Diddy Likely Didn't Cough Up Cassie Settlement Himself, Expert Claims

Diddy has recently settled a bombshell sexual assault lawsuit with Cassie, but a legal expert claims that Diddy may not have written the check at all.

Houston based attorney Symone Redwine went on the Pour Horsemen podcast on Wednesday (November 29) to explain how exactly Cassie could have received money without the Bad Boy mogul actually writing a check.

“They didn’t sue just Diddy — they sued his corporations,” she explained. “And they sued his corporations, and sued in her capacity as an employee. When you do that, it triggers commercial liability insurance and it triggers another policy called directors and officers.”

She continued: “We know he’s the director of the companies as a CEO. So now you got two policies. What happens then is, it takes away Puffy’s ability to settle. It’s not his choice no more. […] So because they added those claims, the corporate insurance carrier got to say, ‘Oh hell no, we’re giving her the money.'”

HipHopDX has reached out to both Symone Redwine and representatives for Diddy for additional comment.

Earlier this month, Cassie filed a disturbing lawsuit against Diddy — who she dated off-and-on from 2007 through 2018 — alleging human trafficking, sexual abuse, assault, and more.

She went on to settle with Diddy less than 24 hours later; however the financial terms were not disclosed.

“I have decided to resolve this matter amicably on terms that I have some level of control,” Cassie (real name Casandra Ventura) said in a statement per the New YorkPost. “I want to thank my family, fans and lawyers for their unwavering support.”

Diddy’s attorney Ben Brafman addressed the settlement in a statement given to HipHopDX on Saturday afternoon (November 18).

“Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing,” the attorney wrote. “Mr. Combs‘ decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims. He is happy they got to a mutual settlement and wishes Ms. Ventura the best.”

related news

Diddy’s Partnership With Prep School Network Ends Following Sexual Assault Allegations

November 28, 2023

On Tuesday (November 28), TMZ reported that Puff has temporarily stepped down as the chairman of Revolt, the network he founded a decade ago. A source told the outlet that the move “was to not allow the accusations he’s facing [to] distract from Revolt’s mission or success.”

Two more lawsuits were filed against Diddy (real name Sean Combs) following the settlement.

The most recent accuses him of raping two women “in 1990 or 1991.” The suit alleges that singer Aaron Hall, best known as a member of the R&B/new jack swing group Guy, also raped both women on the same night.

Denying the claims, a spokesperson for Diddy told HipHopDX: “These are fabricated claims falsely alleging misconduct from over 30 years ago and filed at the last minute. This is nothing but a money grab. Because of Mr. Combs’ fame and success, he is an easy target for anonymous accusers who lie without conscience or consequence for financial benefit.

“The New York Legislature surely did not intend or expect the Adult Survivors Act to be exploited by scammers. The public should be skeptical and not rush to accept these bogus allegations.”

The second person to accuse Diddy of sexual assault was Joi Dickerson-Neal, who claims that the rapper and producer drugged and raped her in the early ’90s, while also filming the act. He denied these allegations as well.