Here's A Breakdown Of Diddy's Legal Troubles

Billionaire media mogul Sean “Diddy” Combs has vehemently denied accusations of violence and sexual abuse that have been lobbed at him over the last six months, even as federal agents raided properties linked to him.

“Enough is enough,” the rapper said in a statement in December.

“Sickening allegations have been made against me by individuals looking for a quick payday,” he said. “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.”

But the accusations got harder to deny on Friday, May 17, when CNN published previously unseen footage from 2016, which appears to show Diddy violently assaulting his then-girlfriend, singer-songwriter Cassie Ventura. The disturbing footage corroborated claims she made in a bombshell lawsuit filed against him in November.

The 54-year-old, who has also gone by Puffy or Puff Daddy, settled the lawsuit with Cassie a day after she filed it, but the floodgates were opened. Over the next several months, more accusers filed lawsuits claiming he was violent or sexually abusive. In March, Homeland Security Investigations agents conducted the raids.

The raids and lawsuits, which come amid a broader reckoning in the music industry, add to a long list of legal troubles Diddy has faced over the years.

Here’s a timeline of allegations made against Diddy throughout his career.

1996: Diddy Found Guilty Of Threatening Photographer With Gun

Diddy was found guilty of misdemeanor criminal mischief in 1996 for using a gun to threaten a New York Post photographer, NPR reported

The incident occurred in 1995 as Gary Miller was taking photos of Diddy’s company cars, according to The New York Times

Diddy and about 10 of his employees surrounded Miller before they “menaced him with a pistol and seized his film,” according to the Times, which also reported that Diddy denied the accusation.

April 1999: Record Executive Claims Diddy Beat Him Up During Meeting

Record label executive Steve Stoute accused Diddy and others of assaulting him over a dispute involving a music video with rapper Nas in April 1999, according to The Washington Post

“He punched me in the face, and then he grabbed the phone and bashed me in the head with it,” Stoute said in a May 1999 interview with the Los Angeles Times

“One minute I’m in the middle of a meeting,” he said, “and the next minute I’m down on the floor and Puffy and his guys are kicking and pounding me. One of them picks up a chair and throws it at me. Then Puffy throws my desk over and they just walk out like nothing happened.”

Diddy faced up to seven years behind bars, but Stout reportedly asked the Manhattan district attorney to drop the charges following an apology from Diddy, according to The New York Times. Though the assault charge was dropped, Diddy reportedly pleaded guilty to harassment and was ordered to attend one day of anger management classes, according to NPR.

December 1999: Woman Claims Diddy Shot Her In The Face At NYC Nightclub

Amid a Dec. 27, 1999, shooting at a New York City nightclub, a bullet hit Natania Reuben in her face. Reuben claimed she saw Diddy and a rapper named Shyne holding a gun at the time of the shooting. Despite a jury acquitting Diddy in 2001, Reuben has insisted Diddy is the person who shot her.

“I would absolutely, unequivocally like the case reopened. It needs to be reopened,” Reuben told NewsNation in March. “And the saddest part to me is, had people taken what I said more seriously and listened more intently, 24 years worth of people probably would not have had to suffer.”

Shyne served time for the shooting after being convicted of multiple charges, including first-degree assault, reckless endangerment and criminal possession of a weapon. Shyne argued he had fired his gun into the air during the conflict, not at Reuben. Reuben has maintained that Shyne is not responsible for her facial injury.

March 2001: TV Host Says Diddy And His Entourage Attacked Him After An Interview

Roger Mills, host of a celebrity TV show, sued Diddy in March 2001, alleging the media mogul and his entourage attacked him and broke his camera following an interview in 1999, Billboard reported.

When Mills asked Diddy about rumors that he was involved in the 1997 killing of rapper Notorious B.I.G., the interview immediately concluded, according to Billboard.

In February 2004, a jury found Diddy not guilty, according to Today.

March 2007: Partygoer Says Diddy Punched Him And Girlfriend At Los Angeles Nightclub

In a March 2007 lawsuit, a man named Gerard Rechnitzer accused Diddy of punching him and pushing his girlfriend at a February 2007 party at Teddy’s at the Hollywood Roosevelt Hotel in Los Angeles, according to CBS News. The lawsuit was settled in March 2008, and the terms were not disclosed, according to TMZ.

Sean "Diddy" Combs watches a football game between UCLA and Washington State on Nov. 14, 2015, in Pasadena, California. His son played for UCLA. Mark J. Terrill/Associated Press

June 2015: Diddy Avoids Charge After Claim That He Hit UCLA Coach With Kettlebell

In June 2015, when Diddy’s son Justin Combs was a defensive back for UCLA’s football team, Diddy was arrested for throwing a kettlebell at Sal Alosi, the strength and conditioning coach for UCLA. He was initially charged with assault with a deadly weapon. However, the Los Angeles County district attorney’s office opted not to press charges against Diddy, according to Variety. The DA’s office referred the case to the city attorney’s office on misdemeanor charges but said “it’s unlikely that charges will be filed” against him, according to NBC News.

May 2017: Diddy’s Former Chef Says She Was Forced To Work Long Hours, Serve Post-Sex Meals

In May 2017, Cindy Rueda, a former personal chef for Diddy, accused him of sexual harassment while she worked for himfrom April 2015 to May 2016, according to KNBC-TV in Los Angeles.

Rueda said she was regularly forced to provide food for Diddy and his guests “immediately following sexual activity,” had unwillingly seen him and others naked or engaged in sexual activity, and had been asked sex-based questions. She claimed she was forced to work long hours without overtime pay, sometimes from 9 a.m. to well past 1 a.m. 

The two settled the lawsuit in February 2019, and the terms were not disclosed, according to KNBC.

September 2022: Producer Claims Diddy Or His Son Is Behind A Man’s Disappearance

Music producer Rodney “Lil Rod” Jones asserted in court documents that Diddy or his son, Justin, shot a 30-year-old friend of Justin, named G, twice inside a bathroom at Chalice Recording Studio in Los Angeles in September 2022, HuffPost reported. Lil Rod also said G disappeared after the shooting.

Lil Rod’s account of the shooting contrasts with a KCAL-TV report citing the police around the time of the shooting. The report, which does not name the individuals involved, said the victim was shot outside.

Attorney Shawn Holley denied Diddy’s or his son’s involvement in the shooting.

“Neither Sean nor Justin were in the vicinity or even aware of what had occurred until afterwards. So I don’t think either of them were interviewed [by police],” Holley said in a March statement to NBC News.

Lil Rod later accused Diddy of orchestrating a cover-up of the shooting.

November 2023: Cassie Files Damning Sexual Assault And Abuse Lawsuit

“Me & U” singer Cassie (Casandra Elizabeth Ventura) filed a 35-page complaint against the media mogul in New York on Nov. 16. The two dated from 2007 to 2018, starting their relationship when she was 19 and he was 37.

Cassie said Diddy raped her, forced her to engage in sex acts with male sex workers and regularly beat her during their relationship. She accused him of blowing up the car of rapper and producer Kid Cudi, who reportedly had a romantic interest in Cassie at one point. Cassie also said Diddy pushed her to abuse substances and that he dangled one of her friends over a balcony.

Grammy-winning singer-songwriter Tiffany Red, a friend of Cassie, corroborated the claims in Cassie’s suit, HuffPost previously reported. Red was briefly alluded to in the lawsuit.

Cassie and Sean
Cassie and Sean "Diddy" Combs leave the Costume Institute Gala at the Metropolitan Museum of Art on May 1, 2017. James Devaney/GC Images via Getty Images

November 2023: Cassie And Diddy Quietly Settle Lawsuit

Cassie and Diddy settled her lawsuit against him the day after it was filed.

“I have decided to resolve this matter amicably on terms that I have some level of control. I want to thank my family, fans and lawyers for their unwavering support,” Cassie said in a statement.

Her attorney Douglas Wigdor added: “I am very proud of Ms. Ventura for having the strength to go public with her lawsuit. She ought to be commended for doing so.”

Diddy also released a statement announcing the settlement of the case:

“I wish Cassie and her family all the best. Love,” he said.

Cassie’s lawsuit seemingly kicked off a few other suits against the hip-hop star.

November 2023: Joi Dickerson-Neal Accuses Diddy Of Rape And Showing Video Of It To Others

On Thanksgiving Day in 2023, Joi Dickerson-Neal accused Diddy of drugging her and raping her in 1991. At the time, she was a student at Syracuse University and he was a talent director at Uptown Records, USA Today reported. She said Diddy had shown recorded footage of the rape to others, including Davante Swing, a member of the R&B group Jodeci. Swing told Dickerson-Neal that “everyone” had seen the revenge porn, according to USA Today.

Diddy’s legal team pushed back against Dickerson-Neal’s claims in court, arguing that laws regarding the incident did not exist at the time. They’ve asked that the revenge porn and human trafficking parts of the case be dismissed with prejudice, meaning it can’t be refiled.

November 2023: A Jane Doe Accuses Diddy Of Raping Her Before Singer Also Rapes Her

In another lawsuit filed on Thanksgiving, an unnamed woman accused Diddy and singer Aaron Hall of raping her at Hall’s home, either in 1990 or 1991.

“While at Hall’s apartment, Jane Doe was offered more drinks and was coerced into having sex with Combs,” the filing says, according to Rolling Stone. “After Combs finished doing his business, Jane Doe laid in bed, shocked and traumatized. As she was in the process of getting dressed, Hall barged into the room, pinned her down and forced Jane Doe to have sex with him.”

Doe also said Diddy came to her home within the following days to choke and assault her, according to Rolling Stone.

December 2023: Another Jane Doe Says Diddy And Others Sex Trafficked Her At Age 17

A woman referred to as Jane Doe filed a lawsuit claiming that Diddy, former Bad Boy Records President Harve Pierre and an unnamed man “gang raped” and “sex trafficked” her in 2003 when she was a 17-year-old high schooler, HuffPost reported. In 2003, Diddy was 34.

She claimed she met Pierre at a lounge in Detroit, was flown out to Daddy’s House Recording Studio in New York City, which Diddy owned, and was given “copious amounts of drugs and alcohol.”

On May 10, 2024, Diddy’s legal team asked a federal judge to dismiss the case with prejudice.

“Mr. Combs and his companies categorically deny Plaintiff’s decades-old tale against them, which has caused incalculable damage to their reputations and business standing before any evidence has been presented,” the filing said, according to The Associated Press. “Plaintiff cannot allege what day or time of year the alleged incident occurred, but miraculously remembers other salacious details, despite her alleged incapacitated condition.”

February 2024: Producer Says Diddy Sexually Harassed Him And Is Running A Racket

Lil Rod filed a lawsuit against Diddy and several associated companies in February, accusing Diddy of sexual harassment, grooming, running a racketeering enterprise and more. 

“Throughout his time with Mr. Combs, Mr. Jones witnessed, experienced, and endured many things that went far beyond his role as a Producer on the Love album,” the 73-page complaint says. “Mr. Combs required Mr. Jones to record him constantly. … As a result, Mr. Jones has secured hundreds of hours of footage and audio records of Mr. Combs, his staff, and his guests engaging in serious illegal activity.”

The Los Angeles home of Sean
The Los Angeles home of Sean "Diddy" Combs is seen in an aerial view during a raid by federal law enforcement agents on March 25. MEGA/GC Images via Getty Images

March 2024: Homeland Security Conducts Bicoastal Raids

The Department of Homeland Security’s investigation division raided several homes linked to Diddy in Los Angeles and Miami on March 25, HuffPost reported.

According to CBS News reporter Nicole Sganga, who cited unnamed officials, the raids may be linked to a sex trafficking investigation. Details about the raid have not yet been released.

 An attorney for Diddy, Aaron Dyer, condemned the raid the following day.

“[T]here was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences,” Dyer told E! News. “There is no excuse for the excessive show of force and hostility exhibited by authorities.”

“This unprecedented ambush — paired with an advanced, coordinated media presence — leads to a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits,” added Dyer.

May 2024: Woman Says Diddy Sexually Assaulted Her And Ruined Her Modeling Career

In a May 21 lawsuit, a woman named Crystal McKinney claimed that Diddy forced her to perform oral sex in 2003 as she pursued a modeling career. She alleged that the assault occurred when Diddy invited her to his studio following a Men’s Fashion Week event in New York City.

In the suit, McKinney said that she passed out after the incident, woke up in a taxi and then realized that she had been assaulted.

According to McKinney, Diddy initially said that he’d help her career, but he instead “blackballed” her and “utilized his significant influence to impede” her professional growth.

May 2024: Cassie Addresses Video Of Diddy Attack

On May 19, following CNN’s release of the 2016 footage that appeared to show Diddy throwing, kicking and dragging Cassie at a Los Angeles hotel, he posted a video saying that he was “disgusted” by his actions.

On May 23, Cassie shared a statement addressing the issue of domestic violence and thanking those who have supported her.

“The outpouring of love has created a place for my younger self to settle and feel safe now, but this is only the beginning,” she wrote. “Domestic Violence is THE issue. It broke me down to someone I never thought I would become. With a lot of hard work, I am better today, but I will always be recovering from my past.”

May 2024: Woman Said Diddy Sexually Assaulted Her Four Times After Promising To Help Her Career

In a lawsuit filed on May 23, a former student at New York’s Fashion Institute of Technology named April Lampros said that Diddy sexually assaulted her at least four times between the mid-’90s and early 2000s, CNN reported.

Lampros also accused Diddy of battery, assault and secretly recording a video of them having sex that he shared with others, among other things.

The lawsuit said that Diddy told her that he’d mentor her and help her with her career in fashion, but “what Mr. Combs displayed as kind gestures quickly manifested into an aggressive, coercive, and abusive relationship based on sex.”

“She felt that if she disobeyed him, he would take away her dreams of pursuing a career in his world. Mr. Combs would also threaten to blacklist her in the industry if she tried to mess with him in any way,” the suit said. “Ms. Lampros’ dreams and everything she’s been working hard for were in the palm of his hands.”

Lydia O’Connor contributed reporting.

Need help? Visit RAINN’s National Sexual Assault Online Hotline or the National Sexual Violence Resource Center’s website.