For decades, Sean Combs was hailed as hip hop’s jack of all trades. The Grammy-winning rapper, producer, businessman and executive of Bad Boy Records has launched the careers of some of music’s biggest names, sold millions of records and became known as the host of some of Hollywood’s most glamorous bashes – including his annual White Party. But as of Monday 16 September, Combs is a man behind bars, charged with sex trafficking and racketeering. Abhorrent accusations via a growing heap of lawsuits continue to form against him.
First accused of sexual harassment by his former personal chef Cindy Ruela in 2017 (the lawsuit was settled outside of court two years later), the allegations against the disgraced mogul didn’t gained steam until late 2023. In March, his mansions across the US were raided by Homeland Security. Involving sex workers, hidden cameras and illegal drugs, the so-called “freak off” parties hosted in them were a breeding ground for his own “emotional, physical and verbal abuse” of victims, according to indictments.
Much like how his moniker has changed over the years — whether known as Puff Daddy in the 90s, P.Diddy in the 00s or simply Diddy in recent years — the 54-year-old’s inner circle has shifted over the last three decades, with his high profile soirees pulling in a hoard of A-List names across music, film and allegedly, even royalty. Here, we look at some of the names from Combs’ inner circle, past and present.
Then
Usher
In addition to The Notorious B.I.G and Mary J Blige, Combs is credited with launching the career of R&B star Usher, after the singer’s record label executive L.A. Reid sent the 14-year-old singer to live with a 23-year-old Combs for a year in 1994. In a 2004 interview with Rolling Stone, Usher — who alongside singer P!nk has been accused of deleting tweets that reference Combs since his arrest — reminisced on how Combs showed him “a totally different set of s*** — sex, specifically”.
“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 continued. Years later, in a 2016 interview with Howard Stern, he described his times at Diddy’s home as “pretty wild”. He is yet to comment on Combs’ arrest.
Justin Bieber
Combs attempted a similar “custodial” tactic with Justin Bieber during Bieber’s rise to fame in 2009, when Combs was 40 years old and Bieber was 15. According to an old video from Justin Bieber’s official channel, Usher, Bieber’s mentor and label executive, signed over “custody” of Bieber to Diddy for 48 hours. “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,” Diddy claims in the video.
“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,” he adds. Diddy asks Bieber what he wants to do over the next 48 hours, to which the young singer says: “Let’s just get some girls, let’s go hang out with some girls.”
The pair continued to spend time together throughout Bieber’s career, and in 2021 Bieber posted a throwback picture of the two of them together to Instagram with the caption “My bro @diddy throwback”. Their friendship continued until as recently as 2023, when Bieber featured on a song for Combs’ latest album.
Kim Porter
Model and actress Kim Porter was in an on-and-off relationship with Combs between 1994 and 2007. Together, they had three children: rapper Christian (known as King Combs) was born in 1998 and twins Jessie and D’lila in 2006 (Combs has three more children from various relationships). He also adopted Porter’s son from a previous relationship, Quincy Brown. Porter passed away in 2018 at the age of 47 due to complications from pneumonia, however, a recent memoir — which the MailOnline reported allegedly comprises Porter’s diary entries detailing the pair's turbulent relationship — has topped Amazon’s best sellers list.
Jennifer Lopez
During a break from his relationship with Porter, Combs dated JLo for two years between 1999 and 2001. Crediting Combs with mentoring her during the early stages of her career, two years after the relationship ended Lopez told Vibe magazine that Combs was unfaithful to her: “I was in a relationship with Puff where I was totally crying, crazy, and going nuts, it really took my whole life in a tailspin.” Lopez has not publicly commented on Combs’ arrest or the allegations made against him.
Ashton Kutcher
They seem like an unlikely pairing, but the billionaire became close with Kutcher after expressing fondness for his iconic 2000’s celeb prank show, Punk’d. “We became fast friends and we just used to hang out, watch football together,” Kutcher told Sean Evans during his 2019 appearance on chat show Hot Ones. When asked by Evans whether he could tell any stories from Combs’ infamous parties, Kutcher joked: “I’ve got a lot I can’t tell… I’m actually cycling through them. Diddy party stories, man, that was some weird memory lane thing.”
Leonardo DiCaprio
In a 2017 interview with Vogue, Combs said that DiCaprio was the “number one” guest on the invite list for his upcoming White Party. But that isn’t the first mention of the pair’s friendship. Images of a young DiCaprio smoking and laughing at one of Diddy’s parties raised eyebrows recently, and in 2019 the Oscar-winning actor was filmed dancing at Combs’ 50th birthday party.
However a source close to DiCaprio told MailOnline that he hasn’t had anything to do with Combs “for years”. “He attended a few of his parties back in the early 2000s — but literally everyone did. They were not freak-offs,” the source said. “He has nothing to do with any of that world, so for anyone to assume that he will get roped into this based on a few grainy photos that are more than 20 years old is ridiculous.”
Naomi Campbell
DiCaprio isn’t the only A-Lister who has rubbed shoulders with Combs’ over the years. As well as Paris Hilton, Mariah Carey, Kim Kardashian, Jay Z, Beyoncé and Sarah Jessica Parker, supermodel Naomi Campbell has also been pictured partying with Combs. She is rumoured to have dated Combs for a short while in the early 2000s. Just last November, Campbell threw him a star-studded birthday party in London, with guests including Janet Jackson and Idris Elba.
Casandra Ventura
A singer, model and actress better known as Cassie, who was swept under Combs’ wing in 2005, signing her to his label and releasing her debut album. The couple entered a relationship in 2007, lasting until 2018 — however, details of Combs’ abuse only came to light in 2023 when Ventura filed a lawsuit against him accusing him of a emotional abuse, violence and sex trafficking.
Combs’ representatives initially denied the allegations, however when CNN made a 2016 surveillance video of Combs grabbing, dragging and kicking Ventura public in May, Combs publicly apologised. In a statement after the video was released, Ventura said that the violence “broke me down to someone I never thought I would become”.
Ventura filed a lawsuit against Combs in 2023 accusing him of a emotional abuse, violence and sex trafficking
Roger Bonds
Appearing on an episode of Piers Morgan Uncensored in May, Roger Bonds — the mogul’s former head of security — said that he witnessed Combs’ alleged violence towards women “around four or five times”, including incidents with Ventura and Porter. “It didn’t surprise me when I saw it because I’ve seen things to this nature before,” he said of the CNN video from 2016. “I’ve gotten in-between things of this nature before — and this was back in 2012.”
Now
Kristina Khorram
As Combs’ Chief of Staff, Billboard reported last year that Khorram “works side by side daily with Diddy and spearheads many of his projects and events”. However when music producer Rodney “Lil Rod” Jones Jr — who worked on Combs’ most recent album — filed a $30 million lawsuit against Combs accusing him of sexual harassment and trafficking in February, Khorram was referred to as “the Ghislaine Maxwell to [Combs’] Jeffrey Epstein”. A member of the billionaire’s staff since 2013, the documents allege that Khorram “ordered sex workers and prostitutes for Mr. Combs” for his freak-offs and instructed his domestic staff to carry ‘fanny packs’ (aka bum bags) containing narcotics so they were available whenever he requested them. Khorram did not respond to the Evening Standard’s approach for comment about these lawsuit allegations.
Yung Miami
Formerly one half of popular rap duo City Girls, Yung Miami dated Combs between 2021 and 2023, with the pair appearing at many high-profile events together, including the 2023 Met Gala. When questioned on the allegations made against him, the rapper (real name Caresha Brownlee) said on her TV show that she couldn’t speak on the allegations because she didn’t have such experiences with Combs, and that he was “a really, really good person to me”. Alongside Khorram, Brownlee is mentioned in Jones Jr’s lawsuit, with the producer accusing her of procuring drugs for Combs. Miami did not respond to the Evening Standard’s approach for comment about these lawsuit allegations.
Nathalie Moar
Moar worked as the head of Combs’ communications for over twenty years, but according to The Mirror has reportedly stepped down since his arrest. Working alongside the disgraced mogul to build his fragrance and clothing empire, she also helped to navigate his public image amid Ventura’s lawsuit and during the raids on his various homes. In an interview with PR Newsweek in 2018, Diddy said of Moar: “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.”
