5 Times Celebrities Called Out Diddy Before His Infamous Arrest

We are three weeks into Sean ‘Diddy’ Combs’ sex trafficking trial. As the trial progresses, several witnesses have stepped forward to share harrowing details of their time in Diddy’s presence. Cassie Ventura and Dawn Richard have both spoken. Kid Cudi has also taken the stand to talk about his troubling encounter with the rap mogul. While the testimonies we’ve heard so far are alarming, if you think back, a lot of people have blown the whistle on Diddy over the years. We’ve collected five examples of celebrities speaking negatively about Diddy and his infamous sex parties.

Aubrey O’Day didn’t testify, but she’s said plenty

Aubrey O’Day has been suspiciously absent from the witness list for Diddy’s trial. She was never subpoenaed to testify. That doesn’t mean she hasn’t shared her story over the years. O’Day, who worked with Diddy on Danity Kane, appeared on The Celebrity Apprentice 5 in 2012 and hinted at contempt for her former manager then. Donald Trump, then a reality TV star, asserted that Diddy was a “good guy,” O’Day opted not to comment, but her face said it all years before his arrest.

Years later, O’Day opened up about working with Diddy to Variety. During a 2019 interview, she said, “Diddy was one of the most intense people you could ever work with. I experienced everything from race [remarks] to sexism, and a lot of it was scary.” She has also suggested she was dismissed from Danity Kane for refusing to live up to Diddy’s expectations, but she insists her talent as a performer was never the issue.

50 Cent has been one of Diddy’s most vocal critics

One of the music mogul’s most outspoken critics is 50 Cent. In the early 2000s, 50 Cent dropped a diss track about Diddy and went head-to-head with him over their liquor brands. He’s trolled him on social media multiple times, too. It wasn’t just a business scuffle, though.

50 Cent questioned Diddy’s behavior and inclination for exploiting artists multiple times before any victim filed a single lawsuit or arrest warrants were issued. He criticized Diddy’s business practices, suggesting that the record producer took credit for work done by others and manipulated creatives for personal gain. In interviews, 50 Cent expressed discomfort with Diddy’s demeanor, recalling instances where Diddy’s comments made him uncomfortable. He suggested the rap mogul had “weird energy” and insisted he wasn’t into “weird s**t.”  

Usher indicated that wild and inappropriate things were taking place in Diddy’s home

While 50 Cent has been openly critical of Diddy, Usher has been much quieter about the rapper. Usher knows him well, though. He actually lived with Diddy when he was just a teen. Usher discussed his experience living with Diddy and hinted at the strange happenings and wild parties nearly a decade before his arrest.

Usher described the year he spent in Diddy’s New York City home as “pretty wild,” noting that he witnessed “very curious things” that he didn’t fully understand at the time during an appearance on The Howard Stern Show. When Howard Stern asked him if he needed to do chores to “stay humble,” Usher scoffed. He went on to recount seeing parties and activities that were eye-opening for someone his age, including instances where he would “open a door and see somebody doing it, or several people in a room having an orgy.” While Usher insists he wasn’t involved in any of the activities, he was emphatic that he wouldn’t want his children exposed to anything he saw.

Katt Williams advised everyone to say “no” to Diddy’s parties

Katt Williams seemed to have a crystal ball and could predict the future. The controversial comedian spoke about distancing himself from Diddy’s infamous parties just months before the record producer landed in a federal prison.

During a January 2024 interview on Club Shay Shay, Williams remarked, “P. Diddy be wanting to party, and you’ve got to tell him no. I did. I got the receipts.” He made additional comments about Diddy and his party later that same year. During a festival appearance, he said that if he’s at a Diddy party, he’s there with “bad intentions” to observe.

Wendy Williams has made several comments about Diddy in the years before his arrest

Wendy Williams was one of the first people to speak out against Combs. While Williams, who is currently fighting a conservatorship, hasn’t been able to speak much about the arrest, she has opened up about her encounters with him years earlier. Williams blamed Combs for getting her fired from her radio gig back in the 1990s and suggested he sent women to intimidate her. She spoke about his relationship with Cassie Ventura in the 2010s and even questioned Jennifer Lopez on her romance with the mogul.

More recently, she appeared briefly, via phone, on The Breakfast Club. During the January 2024 check-in, she spoke openly about Diddy, stating, “You don’t know the things that I knew about Diddy back in the day.” She went on to insist that he will spend the rest of his life in prison. While the prediction hasn’t come true yet, we’ll know sooner rather than later if Williams is correct.