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Kid Cudi 'Prayed' That Cassie Ventura Would One Day Be Free After Terrifying Sean 'Diddy' Combs Relationship: 'It Was So Emotional for Me'

Photo of Kid Cudi, Sean 'Diddy' Combs and Cassie Ventura
Source: MEGA

On 'TODAY With Jenna & Friends,' Kid Cudi showered ex Cassie Ventura with support amid Diddy's trial.

Aug. 14 2025, Published 1:50 p.m. ET

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Kid Cudi has nothing but love and respect for Cassie Ventura.

During the Thursday, August 14, episode of TODAY With Jenna & Friends, the rapper, 41, showed support toward his ex, who has become entangled in Sean 'Diddy' Combs' trafficking trial.

In his new book, Cudi: The Memoir, which was released on August 12, the "Day 'n' Nite" singer looked back on his relationship with the star.

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Image of Kid Cudi briefly dated Cassie Ventura in 2011.
Source: TODAY With Jenna & Friends/YouTube

Kid Cudi briefly dated Cassie Ventura in 2011.

"Over time, I realized she was a prisoner. I just prayed, one day she would be free," he wrote.

Host Jenna Bush Hager asked Cudi if he thinks she's free now, two years after filing a lawsuit against Combs for a decade of abuse.

"I think she has [found freedom], and it's a beautiful thing," Cudi expressed. "When I found out she was getting married, it just touched my heart because I was just like, 'Yes. Yes, Cassie.' When I found out she was having kids, I almost shed a tear. It was so emotional for me to see her kind of thrive and find her happiness and peace. It's a really beautiful thing."

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Kid Cudi Testifies Against Diddy

Source: Call Her Daddy/YouTube

Kid Cudi joined Alex Cooper on 'Call Her Daddy.'

During a Wednesday, August 13, episode of the "Call Her Daddy" podcast, Cudi recalled what it was like taking the stand at Diddy's trial earlier this year to support Ventura.

"I hated every minute of it," he revealed. "I did not want to do it, but then I thought about — when I was up there — I’m here to support Cassie. Cassie is my friend, and I love her and I want to see her do well."

Ventura and Combs dated on and off from 2007 to 2018. Cudi was in a brief relationship with Ventura in 2011 while the couple was on a break.

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Source: TODAY With Jenna & Friends/YouTube

Kid Cudi is happy that Cassie Ventura is 'free.'

In May, Cudi testified that Combs broke into his home while he and Ventura were together. The "Last Night" rapper was accused of ordering someone to set Cudi's car on fire, although no evidence has been revealed.

“It was crazy, man. In the moment, it was just crazy," he exclaimed. "I had a hard time understanding if it was reality. I was like, ‘Am I in a movie? What the f--- is going on?’ … It was just chaotic and intense."

Image of Sean 'Diddy' Combs dated Cassie Ventura for over a decade.
Source: MEGA

Sean 'Diddy' Combs dated Cassie Ventura for over a decade.

During the May trial, Cudi alleged that Combs was "abusive" toward Ventura.

"I’ve always just wanted to see her thrive and do well and be happy. I know she was living a nightmare," he said during the podcast interview. "I just was there to support her. That’s what, kind of, gave me peace with it. When I sat down in that chair, it was just about, 'D---, I don’t want to do this.' To being like, 'Oh man, I got to hold homegirl down and look out for her.'"

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