Cassie gets dragged back into Diddy Freak-Off drama by ex-escort


Continued ties to Diddy’s episode are the last thing we can do Cassie Ventura wants in her life!

The singer is now urging the court to ensure that an alleged campaign of harassment against her by a former male escort related to Diddy is stopped and her peace is upheld.

Cassie Ventura filed an explosive lawsuit against Diddy in 2023, accusing him of persistent abuse during their relationship. The lawsuit was reportedly settled within 24 hours, with payments running into the tens of millions of dollars.

Cassie at the 2017 MET Gala red carpet in New York
MEGA

The singer told the court in her lawsuit that she has become the target of harassment and threats from a male escort who was previously hired to participate in her freak-offs with Sean “Diddy” Combs.

In the document filed on Thursday, June 11 by Cassie’s attorney in response to the lawsuit filed by the ex-male escort, identified as Clayton Howard, Cassie made her grievances known.

According to the singer, Clayton recently posted videos on social media containing statements that her legal team interpreted as threats against her. Cassie confirmed in the filing that Clayton’s words transitioned from criticism to intimidation and immediately set off alarms in her camp about her safety.

Clayton had previously filed a lawsuit claiming that he suffered injuries from his participation in sex parties involving Diddy and Cassie. The former escort was also on the witness stand during criminal proceedings over Diddy’s alleged “freak-off” encounters.

TMZ noted that Cassie’s attorneys also claim that Howard used social media defamation of the singer and that his statements constitute harassment and victim blaming.

Now living abroad, Cassie asks the court to set a hearing so she can seek an order that would limit Howard’s right to continue making public statements about her.

Another former escort describes a darker atmosphere during the final Freakoff days

Last June, another male escort came forward with testimony that he had participated in multiple encounters involving Diddy and Cassie noticed a very significant shift in the last days of their meeting.

The escort, identified as Shawn Dearing, recalled participating in more than a dozen of the events and stated that as their encounters progressed, things became more intense and emotionally disturbing.

He noted that the very last time they met was notable because the air around them felt very heavy and dark, which confirmed his worst fears.

He noticed that Cassie’s typically relaxed and carefree demeanor was absent, and she radiated a reluctant energy. However, she still wanted to please her ex-boyfriend, despite how dark everything felt.

Cassie Ventura’s courage encouraged Shawn Dearing to come clean

Shawn added that another thing he noticed during his time working with the couple was that Cassie was trapped in Diddy’s world and basically acted as if she had no say or choice in the matter.

“In my opinion, in that situation, she was at a loss as to whether this was a beast she could control or not. So she went along, because she had to, because who knows? Who knows where this beast is going, and there’s no way to tame it,” Shawn added.

The escort’s story matched Cassie’s later admission at Diddy’s trial that she had to show up and pretend even though she never wanted to participate in the freak-offs.

Shawn noted that his stint with Diddy and Cassie began in 2014/15 when he was booked through an escort service, and that they would meet at various luxury locations in Los Angeles, including her apartment.

He left the company a few years later when he realized how dark the industry was, and when Diddy tried to hire him again in 2017, he turned down the offer. Shawn confirmed that his testimony at the time was to support Cassie’s testimony and help bring the truth to light.

The ‘Long Way To Go’ singer kicked against Diddy’s bid for release

Sean
Xavier Collin/Image Press Agency/MEGA

The explosion noted that in 2025, Cassie and her legal team pushed back on Diddy’s move to seek release prior to his sentencing, noting that keeping him in custody ensures the safety of eyewitnesses in the case.

In a letter submitted to the court, Cassie’s lawyers wrote to Judge Arun Subramanian to deny any request for immediate release, saying it could cause fear and uncertainty among those who came forward.

Doug Widor, Cassie’s attorney, added that his team is also happy to know Diddy will be held accountable and faces significant prison time. Cassie’s attorney emphasized that her decision to come forward and share her story marked a shift in the entertainment industry.

Doug went on to say that the singer showed exemplary courage during the trial and helped draw attention to the reality of powerful men in Hollywood and how their misconduct often goes without consequences for decades.

Cassie Ventura’s colleague praised her decision to come forward

Kesha at MusiCares 2026 Person of the Year Honoring Mariah Carey
Xavier Collin/Image Press Agency/MEGA

Last year, singer and performer Kesha publicly stated that she would stand by Cassie in her quest to get justice for the years of abuse she suffered during her relationship with Diddy.

In a post on X, Kesha described Cassie as a strong woman who has become a beacon of hope for survivors in similar situations. Despite the verdict in which Diddy was acquitted sex trafficking and racketeering chargesKesha went on to say that she completely believed Cassie’s story.

Kesha’s post received millions of comments and attention from supporters who praised her for speaking out about her experiences. Many commentators described her testimony as impressive and credited her with starting a trend of survivors demanding accountability.

The singer also received praise from users who praised her for using her platform to publicly support another woman in the industry, with several commentators describing solidarity and public support as important in encouraging others to speak out.




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