Last week, Sean “Diddy” Combs was indicted on sex-trafficking and racketeering charges and taken into custody in New York. His arrest brought renewed attention to a spate of disturbing allegations against him, which have been detailed in multiple lawsuits accusing him of abuse, sexual harassment, sexual assault, and nonconsensual pornography. With more specifics expected to emerge when his trial starts, rumors have run wild online about what else Diddy might have used his power and wealth to keep hidden.

One resurfaced video that raised a lot of questions shows the music mogul hanging out with a 15-year-old Justin Bieber. Posted to Justin’s YouTube account in November 2009 and titled “JUSTIN BIEBER’s 48 HRS with DIDDY!!,” the video shows Justin joking about driving one of Diddy’s cars before the pair share that they’re about to spend two days together. “Where we hanging out and what we doing, we can’t really disclose,” Diddy says, “but it’s definitely a 15-year-old’s dream.” He adds, “For the next 48 hours, he’s with me. We’re gonna go buck full crazy.” When Diddy asks Justin what he wants to do, the teen says, “Let’s go get some girls,” prompting the then-40-year-old mogul to call him a “man after my heart.”

In the wake of the sex-trafficking charges against Diddy, the video looks a lot more sinister. Justin probably met Diddy when he was 13, after he was plucked from YouTube obscurity and became a protégé of sorts to Usher — who himself had been mentored by Diddy in the ’90s when he was an up-and-coming teenage musician. (Usher later recalled witnessing some “very curious things taking place” but has mostly reminisced fondly about his time at “Puffy Camp.”)

Although Bieber and Diddy didn’t make music together until last year when Bieber was featured on Diddy’s album, it seems the two spent a fair amount of time together when Bieber was younger. The earliest clip has aged the worst, but another unsettling video appeared on Diddy’s YouTube page in December 2010; in it, Diddy presents Justin with a letterman jacket after asking why they haven’t been hanging out anymore, prompting an apparent bout of nervous stuttering from the young singer. “You ain’t been callin’ me and hanging out the way we used to hang out,” Diddy tells Justin, as the 16-year-old sways back and forth before joking that Diddy doesn’t have his number anymore. (The video turned out to be a promo for Diddy’s album Last Train to Paris.)

Clips from later years appear to show Bieber at various parties and clubs with Diddy and his friends, some of which seem to involve him drinking, though it’s hard to tell how old he is. In yet another resurfaced video, this one from a 2014 episode of Keeping Up With the Kardashians, Khloé Kardashian recovers from a weekend of partying until 5:30 a.m. with a group that includes Bieber and Diddy at an event where “half the people were butt-naked.” (Bieber would have been about 20.)

The two performers certainly spent enough time together for Bieber to be shaken by the news that Diddy had been slapped with a federal sex-trafficking indictment. Following Diddy’s arrest, the Daily Mail claimed Bieber is “so disturbed by the Diddy news and is unwilling to process it or discuss it so he has shut off.” Their source emphasized that “so many people who helped to make him who he is were very close to Diddy and it has completely thrown him.”

People, however, said Bieber is “aware of Diddy’s arrest and all the allegations” but “wants to focus on being a great dad and husband” and has been “in a happy bubble” since his baby arrived.

The Cut has reached out to Bieber’s representatives for comment and will update this post if we hear back.