Close Menu
The Shade RoomThe Shade Room
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • NEWSLETTER
  • CAREERS
  • ADVERTISE WITH US
  • GET FEATURED
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Trending
  • Tory Lanez Files $100M Lawsuit Against California Prison For 2025 Stabbing Attack & Seeks $1M Per Wound
  • Sweet Life! Karrueche Tran & Deion Sanders’ Cozy Selfie Has The Internet Screaming Relationship Goals (PHOTO)
  • Ice Spice Seemingly Shouts Out Wendy’s While Addressing Viral McDonald’s Incident (PHOTO + VIDEOS)
  • Whew! Cleotrapa Enters The Chat As Fans Sound Off On Ice Spice’s McDonald’s Altercation (VIDEOS)
  • Photos Reveal State Of D4vd’s Reported $3.5M Hollywood Home Prior To Arrest In Celeste Rivas Hernandez Case
  • Social Media Reacts As Pooh Shiesty’s NEW Mugshot Surfaces Amid Arrest For Kidnapping & Robbery Of Gucci Mane (PHOTO)
  • Clapback Season! Rihanna Trolls Content Creator Over Baby #4 Speculation After Alleged Pregnancy Photo Surfaces (VIDEO)
  • Footage Of D4vd’s Arrest Surfaces As His Lawyers Speak Out Amid Ongoing Investigation (VIDEO)
  • Whoa! Video Footage Shows Woman Physically Attacking Ice Spice At Los Angeles McDonald’s (WATCH)
  • Akon On Why He Didn’t Sign Drake, A Verzuz With T-Pain + Polygamy & Ne-Yo | SITSR (Exclusive)
The Shade RoomThe Shade Room
The Shade Room Text Logo
Facebook X (Twitter) Instagram YouTube TikTok Snapchat
  • SHOWS
  • CELEBS
  • NEWS
  • BEAUTY & STYLE
  • TSR TEENS
  • TSR SHOP
  • ROOMIE DIARIES
  • ADVERTISE WITH US
The Shade RoomThe Shade Room
Home » All Listicles » Freak-Off Texts, Emails & Mention Of Ryan Leslie: Diddy’s Defense Unleashes Cross-Examination On Cassie (Day Four)
Celebs

Freak-Off Texts, Emails & Mention Of Ryan Leslie: Diddy’s Defense Unleashes Cross-Examination On Cassie (Day Four)

By TSR Admin - 2025/05/15
Facebook Twitter Pinterest
Diddy's Defense Unleashes Cross-Examination On Cassie As His Trial Continues (Day Four)
Share

Day four of the federal criminal trial against Sean “Diddy” Combs commenced on Thursday, May 15. TSR is back on the ground. And the day kicked off with Judge Subramanian requesting the prosecution and defense “to finalize what evidence can and can’t be introduced.” This reportedly before the defense began their cross-examination of Casandra “Cassie” Ventura.

RELATED: Beatings Diddy’s Staff Knew About, Self-Harm & Her Tell-All Book: Cassie Continues Testimony In Federal Trial (Day Three)

#TSRTrialWatch Day 4 begins with Judge Arun Subramanian kicking off today’s hearing by working with both legal teams to finalize what evidence can and can’t be introduced before the defense starts cross-examining Cassie’s legal team.

This follows overnight complaints from…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

Cassie Sits For Cross-Examination In Diddy Trial: 2008-2009 Emails & Texts Read & As “Pop Pop” Nickname Resurfaces

Defense attorney Anna Estevao began the team’s cross-examination with questions about Cassie and Diddy’s relationship.

Defense attorney Anna Estevao begins her cross-examination by asking Cassie about her relationship with Diddy.

Cassie responded yes to a series of questions:
Estevao: “You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well.” Cassie:…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

As the cross-examination continued, Estevao presented Cassie with old texts and email exchanges she shared with Diddy. In a set from 2008, Cassie shared her love for Diddy, while in a set from August 2009, Diddy expressed his love for Cassie.

“I love you sooooo much it makes me cry,” he reportedly wrote in a message.

Additionally, in one text message, Cassie even refers to “Diddy” as “Pop Pop.” As mentioned in her earlier testimony, this was a name she says she used to call her grandfather. And found it “disrespectful” that Diddy asked her to also refer to him the same.

In April 2010, Cassie told Combs: “Going to sleep now so it can be tomorrow faster and you can be home. Love you!!!” Combs replied: “Love my baby.”

Diddy appears relaxed as cross-examination is underway sitting back in his chair, with his legs crossed, conferring with his lead…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

Amid the texts being read, Cassie explained her perspective: “I had fallen in love with him and cared about him very much.”

By: Jadriena Solomon

Cross-Examination Continues: Things Appear To Take A Turn In 2010

As the cross-examination continued, Cassie read an April 2010 email. In it, she “expressed frustration that Combs would rush her off the phone and wasn’t making time for her.”

“That’s not being in a relationship with someone that you love and are in love with … I am really hurt by the way you deal with me, I don’t need your money, I need some attention,” she wote.

By: Jadriena Solomon

Cross-Examination: Texts Mentioning “Freak-Offs” Are Read

Estevao then reads texts from Diddy, reportedly shared in August 2009.

“When do you want to freak off? Lol,” he writes. To which Cassie responds, “I’m always ready to freak off.”

Two days later, Cassie reportedly writes to Diddy again:

“I can’t wait to watch you. I want you to get real hott,” he says.” To which she responds, “Me Too, I just want it to be uncontrollable.”

By: Jadriena Solomon

#1

Court Pauses At Cassie's Request

Cassie Requests Brief Pause Mid Cross-Examination Testimony

After a series of explicit messages were shown in court, the judge granted Cassie’s request for a break, allowing her to step down from the witness stand. The jury was also dismissed for a short recess.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#2

Cross-Examination Continues: Cassie's Asked About Her Prior Romance With Ryan Leslie

When cross-examination resumed, the defense questioned Cassie about having “Mr. Leslie’s initials” tattooed on her body. In response, she affirmed. Ultimately, Cassie was asked how many tattoos she had before meeting Diddy.

She explained she had three, which included one that read, “No Regrets.”

By: Jadriena Solomon

#3

Cross Examination Continues: 2009 Texts Are Read Where Cassie Tells Diddy She Wants More

As cross continues, a 2009 text exchange between Cassie and Diddy is read. In the correspondence, Cassie expresses her desire to have more than a sexual relationship with Diddy.

“I like that. I want it and I want to give you the same,” Cassie wrote, reportedly referring to oral sex. “I just think that I have to trust you beyond it just being sexual. Do you know what I mean? In order for me to be more open with the things we do in bed, I need to feel safe, like home, like this is my husband, and this is THE ONLY man that will ever have this aggressive/sexual side of me.”

The message reportedly ends with, “The last time was a mistake… it made me feel a little dirty and grimy as opposed to sexual and spontaneous.”

By: Jadriena Solomon

#4

Cross-Examination Continues: Cassie Giggles At 2007 Email

As a 2007 email was shared, Cassie giggled in court. The email was reportedly sent by her to Diddy.

“It’s making me giggle because it’s from 2007,” Cassie told the court, reportedly breaking the tension inthe room.

By: Jadriena Solomon

#5

Cross-Examination: Mood Shifts As The Topic Turns To Cassie's Civil Lawsuit & The Freak-Offs

At that point, cross continued with Diddy’s lawyer asking Cassie if she was unaware that her civil lawsuit, and specifically the revelation of the sexual “freakoffs,” involving the 55-year-old, ruined his career.

“I could understand that,” Cassie replied.

As for the freak-offs, specifically, Cassie explained that she “wore wigs and masquerade masks during the encounters to stay hidden.”

“I definitely didn’t want anyone to know,” she explained.

More specifically, Cassie explained that on the first freak off, she followed Diddy’s lead.

“The encounter itself was pretty crazy,” she said. “I really followed his lead on that because I had never done it before.”

By: Jadriena Solomon

#6

Unbothered? Diddy Sits Back as Steamy Texts With Cassie Are Read in Court

As Estevao and Cassie read steamy old texts between her and Diddy aloud in court, Diddy appeared unbothered — sitting back at the defense table with his hands folded and legs crossed.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#7

The defense has Cassie reading multiple pages of texts and emails exchanged between her and Diddy dating back 15 years.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#8

Cross-Examination Continues: Cassie Shares Diddy's Addictions

Before the court broke for lunch, Cassie explained that she believes Diddy was an addict to “success.” Additionally, she explained that “at a point,” he was also addicted to opiates.

Cassie Testifies Diddy Was “Addicted to Success” — and Eventually Opiates
As court broke for lunch, Estevao pressed Cassie on Combs’ alleged addictions.

“Would you say he was an addict?”
Cassie: ” would say he was an addict.”
“To what?”
Cassie: “Success.”

When asked if he was…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

#9

#10

Cross-Examination Continues: Cassie's Time On The Stand Is Discussed

As the trial returns, the defense reveals that they expect Cassie’s time on the stand to be concluded by the end of Friday, March 16.

Trial has resumed and Diddy’s defense team reveals they don’t expect to be don’t question Cassie until the end of the day on Friday, with Judge Subramanian noting that both sides agreed she’d be off the stand by the end of the week, since she’s due to give birth very soon.…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

#11

Cross Examination: FO's Are Mentioned Again

From there, the defense shares additional texts in which Cassie and Diddy discussed their “love” for the freak-offs.

“Loving FO’s were just words at that point,” Cassie told the courtroom.

Per the New York Post, Cassie would sometimes purchase “different sexual supplies, lubricants, [and] outfits” for the FOs from sex shops. Furthermore, one text shared by the defense showed Cassie and Diddy noting their efforts to be cautious to avoid her getting pregnant.

Combs reportedly sent Cassie a message that they would “be extra careful” on that particular occasion.

By: Jadriena Solomon

#12

The defense is presenting a large batch of documents as evidence—some of the docs have as many as 26 pages.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#13

Cross-Examination Continues: Kim Porter Is Mentioned

Per the Post, as cross continued, Cassie testified that she was jealous of Kim Porter. Porter shared three children with Combs and their relationship ran from about 1994 to 2007.

“I had some jealousy toward Ms. Porter, yeah,” Cassie said, noting that Diddy would often spend holidays with Porter and their children, which made her feel “upset.”

By: Jadriena Solomon

#14

Cross-Examination Continues: Gina Huynh Is Mentioned

Additionally, Diddy’s romantic relationship with Gina Huynh was also mentioned. Per Cassie, finding out about his relationship with Huynh prompted “scary” arguments between her and the mogul.

Diddy’s Infidelity:

The defense asks Cassie about Diddy’s relationships with Gina Huynh and Kim Porter during their relationship. Cassie admits finding out about Gina “upset” her, and promoted arguments between her and Diddy.

Cassie: “It was scary.”

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

#15

Cross-Examination: Kid Cudi Is Mentioned Again

As cross continued, the defense moved on to Cassie’s romance with Kid Cudi. It was explained that Cassie’s romance with Cudi began after she was connected to him by Diddy. Furthermore, Diddy explained that a collaboration with Cudi would be helpful for her career.

Cassie became romantic with Cudi while she and Diddy were briefly broken up. During that time, however, Cassie continued to be involved in freak-offs with Diddy.

Defense moves on to Cassie’s relationship with Kid Cudi, which started after Diddy suggested a collaboration with Cudi would be good for Cassie’s career. Cassie says she and Diddy were on a “break” when she started dating Cudi, but she was still doing freak offs with Diddy,

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

#16

Diddy Acknowledges The Audience:

During a brief break, Diddy stood at the defense table and acknowledged reporters in the room, asking “How you doing?” He had a quick huddle with his attorneys before proceedings continued.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#17

Cross-Examination: Cassie Recalls Diddy's Reaction To Her Drug Use

As the cross continued, Cassie recalled Diddy’s alleged reaction to her on-and-off dependence on opiates.

Now to Cassie & Diddy’s drug use—Cassie said although Diddy did provide her with drugs, he once told drug dealers in Los Angeles to stop delivering drugs to her.

“At some point it happened,” she said as she tried to recall exactly when.

She added that Diddy recommended she…

— TheShadeRoom (@TheShadeRoom) May 15, 2025

Additionally, Cassie shared that Diddy’s reaction to her use of drugs when he wasn’t present.

Estevao: Did you ever call yourselves ‘Get High Partners?’

Cassie: We did.

Estevao: Did you take drugs without him knowing it?

Cassie: Yes.

Estevao: What was his reaction?

Cassie: It was explosive.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Jadriena Solomon

#18

The Courtroom Takes Another Break

Judge calls a break after Estevao presents a lengthy document, and starts questioning Cassie about heating up baby oil during freak offs.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

#19

Cross-Examination: Cassie Calls Out Defense For Making Her "Look Like A Side Piece"

On the stand, Diddy’s defense attempted to highlight instances of Cassie’s anger and jealousy by referencing past texts between them. She clapped back, saying, “You’re making me look like a side piece, and that is not what I thought I was.” 

By: Cassandra Santiago

#20

Cross-Examination: Michael B. Jordan Comes Up In Cassie's Testimony

Ahead of the court adjourning for the day, Cassie testified about Diddy suspecting she was being unfaithful to him while she was filming for ‘Honey 3’ in South Africa. Cassie said the man he suspected was Michael B. Jordan.

By: Cassandra Santiago

 

#21

Defense Questions Cassie About 2016 Hotel "Freak Off"

Additionally, the defense questioned Cassie about the “freak off” that happened at the hotel in 2016 that ended with her assault on video. Attorney Anna Estevao presented text messages between the ex-couple, suggesting Cassie agreed to participate ahead of it in sexually explicit language that wasn’t read to the courtroom.

Cassie responded that she could tell by Combs’ language in the texts that he wanted a “freak off” since he questioned her about her plans for the night. She said she wanted to get the act over with so Diddy would be happy and allegedly not ruin a movie premiere she had scheduled for three days later.

Estevao then suggested that on the day of the 2016 beating, Cassie and Diddy had a “bad batch” of the drug MDMA. But the singer only replied, “I have no idea” before her testimony concluded for the day. She’s expected to return to the stand on Friday for additional questioning from both sides.

Court has adjourned for the day, with Estevao ending today’s cross with questions about the freak off at the Intercontinetal in LA that led to Diddy’s brutal assault on Cassie.

The defense reveals former Danity Kane member Dawn Richard will take the stand tomorrow.

— TheShadeRoom (@TheShadeRoom) May 15, 2025

By: Cassandra Santiago

#22

This is a live article. Check back in here with The Shade Room for more updates.

Click here for a recap of the overall trial thus far.

See the links below for Cassie’s previous testimony.

From Freak-Offs To Stompings, Cassie Testifies In Trial About Alleged Violent Relationship With Diddy (Day Two)
Beatings Diddy’s Staff Knew About, Self-Harm & Her Tell-All Book: Cassie Continues Testimony In Federal Trial (Day Three)

 

What Do You Think Roomies?
+1
0
+1
0
+1
1
+1
0
+1
0
+1
0
+1
0
Share.
TSR

TSR

Related Posts

Tory Lanez Files $100M Lawsuit Against California Prison For 2025 Stabbing Attack & Seeks $1M Per Wound

Tory Lanez Files $100M Lawsuit Against California Prison For 2025 Stabbing Attack & Seeks $1M Per Wound

2026/04/18
Sweet Life! Karrueche Tran & Deion Sanders’ Cozy Selfie Has The Internet Screaming Relationship Goals (PHOTO)

Sweet Life! Karrueche Tran & Deion Sanders’ Cozy Selfie Has The Internet Screaming Relationship Goals (PHOTO)

2026/04/18
Ice Spice Seemingly Shouts Out Wendy’s While Addressing Viral McDonald’s Incident (PHOTO + VIDEOS)

Ice Spice Seemingly Shouts Out Wendy’s While Addressing Viral McDonald’s Incident (PHOTO + VIDEOS)

2026/04/17
Latest Posts

Tory Lanez Files $100M Lawsuit Against California Prison For 2025 Stabbing Attack & Seeks $1M Per Wound

2026/04/18

Sweet Life! Karrueche Tran & Deion Sanders’ Cozy Selfie Has The Internet Screaming Relationship Goals (PHOTO)

2026/04/18

Ice Spice Seemingly Shouts Out Wendy’s While Addressing Viral McDonald’s Incident (PHOTO + VIDEOS)

2026/04/17

Whew! Cleotrapa Enters The Chat As Fans Sound Off On Ice Spice’s McDonald’s Altercation (VIDEOS)

2026/04/17

#TSRExclusive

Not you missing out on our newsletter, tap in & sign up!

About
About

TSR is the culture's definitive source for trending celeb news, exclusive interviews, videos, and more.

NMSDC CERTIFIED

Facebook X (Twitter) Instagram YouTube TikTok Snapchat
Latest Posts

Tory Lanez Files $100M Lawsuit Against California Prison For 2025 Stabbing Attack & Seeks $1M Per Wound

Sweet Life! Karrueche Tran & Deion Sanders’ Cozy Selfie Has The Internet Screaming Relationship Goals (PHOTO)

Ice Spice Seemingly Shouts Out Wendy’s While Addressing Viral McDonald’s Incident (PHOTO + VIDEOS)

Featured Posts

Social Media Reacts As Pooh Shiesty’s NEW Mugshot Surfaces Amid Arrest For Kidnapping & Robbery Of Gucci Mane (PHOTO)

Clapback Season! Rihanna Trolls Content Creator Over Baby #4 Speculation After Alleged Pregnancy Photo Surfaces (VIDEO)

Whoa! Video Footage Shows Woman Physically Attacking Ice Spice At Los Angeles McDonald’s (WATCH)

© 2026 The Shade Room
  • Celebs
  • News & Politics
  • Beauty & Style
  • Shows
  • TSR Teens
  • TSR Shop
  • Privacy Policy
  • Terms & Conditions
  • Advertising Guidelines

Type above and press Enter to search. Press Esc to cancel.