A Brief Look at Diddy’s History of Controversies and Allegations

In November, Casandra “Cassie” Ventura filed a federal lawsuit against Sean “Diddy” Combs in New York federal court. Her lawsuit includes graphic claims of sexual assault, physical abuse, and an allegation that Combs, her ex-boyfriend, would force her to have sex with male sex workers while he watched. Ventura’s claims are among the worst, but not the first controversy that the music mogul and entrepreneur has been alleged to be involved in.

Combs has attempted to rebrand himself as “Brother Love” in recent years, even changing his middle name to Love, but he has a prolonged history of violence, dating back to the Nineties. He’s never been convicted of a serious crime but has repeatedly been accused of having violent encounters with everyone from his exes Ventura and Gina Huynh (who alleged physical abuse in 2019) to executive Steve Stoute and rappers like J. Cole and Drake.

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Combs’ attorney Ben Brafman told the New York Times that “Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail. Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday.” The two reached an “amicable” settlement for an undisclosed amount on Nov. 17.

Here is a timeline of Combs’ controversies over the years:

CCNY Tragedy, 1991

Combs co-promoted a celebrity basketball game and concert at City College of New York where nine people died and 29 people were injured. The gym had a capacity of 2,730 people but as many as 5,000 people showed up to the event, which didn’t have enough security to control the throng. After organizers closed the doors and stopped letting attendees in, people outside broke the gymnasium’s doors and rushed the lobby, causing a stampede. Then-New York City Mayor David Dinkins’ administration published a 67-page report called “A Failure Of Responsibility” that cited Combs for hiring inadequate, inexperienced security. Combs settled a slew of lawsuits from family members of attendees who died at the gymnasium, finalizing the last suit in 2000.

Jake Robles Shooting, 1995

Combs and Death Row Records co-founder Marion “Suge” Knight were once friends, but the animosity that fueled the violent rivalry between Death Row and Bad Boy started once Knight’s friend (and security guard) Jake Robles was killed outside an Atlanta nightclub after an argument with the Bad Boy camp. The men were celebrating musician Jermaine Dupri’s birthday at Platinum City Club when, as then-Fulton County Sheriff Deputy Chris Howard told police, an argument began between members of the Bad Boy and Death Row Records entourage. Howard said that he escorted Combs and his guests outside to leave the club, and thought the coast was clear to allow Knight and his entourage to leave. But, as Howard told the Los Angeles Times, “[Knight’s] partner was just about ready to get into the limo when all of a sudden Puffy’s guys came from around the corner . . . and one of them had a gun.” Howard said he chased the man, who handed the gun to another person, who shot Robles “two or three times.” According to the Times, the person then jumped into a “car carrying Combs’ associates.” Robles died weeks later at an Atlanta hospital. Combs has denied involvement in the shooting, which Knight reportedly held him responsible for.

Attacking Steve Stoute, 1998

In 1998, Combs and two other men attacked Steve Stoute after the music executive, then Nas’ manager, erroneously sent MTV a version of Combs and Nas’ “Hate Me Now” music video which contained scenes depicting Combs as Jesus Christ being crucified. Combs wanted the crucifixion scene deleted from the video, and was enraged that it played on-air. Stoute says that Combs and two men barged into his New York City office and attacked him with a champagne bottle. He was charged with second-degree assault and criminal mischief. Stoute claims that his arm and jaw was broken in the attack, but Combs denied any bones were broken to MTV, also telling the network, “I basically went to his office, and what happened in his office, I really can’t speak about but I can say this: the way I handled myself in his office was completely wrong and I’ve since apologized to Steve about that and I felt like, you know, I just disappointed myself.” Combs was sentenced to a one-day anger management class.

Club New York Shooting, 1999

In late December 1999, Combs and his Bad Boy signee Jamal “Shyne” Barrow were partying at Club New York when Diddy knocked a drink out of Matthew “Scar” Allen’s hands. Allen got into an argument with Combs and someone threw money in Combs’ face. Allen also threatened to kill Shyne. Prosecutors allege that amid the fray, all three men drew guns, and Shyne shot three times in the crowded club. Three people were shot. Combs, who was arrested with two nine-millimeter guns in his car, was charged with four weapons charges and for bribing his driver to claim that the guns were his own. A witness at the trial said she saw both Shyne and Combs shoot their weapons, but Combs was acquitted on all charges, while Shyne was found guilty of five of his eight charges and was sentenced to 10 years in prison.

Scuffle with J. Cole, 2013

In 2013, Combs was allegedly involved in an altercation with J. Cole at a 2013 MTV VMAs afterparty. Multiple sources alleged to Complex that a “visibly intoxicated” Combs accosted Kendrick Lamar about his fiery verse on Big Sean’s “Control,” where he bragged he was “King of New York.” Combs allegedly tried to pour a drink on Kendrick before Cole intervened and they got into a fight. The New York Post, however, reported that the scuffle occurred after “J. Cole was saying inappropriate things to Sean Combs and his girlfriend, Cassie.” A witness told them that “Some pushing and shoving happened. No punches were thrown, but it was a visible disturbance.” Both men immediately denied a fight took place, though Cole later rapped, “My last scrap was with Puff Daddy, who would’ve thought it?” on 2021’s “Let Go My Hand.”

Allegedly Punches Drake, 2014

In December 2014, Combs allegedly punched Drake over the rights to the beat that became Drake’s “0 to 100.” The Miami New-Times reported that the two got into an argument outside of LIV nightclub during DJ Khaled’s event for Basel Weekend. Words were allegedly exchanged, and reportedly, “then blows,” with Combs telling Drake, “You will not disrespect me.” Combs has denied punching Drake, telling the radio show The Breakfast Club “I didn’t do nothing to Drake, Drake is my friend.”

Fights UCLA Coach, 2015

In June of 2015, Combs got into a scuffle with then-UCLA assistant football coach Sal Alosi. TMZ reported that Combs was present during a UCLA practice where Alosi chided his son (and then-UCLA player) Justin Combs, telling him, “I don’t care if your dad’s here. This is UCLA. I’m going to treat you just like I treat everyone else.” After the practice, Combs and his son reportedly went to Alosi’s office, where an argument ensued and Combs “grabbed” Alosi. According to one account, Combs was forcibly removed from Alosi’s office and then swung a kettlebell at an intern. A rep for Combs Enterprises noted, “The various accounts of the event and charges that are being reported are wholly inaccurate. What we can say now is that any actions taken by Mr. Combs were solely defensive in nature to protect himself and his son.” The LA district attorney decided not to file assault charges against Combs.

Gina Huynh Alleges Abuse, 2019

In 2019 Combs’ ex Gina Huynh told blogger Tasha K that Combs physically abused her throughout their five-year relationship. She claimed he once stomped her on the stomach, causing her to lose her breath, and also punched her in the back of the head. She told Tasha K that, “He was mentally, emotionally and physically abusing me. He would always compare me to Cassie and tell me that I’m the bad one, she’s a good one.” She also said that “everyone” in Combs’ circle “allowed” the abuse to occur.

Cassie Files Civil Suit Against Combs, 2023

On Nov. 16th, Combs’ ex Casandra “Cassie” Ventura filed a federal lawsuit against Combs in New York alleging years of assault. Her lawsuit contains graphic allegations of Combs raping her in 2018, physically abusing her, intimidating her, and making her have sex with male escorts while he watched. The lawsuit also alleges that Combs blew up Cudi’s car to deter him from seeing Cassie romantically — through a rep, Cudi said the accusations are true. Combs has denied the allegations and alleged that Cassie tried to blackmail him for $30 million before filing the lawsuit. The two settled for an undisclosed amount on Nov. 17, with his attorney Ben Brafman stating that “Mr. Combs‘ decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims.”

Jane Doe Sues for 1991 Rape and Revenge Porn

Five days after Combs and Cassie reached a settlement, a former Syracuse University college student sued Combs for allegedly drugging, raping, and recording her, afterwards allegedly showing others the assault he filmed. The suit, which was obtained by Rolling Stone, claims that after taking the woman to dinner in Harlem in 1991, he drove her to a recording studio where he raped her while, she alleged, she was in “a physical state where she could not independently stand or walk.”  “Days later,” the suit reads, “a male friend revealed to her that he had viewed the ‘sex tape’ along with other men.” A representative for Combs denied the allegations, calling them a “money grab” in a statement to TMZ.

Diddy Faces Third Sexual Assault Suit in One Week

Just before New York State’s Adult Survivors Act’s Nov. 23 deadline, a second anonymous accuser filed a lawsuit against Combs alleging sexual assault. (The law, passed in May 2022, opened a window for people over the age of 18 at the time of alleged sexual offenses to file lawsuits against alleged perpetrators, overriding statutes of limitations that typically cut off legal options — advocates have asked for an extension of the act’s window or the undoing of statutes of limitations altogether.) In this suit, a woman claims Diddy and singer-songwriter Aaron Hall took turns raping her and a friend in 1990 or 1991.  She also alleges that days later, Diddy again attacked her at a home where she was staying. “He was irate and began assaulting and choking Jane Doe to the point that she passed out,” the complaint alleges. “Combs was searching for Jane Doe’s friend because he was worried that she would tell the girl he was with at the time what he and Hall had done to them.” (Reps for Hall and Combs did not immediately return requests for comment on Friday.)

Third Jane Doe Files Lawsuit

On Dec. 6, Jane Doe plaintiff filed a lawsuit against Combs, Daddy’s House Recordings, and Bad Boy Entertainment, alleging that in 2003, when she was 17, she was gang raped by Combs, former Bad Boy President Harve Pierre, and another unidentified man at Combs’ Daddy’s House studio in New York City.  The lawsuit claims that the teen met Pierre in Detroit and was told Combs wanted to meet her. She was flown in on a private jet to Teterboro, NJ, before arriving in Manhattan. The three men allegedly plied the high schooler with “copious amounts of drugs and alcohol.” The graphic lawsuit said that things began to visually “blur” for her when she was assaulted by the three men in the bathroom as she drifted in and out of consciousness, had difficulty breathing, and pled for them to stop. Allegedly, Combs assaulted her first and then watched the other two men while sitting in a chair outside the bathroom. The lawsuit also claims that after Pierre finished assaulting her, she was left in the bathroom alone, where she curled into a fetal position with vaginal pain. Once she “regained her bearings,” she was taken back to an airport and flown to Detroit.

On the same day of the lawsuit, Combs made a statement claiming, “Enough is enough. For the last couple of weeks, I have sat silently and watched people try to assassinate my character, destroy my reputation and my legacy. Sickening allegations have been made against me by individuals looking for a quick payday. Let me be absolutely clear: I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth.”

Tiffany Red Writes an Open Letter Corroborating Cassie’s Allegations

On Dec. 7, Tiffany Red — a Grammy-winning singer-songwriter who has written songs for Zendaya, Joe Jonas, Jason Derulo, and Tamar Braxton, among others — published an open letter to Combs via Rolling Stone alleging that Cassie’s claims were true.

“I’m one of the friends mentioned in her lawsuit, specifically from the night of her 29th birthday, as detailed in the section labeled ‘Mr. Combs Forces Ms. Ventura Into Sex Trafficking,’” she wrote. Red detailed her first encounters with Combs and her working relationship with Cassie as a songwriter and detailed the party where she claimed Combs separated Cassie from her friends. When Cassie and Combs returned later in the evening, Red wrote that they appeared intoxicated and that Combs was verbally abusive to both women, calling Red an “emotional singing bitch,” before departing.

“She later told me you made her have a ‘Freak Off’ — which Cassie described in her lawsuit as an ‘arrangement’ where you would make her perform sexual acts with male sex workers — that night,” Red wrote. “The reason you called me ’emotional singing bitch’ was because you were listening to new songs we wrote during the ‘Freak Off’ that had begun after you came to get her earlier that night. I am disturbed to my core by this.” Red wrote that she saw occasions later where Combs appeared verbally abusive to Cassie and said that she, too, had experienced trauma as a result of Combs’ alleged actions.

Hulu Scraps Family Reality Show

Hulu announced on Dec. 3 that the company would no longer make a reality show centered around Combs and his family. The news arrived as multiple companies severed business ties with the hip-hop mogul following the accusations of sexual abuse and physical violence.

The project — which was under the working title Diddy+7 — was being produced by James Corden’s production company Fulwell 73 for Hulu. The dropped reality show was said to take after Keeping Up with the Karadashians, which is also produced by Fulwell 73 for the streaming service. “It’s going to profile the entire family,” a source told Page Six in March. “They all have businesses — even the kids — and it will feature everyone.”

Combs has stepped aside from his chairman role at Revolt, liquor company Diageo asked a judge to prevent him from appearing on new advertising for DeLéon, and a total of 23 brands have now severed ties with Empower Global, his online marketplace for Black-owned businesses, which launched in July.

Combs Settles with Diageo

Combs reached a settlement on Tuesday, Jan. 16, with the liquor giant Diageo, with whom he shared joint ownership of the tequila brand DeLeón. Combs first sued Diageo in May, accusing the company of labeling Cîroc and DéLeon as “Black brands” restricted to “urban” markets. He sued again in October, asking for an injunction that would force Diageo to comply with how he viewed his DeLéon contract. Weeks later, his ex-girlfriend Cassie filed a lawsuit alleging Combs raped her, beat her, and forced her to have sex with other men while he watched. Two more accusers stepped forward with lawsuits on Thanksgiving Day. Though Combs has denied the accusations, Diageo had been pushing a judge in New York to deny Diddy’s request for control over an incoming $15 million marketing budget for DeLéon Tequila.

“Sean Combs and Diageo have now agreed to resolve all disputes between them. Mr. Combs has withdrawn all of his allegations about Diageo and will voluntarily dismiss his lawsuits against Diageo with prejudice,” a joint statement from both parties obtained by Rolling Stone reads, meaning the mogul can’t refile the lawsuit in the future. “Diageo and Mr. Combs have no ongoing business relationship, either with respect to Cîroc vodka or DeLeón tequila, which Diageo now solely owns.”

Sean Combs Sued for Sexual Assault by ‘Love Album’ Producer

On Feb 27, Combs was sued by producer Rodney “Lil Rod” Jones for $30 million for sexual assault. The producer worked with Combs on his The Love Album and says that he was subjected to sexual misconduct for the duration of the production process. He also claimed that Combs owes him $50,000 for his work on the Grammy-nominated album.

Jones’ 70-page lawsuit, filed in the Southern District of New York, alleges that while working on the album and living with Combs in New York, California and Florida, Combs repeatedly groped his “anus and crotch without consent,” and attempted to “groom him into accepting a homosexual relationship” by showing him explicit videos, claiming it was “a normal practice in the music industry.” He claims that Combs would walk around the house naked and force him to watch him shower, and alleges that when he told Combs’ chief of staff Kristina Khorram about Combs’ actions, he was told, “you know, Sean will be Sean.”

The lawsuit implicates others, including Combs’ son Justin, who’s accused of procuring underage girls for parties where Combs drugged visitors and secretly recorded their sex acts. Jones claims he was also drugged at a party and woke up “naked, dizzy, and confused” in a bed with “two sex workers and Mr. Combs.” He claims that Combs frequently displayed guns as an intimidation tactic and threatened to “eat Mr. Jones’ face.”

After the lawsuit became public, adult film actor D’Angelo “Knockout” Marquis claimed that photos that the lawsuit purported as producer Stevie J engaged in a sexual act were actually stills from one of his videos.

Diddy’s lawyer Shawn Holley called Jones a “liar” who is “shamelessly looking for an undeserved payday.” He added, “His reckless name-dropping about events that are pure fiction and simply did not happen is nothing more than a transparent attempt to garner headlines.” Justin Combs’ lawyer also responded to the lawsuit, noting, “Justin Combs categorically denies these absurd allegations. They are all lies! This is a a clear example of a desperate person taking desperate measures in hopes of a pay day. There will be legal consequences for ALL defamatory statements made about the Combs family.”

Authorities Raid Sean Combs’ Homes in Los Angeles and Miami

On March 25, law enforcement officials carried out simultaneous raids of Combs’ homes in Los Angeles and Miami. The investigation was led by the Department of Homeland Security, and news footage from the Miami raid appeared to show two men in handcuffs sitting outside the house.

“Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners,” a Homeland Security Investigations spokesperson said in a statement. “We will provide further information as it becomes available.”

Amidst the raids, a source told Rolling Stone that four Jane Does and one John Doe had already sat for interviews with Southern District of New York investigators for an investigation related to an alleged sex trafficking and RICO case. More interviews had been scheduled the source added.

Video of Combs Kicking an Dragging Cassie at a Hotel Surfaces

On May 17, a newly-surfaced March 2016 surveillance video captured Combs chasing, kicking, and dragging his then-girlfriend Cassie down a hotel hallway.

The video footage was dated March 5, 2016, according to CNN, and seems to correspond to an alleged incident from a sex-trafficking lawsuit filed by Cassie (real name Casandra Ventura) last November. Ventura noted in her lawsuit that video of the alleged attack existed, but she believed Combs had paid the hotel $50,000 for the security footage.

“The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs,” Ventura’s attorney Douglas Widgor said in a statement. “Words cannot express the courage and fortitude that Ms. Ventura has shown in coming forward to bring this to light.”

The security footage, which has no sound, showed a barefoot Ventura quickly walking out from a hotel room with personal items in her hand while wearing an oversized hoodie. In her lawsuit, Ventura claimed she was at the hotel because Combs had her participate in a “freak-off” — where she was forced to have sex with male sex workers while Combs watched.

During the freak-off, Combs “punched Ms. Ventura in the face, giving her a black eye,” the lawsuit claims, and Ventura waited until Combs was asleep to sneak out of the hotel.

UPDATE: This article was updated most recently on May 17, 2024 at 7:30 p.m. ET to include the surveillance footage of Diddy kicking an dragging Cassie in a hotel hallway in 2016.

It was previously updated on March 25, 2024 after authorities raided Combs’ homes in Los Angeles and Miami, and on Feb. 28 at 2:30 p.m. ET to include Combs being sued by producer Rodney “Lil Rod” Jones for $30 million for sexual assault. It was also updated on Jan. 16 at 4:41 p.m. ET to include that Combs and Diageo reached a settlement with Diageo, and on Dec. 13, 2023, 12:38 a.m. ET: This post was updated to reflect news that Hulu would no longer be making Sean Comb’s family reality show.

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