Sean 'Diddy' Combs Apologizes After Cassie Assault Footage: A Timeline of His Lawsuits

Sean 'Diddy' Combs has been faced with several lawsuits.

The first bombshell dropped on the afternoon of Nov. 16, 2023 when singer Cassie Ventura sued Sean "Diddy" Combs and accused him of rape, among other allegations of wrongdoings.

The 35-page lawsuit, riddled with graphic and disturbing claims, soon set off a litany of allegations brought forward by three other women who also accused the embattled rap mogul of sexual misconduct. Ventura and Diddy reached a settlement a day after her filing. 

"Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing," said Diddy's attorney, Ben Brafman, in a statement to ET. "Mr. Combs' decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims. He is happy they got to a mutual settlement and wishes Ms. Ventura the best."

Combs' legal troubles continued on March 25, when federal agents raided his homes in Los Angeles and Miami in what Homeland Security Investigations said was part of an ongoing investigation. It's been reported that the probe, being helmed by the Southern District of New York, is tied to sex trafficking allegations.

In a statement to ET, Diddy's attorney, Aaron Dyer, blasted the feds for its "gross overuse of military-level force" amid the execution of search warrants, adding, "Mr. Combs is innocent and will continue to fight every single day to clear his name."

In the months since the raid, Rodney "Lil Rod" Jones filed his own lawsuit against Combs, Diddy's son faced his own allegations, and in May 2024, Ventura's claims resurfaced due to recently unearthed security footage.

To better understand how we got here, ET takes a look back at Cassie's lawsuit against Diddy and the ensuing fallout.

Cassie Sues Diddy

Cassie claimed in court documents that Diddy began a pattern of control and abuse within a few years of signing her to his Bad Boy records label. She claims Diddy "lured" her "into an "ostentatious, fast-paced, and drug-fueled lifestyle, and into a romantic relationship with him -- her boss, one of the most powerful men in the entertainment industry, and a vicious, cruel, and controlling man nearly two decades her senior."

She claimed Diddy's control over her included him introducing her "to a lifestyle of excessive alcohol and substance abuse and required her to procure illicit prescriptions to satisfy his own addictions." Among the number of disturbing allegations made in her lawsuit included claims that Diddy would often punch, beat, kick and stomp on her, resulting in bruises, burst lips, black eyes and bleeding.

Cassie also claimed she was "trapped" by his "cycle of abuse, violence, and sex trafficking." More specifically, Cassie claimed Diddy would force her to engage in sex acts with male sex workers while masturbating and filming the encounters, which the singer claimed Diddy referred to as a "freak off," or "FO." The court documents claimed that Diddy "would repeatedly tell Ms. Ventura at random moments that he wanted an FO, and Ms. Ventura was eventually expected to facilitate the location and the hiring of male sex workers."

Cassie Ventura and Sean Combs at the Met Gala on May 7, 2018 in New York City. - Getty

Diddy has vehemently denied these allegations.

The "Me & U" singer went public with her relationship with Diddy in 2012, though they were romantically linked as far back as 2007. In 2008, they collaborated on his song, "Swagga Like Puff," and in 2009, they worked together on her song, "Must Be Love."

They split in October 2018.

Cassie and Diddy Reach Settlement 

Some 24 hours after she filed her lawsuit in Manhattan Federal Court, Cassie and Diddy reached a settlement.

In a statement to ET, Diddy said, "We have decided to resolve this matter amicably." He added, "I wish Cassie and her family all the best. Love."

"Just so we’re clear, a decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing," Diddy's attorney, Ben Brafman, also said in a statement to ET. "Mr. Combs' decision to settle the lawsuit does not in any way undermine his flat-out denial of the claims. He is happy they got to a mutual settlement and wishes Ms. Ventura the best."

Sources close to the situation tell ET, "The decision to settle quickly and privately was largely influenced by considerations for Diddy's family."

Diddy Faces More Lawsuits

Less than two weeks after he and Cassie settled their lawsuit, Diddy faced two more accusations of sexual assault in a lawsuit that echoed many of Cassie's allegations.

According to court documents, a second woman named Joi Dickerson-Neal alleged that Combs drugged and sexually assaulted her when she was a college student at Syracuse University in 1991. The complaint claimed that Dickerson-Neal knew Combs through shared acquaintances and appeared with him in a music video for "Straight From the Soul," by Finesse and Synquis. 

Dickerson-Neal claimed she "reluctantly agreed" to a dinner with Combs, where he allegedly slipped a drug in her drink when she left to use the restroom, and soon "couldn't independently stand or walk." The music executive allegedly "pushed" Dickerson-Neal to stick with him as he "attended to a few things in the city" and later brought her to "a place he was staying to sexually assault her." 

Sean Combs at Howard University on Oct. 20, 2023 in Washington, DC. - Getty

"Days later, a male friend revealed to her that he had viewed the 'sex tape' along with other men," the court documents alleged. "Horrified, Ms. Dickerson asked how many others saw it, to which he responded, 'everyone.'"

A third woman, who filed the suit as a Jane Doe, claimed Diddy and R&B singer Aaron Hall assaulted her and her friend at the latter's apartment more than three decades ago.

Doe claimed that she met the men at an event hosted by Uptown Records distributor MCA Records at the company's offices. "Combs and Hall were very flirtatious and handsy with Jane Doe and her friend, offering them drinks throughout the night," the lawsuit states. Later at Hall's apartment, Doe alleges she "was coerced into having sex with Combs."

"After Combs finished doing his business, Jane Doe laid in bed, shocked and traumatized," the lawsuit states. "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."

On Dec. 6, 2023, a fourth woman accused Diddy of sexual assault. The woman claimed Diddy participated in a "gang rape" of a then-17-year-old in 2003. After that lawsuit came to light, Diddy spoke out on social media and said, "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," he continued. "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."

Music producer Rodney "Lil Rod" Jones also sued Diddy and accused him of sexual assault, harassment and not paying him for work done on The Love Album. In that lawsuit, Jones went on to also claim that 50 Cent's ex, Daphne Joy, was one of Diddy's sex workers.

50 Cent's Documentary 

On the same day Diddy faced the fourth accuser, 50 Cent took to social media to share that his production company was working on a Diddy documentary about the myriad of sexual assault allegations made against him. 

A representative for Curtis Jackson & G-Unit Film and TV confirmed the news to ET in a statement. 

That day, 50 Cent shared a snippet of what he's filmed so far, which included former Bad Boy Records rapper Mark Curry alleging that Diddy would spike bottles of alcohol and serve them only to women who attended the parties he hosted.

50 Cent and Diddy. - Getty

Curry also alleged that Diddy warned his crew not to drink from those bottles and only drink from the bottles he set aside for him and the rest of his crew. According to 50 Cent, proceeds from the documentary will benefit victims of sexual assault and rape.

Celebrities Speak Out

Members of the R&B group Danity Kane spoke out in support of Cassie. The girl group -- which included, at various times, Aubrey O'Day, Wanita "D. Woods" Woodgett, Dawn Richard, Aundrea Fimbres and Shannon Bex --  was formed on Diddy's iteration of Making the Band in 2005 and later signed to the rapper and producer's Bad Boy Records. 

O'Day shared her thoughts in a statement to ET, saying, "I am in full support of Cassie. It isn't easy to take on one of the most powerful people in this industry and be honest about your experience with them. I know what her heart is feeling right now, because I have done so as well. May her voice bring all the others to the table, so we can start having more transparent conversations about what is actually happening behind the scenes. There is a lot more to all of our stories!"

After the feds raided Diddy's homes, O'Day took to her Instagram Stories to share a headline detailing the raids. She also added her commentary with a cryptic message: "What you sow, you shall reap."

Diddy's Homes Raided

The rap mogul's homes in Los Angeles and Miami were raided by federal law enforcement on March 25. 

In a statement to ET, Homeland Security Investigations shared, "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."

ET has reached out to Diddy's reps and attorneys for comment.

TMZ reported that law enforcement sources said the case is being handled out of the Southern District of New York, and that it appears to be tied to sex trafficking allegations. The outlet also reported that two of the handcuffed men in the helicopter footage appear to be Diddy's sons, Justin and Christian "King" Combs.

Diddy Spotted in Miami

Diddy was photographed pacing around the Miami-Opa Locka Executive Airport at approximately 3 p.m. on the day his homes were raided. He had his cell phone in his hand and appeared to be alone.

In a video obtained by TMZ, Combs can be seen walking around freely outside the customs office at the airport, reportedly hours after the raids were initiated.

The So-Called 'Mule'

According to an arrest affidavit obtained by ET, Brendan Paul was arrested on Monday, March 25, 2024 at 4:30 p.m. at Miami-Opa Locka Executive Airport. Paul, 25, was taken into custody for being in possession of cocaine and marijuana candy.

Paul is the same person mentioned in music producer Rodney "Lil Rod" Jones' lawsuit against Diddy. According to court documents obtained by ET, Jones accuses Paul of being Combs' "mule" and that Paul "acquires and distributes Mr. Combs [d]rugs, and [g]uns."

Mugshot of Brendon Paul. - Department of Homeland Security

It's unclear if Paul's arrest is connected to the probe that's embroiled Diddy, but the same law enforcement agency that raided Diddy's homes also took Paul into custody.

In a statement to ET, Paul's attorney, Brian Bieber, said, "We do not plan on trying this case in the media all issues will be dealt with in Court."

Jones sued Diddy, among other things, for unpaid work he produced on Diddy's The Love Album.

What's Possibly Next

Neama Rahmani, a former federal prosecutor and president of West Coast Trial Lawyers who is not involved with this case, tells ET that the fact that the case seems to be being helmed by the U.S. Attorney's Office in New York means Diddy is in dangerous legal waters.

"The case seems to be coming out of the U.S. Attorney's Office in New York, which is one of the most prestigious in the country, which leads me to believe that this may be related to the allegation that came out initially when Cassie filed her lawsuit in November," Rahmani says.

He adds, "The government likely has a very strong case against Diddy. They don't execute these types of search warrants until they have talked to witnesses, have gathered evidence, and they believe they have an ironclad case. Not only that, they have to get a federal judge to sign off on the search warrant, so I believe the case against Diddy is very strong."

If a trial takes place, don't expect cameras in the courtroom.

"That's because of the federal rules of criminal procedure," Rahmani says. "So, we'll see the courtroom sketch artists that we typically see in federal cases."

50 Cent's Ex Speaks Out

In Rodney "Lil Rod" Jones' sexual assault and harassment lawsuit against Diddy, the music producer claimed that 50 Cent's ex, Daphne Joy, was one of Diddy's sex workers. In court documents, Jones claimed Joy was one of three women Diddy "bragged about" paying a "monthly stipend" for their sex work. Joy has since responded to the claim as categorically false.

"I am deeply hurt by the lies in Rodney Jones' lawsuit," Joy said in a statement shared on social media. "The claim that I am a sex worker is 100% false and character assassination. I am retaining an attorney to explore all legal remedies against both Rodney and his attorney."

Joy dated the "In Da Club" rapper for a year until they split in 2012, just months after their son, Sire, was born. 

Soon after denying Jones' claims, Joy shared a statement on Instagram in which she accuses 50 Cent of rape and physical abuse.

"We moved to New York to give you the opportunity to be a father to your son and you saw him 10 times out of the 2 years that we lived 1 mile away from you. I am tired of upholding and protecting an image to our son that you have never even earned," she wrote in her statement. "Let’s put the real focus on your true evil actions of raping me and physically abusing me. You are no longer my oppressor and my God will handle you from this point on. You have permanently damaged the last hope I had for you as a father to preserve our family with these last and final false claims made against me. You have broken our hearts for the last and final time."

In a statement to ET, 50 Cent denied the accusation and claimed Joy's "baseless accusations" are in response to him filing for sole custody of their son, Sire.

"The disturbing allegations in the sworn pleadings recently filed in a court case related to Daphne Joy the mother of my 12-year-old child, has required me to take all necessary legal actions to protect my son Sire," the statement read. "The most recent false and baseless accusations by Daphne Joy are clearly in response to my decision to seek sole custody of my son. My son Sire is my main priority and keeping him in a safe environment is my only focus at this time."

Christian Combs Faces Lawsuit

Amid his dad's legal woes, Christian Combs was accused of sexually assaulting Grace O'Marcaigh, a yacht employee, while on a boat chartered by Diddy, who was also named in the suit.

O'Marcaigh claimed she was pressured to take shots with the younger Combs, and alleged that he became aggressive when he wanted her to continue taking shots. She further claimed that he violently grabbed her arm and forced her to take another shot, which she alleged was spiked, before he allegedly touched her legs, breasts, anus and vagina, and tried to kiss her neck, face and hands.

O'Marcaigh claimed that Lil Rod has an audio recording of the alleged incident, and she included a transcript of that purported recording in her lawsuit. The lawsuit also included photos of O'Marcaigh's alleged injuries. 

In a statement to ET, Diddy and Christian's attorney, Aaron Dyer, told ET in part, "We will be filing a motion to dismiss this outrageous claim."

Model Addresses Claims

In addition to claiming that Daphne Joy was one of Diddy's sex workers, Lil Rod's lawsuit against Diddy alleged the same thing about model Jade Ramey. She spoke out in an exclusive statement to ET through her publicist, Eve Sarkisyan, at YES Public Relations, and, like Joy, denied Lil Rod's claim.

"Yes, I dated someone. Dating someone doesn't directly correlate to any of the false allegations made," Ramey said. "How unfortunate we've entered a time where caring for someone or falling in love is worthy of scrutiny in the court of public opinion. What may be amusing for you is real life for others, and my feelings have never been for entertainment, nor are they up for discussion."

"We need to be more conscious as a society when ridiculing people’s lives and relationships merely for enjoyment," her statement continued. "I appreciate everyone’s kind messages and support during this time. Thank you."

Video of Diddy Assaulting Cassie Is Released

Ventura's allegations against Diddy were put back into the spotlight on May 17, 2024, when CNN published previously unreleased security footage that showed Diddy grabbing, shoving, dragging, and kicking his then-girlfriend.

The video, which was compiled from multiple camera angles, was dated March 5, 2016. The incident shown in the clips corresponded to an incident highlighted in Ventura's explosive lawsuit.

In the video, Ventura is seen exiting a hotel room and walking to a bank of elevators. Diddy, holding a towel around his waist, runs after the model and grabs her by the back of the neck, throwing her to the floor. He then turns to kick her as she lies on the ground.

Diddy retrieves Ventura's dropped purse and weekend bag from the floor near the elevators before turning to kick Ventura again. He then begins to drag Ventura by the neck of her sweatshirt toward a room before walking away.

"The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs," Douglas H. Wigdor, Ventura's lawyer, told ET in a statement. "Words cannot express the courage and fortitude that Ms. Ventura has shown in coming forward to bring this to light."

The Los Angeles District Attorney Responds

In the wake of the video's release, the D.A.'s office reacted to the "extremely disturbing and difficult to watch" clip in a statement released on social media.

"If the conduct depicted occurred in 2016, unfortunately we would be unable to charge as the conduct would have occurred beyond the timeline where a crime of assault can be prosecuted," the statement read. "As of today, law enforcement has not presented a case related to the attack depicted in the video against Mr. Combs, but we encourage anyone who has been a victim or witness to a crime to report it to law enforcement or reach out to our office for support from our Bureau of Victims Services."

Diddy Breaks His Silence on the Video

Days after CNN published the video of Diddy assaulting Ventura, the rapper took to Instagram to share a video message.

"It's so difficult to reflect on the darkest times in your life, but sometimes you got to do that. I was f**ked up -- I hit rock bottom -- but I make no excuses," he said in the video. "My behavior on that video is inexcusable. I take full responsibility for my actions in that video. I was disgusted then when I did it. I'm disgusted now. I went and I sought out professional help. I got into going to therapy, going to rehab."

"I had to ask God for his mercy and grace," he said. "I'm so sorry. But I'm committed to be a better man each and every day. I'm not asking for forgiveness. I'm truly sorry."

Ventura's legal team responded to the video in a statement to ET. 

"Combs' most recent statement is more about himself than the many people he has hurt," Meredith Firetog, partner at Wigdor LLP, said. "When Cassie and multiple other women came forward, he denied everything and suggested that his victims were looking for a payday. That he was only compelled to 'apologize' once his repeated denials were proven false shows his pathetic desperation, and no one will be swayed by his disingenuous words."

If you or someone you know is experiencing domestic violence, call the National Domestic Violence Hotline at 1-800-799-7233, or go to thehotline.org. All calls are toll-free and confidential.

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