As Sean ‘P Diddy’ Combs awaits trial on sex trafficking charges, we take a look back at the superstar’s inner circle, including Justin Bieber, Usher and more

P Diddy, one of the world’s most successful music producers, was once surrounded by a plethora of famous faces. The Bad Boy star, 54, was always in good company, rubbing shoulders with stars from music, film and even royalty.

However, he now finds himself far removed from the glitz and glamour of Hollywood as he awaits trial for sex trafficking charges (which he denies), at the Metropolitan Detention Center in Brooklyn, New York. As the world anticipates the rapper’s next hearing on October 9, let’s take a look at some of the notable names from Combs’ past and present inner circle.

Usher is one such name. Diddy is credited with launching the career of R&B star Usher after record label executive L.A. Reid sent the then 14-year-old to live with the then-23-year-old rapper for a year in 1994.

In a 2004 interview with Rolling Stone, Usher recalled how the father-of-six introduced him to “a totally different set of s*** – sex, specifically”. He said: “There were always girls around. You’d open a door and see somebody doing it, or several people in a room having an orgy,” reports the Mirror.

Years later, in a 2016 interview with Howard Stern, he described his times at Diddy’s home as “pretty wild.” Usher has yet to comment on Combs’ arrest. Justin Bieber is another name associated with Diddy.

Justin Bieber and Diddy struck up a friendship at the dawn of Bieber’s career when he was just 15, with Diddy already in his forties. The duo became buddies back in 2009 after meeting at the VMAs, shortly after Justin was signed by Usher.

On Jimmy Kimmel’s show, Justin was asked about his hangouts with Combs, to which Diddy responded: “He knows better than to be talking about the things he does with big brother Puff on national television. Everything ain’t for everybody.”

Jennifer Lopez, known as J-Lo, dated the Bad Boy Records mogul for two years until their split in 2001. They were one of the most glamorous couples in the entertainment industry at the time.

However, post-breakup, Lopez didn’t mince words about their past relationship. When radio host Big Boy hypothetically asked her, “You’re on a raft in the middle of the ocean and you look in the ocean, you see two people floating. You can only pull up one because that’s how much room you have on the raft. You look in the ocean, you see Ben Affleck and you see Diddy,” J-Lo sharply replied: “I’d let both those mother f*****s drown!”

In a 2017 interview with Vogue, Combs revealed that Leonardo DiCaprio. was the “number one” guest on his invite list for his upcoming white party. This isn’t the first time their friendship has been noted.

Recently, photos of a young DiCaprio smoking and laughing at one of Diddy’s parties have caused a stir. In 2019, the Oscar-winning actor was even caught on camera dancing at Diddy’s 50th birthday bash.

Cassie Ventura, who dated Diddy from 2007 to 2018, only brought allegations of abuse against Combs to light in 2023 when she filed a lawsuit accusing him of emotional abuse, violence, and sex trafficking. Initially, Diddy’s representatives denied these claims.

However, when CNN released a 2016 surveillance video showing Combs physically assaulting Ventura in a hotel in May, the rapper publicly apologized. After the video’s release, Ventura stated that the violence “broke me down to someone I never thought I would become.”

Yung Miami, formerly one half of the popular rap duo City Girls, was in a relationship with Diddy between 2021 and 2023. The pair were often seen together at high-profile events, including the 2023 Met Gala.

Miami recently broke her silence about the allegations against her ex-boyfriend, stating that she can’t speak to those who have accused the disgraced rapper of abuse as “that wasn’t my experience.”

Yung Miami, whose real name is Caresha Brownlee, discussed the allegations during a chat with Saucy Santana on the season two premiere of her Revolt TV show, Caresha Please. Nathalie Moar, who worked as the head of Combs’ communications for over two decades before stepping down following his arrest, played a key role in building his fragrance and clothing empire alongside the Tell Me star.

She also helped manage his public image during Cassie Ventura’s lawsuit and the raids on his homes. In a 2018 interview with PR Newsweek, Diddy praised Moar, saying: “We’ve been through so much together. She’s involved in all aspects of my business, and her leadership, passion, and hard work continue to exemplify the level of excellence I demand from my team.”