In a shocking throwback moment, Sean “Diddy” Combs was caught on camera jokingly telling Justin Bieber to keep quiet about “the things he does with Puff.”

The disgraced rapper featured with the young singer, who was just 16 at the time, on a 2011 episode of Jimmy Kimmel Live. Now 54, Diddy is in federal custody, awaiting his day in court on charges including sex trafficking, transportation for prostitution, and racketeering. He pleaded not guilty to the charges. He’s also battling numerous allegations of sexual abuse and violence, all of which he has denied.

A clip that has recently resurfaced shows late night host Jimmy Kimmel questioning a then 41-year-old Diddy about his connection with Justin, asking, “What’s going on with you guys? Are you working together?” To which Diddy responded, “Nah. I think that we have become friends in a strange way.”

Justin chimed in with a quip, likening their friendship to “Rob and Big” nodding to the dynamic between skateboard celebrity Rob Dyrdek and his late bodyguard Christopher “Big Black” Boykin, who starred in their own MTV reality show in the 2000s, reports the Mirror.

Diddy elaborated, saying, “I mean, to a lot of us, he’s like a little brother. You know what I’m saying? He’s not afraid to call and ask for advice. He’s somebody that industry-wise, the record industry is a strong family. He’s somebody that we definitely have our arms around and we want to protect him, because he’s such genuinely a nice person besides his talents. He’s one of the greatest kids you could ever know.”

Jimmy teased Justin with, “You know, Diddy bought his son a Bentley, maybe he can buy you one also while he’s at it.” The crowd erupted in laughter as Justin shot back: “He got me a Lamborghini. I haven’t gotten it yet though.” Continuing the banter, Jimmy asked, “When is it coming, that Lamborghini? We talked about this last time.”

Diddy humorously retorted: “He had the Lamborghini for a day or two and he had access to the house. And he knows better than to be talking about the things he does with big brother Puff on national television. Everything ain’t for everybody.” The Mirror reached out to Justin and Diddy’s reps for a statement about this resurfaced clip.

Back in 2009, the two struck up a friendship after running into each other at the VMAs. During that period, Justin was being mentored by Usher, who has a history himself with Diddy during his early career days. Diddy was a mentor to Usher.

Subsequently, Usher has come forward about the guidance received from Diddy, claiming that the hip-hop mogul introduced him to the world of sex, drugs, and alcohol way before his time. In a candid MTV interview in 2010, Usher articulated that he “wouldn’t pass on any of the advice he gave me.”