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Drake allegedly clashed with Diddy over Cassie

Cassie's testimony in Diddy trial may have opened a can of worms involving Drake

By TCP News Desk May 15, 2025
Drake allegedly clashed with Diddy over Cassie
Drake allegedly clashed with Diddy over Cassie

As the high-profile trial of Sean "Diddy" Combs continues, disturbing revelations and testimonies continue to emerge from the courtroom.

The rapper was arrested and indicted in the Southern District of New York on September 16, 2024, on charges of racketeering, sex trafficking by force and transportation for purposes of prostitution.

The first few days of the trial saw Diddy’s former longtime partner Casandra Ventura, better known as Cassie, take the stand to chronicle the alleged abuse she has suffered at the hands of the music mogul.

The 38-year-old revealed that she was assaulted by Diddy prior to attending Drake’s OVO Fest in Toronto.

The prosecutors also showed a picture of Cassie with French Montana at the festival, in which she had covered her facial injuries with her hair.

The revelation prompted hip-hop podcaster DJ Akademiks to speculate what actually happened at the event.

Akademiks believes that the Canadian artist attempted to hook up with Cassie, resulting in an alleged nightclub altercation in 2014 between Drake and Diddy.

The podcaster went on to suggest that Drizzy’s 2016 song 4PM In Calabasas is actually a Diddy diss track.

While it is all mere speculation at this point, Akademiks' claims are not entirely outside the realm of possibilities considering what has transpired following Diddy’s arrest.

How long did Cassie and Diddy date?

Cassie Ventura and Sean “Diddy” Combs were in a long-term relationship from 2007 to 2018.

RELATED: Diddy allegedly attacked Cassie before Drake's festival