Kid Cudi’s past relationship with singer Cassie has resurfaced in the spotlight amid Sean “Diddy” Combs’ ongoing criminal trial. On May 14, Cassie— also known as Casandra Ventura—testified in Manhattan federal court as a key witness in the sex-crimes case against Combs. She revealed that her romance with Cudi allegedly triggered a violent reaction from the music mogul. The explosive testimony has added another layer of drama to the already high-profile proceedings. Here are five key things to know about their relationship:
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Cassie And Kid Cudi Met In 2011
In 2011, while her relationship with Sean “Diddy” Combs was on shaky ground, Cassie began dating rapper Scott Mescudi, better known as Kid Cudi. The two first connected through work, and their professional relationship soon turned romantic. However, Cassie admitted she didn’t tell Combs about the new relationship at the time. Her decision would later become a key detail in her explosive testimony during Combs’ federal trial.
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
Diddy Learned About Their Relationship During A “Freakoff”
Cassie said Diddy found out about her and Kid Cudi during one of his infamous “Freak Offs” — disturbing events where she claims he forced her to have sex with other men. She testified that he discovered the relationship after going through her phone and seeing emails between her and his assistant, Capricorn Clark, discussing plans to have her toiletry bag dropped off at Cudi’s house the next day. That’s when he allegedly snapped. Cassie recalled him grabbing a wine opener, placing it between his fingers, and lunging at her in a fit of rage.
She Contacted Kid Cudi Via Burner Phone
Cassie revealed that she used a burner phone to contact Kid Cudi during their relationship. She said she went to those lengths because she didn’t want Diddy to find out she was dating the ‘Pursuit of Happiness’ rapper. The secret communication was part of her effort to keep the romance hidden from Combs.
