As it stands, rapper and businessman Sean Combs – famously known as P. Diddy – is ensnared in a host of legal situations. 54-year-old Combs has been hit with various lawsuits, is facing numerous charges and is currently behind bars while awaiting trial. It’s fair to say that Diddy’s legal issues began in earnest in late 2023 when ex-girlfriend Cassie Ventura filed suit against him. Now, it would seem that Ventura is allegedly being viewed as a “pioneer” for suing the star early on, and an insider dropped claims about how she feels about that.
The 38-year-old singer has seemingly remained quiet since Diddy was arrested in New York back in September. Now, a source tells ET that Cassie Ventura is purportedly doing well at this time, saying that her former boyfriend’s arrest is “a huge weight off her shoulders.” The unnamed individual also claims the songstress is “honored” to be viewed as a “pioneer” when it comes to her role in the “Workin” rapper’s fall from grace. Additionally, it’s said that Ventura “feels much more confident about her safety with Diddy being in jail.”
Known mononymously as Cassie, the Connecticut native dated Sean Combs between 2007 and 2018. She filed suit against the Sean John founder in November 2023, accusing him of alleged rape, violence and sex trafficking. As noted by NPR, Cassie and Combs’ legal teams settled the lawsuit only a day after it was filed. Specific details were not provided, though it was said that the deal was to “to their mutual satisfaction.”
In May 2024, a previously unreleased 2016 security footage from a hotel was released and apparently confirmed the “Is It You” singer’s claims against her former boyfriend. The video – which was recorded at the InterContinental Hotel in Los Angeles – showed Diddy following Cassie after she exited a room and then throwing her to the ground by her neck. The Grammy winner then proceeded to kick Cassie multiple times while she was on the ground, before dragging her by her sweatshirt and eventually throwing an object at her.
The “Last Night” performer eventually released a video in response to the footage, apologizing for his actions. Meredith Firetog, one of Cassie’s lawyers, chastised the apology, asserting that the rapper’s statement was “more about himself than the many people he has hurt.” Also speaking out was Cassie’s husband, Alex Fine and, while he didn’t mention Diddy by name, he did condemn anyone who would condone domestic violence. Reactions from Slim Thug, Kelly Price and more also surfaced, with them expressing their personal disappointment over the video.
Since then, some who were in Diddy and Cassie’s orbit while they were together have made claims about the supposed dynamics of their relationship. Their former bodyguard, Roger Bonds, claimed to have broken up a fight between them following one of Jay-Z’s parties years ago. Bonds claimed that, at the time, Cassie punched Diddy in the face and, while recalling another instance, the ex-bodyguard alleged that the latter did the same to his then girlfriend.
As for the charges that Puff Daddy is currently facing, a 14-page indictment laid out alleged offenses including racketeering, sex trafficking and transportation to engage in prostitution, bribery and more. One of the biggest points of interest in regard to the claims are the alleged “Freak Offs” that Puffy would hold. It’s been said that as part of the events, women were coerced into performing sexual acts for guests and that they were recorded.
Sean Combs is currently awaiting trial in the Brooklyn-based Metropolitan Detention Center after being denied bail multiple times. His court date is reportedly set for May 5, 2025. As of right now, it remains to be seen what lies ahead for the embattled hip hop mogul. The same is true for whether Cassie Ventura decides to speak out on the case as well as her apparent status as the first high-profile person to sue Diddy in this long line of lawsuits.
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