In Hindsight, Wendy Williams Was On to Diddy

Oh, where is “The Wendy Williams Show” when you need it? The former talk show host was no stranger to calling out Diddy, so we know she would’ve had a field day with the mogul’s federal indictment, the allegations and all of his other pending lawsuits.

Despite the two celebs seemingly on good terms after he appeared on her talk show back in 2017, Diddy and Williams have a checkered history. Before Williams made it to TV, she repeatedly called Puffy out on her Hot 97 radio show. The two had a tumultuous relationship, and in an interview with media legend Sway, she implied Diddy played a key role in jeopardizing her career.

Williams eventually found her footing with the 2008 arrival of her daytime television show, “The Wendy Williams Show,” and you better believe she never took her foot off of Diddy’s neck. In fact, Diddy and his early legal troubles became trending topics during many of Williams’ Hot Topic segments. But the most frightening part of it all is Williams seemed to warn the public about Diddy’s “controlling” tendencies toward Cassie.

In 2015, Williams even speculated Diddy was overbearing and controlling his then-girlfriend, Cassie Ventura. “When you date a mogul, it’s really difficult to avoid them because if you use your head you never know when they’ll pop up on the scene,” she told her live audience. “He can hire a plane right now…land on the roof of the hotel she’s staying, pay people off at the front desk, ‘Give me a key and let me up in her room.’”

And when Diddy and Ventura officially called it quits in 2018, Williams spoke out against him for publicly trying to win her back. Williams said, “I think this was a grand overture from Puffy. I don’t believe he really wants her back.” She continued, “I believe he probably treated her, at some point, like a possession.”

In hindsight, Williams was onto something here. Ventura filed a civil lawsuit in 2023 against the 54-year-old that cited physical and sexual abuse, which aligns with Williams’ claims. And after hotel footage showed Diddy physically assaulting Ventura in 2016, he even came out and apologized for his actions.

From Williams alleging Diddy sent girl group Total to jump her outside of Hot 97 to the talk show host suggesting Diddy was too busy partying and being a “playboy” to settle down with just one woman, Williams always seemed to have the inside scoop on Puff Daddy and the ongoing allegations surrounding him.

When Williams brought Diddy on her show, he gave her much-needed flowers. “I just want to say how proud I am of you because I don’t think people really get it that you were the first one to really cover hip-hop culture,” he said. “You started shedding light on our culture and our people, so thank you very much.”

Now, Williams is receiving treatment at a wellness facility after ongoing health issues. And Diddy is sitting in a jail cell after being denied bond on federal racketeering and sex trafficking charges.