Wendy Williams' Brutally Honest Comments About Diddy Resurface

The following article includes allegations of domestic abuse and sexual assault.

After Diddy was hit with allegations that he sexually assaulted his ex-girlfriend Cassie and multiple other women, some of Wendy Williams' old comments about him started recirculating on the internet. Williams' fans also can't help but wonder what she would say about the rapper if she were still holding court on daytime TV today. "Wendy Williams would've had a time with what's going on with Diddy," one person tweeted. In addition to court docs to read aloud, Williams would have photos of the feds raiding Diddy's homes to flash up on her famous big screen.

One of the most unforgettable moments on "The Wendy Williams Show" was when Diddy sat down for an interview with Williams in 2017. After years of bad blood, they managed to bury the hatchet and have a civil conversation. It was a real love-fest, with Williams gushing about how great her guest smelled, remarking on his youthful visage, and marveling over how expensive his outfit looked. She even went all red carpet reporter by having the camera zoom in on his shining Saint Laurent boots. 

Diddy was a gracious guest. "I want to just tell you how proud I am of you because I don't think you get enough credit for being the first one to really cover our culture ... hip-hop culture and also hip-hop celebrities," he said. But according to Williams, there was a time when Diddy was so angry about the way she covered his personal life that he sought revenge.

When Wendy Williams worked as a radio host for Hot 97 in the '90s, she suggested on-air that Diddy might be gay. She believes the Bad Boy Records founder retaliated by using his influence as a well-connected music mogul to orchestrate her firing in 1998. "Did Puffy have a hand in it? It is my belief," she told New York Magazine in 2005. In an interview with "The Art of Dialogue," Diddy's former bodyguard, Gene Deal, recalled that Williams planned to use a photo of a man pulling Diddy's pants down to back up her claim. However, Deal said the picture was snapped when a partygoer pantsed Diddy as a joke. The person who took it sent it to Williams, who sensationalized it on her radio show. "Wendy Williams said she had him in a compromising position," Deal recalled.

Williams also addresses her belief that Diddy got her fired in her book "The Wendy Williams Experience," which was published in 2005. "The hell he put me through, I will never forget. But I don't hate him," she writes. After recounting some of Diddy's brushes with the law, she adds, "There seems to be this black cloud over Puffy." Despite their yet-to-be-resolved beef, Williams expresses an interest in interviewing Diddy someday. "I can say that I will not be asking him, 'Are you gay?'" she writes. She was true to her word when he appeared on her show over a decade later.

When Diddy appeared on "The Wendy Williams Show," the topic of his relationship with Cassie came up. As Diddy described his feelings for his then-girlfriend, who was also one of the musicians signed to his record label, Williams seemed to swoon a bit, letting out little gasps of awe. However, she also told Diddy, "I'm shocked that you and Cassie have gone this far." Diddy and Cassie broke up the following year.

Williams seemed to have no inkling of the explosive allegations Cassie would later make against Diddy. In a civil suit, Cassie accused her ex of rape, assault, and sex trafficking. But Williams did have some thoughts about the pair's power dynamic, which is something Cassie touched on in her lawsuit. "I believe he probably treated her at some particular point like a possession," Williams said on "The Wendy Williams Show." During another episode, she suggested that Diddy could make it difficult for Cassie to ever completely extricate him from her life because he could use his wealth and power to follow her wherever she went. Cassie was filming a movie in South Africa at the time, and Williams used that detail to concoct a hypothetical scenario. "He can hire a plane right now ... land on the roof of the hotel where she's staying, pay people off at the front desk, [and say], 'Give me the key and let me up in her room,'" Williams said.

While Wendy Williams pointed out that there were plenty of flaws in Diddy and Cassie's relationship on "The Wendy Williams Show," she also said that she wanted the pair to make up after their 2018 breakup. "I'm sad about this, y'all, I thought they were going to get married," Williams told her audience. She added that she hoped the pair would reconcile, quickly get engaged afterward, and have a child together. In another episode of her show, Williams suggested that Cassie might find it difficult to navigate life on her own after the split because she had started dating Diddy when she was just 21 years old. Williams pointed out that Diddy had likely taken care of his girlfriend's accommodations and transportation during the 11 years that the couple dated, so Cassie was going to experience a huge lifestyle change. "She probably doesn't know how to apply for a mortgage," Williams mused.

Williams didn't view Diddy's rumored rebound romance with model Jocelyn Chew as an impediment to Diddy and Cassie resuming their relationship, although Chew's young age made her wonder whether Diddy had decided that then-32-year-old Cassie was too old for him.

If the split was going to stick, Williams suggested it was for the best that the exes never had any kids together. "Cassie doesn't have to deal with any of that baby mama drama and all that mess," she said.

Wendy Williams has made some contradictory remarks about Diddy on "The Wendy Williams Show." During one episode, she called him out over his treatment of some of the artists he has signed to Bad Boy Records, including Danity Kane member Aubrey O'Day. Williams suggested that Diddy didn't do enough to further the careers of the "Making the Band" star or "Bad Boy for Life" rapper Black Rob, saying, "When Puff is done with you, he drops you." She added, "He's used to having people do what he wants, and when they don't, then he's used to seeing them buried under the bus afterwards."

However, in 2019, Williams jumped to Diddy's defense after O'Day accused him of the same behavior the talk show host had previously decried. O'Day had reacted to the news that Diddy was rebooting "Making the Band" by tweeting, "You know he can't finish any artist he starts." Williams' response was to scold O'Day and suggest that Danity Kane didn't deserve to be successful. "You weren't listening to the master," she said on her show. Williams went on to list a few artists who had long careers after signing with Bad Boy Records, including Lil' Kim and Mary J. Blige. "Where do you want to go with this, Aubrey? Get your facts," she concluded.

Wendy Williams has had so much to say about Diddy on her show over the years. She even told "The Wendy Williams" audience that Diddy commanded the three members of his label's R&B group Total to attack her outside the Hot 97 offices in the '90s. However, she didn't mention him by name. "Once upon a time there was a music mogul who sent his all-girl group to beat my a**," the talk show host recalled. While the experience left her understandably upset at the time, she said that it made her aspire to further her career.

Once Williams moved from radio to TV, Diddy provided her with plenty of material for her "Hot Topics" segments. And fans rewatching clips of her show still find her personal anecdotes about Diddy riveting. "Wendy can tell the Total story 100 times and I will listen. It never gets old," reads one YouTube comment.

In "The Wendy Williams Experience," Williams informs her readers that she's actually grateful to Diddy, thanks in part to his many legal woes, romantic entanglements, and beefs with other musicians. Of the man she would eventually make amends with, she writes, "If he doesn't like what's written about him, he has only himself to blame. Puffy is a person who stays in the news. That is one thing he has done for my career — giving me much to talk about. And I love him for that."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).