Aunty Wendy tried to tell us for years and suffered greatly for it!
Allow us to take you down memory lane. Over the years, Wendy Williams has had a tumultuous relationship with Sean “Diddy” Combs, beginning with her criticisms and exposès of him on her Hot 97 radio show in the ’90s, leading to her firing in 1998. Despite this, she found success with her own talk show. Their relationship seemed to mend when Diddy appeared on her show in 2017, but Williams has made several remarks about him since, including claims of being nearly jumped by a group from Diddy’s label, mocking his name changes, expressing contempt in her book, speculating on power dynamics in his relationships, and commenting on his playboy lifestyle. She also criticized his public attempts to win back Cassie after their split, labeling it as manipulation. (Via US Weekly & The Daily Beast)
Getting Jumped
Before getting fired from Hot 97, Williams claimed in 2005 during her radio show, The Wendy Williams Experience, that she was almost jumped by the girl group Total, who was signed to Diddy’s record label Bad Boy Records. Williams recalled the alleged moment and hinted that Diddy was involved during a 2019 episode of her talk show.
“Once upon a time, there was a music mogul who sent his all-girl group to beat my ass in front of the radio station. Fact!” she claimed. “I finished my shift, round up my headphones, put my bag [on] my arm and I see everybody lined up at the window looking down on the sidewalk.”
Williams explained that she was dating ex-husband Kevin Hunter at the time and they had encountered the musical act.
“I find this girl group, jump out of a gypsy cab, to come after me,” she alleged. “To beat my ass! For what? You know what I said was true. You all were broke and you were living in the projects, and that was that.”
Her Firing
During a 2013 interview with Vlad TV, Williams tiptoed around her firing from Hot 97 and how it revolved around her speculation about hip-hop musician’s sexuality.
“There was a radio personality once upon a time and her name was Wendy Williams and she was practically burned at the stake for talking about such and now it’s all come full circle,” she teased. “There were many situations back in the day in my career and it’s all coming full circle.”
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Former Badboy President Kirk Burrowes detailed the East Coast-West Coast feud between Bad Boy and Death Row Records in the 1990s and Williams’ involvement. Burrowes claimed that Combs’ infant son and the boy’s mother, Mysa Hylton, were paid to take a picture with Combs’ rival, Suge Knight.
“It got back to the east that [Mysa] was there in the office and that Suge was meeting Justin Combs and possibly holding him in his arms, and that there was a photographer taking a picture,” Burrowessaid. “That wasn’t the picture we needed to see on our end or that we wanted the world to see—at all.”
Somehow, Williams got wind of the photo and announced that she had big news coming on her syndicated radio show, and the Bad Boys team had to intervene to prevent the photo from spreading to the public.
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Later, Williams had a theory that Combs engaged in sexual activity with other men, and she received a photo of a man allegedly pulling Combs’ shorts down while he was on vacation in Cancun. During an Art of Dialogue interview in 2022, Combs’ former bodyguard Gene Deal said Combs got Williams fired from her job at Hot 97 before she could address the photo on the air.
“The power [Combs] had with the radio stations in New York, motherfuckers didn’t breathe hard if [Combs] didn’t want them to. …[Combs] got one of the hottest DJs off Hot 97 because she wanted to put up a picture of him getting his pants pulled down,” Deal said. “[Combs] 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, any of the record labels executives that was cool with him, everyone was going to boycott their station.
“We was out in L.A. for about three days,” Deal added. “Before we landed back in New York, Wendy Williams was in the radio station in Philly. It was over for her. She was fired.”
His Name Changes
Williams, who always refers to the rapper as Puffy, poked fun at him constantly changing his name throughout his career.
“I don’t like when people change their names in the middle of our relationship,” she quipped in a 2015 episode of The Wendy Williams show. “Like don’t tell [to] me call you Diddy, I know you as Puffy, that’s it.”
Her Book Revelations
In her 2004 book, The Wendy Williams Experience, she wrote that she had “a certain level of contempt for Puff” because he “single-handedly tried to ruin” her career.
“The hell he put me through,” she penned. “I will never forget. But I don’t hate him.”
Alluding to Controlling Tendencies
After Diddy and Cassie (real name Cassandra Ventura) briefly broke up in 2015, Williams speculated that there was a balance of power issue between the record producer and singer.
“My thing about 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 said on The Wendy Williams Show. “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.’ I’m already paranoid as a person.”
Calling Out His Playboy Nature
Williams quipped that she didn’t think Diddy would want to settle down when he reached the age range of “68 to 78” due to his party boy lifestyle.
“He’ll pick [a woman] and settle down but right now I don’t think he will,” Williams claimed on a 2015 episode of her series. “I think he’s leading this playboy lifestyle where he’s got these women in his life … where he’s got them hypnotized.”
On His Guest Appearance
Three years after his interview with Williams, the talk show host opened up about the rivals’ full circle moment. “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,” she said during a 2019 interview on the Sway’s Universeradio show. “Bad Boy for life.”
Weighing in on Cassie and Diddy’s Split
When Diddy and Cassie called it quits for good in 2018, Williams was initially rooting for the pair to get back together since Diddy publicly declared his love for Cassie on Williams’ talk show. However, after seeing Diddy attempt to win Cassie back on social media, Williams labeled his behavior as manipulation.
“I suggest don’t use social media though to reach out. I think this was a grand overture from Puffy. I don’t believe he really wants her back,” she said at the time. “I believe he probably treated her, at some point, like a possession. If you really cared then you’d reach out privately not publicly.”
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