Wendy Williams’ Warnings About Sean ‘Diddy’ Combs, Explained
Wendy Williams didn’t shirk away from the entertainment world’s big stories. Her reporting ruffled many feathers throughout her career. One celebrity whom she followed closely was Sean “Diddy” Combs. Williams dropped one warning after another regarding the mogul’s behavior on her radio show and, later, syndicated talk series.
Wendy Williams warned her followers about Sean ‘Diddy’ Combs’ behavior for years
The conflict between Wendy Williams and Sean “Diddy” Combs lasted years. She believed he was behind her firing from Hot 97, where she was the afternoon drive-time DJ from 1994 until 1998. Reportedly, Combs attempted to silence Wendy to prevent further speculation about his personal life on her show.
During this period, Williams frequently talked about Diddy (then known as Puff Daddy) and his personal life, particularly his relationships. Williams was known for addressing sensitive and speculative topics that other media outlets rarely covered, and this didn’t sit well with Combs.
When she helmed the syndicated Wendy Williams Show, Williams continued to speak out against Combs. She dove deep into his personal relationships, particularly his breakup with Cassie Ventura.
She said in a YouTube clip, “Reportedly, they broke up because Puffy was cheating on her with another woman. Either she will go back with him or not because once you date a superstar, you’d be stupid not to use that to bounce to the next superstar.”
“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 and 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.’” She added that the idea frightened her.
Subsequently, in November 2023, Ventura filed a lawsuit against Combs. She accused him of rape and physical and emotional abuse during their 11-year relationship.
Wendy Williams had ‘contempt’ for Sean ‘Diddy’ Combs
In her 2004 book, The Wendy Williams Experience, Williams wrote that she had “a certain level of contempt for Puff” because he “single-handedly tried to ruin” her career. She commented on “the hell he put her through.” She added that she didn’t “hate” Combs, but would “never forget” what he did to her.
There was also a rumor that Combs allegedly sent the R&B girl group Total (from his Bad Boys label) to physically confront Williams in the 1990s outside of the Hot 97 studio. This claim has never been officially confirmed. Members of Total subsequently denied being involved in any physical altercation with Wendy Williams.
During a 2015 Wendy Williams Show episode, Williams also discussed Combs’ playboy lifestyle. “He’ll pick [a woman] and settle down, but right now, I don’t think he will. I think he’s leading this playboy lifestyle where he’s got these women in his life where he’s got them hypnotized.”
Wendy and Diddy eventually reconciled
In an interview with Sway, Wendy Williams implied Diddy played a crucial role in jeopardizing her career. “We had real bad blood for a while, the worst blood.”
The two eventually reconciled. He appeared on The Wendy Williams Show in 2017. “I know I pissed a lot of people off, including you,” Williams said as Combs nodded in agreement. “But this is a full-circle moment, everybody. Get into adult conversation.”
Williams is battling frontotemporal dementia and aphasia and has not publicly addressed Combs’ recent arrest on sex trafficking and racketeering charges. Combs remains in federal custody.
How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.
