What Happened Between Kid Cudi and Cassie? A Look Back at Their Brief Relationship — and Diddy’s Alleged Role in Their Split

Kid Cudi had a brief relationship with Casandra “Cassie” Ventura — and is now testifying at Sean “Diddy” Combs‘ sex trafficking trial because of it.

In 2011, the “Pursuit of Happiness” singer, whose real name is Scott Mescudi, dated Ventura amid her on-again, off-again relationship with Combs, which officially ended in 2018.

Now, Combs is on trial on charges of racketeering, sex trafficking and transportation to engage in prostitution, for which he has pleaded not guilty. During the first week of the trial, Ventura took the stand and detailed the alleged abuse she suffered throughout their decade-long relationship, from claims of being forced to participate in his “freak offs” to being assaulted in a hotel in 2016.

While on the stand, Ventura also opened up about dating Mescudi for a short period, but allegedly having to break it off out of fear of Combs’ reaction.

On May 22, Mescudi, who is now engaged to Lola Abecassis Sartore, was called in to give a testimony of his own — and provided more details about Diddy’s alleged response to his and Ventura’s romance.

Here’s everything to know about Cassie and Kid Cudi’s relationship — and what the rapper said about Diddy’s reaction to it during the mogul’s sex trafficking trial.

Cassie dated Kid Cudi in 2011 amid a break from her relationship with Diddy

Although Ventura and Mescudi met at an event in 2008, the pair didn’t begin dating until 2011, as he revealed during trial, per NBC News.

At the time, Ventura was on a break from Combs, whom she filed a lawsuit against in 2023 accusing him of rape, physical abuse and coercing her into drug-fueled sex acts with male escorts, which he allegedly filmed and used as blackmail.

Per the lawsuit, Ventura’s relationship with Mescudi came during a “rough patch” between her and Combs.

Cassie said Diddy “lunged” at her after finding out about her romance with Kid Cudi

In 2012, Combs allegedly returned from a trip and demanded that Ventura participate in one of his “freak offs” — elaborate and produced sex performances that the mogul allegedly orchestrated and coerced women to participate in with male sex workers — per her lawsuit.

According to the suit, Ventura “acquiesced” — and things allegedly took another dark turn when Combs found out about her relationship with Mescudi during the “freak off.”

After Combs came across an email between her and Mescudi’s staff about a toiletry bag, Ventura claimed that the Bad Boy Records founder “lunged” at her with a corkscrew between his fingers.

“I just remember him putting a wine opener between his fingers and lunging at me,” she recalled during her testimony.

Cassie fled to Kid Cudi’s home, but alleged that Diddy beat her when she eventually returned

After the corkscrew incident, Ventura went to a hotel and called Mescudi from a burner phone — which she said during testimony she only had because she wanted to avoid Combs finding out about her new romance.

Per the lawsuit, she eventually went back to Combs because she felt like “she could not escape Mr. Combs and his network of enforcers.”

During testimony, Ventura provided more details about what allegedly happened when she returned in an attempt to resolve the situation, claiming that an “irate” Combs beat her and threatened to release “freak off” videos and hurt both her and Mescudi.

“Sean kicked me in the back, I fell on the floor and then left,” she said. “I had a large bruise on my back and bruises on other places — he literally kicked me with the bottom of his foot.”

Ventura went on to say that she returned to her hotel room, which was allegedly “torn up” with urine on the floor and feces in the toilet. She also claimed that Combs told her “he was going to hurt Scott and I,” among other allegedly harmful threats toward the rapper.

Diddy was accused of blowing up Kid Cudi’s car in a jealous rage

Shortly after finding out about their relationship, Combs allegedly threatened to blow up Mescudi’s car, as detailed in the lawsuit.

“In February 2012, during Paris Fashion Week, Mr. Combs told Ms. Ventura that he was going to blow up Kid Cudi’s car and that he wanted to ensure that Kid Cudi was home with his friends when it happened,” the suit alleged. “Around that time, Kid Cudi’s car exploded in the driveway.”

Ventura maintained the claim during her testimony, saying, “He mentioned when we were out of the country that Scott’s car would be blown up and he wanted his friends to see it.”

According to The New York Times, Mescudi confirmed in November 2023 that his car blew up.

During his May 22 testimony, the musician was asked about the incident and recalled thinking, “What the f—.”

Mescudi claimed he got a call from his dog sitter that his car was on fire, and a friend sent him a photo of his damaged Porsche convertible.

“The top of my Porsche was cut open and that’s where they inserted the Molotov cocktail,” he said, without mentioning Combs’ name in connection with the explosion.

Diddy allegedly extorted $20,000 from Cassie’s mom during her daughter’s relationship with Kid Cudi

On May 20, Ventura’s mother Regina testified in Combs’ trial, claiming that her family paid $20,000 to him out of concern for her daughter’s safety.

She alleged that Combs threatened to release explicit videos of Ventura once he found out about her new relationship with Mescudi, and claimed that he demanded $20,000 because he was “angry” about the money he had spent on her while she was dating someone else.

“I was physically sick. I did not understand it, the sex tape threw me. He was trying to hurt my daughter,” she said during her testimony. “We took a home equity loan and that was the only way we could get the money.”

Kid Cudi testified that Diddy broke into his home and “messed with” his dog

During his testimony, Mescudi claimed that Combs broke into his home in December 2011 to confront him. The rapper testified that Ventura had called him early in the morning on the day of the break-in, when the two got on a call with one of Combs’ employees, who “seemed very scared.”

He said the employee informed him that Combs and an associate were inside Mescudi’s home, leading the rapper to contact the mogul directly. The Bad Boy Records founder allegedly said, “I just want to talk to you,” before adding that he was at Mescudi’s home “waiting” for him to come.

Mescudi claimed that Combs was not there when he arrived back home, but that several things were out of place, including his security camera being turned away and his dog being locked inside the bathroom.

“I was looking for [Combs]. I wanted to confront him, I wanted to fight him, you know?” Mescudi recalled, claiming that he instead called the police.

While on the stand, Mescudi said he later went to spend Christmas with Ventura’s family, during which Combs allegedly called him several times to ask about their romance.

“He wanted to get to the bottom of it and figure it out,” Mescudi said. “But post-break-in, I didn’t want to talk to him. I told him, ‘You broke into my house and messed with my dog, I don’t want to talk to you.’ “

If you or someone you know has been sexually assaulted, please contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673) or go to rainn.org.