From Usher to Jay-Z: Diddy's celebrity ties that have come under scrutiny after his arrest

More celebrities are now under the lens for their association with rapper Sean "Diddy" Combs after his arrest on September 16 for alleged "racketeering, s*x trafficking and transportation to engage in prostitution."

His 14-page indictment shed light on the Bad Boy Records founder's alleged "freak offs", described as elaborate s*x parties where the rapper allegedly drugged and forced women to have s*x with male escorts and filmed them without consent.

Authorities allegedly found evidence of these events when they conducted a raid in March. As news of the evidence hit social media, netizens dissected the rapper's relationships with his celebrity friends. Diddy's parties are widely known in the entertainment industry, usually boasting a star-studded guest list.

Photos from his 2000 White Party resurfaced on social media, with people spotting many familiar faces like Jennifer Lopez (Diddy's then-girlfriend), Leonardo DiCaprio, Sarah Jessica Parker, and the late singer Aaliyah, among others.

His other parties over the years welcomed guests like Paris Hilton, the Kardashians, Mariah Carey, Pamela Anderson, Ashton Kutcher, and Kelly Osbourne. However, there is no evidence pointing to the above celebrities being involved in the "freak offs".

Combs' guest list is not the only thing under scrutiny. His association with musicians like Usher, Jay-Z, Jennifer Lopez, and Justin Bieber came under the spotlight after his arrest.

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Diddy's ties with his celebrity friends explored

One of Diddy's recent celebrity friends under scrutiny was Usher after the singer's X profile was scrubbed over the weekend. While he claimed he was hacked, netizens were curious about the timing of the hacking in relation to Diddy's arrest.

Usher lived with Combs when he was around 15 years old while working on his debut album. In a 2004 interview with Rolling Stone, the singer claimed Combs' home was filled with girls and there was always an orgy going on.

“There was always girls around. You’d open a door and see somebody doing it, or several people in a room having an orgy,” he said.

However, in a 2016 Howard Stern interview, he backtracked his answer. But he added that living with the rap mogul was "pretty wild" and answered with an emphatic "no" when asked if he would send his kids to "Puffy camp."

Combs' past relationship with Jennifer Lopez was re-visited after his arrest. The couple, who dated between 1999 and 2001, found themselves in legal trouble after an outing at a New York nightclub left three people injured in a shooting.

Natania Reuben, a victim, alleged that the shooting happened after an altercation between Combs and another patron. She also claimed that the rapper opened fire and shot her in the face.

Combs, his bodyguard Anthony Jones, his protege Shyne, and Lopez, were arrested after police found a stolen gun in their car. Lopez's charges were dropped, Jones and Combs were acquitted after a trial in 2001 and Shyne was found guilty on five charges.

Neither Usher nor Jennifer Lopez have commented on Diddy's s*x trafficking charges and arrest.

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Netizens find an old video of 15-year-old Justin Bieber spending 2 days with Diddy

A 2009 YouTube video of Justin Bieber, then 15, spending 48 hours with Diddy recently gained traction. In the video, Bieber said he wanted to "get some girls" and have fun. The rapper replied they were going to go "buck fool crazy" over the 2 days, adding:

“Where we’re hanging out and what we’re doing, we can’t really disclose, but it’s definitely a 15-year-old’s dream. I have been given custody of him. He’s signed to Usher – I had legal guardianship of Usher when he did his first album. I don’t really have legal guardianship of him, but for the next 48 hours he’s with me. And we’re gonna go buck fool crazy.”

In a 2014 episode of Keeping Up With The Kardashians, Khloé talked about attending a Diddy party where half the people were "butt-naked", mentioning Bieber in the list of people also in attendance.

The two videos had fans speculating about the relationship between Combs and Bieber, pointing out that Bieber was very young when he got his start in the industry. However, the pair remained friendly over the years and collaborated on Combs' 2023 song Moments.

Combs' close friendship with fellow rapper Jay-Z also gained scrutiny. The rappers' friendship spanned decades, with the two first collaborating on the track Young G's from Combs' debut album in 1997. In 2015, the two also discussed getting into business together and have been pictured in each other's company several times.

Recently, an old video of Combs slapping Jay-Z's butt on stage was shared on X. Their friendship was also mocked by 50 Cent, who posted a "missing" photo of Jay-Z following the raids in Diddy's homes in March.

Neither Jay-Z nor Justin Bieber have commented on Diddy's arrest.