Diddy lawyers grill Cassie on 11-year relationship; 'freak offs' continued while dating Kid Cudi

NEW YORK - Cassandra "Cassie" Ventura returned to the witness stand for a third day in Sean "Diddy" Combs’ federal sex trafficking trial, facing increasingly intense cross-examination.

The case continues to shed light on their allegedly dark and abusive relationship that lasted over a decade.

Diddy’s legal team has been actively questioning Cassie, with defense attorneys presenting sexually explicit messages exchanged with Sean "Diddy" Combs to argue her participation in "freak offs" was consensual.

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4:35 p.m.

Freak-offs continued while dating Kid Cudi

Cassie said that she continued to have "freak-offs" with Combs even when dating rapper Kid Cudi because it "was a job." She talked about have a burner phone while dating Kid Cudi due to being scared of what Combs would do

3:50 p.m.

Cassie responds to drug use

Cassie said Diddy once communicated to drug dealers in Los Angeles to stop delivering drugs to her.

She also acknowledged that Diddy had recommended that she get help for her drug issues. Cassie said Diddy only wanted her to do drugs with him rather than with friends.

3:34 p.m.

Cassie expresses occasional frustration

"This isn’t about what I feel is relevant right now, right?" Cassie said, glancing at the judge, Arun Subramanian. "Because there’s a lot we skipped over."

At one point, Cassie complained that jurors weren’t hearing the full context of the text messages the defense was highlighting.

2:10 p.m.

Texts show Cassie and Diddy making plans for ‘freak offs’

Defense shows Cassie texts between her and Diddy discussing supplies for the freak offs. 

2:01 p.m.

Cassie is back on the stand for more defense questions

Who is in the courtroom?

The judge, 12 jurors, six alternates, a dozen lawyers, a packed courtroom audience and Combs — who has remained observant throughout.

1:31 p.m. 

Defense wants Cassie to return next week

The judge said there had been pre-trial discussions for months about the need to finish Cassie’s testimony this week, given her advanced pregnancy.

12: 33 p.m.

Is Diddy an addict?

"Would you say he was an addict?" the lawyer asked. "I would say he was an addict," Cassie responded.

"What was he addicted to?" Estevao asked. "Success," Cassie initially said.

When the lawyer asked if Combs was addicted to opiates, Cassie said: "At a point, yes."

Estevao asked her how she knows. Cassie answered: "Because he told me."

-Larry Neumeister

12:25 p.m.

Defense asks Cassie about swinger lifestyle

Defense asks Cassie directly if she thinks "freak-offs" were related to this lifestyle.

She responded: "In a sexual way," Cassie responded, before adding: "They’re very different."

-Adeja

12: 15 p.m.

Was this all about a swingers lifestyle?

11:59 a.m.

Cassie says she sometimes watched Combs having sex with other women

Under questioning Cassie says that on at least four occasion during their relationship, she watched Diddy have sex with other women. She says Diddy told her it was part of a "swingers lifestyle."

11:51 a.m. 

Questioning takes a turn

Nearly two hours in, the cross examination shifted in tone as Anna Estevao asked Cassie if it’s fair to say she ruined Combs’ career by suing him and revealing "freak-offs" in 2023.

-Adeja Shivonne

10:51 a.m.

Cassie asks for a short break

The judge agreed, to let Cassie leave the witness stand after more explicit messages were put on display. The jury has also been given a break.

10:48 a.m.

Questioning turns to ‘freak offs’

— "When do you want to freak off? Lol" Combs asked in August 2009.
— "I’m always ready to freak off," she replied.

Two days later, Cassie sent an explicit message to Combs.

— "I can’t wait to watch you. I want you to get real hott," he replied.
— "Me Too, I just want it to be uncontrollable," she said.
-Michael R. Sisak, Larry Neumeister

10:35 a.m.

A loving, caring counterpoint

The defense has Cassie reading out loud from the warm emails and messages she exchanged with the hip-hop star early on.

-Michael R. Sisak

10:20 a.m.

Diddy appears relaxed 

Diddy reportedly is sitting back in his chair, legs crossed, conferring with Agnifilo, who’s seated next to him.

-Adeja Shivonne

10:08 a.m.

Defense introduces their ‘love’ texts. ‘I love you sooooo much it makes me cry’

In one 2008 email, Cassie told Combs she was a lucky woman. "I love you sooo much," she wrote after Combs thanked her for flying to Atlanta to be with him.

10:00 a.m.

Cassie is questioned about her feelings

— "You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well."
— "Yes."— Your love of Combs explained explained "why it hurt so badly when he lied."
— "Yes."
— "When he cheated on you," Estevao continued.
— "Yes, Cassie said.

9:45 a.m. 

Cassie arrives in black suit

Cassie returned to the witness stand in a black suit and a light colored blouse underneath.

-Adeja Shivonne

9:40 a.m.

Judge talks about evidence

During a nearly one hour long discussion Thursday morning about evidence that can be introduced on cross examination, the judge noted that with one of his rulings, "99.9 percent of evidence is not being impaired."
 

 9:24 a.m.

Judge lays out ground rules

Judge Arun Subramanian talks to lawyers about evidence as final ground rules are set before the cross examination by defense begins.

He denied a request by defense lawyers to introduce text communications between Diddy and Cassie that would include references to specific sexual acts.

-Adeja Shivonne, Associated Press

9:00 a.m. 

Cross-examination of Cassie expected to begin soon in Manhattan federal court

Defense lawyers say they’ll be scrutinizing how infidelity fueled the combustible nearly 11-year relationship between the R&B singer and the music mogul who controlled her career.

Diddy's lawyers told the judge that questioning Cassie about infidelities is important.

"Everybody knows that we are going to bring up infidelities, that we’re going to want to bring up text messages of infidelities, and these text messages are often in colorful language," Agnifilo said.

-Adeja Shivonne

What happened in court Wednesday?

On Wednesday, she told the court that Combs demanded she have "hundreds" of sex acts with male sex workers — which he allegedly recorded, watched, and controlled, sometimes for hours or days. 

Cassie said she didn’t feel she could refuse, fearing he would release the footage and "make her look like a slut."

When a prosecutor asked Cassie how many "freak-offs" she participated in, she said: "Impossible to know. Hundreds?"

Now 38 and pregnant with her third child with husband Alex Fine, Cassie has painted a disturbing picture of the long-term relationship she had with Diddy— one she says was marked by manipulation, abuse, and control behind the glitz and glamor of red carpets and celebrity events.

The case is drawing renewed attention not only for its disturbing allegations, but also for what it may reveal about Diddy’s past romantic entanglements and his image as a music mogul.

Diddy’s attorneys admit he could be violent at times but argue the sexual encounters were consensual. They contend his actions do not amount to sex trafficking or racketeering, the charges he faces.

• MORE: Cassie details relationship with Diddy: 'Freak offs' and being signed to Bad Boy
• Al B. Sure! on Diddy allegations, Kim Porter's death: 'She was in the best of health

When did Cassie and Diddy date?

Cassie, Diddy timeline

Cassie said she met Diddy in 2005 when she was 19, and he was 37. 

He signed her to a 10-year contract with his Bad Boy Records label. Within a few years, they began dating — a relationship that, according to her testimony, quickly turned toxic.

Cassie and Diddy officially ended their relationship around 2018. 

Cassie's husband Alex Fine

The following year, she married her personal trainer, Alex Fine, in September 2019. 

The couple has two daughters, born in December 2019 and March 2021. 

On Nov. 16, 2023, she filed a lawsuit against Diddy, accusing him of years of abuse, violence, and sex trafficking. 

On Feb. 19, 2025, Cassie and Fine announced that they’re expecting their third child.

• MORE: Diddy family tree: The rapper’s kids, their moms, and Kim Porter explained
• MORE: Who was Kim Porter? Diddy's ex partner, mother of 3, since passed

How many kids does Diddy have?

As his legal issues unfold, scrutiny falls on his close associates and family, including his children and his mother, who have appeared in NYC court alongside him to watch, although it's unclear what their views on his situation are amid the ongoing trial. 

The lack of public statements from Diddy’s family has added to the intrigue surrounding Kim Porter, the late mother of three of his children, and her untimely death.

So, who are they? 

Quincy is the biological son of singer and producer Al B. Sure! and model Kim Porter.

Christian Combs, also known as "King Combs," is the biological son of Diddy and model Kim Porter. 

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Justin Combs is the first biological son of Diddy and Misa Hylton's son.

Born in 2006, Jessie and D'Lila are the twin daughters of Kim Porter and Diddy.

Chance, also born in 2006, is the daughter of Sarah Chapman and Diddy, and she is Sarah’s only child.

 Love Sean is Diddy’s seventh child and the daughter of Dana Tran. 

What is racketeering?

Sean "Diddy" Combs is facing a federal RICO charge accusing him of running a criminal operation through his companies including Bad Boy Entertainment and Combs Global from 2004 to 2024. 

Prosecutors allege he and his associates engaged in kidnapping bribery drug distribution forced labor and sex trafficking. 

The indictment claims Diddy orchestrated a long running sex trafficking scheme involving coercion and abuse. 

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The RICO statute allows authorities to pursue both him and anyone tied to the alleged criminal enterprise.

Diddy has pleaded not guilty to one count of racketeering conspiracy, two counts of sex trafficking by force, fraud or coercion, and two counts of transportation to engage in prostitution.

How long has Diddy been in jail?

Diddy was arrested in Oct. 2024 at a New York City hotel. 

Since his arrest, Combs has been held at a federal detention center in Brooklyn. 

Diddy Trial