Before the controversial life of the Grammy-winning rapper behind the doors was unraveled, with the constant lawsuits and numerous allegations against him, one name that consistently emerged as a voice of caution was the talk show host Wendy Williams.
Known for her candid commentary, Williams has a long history of calling attention to the rapper’s actions, whether addressing her abrupt firing from Hot 97 radio or sharing her critiquing his long relationship with Cassie Ventura.
Wendy Williams Alleged Diddy Had Her Fired From Hot 97
Wendy Williams, who was diagnosed with dementia in 2023 has now been declared “cognitively impaired and permanently incapacitated” by her legal guardian Sabrina Morrissey.
Williams has been known for her bold and often controversial commentary, including her strained relationship with music mogul Sean Combs, aka P. Diddy, which dates back to her time on the popular Hot 97 radio show.
Williams was fired from Hot 97 in 1998 after making provocative claims about Diddy’s label Bad Boy Records, and speculation surrounding the hip-hop mogul’s s*xuality, as per US Weekly.
Years later, after achieving success with The Wendy Williams Show, Williams suggested in an interview with Vlad TV that Diddy was behind her firing. She remarked:
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 — There were many situations back in the day in my career and it’s all coming full circle.
Her former co-host Charlamagne Tha God later addressed the claims, stating, “Wendy got fired from Hot 97 by Diddy because that’s when Bad Boy was smoking hot and, yeah, she got fired for putting that out there,” in an appearance on The Art of Dialogue podcast.
Wendy Williams Claimed Diddy Sent R&B Group Total to Confront Her
While Williams was fired from the radio show in 1998, the alleged beef between her and the popular rapper is believed to have started well before her dismissal.
The talk show host later revealed on her radio show The Wendy Williams Experience in 2005 that she was nearly attacked by Total, a popular R&B group signed to Diddy’s Bad Boy Records.
She alleged that it was Diddy who orchestrated the incident, stating:
Once upon a time, there was a music mogul who sent his all-girl group to beat my a*s in front of the radio station. Fact! — 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.
“I find this girl group, jump out of a gypsy cab, to come after me,” she further alleged before adding, “To beat my a*s! For what? You know what I said was true. You all were broke and you were living in the projects, and that was that.”
Additionally, Williams has also been vocal about what she described as the toxic nature of Diddy’s relationship with his ex-girlfriend Cassie Ventura, who later filed a lawsuit against the hip hop star in 2023 before the ongoing investigation on the rapper.
Wendy Williams Highlighted Power Imbalance in His Relationship with Cassie Ventura
Along with claims about how the rapper tried to ruin her career, Wendy Williams has also spoken out about his problematic behavior, including his playboy image and his relationship with Cassie Ventura.
Combs and Ventura were in an 11-year relationship, marked by several highs and lows. During a brief split in 2015, Williams highlighted the power imbalance between in their relationship, stating,
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 — 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.
Even after Diddy appeared on The Wendy Williams Show in 2017, Williams continued to speak out. Following the couple’s split in 2018, she called Diddy’s attempts to win Ventura back through public gestures manipulative:
“I believe he probably treated her, at some point, like a possession. If you really cared then you’d reach out privately not publicly,” she stated reflecting on their split.
In addition to his problematic nature and relationship with Ventura, Williams also critiqued his “playboy lifestyle,” in a statement that has gained a more chilling meaning in the wake of recent revelations.
“I think he’s leading this playboy lifestyle where he’s got these women in his life … where he’s got them hypnotized,” she said while sharing her belief that Diddy would want to settle down only later in his life, between 68 and 78, due to his party boy lifestyle.
Wendy Williams Called Diddy a “very dangerous man” in Her Book
Wendy Williams’ allegations about Sean ‘Diddy’ Combs extend beyond her shows and interviews, as she also detailed her claims in her book, dedicating multiple chapters to the hip-hop mogul.
In her book, Williams clarified that she does not hate Diddy, despite all his alleged attempts to ruin her career. She said in her book, The Wendy Williams Experience,
For the record, I do not hate Sean “Puff Daddy, Puffy, P. Diddy” Combs… I do, however, hold a certain level of contempt for Puffy. He single-handedly tried to ruin me, tried to ruin my career. He spent a lot of money and used a lot of his influence to try to crush me in New York in the late 1990s.
She further stated,
It’s old news, and I don’t really want to rehash the gory details, but I will say that Puffy almost accomplished his goal. And the hell he put me through, I will never forget. But I don’t hate him.
Williams also addressed Diddy’s controversial history in the entertainment industry, addressing topics such as the 1999 Club New York shooting, the tragic death of Notorious B.I.G., and his relationship with Misa Hylton, with whom he shares a son, Justin Combs.
Describing him as “a very dangerous man” in her book, Williams wrote, “Puffy hides his [fear and intimidation] behind shiny suits, which makes him more dangerous because you don’t necessarily see him coming.”
Prior to the concerning updates regarding her health, Williams has spoken out on Diddy’s arrest and indictment on charges of racketeering and s*x trafficking. “You know how I feel about that? It is about time,” she said in an interview with Daily Mail. Diddy has denied the allegations against him and pleaded not guilty.
