Here's A Breakdown Of Diddy's Legal Troubles

Billionaire media mogul Sean Diddy Combs pleaded not guilty to federal racketeering and sex trafficking charges on Tuesday. Correspondingly, he has vehemently denied accusations of violence and sexual abuse that have been lobbed at him over the last several months, even as federal agents raided properties linked to him and a damning video surfaced of him attacking a woman.

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 May 17, when CNN published previously unseen footage from 2016 that 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 rapper, 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 in Los Angeles and the Miami area .

And, on Monday, the media mogul was arrested when a federal indictment was unsealed in New York City. 

His arrest, 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. 

Heres 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 Diddys 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 Im in the middle of a meeting, he said, and the next minute Im 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 Teddys 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 .

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

In June 2015, when Diddys son Justin Combs was a defensive back for UCLAs 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 attorneys office opted not to press charges against Diddy, according to Variety . The DAs office referred the case to the city attorneys office on misdemeanor charges but said its unlikely that charges will be filed against him, according to NBC News .

May 2017: Diddys 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 him from 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 Mans 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 Rods 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 Diddys or his sons involvement in the shooting.

Neither Sean nor Justin were in the vicinity or even aware of what had occurred until afterwards. So I dont 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 Cassies suit, HuffPost previously reported . Red was briefly alluded to in the lawsuit.

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.

Cassies 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.

Diddys legal team pushed back against Dickerson-Neals claims in court, arguing that laws regarding the incident did not exist at the time. Theyve asked that the revenge porn and human trafficking parts of the case be dismissed with prejudice, meaning it cant be refiled.

November 2023: A Jane Doe Accuses Diddy Of Raping Her, Alleges Aaron Hall Also Raped Her

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

While at Halls 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 Daddys House Recording Studio in New York City, which Diddy owned, and was given copious amounts of drugs and alcohol.

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

Mr. Combs and his companies categorically deny Plaintiffs 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.

March 2024: Homeland Security Conducts Bicoastal Raids

The Department of Homeland Securitys 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 Mens 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 hed 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 Yorks 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 hed 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 shes been working hard for were in the palm of his hands.

September 2024: Diddy Hit With $100 Million Default Judgment

Derrick Lee Cardello-Smith, who is incarcerated in Michigan, sued Diddy in June for alleged sexual assault in 1997. Cardello-Smith said Diddy drugged and sexually assaulted him when he was working a party for Diddy in Detroit. 

Cardello-Smith also alleged that Diddy visited him in jail in August to offer him $2.3 million to close the suit. 

However, when the music artist did not show up for a hearing in September, the judge awarded Cardello-Smith a default judgment of $100 million. Diddy is expected to pay Cardello-Smith $10 million per month starting Oct. 1. 

Mr. Combs has never heard of him let alone been served with any lawsuit, Diddys attorney Marc Agnifilo told The Los Angeles Times . Mr. Combs looks forward to having this judgment swiftly dismissed.

September 2024: Dawn Richard Files Suit Against Diddy Claiming Assault, Threats To Her Life

Dawn Richard, a former member of Danity Kane and Diddy Dirty Money, filed a 58-page complaint against Diddy in which she accused him of sexual assault, threats to her life, withholding pay and more. 

Richard claimed in the complaint that Diddy forced her to have meetings while he or both of them were undressed, often required Richard and her band members to record and rehearse for stretches of 36 to 48 hours without breaks, and once kept her locked in a car for more than two hours.  

Diddy flagrantly exploited Ms. Richards musical talent as a singer and writer while withholding her rightful earnings, stealing her copyrighted works, and subjecting her to years of inhumane working conditions which included groping, assault, and false imprisonment, among other violations.

Richard also claimed to have witnessed Diddy abuse his ex-girlfriend Cassie and recalled an instance where his other ex-girlfriend, Kim Porter, left his studio injured and in tears.

Moreover, she described an instance in which Diddy arranged for young women and underage girls to party, drink and do drugs with him and other celebrities around the 2009 Soul Train Awards. 

Many of them appeared lethargic or passed out while Mr. Combs and his guests performed sexual acts on them, the complaint said. Mr. Combs repeatedly said things like this is a buffet, enjoy yourselves; this is what we do, this is how we party.

September 2024: Federal Agents Arrest Diddy On Sex Trafficking And Racketeering Charges

Federal agents arrested Diddy on Sept. 16 on three federal counts of sex trafficking and racketeering, which he pleaded not guilty to the following day. 

Moreover, a judge denied bond for the music mogul due to concerns he may attempt to flee or intimidate witnesses. Diddy is being held alone in the Special Housing Unit of the Metropolitan Detention Center in Brooklyn, New York, according to CNN . 

Prosecutors accused Diddy of abuse that was at times, verbal, emotional, physical and sexual.

Members and associates of the Combs Enterprise engaged in, and attempted to engage in, among other activities, sex trafficking, forced labor, interstate transportation for purposes of prostitution, coercion and enticement to engage in prostitution, narcotics offenses, kidnapping, arson, bribery, and obstruction of justice, they said in court documents.

Diddys attorney Marc Agnifilo addressed his clients arrest on Monday.  

We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorneys Office, Agnifilo told TMZ  in a statement . Sean Diddy Combs is a music icon, self-made entrepreneur, loving family man, and proven philanthropist who has spent the last 30 years building an empire, adoring his children, and working to uplift the Black community.

On Tuesday, Agnifilo said that Diddys spirits are good and that hes confident.

Lydia OConnor contributed reporting.

Need help? Visit RAINNs National Sexual Assault Online Hotline  or the National Sexual Violence Resource Centers website .