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Attorney Symone Redwine Explains How Insurance Claims Factored Into Diddy’s Settlement With Cassie

Attorney Symone Redwine Explains How Insurance Claims Factored Into Diddy’s Settlement With Cassie

Diddy Combs

Symone Redwine, TikTok screenshot/Diddy, Instagram

It’s been a rough few weeks for Sean “Diddy” Combs. First, on Nov. 16 he found himself in the midst of a sexual assault lawsuit filed by singer Cassie, whose real name is Cassandra Ventura, whoaccused Diddy of rape and physical abuse throughout their decade-long relationship. They settled it one day later for an undisclosed amount. Then, two more sexual assault suits followed. Combs continued to deny all of the allegations.

But what’s intriguing is the Cassie settlement. According to Houston-based attorney Symone Redwine, Diddy, who has an estimated net worth of $850 million, might not have paid the settlement himself. He also might not have had he control on whether to decide to pay or not.

Redwine says insurance might have played a role in this high-profile case–and been the ones who made the decision to settle.

Cassie accused Combs of using his industry connections to manipulate and control her. She described their relationship as “a cycle of abuse, violence, and sex trafficking.” Cassie also claimed that Diddy introduced her to a fast-paced and drug-fueled lifestyle, which included forced sexual encounters with male prostitutes, threats, and beatings.

Less than 24 hours after Cassie filed the lawsuit, news broke that the two parties had reached a settlement. Diddy’s attorney, Ben Brafman, clarified that settling the lawsuit did not constitute an admission of wrongdoing on Diddy’s part.

Redwine provided a unique perspective on the settlement when she appeared on The Pour Horsemen Podcast on Nov. 29 to explain the role of insurance claims in this high-stakes case. Redwine pointed out that Cassie’s legal team didn’t just target Diddy; they also sued his corporations, including Bad Boy Records, Epic Records, Bad Boy Entertainment, and Combs Enterprises. This strategic move had far-reaching implications.

Houston-based Redwine is a law professor at Texas Southern University School of Law,

“When you do that, it triggers commercial liability insurance, and it triggers another policy called directors and officers,” Redwine explained. She noted that Diddy, as the CEO and director of these companies, now faced the involvement of two insurance policies. The important point is that this shift in litigation strategy transferred control of the settlement process away from Diddy.

“It’s no different than if you hit somebody with your car,” she said. “Let’s say you have State Farm [insurance], State Farm gets to decide to settle, not you.”

She went on to explain, “They didn’t sue just Diddy — they sued his corporations. 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 anymore. […] So because they added those claims, the corporate insurance carrier got to say, ‘Oh hell no, we’re giving her the money.’”

Redwine noted that it took away Diddy’s ability to dictate the terms of the settlement, making it the insurers’ prerogative, Newsweek reported.

And she added, “More than likely, what will happen is those insurance companies have the ability to say, ‘We won’t renew your policy if he continues to be a director or officer.'” This could be the reason why Diddy temporarily stepped down for the board of his Revolt TV company.

Symone Redwine, TikTok screenshot, https://www.tiktok.com/@houstonpourhorsemenpod/video/7306667240055770414/Diddy, Instagram, https://www.instagram.com/diddy/?hl=en