‘You never knew what was going to happen’: Usher’s stories about Diddy’s ‘freak-offs’ become more horrifying when you factor in how young he was

Sean “Diddy” Combs’ federal indictment on sex trafficking, racketeering, and other charges has raised the question, “Who knew about Diddy’s crimes, and who might have been involved?” Usher lived with Diddy when he was 14 years old, and years later, the singer opened up about that time in his life.

In retrospect, what Usher told both Howard Stern on his show and Rolling Stone is consistent with what’s now known about Diddy’s “freak offs,” or massive celebrity sex orgies involving male and female commercial sex workers sometimes transported across state lines. Years before Diddy’s crimes were exposed in court, what Usher said barely raised an eyebrow at the time, but now, what Diddy is accused of, combined with the R&B singer’s young age, makes Usher’s experience that much more disturbing.

Usher’s ‘Rolling Stone’ interview

Usher spoke with Rolling Stone about living with Diddy as a teenager in 2004. About two decades earlier, Usher moved to New York to work with Diddy, who was already a powerful figure in the music business, so that Diddy could help launch the young singer’s career.

In that Rolling Stone interview, Usher said Diddy introduced him to sex. “There was always girls around. You’d open a door and see somebody doing it, or several people in a room having an orgy. You never knew what was going to happen,” Usher said (via the Rolling Stone).

Usher’s 2016 Howard Stern interview

Usher’s teenage experience with Diddy’s “freak offs” was brought up again in 2016 in an Usher interview on The Howard Stern Show. In that Stern interview, Stern seemed to know about Diddy’s reputation for sex parties and asked Usher pointed questions about whether he participated in them in the ’90s.

Usher told Stern he saw some things but didn’t “indulge.” He added, “I don’t know if I could indulge and even understand what I was looking at. It was pretty wild. It was crazy. There were very curious things taking place, and I didn’t necessarily understand it.” As a teenager, Diddy exposed Usher to “a totally different set of s**t — sex, specifically,” Usher said.

L.A. Reid, a high-powered music executive behind Island Def Jam Music, arranged to have Usher live with Diddy in what Usher says was called “Puffy flavor camp.” Would Usher, a father, let his kids go to “Puffy flavor camp?” Stern asked Usher in 2016. “Hell no,” Usher said.

Usher’s deleted Tweets

Usher is not the only high-profile celebrity caught up in the Diddy scandal. Others include Justin Bieber, who also worked with Diddy as a teenager, Mary J. Blige, Ashton Kutcher, and Jennifer Lopez, to name a few. Shortly after Diddy’s indictment, Usher’s Tweets (now X posts) were deleted, and many thought that meant Usher had something to hide.

According to Usher, however, his account got hacked, and the timing was a mere coincidence. But some of Usher’s social media followers didn’t buy that explanation. “u got hacked and the hackers decided to delete all your tweets instead of tweeting random stuff?” one comment said. “lmfaoo yea a hacker gonna waste time deleting tweets for no reason on ur account 😂😂,” another added.

The singer, Pink, another Diddy associate, also wiped her X account about the same time Usher’s posts vanished. So far, Pink has not posted or commented about why that happened. What’s clear is the Diddy scandal fallout has only started. The full extent of Usher’s involvement may never be known. But Diddy’s crimes, it seems, were an open secret in the music industry.