A Look Back At Wendy Williams Spilling Tea About Diddy

Wendy Williams and Diddy haven’t always seen eye to eye. In fact, they publicly acknowledged their contempt for one another. Williams gained a reputation for often stirring the pot, garnering more than a few celebrity adversaries along the way. As far as Diddy goes, Wendy had more than a lot to say about his life and career.

With the allegations and the ongoing investigations involving Diddy, it took no time for netizens to fish out several celebrities who have dropped hints about the mogul’s controversial lifestyle. Wendy leads the pack and has spoken out against Diddy several times. Here is a retrospective look at all Wendy Williams had to say about Diddy.

In 2009, on her radio show, The Wendy Williams Experience, Williams recounted an incident where she allegedly nearly faced a confrontation with the girl group Total, who was signed to Diddy's Bad Boy Records label. She alleged that Diddy had sent the girl group to beat her up while she was still working at Hot 97. “I got off the air one day, them Total b*tches were downstairs, and everybody upstairs at the radio station was looking down, egging it on… Waiting for something to go down,” she said. Williams later explained that her then-boyfriend had prevented the situation from escalating.

During her tenure at Hot 97, Wendy Williams developed a hypothesis regarding Diddy's potential involvement in sexual encounters with other men. Allegedly, she obtained a photograph depicting a man purportedly pulling down Combs's shorts while he vacationed in Cancun. In a 2013 interview with Vlad TV, Wendy Williams delicately addressed her departure from Hot 97. Specifically, she hinted that it was linked to her speculation concerning Diddy’s sexuality. 

“There was a radio personality once upon a time and her name was Wendy Williams,” she began. “And she was practically burned at the stake for talking about such and now it’s all come full circle. There were many situations back in the day in my career and it’s all coming full circle.” Several years later, her allegation was corroborated by Diddy’s former bodyguard, Gene Deal. 

In a 2022 interview with Art of Dialogue, he said: “Diddy got one of the hottest DJs off Hot 97 because she wanted to put up a picture of him getting his pants pulled down. Diddy told Hot 97 if they didn’t get rid of her before he got back in New York, that they was not going to get any music from any of his friends… Before we landed back in New York, Wendy Williams was on the radio station in Philly. It was over for her. She was fired.”

Us Weekly reported that in her 2004 book titled The Wendy Williams Experience, the talk show host expressed that she held a level of disdain towards Diddy. She also alleged that he had "single-handedly attempted to sabotage" her career. She wrote: “The hell he put me through, I will never forget. But I don’t hate him.”

Following a brief breakup between Diddy and Cassie Ventura in 2015, Wendy Williams made some heavy claims. She speculated about a potential power dynamic imbalance between the record producer and the singer. On her televised talk show in 2015, Williams suggested that Combs might have exhibited controlling behavior. “My thing about when you date a mogul, it’s a really difficult thing to avoid them because if you use your head, you never know when they’ll pop up on the scene,” she said. Evidently, Williams's words held significance. Cassie famously  filed a lawsuit against Diddy in 2024, alleging rape, as well as physical and emotional abuse. Barely a day after the lawsuit's filing, Diddy and his legal representatives reached an undisclosed settlement with Cassie.

During a 2015 episode of her show, Williams humorously remarked that she doubted Diddy would consider settling down, given his penchant for the party lifestyle. She quipped: “He’ll pick [a woman] and settle down but right now I don’t think he will,” Williams claimed. “I think he’s leading this playboy lifestyle where he's got these women in his life… where he’s got them hypnotized.” Once again, this has been alleged to be leaning toward the truth. According to Lil Rod’s recent lawsuit against the mogul, Diddy has quite several women under his thumb. 

Wendy Williams and Diddy ultimately seemed to make up in 2017. The artist and producer made a highly anticipated guest appearance on The Wendy Williams Show. Williams expressed to Combs, revealing to the audience that it had been 15 years since they last saw each other. “I know I pissed a lot of people off, including you. But this is a full circle moment.” In 2019, the talk show host reflected on Diddy's appearance on her show. Speaking to Sway's Universe, she quipped: “He showed up, he smelled great, his stomach was flat. Heather, he was handsome and he ain’t going nowhere. Can’t be stopped now. Bad Boy for life." It’s uncertain whether she alluded to his influence and power, but Williams’s sudden admiration for Diddy raised eyebrows. 

In 2018, amidst one of Diddy and Cassie’s tumultuous break-ups, Wendy Williams didn't shy away from addressing their breakup on her show. She openly expressed her views, suggesting Cassie might have invested her time in a man considerably older than her, given Diddy's 17-year seniority. Following the announcement of their split, Diddy made a public attempt at reconciliation through social media about a week later. Initially supportive of their reunion, especially after Diddy's heartfelt declaration of love for Cassie on her talk show, Wendy Williams later criticized his actions as manipulative. She commented: “I suggest don’t use social media, though, to reach out. This was a grand overture from Puffy. I don’t believe he really wants her or wants her back. I believe he probably treated her at some particular point like a possession… If you really care, then you’d reach out privately, not publicly.”