Sean ‘Diddy’ Combs’ Celebrity Ties—Including Usher, Bieber, J. Lo—Under Fresh Scrutiny

Topline

Sean “Diddy” Combs’ arrest on sex trafficking charges and various sexual assault lawsuits have sparked renewed scrutiny of the many celebrities he has dated, mentored and even invited to his famous parties, comprising a list of industry giants who have largely kept quiet over the emerging scandal.

Key Facts

What Is Combs’ Relationship With Usher?

Usher and Combs became acquainted in 1994, when producer LA Reid—who had signed Usher to his record label—sent him to live, when he was about 15 years old, with Combs at his home in Scarsdale, New York, while he worked on his self-titled debut album. In 2004, Usher told Rolling Stone Combs “introduced me to a totally different set of shit — sex, specifically,” while he lived at his New York home. “There was always girls around. You’d open a door and see somebody doing it, or several people in a room having an orgy,” Usher said. But through the years, Usher has remained tight-lipped about the experience, and does not talk much about his relationship with Combs. He addressed living with Combs in a 2016 interview with Howard Stern, but gave few details. Stern asked if it was “filled with chicks and orgying non-stop,” to which Usher replied, “Not really.” Usher said living with Combs was “pretty wild” and there were “very curious things taking place, and I didn’t necessarily understand.” When Stern asked if Usher would ever send his kids to “Puffy camp,” he replied, “Hell no.” Last week, all of Usher’s posts on X disappeared, fueling rumors it was somehow related to Combs. But Usher wrote in a post on X Sunday that his account was “hacked and damn y’all ran with it,” and his previous posts reappeared. Usher has not commented on Combs’ arrest or sexual assault allegations.

What Is Combs’ Relationship With Justin Bieber?

Bieber, who was discovered at 13 by former marketing executive Scooter Braun, signed to Raymond Braun Music Group, a joint venture between Braun and Usher they created specifically for Bieber. In a video Bieber uploaded to his YouTube channel in November 2009, when he would have been 15 years old—which has attracted renewed attention—Combs announces that Bieber is spending “48 hours with Diddy,” saying, “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.” In the video, Combs says he doesn’t have legal guardianship of Bieber for the 48-hour period like he had when Usher stayed with him. He then asks Bieber what he wants to do, and Bieber says, “Let’s go get some girls.” Combs replies, “A man after my own heart, that’s what I’m talking about.” In another video uploaded to Combs’ YouTube channel in December 2010, when Bieber was 16, Combs teaches Bieber how to “swag walk,” and tells Bieber, “You starting to act different, huh? You ain’t been calling me and hanging out how we used to hang out.” In the years since, Bieber and Combs were pictured together less frequently but appeared to remain on good terms. In a 2014 episode of “Keeping Up with the Kardashians,” Khloé Kardashian said she went to a party where “half the people were butt-naked.” Her sister Kourtney asked who was there, rattling off a list of names: “Diddy, Quincy [Combs]

, Justin Bieber, French Montana,” to which Khloé said, “So far, so good.” Bieber would have been 19 or 20 in 2014. Combs also attended Bieber’s 22nd birthday party in 2016, where he gave Bieber a Bad Boy Records jacket. Bieber also posted a throwback picture of himself and Combs on Instagram in July 2021, captioned: “My bro @diddy throwback.” Bieber and Combs did not collaborate musically until Bieber was featured on Combs’ song “Moments” in 2023, which Bieber called a “wild full circle moment.” Bieber has spoken of feeling traumatized by his child stardom, though he has never elaborated on the cause. An interview clip of Bieber went viral in 2020, in which he said he felt protective of a then-18-year-old Billie Eilish, stating he had a difficult time with people in the music industry “telling me they loved me, and, you know, just turn your back on you in a second.” Bieber hasn’t addressed Combs’ arrest or sexual assault allegations. CBS News reported Tuesday a song that went viral on TikTok in which Bieber appears to say he “lost himself at a Diddy party” that cost him “cost me way more than my soul” is fake and likely AI-generated.

The Combs-Jennifer Lopez Relationship Explained

Lopez and Combs dated in an on-again, off-again relationship between 1999 and 2001, though they have seldom addressed the relationship in the decades since. The two were involved in an incident in 1999 while attending a nightclub in New York, in which gunfire left three people injured. Natania Reuben, one of three people shot, alleged at the time Combs had shot her—doubling down on the allegation in March after the FBI raids on his homes, stating she would have part of the bullet still in her face removed to be used as evidence. During the altercation, Combs was with Lopez, his bodyguard Anthony “Wolf” Jones and the then 21-year-old rapper Jamal “Shyne” Barrow, and after the four fled the scene their car was chased down by police, who discovered a stolen gun in the car. The four were arrested and charged, though charges were quickly dropped against Lopez. The other three faced a weeks-long trial in which Combs and Jones were acquitted. But Barrow was found guilty of five charges including criminal possession of a weapon, first-degree assault and reckless endangerment, though he was acquitted of attempted murder, and served nine years in prison. Barrow—who transitioned to politics after his prison sentence and serves as the opposition party leader in Belize’s House of Representatives—alleged Combs set him up in a press conference last week, accusing him of calling “witnesses to testify against me,” adding Combs “pretty much sent me to prison.” Meanwhile, Lopez confirmed in 2003 that Combs had been unfaithful to her during their relationship, but has rarely ever spoken of him since. In 2014, Lopez said Combs “gave me so many cues and taught me so many things,” stating there’s “still so much mutual respect, admiration and love there.” During a 2015 appearance on “The Wendy Williams Show” that resurfaced on social media, Williams suggested Lopez could reunite with Combs, to which Lopez’s mother made a “no” gesture from the audience. Pictures of Combs and Lopez at his parties have recently also recirculated on social media. In her 2024 documentary “The Greatest Love Story Never Told,” about her relationship with her now-ex Ben Affleck, Lopez said she had been “manhandled and a couple of other unsavory things” in previous relationships, but did not name Combs or any other specific ex. Lopez has not commented on Combs’ arrest or sexual assault allegations.

Combs’ White Parties: Including Dicaprio, Paris Hilton, Mariah Carey

Combs was famous for his “white parties”—lavish events in which guests had to wear all white—for which Combs likened himself to a modern Jay Gatsby. The annual summer events, held throughout the 2000s, attracted hordes of A-list stars, including Leonardo DiCaprio, whom Combs said in a December 2017 Vogue interview is the “number one” person on the invite list. DiCaprio has been photographed at several of Combs’ parties, including his white parties and his 50th birthday celebration in 2019, though the two have seldom discussed each other publicly. Other celebrities photographed at the white parties include Kim Kardashian, Paris Hilton, Sarah Jessica Parker, Mariah Carey and Combs’ exes Lopez and Kim Porter. Combs’ indictment does not suggest criminal activity happened at his white parties.

What Was Combs’ Relationship To Rapper Meek Mill?

Mill, who has reportedly partied with Combs on multiple occasions (including a 2014 Grammys party hosted by Mill that was broken up by police), has repeatedly denied rumors that he and Combs had a sexual relationship. Mill and Combs collaborated several times between 2012 and 2015: Mill is featured on Combs’ song “I Want The Love,” and Combs is featured on Mill’s “Cold Hearted.” Rumors circulated social media after a lawsuit filed by producer Rodney “Lil Rod” Jones alleged Combs had sex with a Philadelphia rapper who dated Nicki Minaj (Mill is from Philadelphia and dated Minaj between 2014 and 2016). In a string of posts on X in February, days after Jones filed his lawsuit, Mill denied that he is gay without naming Combs. Mill posted on Monday he would pay an investigative team $100,000 to find out how he was being linked to Diddy in the media, suggesting a conspiracy to smear his name. Mill has not directly commented on Combs’ allegations, but posted in April: “I don’t believe no Diddy story” saying, “once they lied about me.”

Combs’ Relationship With Cassie

Singer Cassandra Ventura, known as Cassie, filed the first of what became a string of lawsuits against Combs for sexual assault when she sued him in November 2023. The two dated between 2007 and 2018, beginning when Ventura was 19 years old. In Ventura’s lawsuit, she alleged Combs had subjected her to years of physical and sexual abuse and one instance of rape in 2018, in which she said Combs forced his way into her home. Ventura also alleged Combs coerced her to perform in what he called “freak-offs,” in which he would force her to perform sex acts that he directed with male sex workers, in encounters that could last for days at a time. Prosecutors described the “freak-offs” in their indictment of Combs, stating he would wield his “power and prestige” and use “force, threats of force, and coercion” to force victims to engage in sex acts with sex workers, which he often recorded. Combs denied all allegations in Ventura’s lawsuit. The two reached a settlement for an undisclosed amount the day after Ventura filed her suit. In May, CNN published video footage from the InterContinental Hotel in Los Angeles, recorded in 2016, which depicts Combs shoving Ventura to the ground and kicking her, appearing to match some allegations from Ventura’s lawsuit. Days after the video was published, Combs apologized to Ventura in a video posted to his Instagram account, calling his behavior “inexcusable.” Ventura thanked supporters in an Instagram post, stating domestic violence “broke me down to someone I never thought I’d become.”

What Is Combs’ Relationship To Kid Cudi?

Prosecutors alleged in a memo filed to a New York judge that Combs and co-conspirators kidnapped an unnammed individual in an effort to break into the residence of another unnammed individual, referred to as “Individual-1,” on Dec. 22, 2011, alleging the co-conspirators set fire to Individual-1’s car two weeks later. The allegations mirror an incident detailed by Ventura in her lawsuit, in which she says Combs said he wanted to set fire to rapper Kid Cudi’s car after discovering he and Ventura had a brief relationship during a rough patch while Ventura and Combs were together. Kid Cudi’s spokesperson verified Ventura’s account of the incident, telling the New York Times in November: “This is all true.” Ventura said Combs discovered her relationship with Kid Cudi during a “freak-off” he had “demanded” she participate in by discovering emails the two had shared on Ventura’s phone. Combs became “enraged,” Ventura’s lawsuit states, and he allegedly lunged at her with a corkscrew. Combs told Ventura, she claims in the suit, that he wanted to blow up Kid Cudi’s car and that he hoped the rapper would be home for the incident. Ventura said the car blew up around that time, leaving her “terrified, as she began to fully comprehend what Mr. Combs was both willing and able to do to those he believed had slighted him.”

What Is Combs’ Relationship To Jay-Z?

Combs and Jay-Z are regular collaborators and have had a decades-long friendship. Jay-Z appeared on Combs’ debut album, “No Way Out,” in 1997, on the track “Young G’s, and was a guest performer on Combs’ “No Way Out Tour.” As two of the wealthiest-ever rappers—Forbes estimates Jay-Z’s net worth to be about $2.5 billion, and Combs’ was once estimated to be worth as much as $740 million—Combs and Jay-Z jointly donated $1 million to Hurricane Katrina victims and, in 2015, discussed getting into business together. “Me and Jay – we’ve talked about it. We said we want to pick the best one,” Combs said in 2015. The two have been photographed together on many occasions—in recent years, at the 2020 pre-Grammy Awards Gala, and in 2022 to honor DJ Khaled on the Hollywood Walk of Fame. Social media users have recirculated a years-old video of Combs appearing to slap Jay-Z’s butt while the two were on stage together. Jay-Z has not commented on Combs’ arrest or sexual assault allegations—to the ire of Combs’ longtime rival, 50 Cent, who has repeatedly trolled both Combs and Jay-Z on Instagram. “Anybody seen Jay LOL,” 50 Cent posted on Instagram in March after the FBI raids on Combs’ homes, alongside a picture of Jay-Z’s face on a milk carton with the word, “Missing.” “Jay in hibernation he ain’t coming outside till this shit with puff blow over, no brunch, no lunch, No dinner. LOL,” 50 Cent posted in May.

Conspiracies That Combs Was Involved In The Murders Of Tupac And The Notorious B.i.g.

Combs has long been the subject of allegations that he was involved with the killings of rappers Tupac Shakur and The Notorious B.I.G., though no connection has ever been proven, and Combs has never been charged in connection with their killings. The allegations have resurfaced amid his arrest and have been promoted by rappers 50 Cent and Eminem. Shakur was fatally shot in a 1996 drive-by shooting, and 27 years later, South Side Compton Crips gang member Duane “Keefe D” Davis was arrested and charged for allegedly providing the gun and green-lighting Shakur’s killing. Davis reportedly told authorities Combs had promised him $1 million to kill Shakur, a key West Coast rapper in the East-West Coast rap rivalry. Davis, however, has since disavowed some of his prior interview comments and memoir as “entertainment.” 50 Cent has repeatedly insinuated Combs ordered Shakur’s killing, though Combs denied these allegations as “nonsense.” The Notorious B.I.G., whose real name is Christopher Wallace, was killed in a 1997 drive-by shooting in which Combs was reportedly with the rapper but departed a party in a different vehicle. 50 Cent alleged in a 2006 diss track titled “The Bomb” that Combs knows who killed Wallace, and he has since accused Combs of continuing to profit off of Wallace’s name through posthumous music releases. Eminem accuses Combs of having connections to both killings in his song “Fuel – Shady Edition,” released earlier this month: “Notorious B.I.G.’s death was the domino effects of Tupac’s murder / Like facial tissue, whose card should I clean next? Puff’s? / Til he’s in police handcuffs, guilty, will he step up?”

Further Reading

Sean ‘Diddy’ Combs And Bodyguard Accused Of Filming Drugged Woman’s Assault: A Complete Timeline Of Allegations Against Him (Forbes)