What old Wendy Williams show clips predicted about Diddy, Cassie amid trial

USA Today

03-06-2025

What old Wendy Williams show clips predicted about Diddy, Cassie amid trial
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Wendy Williams Says She Is Not Incapacitated In New Interview
In a pre-taped phone interview with 'The View,' the former talk show host addressed her recent hospital visit and independent psych evaluation.
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"My thing about when you date a mogul, is that it's really difficult to avoid them," Wendy Williams blurted out from her iconic plush purple chair.
"You never know when they're going to pop up on the scene," she continued. In December 2015, a "hot topic" on the talk show host's eponymous daytime program focused on the sudden breakup of music mogul Sean "Diddy" Combs and his much younger then-girlfriend Casandra "Cassie" Ventura Fine.
The former radio personality was a longtime frenemy of Combs, often using "The Wendy Williams Show" to gab and gossip about the "I'll Be Missing You" hitmaker's personal life.
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Fast forward nearly a decade: Combs was arrested in September on charges of racketeering, sex trafficking and transportation to engage in prostitution following a monthslong federal investigation. He was indicted but has pleaded not guilty on all counts. And as his federal sex-crimes trial enters its fifth week, fans have resurfaced Williams' comments on Combs and are wondering if she predicted his fate.
"Puffy," as Williams called him, now sits in Brooklyn prison. (The daytime diva herself lives in her own self-described "prison" amid a controversial guardianship; her show ended in 2022 after a prolonged health-related absence.)
Ventura Fine, now a lowkey mom-of-two remarried to an up-and-coming actor, became the star witness in Combs' trial. And with Williams off air, loyal "Wendy watchers" are using archival online clips as reruns.
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In the 2015 clip, Williams quipped that Ventura Fine "broke up with (Combs), and I'm sure she'll be back soon ... or she's got cache now." Williams was right. Ventura Fine returned, testifying in court last month that although she "loved (Combs) very much," she was often coaxed back by his violent threats.
Williams predicted that Ventura Fine could end up with another mogul – one of many observations the talk show host foreshadowed about Combs and the "Me & U" singer.
"Once you date a superstar, you'd be foolish not to use that cache to bounce to the next superstar," Williams said. "At this point in her life, she's spent eight years of her life being flown around the world in private places and doing the best and wearing the best."
Williams added that Ventura Fine had "allegedly been avoiding Puffy."
"I thought she was a professional girlfriend, but apparently, she's over in South Africa filming 'Honey 3.' Now honey, I didn't even know there was a 'Honey 2,' OK?" Williams said with her signature shade.
In court, it was revealed that Ventura Fine was once romantically linked to "Sinners" actor Michael B. Jordan while filming musical drama "Honey 3: Dare to Dance" in 2015. Her ex-best friend Kerry Morgan testified that she "was trying to leave" a "jealous" Combs and started talking to Jordan shortly before the two-month trip.
"He can hire a plane right now, zoom it to South Africa, land on the roof of the hotel where she's staying, pay people off, give me the key and let me up in her room. Like I'm already paranoid as a person, but to know that a person could swoop down on me in the middle of nothing would scare the bejesus out of me," Williams said.
Two years later, in 2017, fans zeroed in on a lengthy interview between Williams and Combs that seemingly featured awkward tension when Wiliams said "as the mother of a now 16-year-old..." before Combs interrupted her and said, "Mhm, who I met backstage. He's a great young man."
Williams, appearing to stumble through her sentence, telling a "nervous" Combs that "you represent a lot to a lot of people in general," adding that the music mogul is "an example to people who aren't Black, like, 'Yes we can, yes we can.' You're an example to boys, like your boys, my boys, their boys, boys in general."
But the next year, Williams revisited the pair's relationship as a topic of discussion. "Puffy's 48. Cassie's 32. 11 years of her life. I was asked during our morning meeting, 'Do I think that she wasted 11 years.' I said, 'well, in a lot of ways, yeah,'" Williams said.
"She probably doesn't know how to apply for a mortgage; she has probably always been on his insurance, so she needs an insurance card, signor or something," Williams said in 2018, chiding the audience for laughing. At the time, the "Wendy" show host added, "I like them together and, on the other hand, it wasn't 11 years wasted because Puffy introduced her to a world that she would never know."
But in her testimony at the start of the trial, Ventura Fine painted a far more sinister picture: For over a decade, the model and actress alleges that she was forced to participate in Combs' "freak offs" – sex performances with various male escorts around the world. When she attempted to leave, Ventura Fine said that Combs and his associates tracked her down and threatened to release "freak offs" footage.
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As the trial began, some social media users missed Williams' blunt delivery, a change of pace from present daytime television's overly positive tone of "spirit tunnels" and song covers.
"She would've been having a field day on hot topics right now," one person commented. Another person said, "I can hear Wendy saying 'clap if you think Puffy is guilty.'"
In late May, another X commenter said that "Wendy Williams would've had the highest ratings in daytime history covering Diddy's trial this week!"
On TikTok, another popular platform for Williams fans, one TMZ video about the host's guardianship on radio show "The Breakfast Club" was flooded with supportive comments after her former mentee Charlamagne Tha God mentioned that she "got fired from Hot 97 years ago because of Diddy" and she said, "Diddy done."
"She sounds like she got her life back," one said as another commented, "Why can't she just start doing a weekly gossip podcast." "She got me with Diddy done," another user said.
Contributing: Aysha Bagchi, Patrick Ryan, Edward Segarra