The rapper has pleaded not guilty to all charges as prosecutors continue to paint him as the ringleader of a criminal enterprise.
He has denied all allegations against him and insists he's only engaged in consensual sex.
If you or someone you know is affected by any of the issues raised in this story, call the National Sexual Assault Hotline at 1-800-656-4673.
Read our Diddy trial updates blog for the latest updates from court...
Cassie's cross-examination ends
The defense's cross-examination of Cassie Ventura has ended.
The prosecution is now finishing up their re-direct questioning.
Cassie is expected to leave the witness stand by the end of the day.
Cassie denies financial troubles
The defense tried to paint a picture of Cassie Ventura struggling with money.
Defense lawyer Anna Estevao asked if "financial issues" caused Cassie and her family to move back in with her parents in Connecticut before November 2023.
Cassie said no and that they just wanted to live on the East Coast.
She was also asked about a planned music tour to Australia and New Zealand that she canceled after she settled her lawsuit against Combs for $20 million in November 2023.
“When you saw you were going to get the $20 million, you canceled the tour because you didn't need it anymore, right?” Estevao said.
"That wasn’t the reason why,” Cassie fired back.
'Want to freak-off one last time?'
Sean Combs' defense lawyer ended her cross-examination by showing text messages between Cassie Ventura and Sean Combs from over a decade ago.
"Want to freak off one last time?" Combs wrote in 2012.
Cassie responded, "I don't want it to be the last time."
She then said she wanted to have a "freak-off" for the "first time for the rest of our lives."
Combs congratulated her on pregnancy
Cassie Ventura testified that Sean Combs reached out to her multiple times after their breakup in 2018, but she never responded.
Combs congratulated on her first pregnancy with husband Alex Fine before she gave birth in December 2019.
He texted her to tell her he had a dream about her.
In 2020, he texted her, "You're one of the greatest women in the world and don't ever forget that."
She responded that the messages "blew her mind" because that's what she wanted to hear when they were together.
In one text, she told Combs, “I wouldn’t be at this beautiful point in my life if I hadn’t been with you.”
'You were always my ride or die'
Cassie Ventura is reading out texts from after the end of her relationship with Sean "Diddy" Combs.
She texted him, "We should talk and have closure."
Combs responded with a tear face emoji.
"You were always my ride or die," he said.
Cross-examination is almost over
The court is back from lunch.
Defense attorney Anna Estevao said the cross-examination of Cassie Ventura is almost over.
Cassie appeared to be relieved and said, "thank you."
Cassie's husband called when she was with Combs
Cassie Ventura testified that during the last time she had sex with Sean "Diddy" Combs, she got a FaceTime call from her now-husband Alex Fine.
Cassie said she didn't answer the call from Fine, a personal trainer who is the father of her two children.
The last time she had sex with Combs in September 2018 was a few days after Combs allegedly raped her following their break-up.
After the consensual encounter, she texted Combs that she had a great time.
Cassie said Fine punched a wall when he found out about the alleged rape.
Court takes lunch
The court is now taking a lunch until 1:10 pm.
After lunch, Cassie Ventura is set to finish cross-examination.
New courtroom sketches revealed
Court sketches from Friday morning show Sean Combs listening as Cassie Ventura continues to face cross-examination.
Combs was also seen hugging defense lawyer Anna Estevao when he walked into the trial this morning.
Sean Combs watches as his lawyer Anna Estevao cross-examines Cassie Ventura on May 16, 2025Credit: Reuters 
Combs embraced Estevao when he walked into the courtroom on FridayCredit: Reuters
'I never saw him again'
Cassie Ventura saw Sean "Diddy" Combs for the last time until trial at the funeral of Kim Porter, his ex-girlfriend, in November 2018.
A few days later, she texted Combs after he posted on social media that Porter was his "soulmate" and said it was hurtful.
“What was the 11 years all about?” Cassie wrote at the time.
She said on the stand, "I never saw him again."
When the defense lawyer asked, "He let you go, right?" Cassie responded, "I don't know about letting me go."
This morning's recap of mistrial drama and Chris Brown
Cross-examination has gone longer than expected - and prosecutors are worried that the trial could be thrown out if they ask Cassie, who is eight months pregnant, to continue on Monday.
Prosecutors told the judge there could be a mistrial if Cassie goes into labor with her third baby with husband Alex Fine over the weekend, leaving her testimony unfinished.
This puts added pressure on the defense to finish their cross-examination today after they kicked off Friday's questioning by asking Cassie about the men she dated while she was with Combs.
Cassie testified this morning that Combs would fly into jealous rages when he found out about her flings with other men, despite his dating other women while they were together.
In August 2016, Combs took her phone when he learned she was dating a football player and called him. The player wasn't named.
Cassie was also asked about an instance in 2013 where Combs took her phone after he suspected she danced with singer Chris Brown.
But she couldn't remember the argument and denied the encounter, saying, "I wasn't dancing with Chris Brown."
Defense tries to poke holes in timeline
Sean Combs' defense team is trying to point out inconsistencies in Cassie Ventura's timeline about when Combs allegedly raped her after they broke up.
In her civil lawsuit, filed in November 2023, Cassie first said the attack took place in September 2018.
Now, the defense is saying Cassie is telling a different story because she remembers the alleged rape as happening in August 2018.
The defense pointed out that in August of that year, Combs texted Cassie, "I know I look bad to you.
"I could tell I didn't turn you on yesterday. I fell off."
'I don't hate him'
Cassie told defense attorney Anna Estevao she doesn't hate her ex-boyfriend even after accusing him of raping her in 2018.
“I don’t hate him,” Cassie testified.
“Do you still have love for him?” Estevao asked.
“I have love for the past and what it was,” Cassie responded.
Cassie reveals reason for break-up
Cassie Ventura testified that she broke up with Sean Combs for good in August 2018.
She said she decided to end the relationship after she saw a picture of Combs with another woman named Gina, whom he dated on-and-off for years.
“I just don’t trust anymore," Cassie texted him.
"That last shot put the nail in the coffin."
She continued, "I promised myself I wouldn’t be with you anymore if you did that to me again."
Cassie also said about Combs' infidelity, "you lied to me," and "she never went away."
Cassie speaks more about alleged rape
Cassie Ventura alleges that Sean Combs raped her in 2018, after they had broken up and she was already dating her now-husband Alex Fine.
She said while she was dating Fine, she met with Combs for dinner at an Italian restaurant in Malibu.
Cassie testified that Combs invited her to go to the musical festival Burning Man with him, even though they had broken up.
She added that he was acting differently during the dinner.
“He was acting strangely, yes,” Cassie testified.
Cassie suggested 'freak-off with a girl'
A text exchange from 2010 showed Cassie Ventura suggesting a "freak off w/ a girl" instead of a man to Sean "Diddy" Combs.
"Yes that's what I'm suggesting," Cassie said under cross-examination.
Combs responded, "What makes you wanna do that?"
They moved past the conversation. It's unclear if a woman ever joined in the "freak-offs" with Cassie and Combs.
Breakup texts shown
Texts are being shown to the jury from around the time that Sean Combs and Cassie Ventura broke up for the final time in 2018.
“Can I not get a chance to make things right?” Combs texted Cassie at the time.
“I haven’t taken care of you?”
Cassie replied, "You took care of me materialistically, not where I needed it.
“I needed you to love me and put me first.”
Text exchange from 2010
A text exchange between Sean Combs and Cassie Ventura from April 2010 is being read out in court after it was referenced during direct questioning by prosecutors earlier this week.
Cassie already testified that she planned to tell Combs she didn't want to have "freak-offs" anymore, but didn't because she was intimidated by his response.
Below is the exchange:
Cassie: I want to talk to you about something tomorrow. Going to sleep. Love you.
Combs: Is it going to stress me out? What is it about
Cassie: Freak-off. It can wait. It’s not a big deal.
Combs: Now you don’t want to do it anymore. Oh, I already know. You so predictable.
Cassie: Really? OK. Since that’s definitely what it was, we’ll leave it at that then, since I’m so predictable. Have a good night.
Combs: Whatever, Baby. I’m not going to play no games with you and you ain’t gonna keep shutting me down.
Cassie: I’m not shutting you down. I never do. If anything, it’s always the other way around. I wasn’t going to say I didn’t want to do it anymore.
Cassie and Chris Brown pictured
While Cassie Ventura denied dancing with singer Chris Brown in 2013 during cross-examination today, the two have been spotted hanging out multiple times throughout the years.
Cassie Ventura speaking to Chris Brown at a party at Chateau Nightclub in Las Vegas on September 1, 2012Credit: Getty 
Chris Brown and Cassie, who denied dancing with Brown in a 2013 instance that made Sean Combs so angry he took her phone awayCredit: Getty Texts shown about "freak-off" drugs
The jury saw a message from Sean "Diddy" Combs to Cassie Ventura in January 2016.
Combs was speaking about having a "freak-off" without taking ketamine, or K.
“I HATE K!!! So you let me know when," he texted.
"Pls don’t be mad and think that’s all I wanna do.
“A successful Fo is when we remember and we don’t be fiending to do it the right way."
Cassie was treated for mental health problems
Cassie testified she went to an inpatient treatment center for 45 days in early 2023 for her mental health programs, where she started writing her book.
She said she underwent psych treatments including neuro feedback therapy and EMDR trauma therapy to recover from her traumatic memories.
Cassie said she's taken Buprenorphine, which treats opiate addiction, since she was prescribed it in 2022.
Cassie said it wasn't cheating
As the defense grilled Cassie Ventura about her infidelities when she was dating Sean Combs on Friday morning, Cassie insisted it wasn't cheating.
“If I was with anyone else besides him, I don’t know that I would call it cheating," Cassie testified.
“When you’re not with somebody, it’s not cheating.
"I feel like it’s a technicality in a boyfriend-girlfriend relationship. We weren’t married."
Cassie makes threats in new audio
An audio recording of Cassie Ventura confronting a man she thought had a "freak-off" video in March 2014 has been played for the jury.
“I’m going to kill you, and then he’s gonna kill you again,” Cassie said in the recording.
"If you don't show me, I will kill you and cut you up," she said.
She continued, "I've never killed anyone in my life."
"It's not going to be blood on my hands, someone else is going to do it. I'm not playing with you."
On the stand, Cassie confirmed it was her speaking in the recording.
Defense mentions Chris Brown
Defense lawyer Anna Estevao asked Cassie Ventura if she remembers when Sean Combs took her phone after he found out she was dancing with R&B singer Chris Brown.
But Cassie denied dancing with Brown.
"I was not dancing with him," Cassie said.
Cassie testified Combs took her phone, car, and passport from her when he was angry at her.
Combs' family members arrive
Sean Combs' son, King Combs, and stepson, Quincy Brown, have arrived at the trial on Friday morning.
Combs' son Justin Dior Combs was also seen walking into the courthouse.
Quincy Brown, left, and King Combs, right, arrive at Manhattan Federal Court on May 16, 2025Credit: AFP 
Quincy Brown, left, and Justin Dior Combs arrive at the US Courthouse in Manhattan on FridayCredit: Reuters