Usher was sent to live with Sean ‘Diddy’ Combs in the mid-90s in a bid to save his music career, but the singer has since admitted his time in New York was ‘the hardest days’ of his life

Singer Usher’s past relationship with Sean ‘Diddy’ Combs is being examined by fans in the wake of the rapper’s arrest earlier this month.

Combs, 54, was arrested at a New York City hotel on Sept. 16 and later jailed without bail on federal charges of sex trafficking, racketeering and transportation to engage in prostitution. Combs denies the charges, with his lawyer describing the music mogul as “an innocent man with nothing to hide.”

The hip-hop tycoon is credited with helping launch the careers of many musicians, like Biggie Smalls, Mary J Blige and Usher. Usher, who rose to prominence in the mid-90s and 00s with hits like Yeah and Confessions part II, first met Combs as a teenager as he faced being dropped from his label.

After being signed by L.A. Reid, the co-founder of LaFace, as a 14-year-old, Usher lost his voice while preparing his debut album and struggled to adjust his vocals. Reid considered dropping Usher but eventually sent him to New York in the spring of 1994 to live with Combs, something Reid dubbed ‘Flavour Camp’.

In an old interview, Usher admitted he quickly adapted to Combs’ lavish lifestyle but admitted his time in New York as a teenager were “the hardest days” of his life and he had to “knuckle up, figure s**t out in New York”. In the wake of Combs’ arrest and imprisonment, historic footage of Usher discussing his time with Combs have resurfaced online.

In one clip, Usher can be seen talking to broadcaster Howard Stern and quizzed about whether Combs’ home was a hotbed for “place was filled with chicks and orgying nonstop”. Answering The Howard Stern Show host, Usher said: “Not really… I got a chance to see some things … I don’t know if I could indulge and even understand what I was looking at.”

He elaborated: “It was pretty wild. It was crazy. There were very curious things taking place and I didn’t necessarily understand it.” Asked if he would allow his own kids to attend Flavour Camp at Combs’ residence, Usher bluntly declared: “Hell no!” Elsewhere during the chat, Usher recalled how he was “like the little brother – they called me Baby Boo.” Asked if Combs enforced any rules, Usher admitted: “He wasn’t disciplinary. He was letting me be a young man.”

Usher’s interview with Stern came over a decade on from the singer’s candid 2004 Rolling Stone interview where he divulged how Diddy had exposed him to “a totally different set of s**t – sex, specifically”. Reflecting on those days, Usher disclosed: “Sex is so hot in the industry, man. 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.”

Combs was arrested on Monday September 16 in New York City on sex trafficking and racketeering charges. He’s been denied bail multiple times and is currently being held in the Metropolitan Detention Centre (MDC) in Brooklyn. Combs has pleaded not guilty to the charges and has denied all wrongdoing. His attorney Marc Agnifilo told the press outside court on Tuesday September 17: “Mr Combs is a fighter, he’s going to fight this to the end. He’s innocent. He came to New York to establish his innocence. He’s not afraid, he’s not afraid of the charges.”

Usher is yet to comment on Combs’ legal woes but eyebrows were raised last week when the OMG singer’s Twitter (X) account wiped thousands of tweets. On Sunday, Usher returned to Twitter to clear the air about his social media drama, claiming his account was “hacked”. He quipped: “Account got hacked and damn y’all ran with it! See you tonight at Intuit Dome.”

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