The details in the court documents are horrific. In a bombshell lawsuit filed on November 16, Sean “Diddy” Combs’ longtime partner Cassie (full name: Casandra Ventura) accused him of rape, beatings, sex trafficking and more. The alleged events took place during their 13-year on-again-off-again relationship. “After years in silence and darkness,” Cassie said in a statement, “I am finally ready to tell my story.”
Then, everything changed in an instant. The next day, on November 17, Diddy, with no admission of liability, settled with Cassie for an undisclosed sum. (One source estimates the payout at $30 million.) Meanwhile, others have come forward with their own horror stories about the music mogul, who vehemently denied Cassie’s claims. “And now fans can’t help but wonder what Jennifer Lopez knows and have been asking if she had a similar experience,” the source says of the A-lister, who dated Diddy from 1999 to 2001 over two hellish years punctuated by cheating rumors and a nightmare arrest following a chaotic nightclub shooting. “Her time with Diddy was certainly tumultuous.”
Cassie, who met Diddy when she was 19 and he was 37, claims that during the relationship she often endured “savage” beatings that left her with black eyes and burst lips. She also alleges that he forced her to perform sex acts with male prostitutes while he filmed, and that he raped her when they broke up. (Contrary to reports that he could face prison time, the NYPD has clarified that Diddy is not currently under criminal investigation.) Diddy, 54, also flew into jealous rages, the legal docs claim, and threatened to blow up Kid Cudi’s car because he showed interest in Cassie, 37. (Kid Cudi’s car was eventually blown up, with no one in it.) Diddy also “exerted complete control” over every aspect of her life, Cassie claims, until she finally managed to leave him for good in 2018.
By contrast, Jennifer has said that dating Diddy helped her learn how to stand up for herself. While working on her first album, he had a “rough way” of guiding her career, she’s revealed, adding that his criticism could be blunt. “He communicated very plainly, like, ‘You need to do this, you need to do that, don’t forget,’” the singer, 54, once said. “And he would share his knowledge with me whether I asked for it or not.”
At times, she suspected he was unfaithful. “I never caught him, but I just knew,” Jennifer said in 2003, adding that during the relationship, “I was totally crying, crazy and going nuts. It really [sent] my whole life [into] a tailspin.”
Things got darker. In 1999, Jennifer spent several hours in jail after she and Diddy were caught fleeing the scene of a NYC nightclub shooting that injured three people — with a gun in the trunk of their Lincoln Navigator. Jennifer was quickly absolved, while Diddy and his protégé Jamal “Shyne” Barrow were arrested on weapons charges.
Shyne, 45, was convicted on two counts of assault, reckless endangerment and gun possession and spent nine years in prison. For his trial, Diddy hired a legal team that included O.J. Simpson attorney Johnnie Cochran. “Jennifer Lopez is a very famous actress. To think Mr. Combs is walking around with her with a loaded gun … it’s so ridiculous that it stretches the imagination,” one of the defense lawyers argued, though witnesses said they’d seen Diddy with a weapon. And his driver testified that his boss had bribed him to claim it was his gun. (In her filing, Cassie alleges that Diddy demanded that she “carry his firearm in her purse just to make her uncomfortable and demonstrate how dangerous he is.”)
Diddy was found not guilty. Years later, Jennifer was called to give a deposition in a civil suit related to the shooting. “She would have had to tell all under oath,” says a source, but Diddy reached a settlement with the nightclub shooting victims.
Jennifer won’t have to testify in this case, either. Despite settling Cassie’s suit quickly, Diddy’s lawyers made it clear the agreement is “in no way an admission of wrongdoing.” Still, experts note that going to trial would have meant that more embarrassing details about his private life would be made public. “That could potentially include videos, text messages and depositions from his exes, including Jennifer,” says the source, noting that several other women have expressed support for Cassie or shared their own stories of abuse.
Jennifer has never accused Diddy of abuse. Without naming names, she wrote in her 2014 memoir, True Love, “I’ve never gotten a black eye or a busted lip, but I’ve felt abused in one way or another: mentally, emotionally, verbally. I know what it feels like for your soul to be diminished by the way your loved one is treating you.”
All these years later, Jennifer and Diddy seem to get along. “They’re still on friendly terms, even though they’re not in regular contact,” says the source, noting that the pair were most recently spotted greeting each other warmly at the final show of her Las Vegas residency in 2018.
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But other famous friends are distancing themselves from him, notes the source. Diddy’s longtime pal Ashton Kutcher — who was just burned after vouching for convicted rapist Danny Masterson — along with Diddy’s former fling Cameron Diaz and friends Beyoncé and Jay-Z, have remained silent. Says the source, “They’re clearly staying out of it.”
Apparently so is Jennifer. “Their relationship ended more than two decades ago — she has definitely moved on,” says the source. “Why would she want anything to do with Diddy’s latest legal nightmare?”
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