Diddy Demanded $20K from Cassie’s Mom After Discovering Her New Romance

Diddy Demanded $20K from Cassie’s Mom After Discovering Her New Romance

  • Cassie Ventura’s mother, Regina, is making headlines after alleging that Diddy flew into a rage over her daughter’s new romance
  • Regina Ventura revealed that the music mogul demanded $20,000 to “recoup” what he’d spent on Cassie’s career after learning of the affair
  • In a chilling twist, Cassie allegedly told her mom that Diddy threatened to leak their wild videos after she went public with Kid Cudi

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Regina Ventura, mother of Sean ‘Diddy’ Combs’ ex-girlfriend Cassie Ventura, dropped another bombshell as she testified during the ongoing trial.

Regina Ventura
Regina Ventura, mother of Cassie Ventura, was spotted outside the Manhattan Federal Court. Images: John Lamparski, The Hollywood Reporter / Getty Images, drivetowardssuccess / Instagram
Source: UGC

She made some damming allegations against Diddy, who faces a string of grave charges.

Diddy demanded a $20K 'payback' after Cassie's new romance

Earlier this week, Regina revealed that Sean ‘Diddy’ Combs was unhappy with her daughter’s relationship with Kid Cudi, whose real name is Scott Mescudi.

She said the music mogul demanded $20,000 to recoup the money she had splurged on Cassie Ventura's career during their relationship.

The court heard:

“He was angry that he had spent money on her, and she went with another person."

Sean ‘Diddy’ Combs and Cassie Ventura's relationship lasted over a decade before calling it quits.

Alleged threats revealed in Cassie's letter

Regina Ventura also noted that this happened after being made aware of the threats her daughter received from the hip-hop mogul in Cassie's letter.

The court heard that Cassie told her mother that Sean ‘Diddy’ Combs was threatening to leak videos from their wild parties after going public with her relationship with Cudi.

In the letter, Cassie also told her mother that the music mogul threatened to hurt her.

Regina Ventura
Regina Ventura, mother of Cassie Ventura, was spotted leaving the Manhattan Federal Court during Sean "Diddy" Combs' trial. Image: John Lamparski
Source: Getty Images

Regina has it that around the same time, Sean ‘Diddy’ Combs contacted her about the $20 0000.

Scared about her daughter’s safety, Regina Ventura and her husband took a home equity loan and wired the money to a Bad Boy account.

However, she has it that despite following instructions, the money was returned about five days later.

Netizens react to Regina Ventura’s explosive claims

Regina Ventura’s claims have since left many connecting the dots.

Some find it puzzling that Sean ‘Diddy’ Combs requested $20,000, yet he was rumoured to be a multimillionaire then.

Others questioned why he would return the money after five days after demanding a ‘recoup.’

@Jiz said:

"Diddy demanded 20k? The sums don’t add up."

@gnxtvoff commented:

"Now they are just lying, and these lies will let him walk free or get a reduced sentence. Dude was worth nearly half a billion in 2011."

Another star dragged into Diddy's mess

Meanwhile, Briefly News reported that another big American singer and songwriter was dragged into Diddy’s mess after being named a person of interest by a witness.

A witness, Dawn Richard, revealed that some of the abuse incidents happened in the presence of other celebrities during the parties, including the award-winning star.

Since then, the news has thrust the singer and songwriter into the spotlight, and many have demanded his side of the story.

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Source: Briefly News

Authors:
Leeroy Mukotekwa avatar

Leeroy Mukotekwa (Editor) Leeroy Mukotekwa joined Briefly News in May 2025 and is an entertainment writer. He holds an Honours Degree in Media from Midlands State University, majoring in journalism. He began his career as a Line Editor at the Midlands Observer before transitioning into blogging. Leeroy also spent over two years writing for The South African. Email: leeroy.mukotekwa@briefly.co.za

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