Times Wendy Williams Was Brutally Honest About Diddy

Trigger warning: This article contains references to sexual assault, violence, and abuse.

Talk show host and producer Wendy Williams has always been known for having brutally honest interviews with guests and controversial commentaries on the biggest stars in the entertainment scene. One of these instances was the time she pointed out that Megan Thee Stallion had three Grammy Awards and Nicki Minaj had none because the former earned it from "being kind to the people around her." Williams also took a jab at Beyoncé and even said that she'll only watch Beyoncé's documentary with closed captions, hinting the superstar sounds uneducated.

Another artist Williams has had constant clashes with is rapper and producer Sean "Diddy" Combs — a feud that has now spanned over two decades. The American music executive is no stranger to issues surrounding his personal life and major career decisions, which is why he didn't escape the broadcaster's criticisms, but Combs' controversies are not on the same level as showbiz news that dies down the next morning. They go as far as house raids and multiple lawsuits. 

So, here's every time Williams tried to warn us about Combs.

The host alleged that Sean "Diddy" Combs sent a girl group to hurt her. "Once upon a time, there was [a] music mogul who sent his all-girl group to beat my a** in front of the radio station," Wendy Williams hinted during a 2005 episode of her show, "The Wendy Williams Experience." After she finished one of her Hot 97 radio shifts, she allegedly saw a girl group come out of a cab to confront her, and that if it weren't for her boyfriend then, now ex-husband Kevin Hunter, things would've escalated badly.

Williams actually named who was behind the incident: R&B group Total, which was signed under Bad Boy Records, the music company founded and run by Combs since 1993. She mentioned that the group's members were downstairs, with everyone in the station watching and encouraging the situation. "It's Total outside, and they're about to set it on you," Williams said her boyfriend at the time told her during an interview.

The trio, composed of Kima Raynor, Keisha Spivey, and Pamela Long, was the first group to be signed under the music label (along with artists The Notorious B.I.G. and Craig Mack). The group released two albums before Spivey reportedly left Total: a self-titled album in 1996, and "Kima, Keisha, Pam" in 1998. Among their well-known songs include "Kissin' You," a feature on Mase's "What You Want", and "Can't You See" (featuring The Notorious B.I.G.).

The Emmy-nominated host had a theory: Sean "Diddy" Combs is gay. Williams had got her hands on a photo of Combs while on vacation in Cancun. What was shown is a man allegedly pulling Combs' pants down. This led Wendy Williams to believe that Combs engaged in sexual activities with other men. This was something Combs didn't take lightly, so he supposedly used a few connections to get her fired from Hot 97.

Combs' former bodyguard Gene Deal revealed that Combs did pull some strings to prevent Williams from addressing the said photo on air. Deal alluded to Combs' power over radio stations in New York. "Puff told Hot 97 if they didn't get rid of her before he got back in New York, they were not going to get any music from any of his friends, any of the record label executives that were cool with him, everyone was going to boycott their station," Deal said in an "Art of Dialogue" interview.

Deal confirmed that Combs was in Los Angeles for three days, and before they landed in New York, Williams was already dismissed from her Hot 97 post. Williams also hinted at the conspiracy firing during a 2013 VladTV interview, where she talked about homosexuality in the hip-hop music industry.

On "The Wendy Williams Show" in 2018, Wendy Williams speculated that Sean "Diddy" Combs was controlling of Cassie Ventura. She also claimed that Ventura was wasting her time with Combs, a man 17 years older than her. "Puffy is 48, Cassie is 32, 11 years of her life. I was asked during our morning meeting, do I think that she wasted 11 years? I said, 'Well, in a lot of ways, yeah,'" she stated.

On her show in 2015, Williams also said that it was possible their relationship was toxic, saying, "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 claimed, "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.'"

Ventura filed a lawsuit against the record executive in 2023. She accused him of rape and physical and emotional abuse during their long-term relationship. Ventura's lawsuit claims she suffered through years of abuse and demands, including being regularly punched, kicked, and stomped on, even raped in her own home for trying to leave the relationship. When Ventura had a fling with rapper Kid Cudi during a brief split with Combs, it was reported that Combs threatened to blow up Cudi's car — which did explode in the rapper's driveway soon after.

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).

A week after Cassie Ventura's case was closed, another woman accused Sean "Diddy" Combs of drugs and rape, this time on a university student in 1991. Complainant Joi Dickerson-Neal accused Combs of filming the assault and sharing the footage in the music industry, damaging her reputation, career, and mental health. The lawsuit mentioned that Dickerson-Neal appeared in a music video with Combs, and that they had common friends.

An anonymous woman also alleged Combs of sexual assault 30 years ago. According to her, Combs and R&B singer-songwriter Aaron Hall took turns raping her and a friend after an event in New York City. The lawsuit states the group went to Hall's apartment, where she was pressured into drinking more and coerced into sex with Combs. Later, it alleges Hall forced himself into the room and sexually assaulted her as well. 

A month later, another allegation against Combs followed, claiming Combs was involved in the sex trafficking of a 17-year-old high school junior back in 2003 to the music executive Harve Pierre, and another unnamed assailant. The file included blurred photos of the accuser sitting on Combs' lap, who was 34 at the time. She claimed the three men made advances, complimenting her looks and pressuring her into showing off her body.

In a 2015 episode of her show, Wendy Williams said that due to Sean "Diddy" Combs' party boy lifestyle, she doesn't think he's the type to settle down anytime soon — even when he's "68 to 78." "He'll pick [a woman] and settle down but right now I don't think he will," Williams said. "I think he's leading this playboy lifestyle where he's got these women in his life ... where he's got them hypnotized."

In the book "The Wendy Williams Experience," she also expressed a disdain towards Combs, accusing him of attempting to derail her career single-handedly. "The hell he put me through," she wrote. "I will never forget. But I don't hate him." 

Combs' also went by the alias Puff or Puffy when he was starting in the industry, because he was called such when growing up. The name was a friend's nickname to him because Combs admittedly had a temper. This constant changing of his name was something Williams also poked fun at on her show. "I don't like when people change their names in the middle of our relationship," she said. "Like don't tell [to] me call you Diddy, I know you as Puffy, that's it."