Cassie Ventura and P Diddy’s Relationship Explained

Sean “Diddy” Combs is making headlines again over a sex trafficking investigation and it has reminded people of the lawsuit brought against him by ex-girlfriend, Cassie.

The R&B singer, whose given name is Cassandra Ventura, first started dating the music mogul, who is also known as P Diddy or Puffy, way back in 2007.

They split after 11 years of dating in 2018 and in November 2023, she slapped him with a lawsuit claiming a variety of allegations including that he abused her, forced her to have sex with male sex workers while he filmed them, rape, threats and introducing her to “an ostentatious, fast-paced and drug-fueled lifestyle.”

Combs settled the suit just one day after it was filed and denied her claims.

Newsweek contacted Combs’ representatives by email.

But their relationship has come under a new spotlight just hours after Homeland Security conducted a raid on two of Combs’ properties as part of a sex trafficking investigation.

“Earlier today [Monday], Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners. We will provide further information as it becomes available,” a spokesperson for HSI told Newsweek in a statement.

It is not known if Combs is a person of interest in the investigation, but his sons, Justin, 30, and King Combs, 25, were seen in handcuffs outside the L.A. home.

Cassie broke her silence about the raids in a statement via her attorney, who is also representing a woman identified as Jane Doe in another lawsuit against Combs.

“We will always support law enforcement when it seeks to prosecute those that have violated the law. Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct,” Douglas Wigdor told Newsweek in a statement.

The raids also come amid a string of lawsuits leveled against the music producer since Cassie’s legal action last year. Two women sued him for sexual assault, with one alleging he also trafficked her.

Then in February, music producer Rodney “Lil Rod” Jones sued Combs alleging he was sexually assaulted, drugged, trafficked and threatened by Combs who also forced him to procure sex workers and drugs for him. In his lawsuit, Jones claimed the music mogul hosted drug-fueled parties where underage girls were allegedly in attendance and that at one such party, the attendees were allegedly forced to lie about a shooting that took place.

Combs has claimed his innocence in all cases.

Cassie & Diddy: A Timeline

The pair first met in 2005 when Cassie was 19 and Combs 37. She was an up-and-coming singer who was signed to his Bad Boy Records and soon released her debut album, Cassie.

The pair began dating in 2007 after he “aggressively” pursued her, according to her lawsuit against him. They would go on to be involved in a more than a decade off-and-on-again relationship.

The ex-couple did not publicly reveal their relationship until 2012 and rumored to have got engaged in 2014 before calling it quits in 2015. They soon reunited later in 2015, but reportedly hit the skids again in 2016 after a heated argument, in which Cassie’s mother complained to police who wrote a domestic incident report.

Cassie and Combs finally broke up for good in 2018 and she confirmed it in October of that year when her team told media, “they are indeed no longer together and haven’t been for months.”

Combs shared some insight in what it was like to be in a relationship with him.

“If I’m in a relationship with you, like 25 percent of your time, you’re gonna just feel like, ‘Aw man, I hate being here, this guy, aw man, he cheated on me, he lied on me,'” he told The Breakfast Club radio show in August 2015. “But then there’s 75 percent of ‘I’mma make you the happiest woman in the whole wide world,’ and I promise you’ll smile the most.”

Cassie went on to marry model Alex Fine and they share two children, daughters Frankie Stone, 4, and Sunny Cinco, 3.

Cassie’s Lawsuit

The singer launched explosive legal action against her ex in November where she accused him of rape and physical abuse throughout their relationship and alleged he used his industry connections to keep her from leaving him. She described the relationship as “a cycle of abuse, violence, and sex trafficking.”

“Throughout their relationship Mr. Combs was prone to uncontrollable rage, and frequently beat Ms. Ventura savagely,” the filing claims.

“These beatings were witnessed by Mr. Combs’ staff and employees of Bad Boy Entertainment and Mr. Combs’s related businesses, but no one dared to speak up against their frightening and ferocious boss.”

After she broke up with Combs, Cassie was briefly linked to rapper Kid Cudi and in that time, the music producer threatened to blow up his car, and it blew up shortly after, according to the lawsuit.

“This is all true,” a spokesperson for Cudi told The New York Times in November.

She also claimed that when she tried to break up with him in 2018 that Combs allegedly overpowered her and raped her.

Before the settlement, Combs denied her allegations through his attorney Ben Brafman.

“Mr. Combs vehemently denies these offensive and outrageous allegations,” he said at the time.

“For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail.”

After the case was settled, Brafman was quick to defend his client once again.

“Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing,” he said.

“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.”

If you or someone you know has been the victim of sexual assault, please call the RAINN national helpline for support: 800.656.HOPE (4673).