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A Timeline of Diddy’s Legal Troubles and Accusations: From Cassie Lawsuit to Multiple Arrests

Paige Strout
12 min read
A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
Generate Key Takeaways

Sean “Diddy” Combs has been under investigation for at least a year after being accused of sexual assault by multiple people.

The rapper and music mogul, 54, made headlines in November 2023 after his ex-girlfriend Cassie accused him of sexual abuse in a bombshell lawsuit. She accused Diddy of beating her, forcing her to take drugs and have sex with male prostitutes on camera. She alleged that the incidents took place at Diddy’s homes across the U.S.

In the lawsuit, Cassie also claimed that Diddy threatened to blow up Kid Cudi’s car after she had moved on with him following their 2018 split. (Cassie has been married to Alex Fine since 2019.)

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Diddy’s lawyer Ben Brafman denied the accusations on his behalf at the time, stating that Cassie’s lawsuit was “riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’ reputation and [is] seeking a payday.”

Breaking Down All of the Allegations Against Diddy: Cassie’s Assault Lawsuit and More

The case was settled just one day after Cassie’s filing. “I have decided to resolve this matter amicably on terms that I have some level of control,” she told Us Weekly in a statement through her attorney Douglas Wigdor. “I want to thank my family, fans and lawyers for their unwavering support.”

In a statement of his own, Diddy said: “We have decided to resolve this matter amicably. I wish Cassie and her family all the best. Love.”

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Scroll down for a timeline of Diddy’s sexual assault legal troubles:

November 2023

Following Cassie’s case settlement, a 2004 New York Magazine interview with Kimora Lee Simmons resurfaced, in which she claimed that Diddy “threatened to hit her” while she was pregnant. The interview noted that Diddy “eventually got down on his knees in public to apologize.” (Kimora is a mother to five kids, whom she shares with multiple partners. Diddy did not address her comments at the time.))

Diddy was soon hit with another lawsuit from a woman named Joi Dickerson-Neal. In court docs obtained by Us filed on November 23, Dickerson-Neal claimed that the musician “drugged, sexually assaulted and abused” her when she was a college student in 1991 and was a victim of “revenge porn” Diddy created and released. Diddy’s spokesperson called the lawsuit a “money grab” in a statement to CNN.

A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests

December 2023

An anonymous woman, dubbed Jane Doe, filed a lawsuit against the music mogul claiming she was sex-trafficked and gang-raped by Diddy and other men when she was 17 years old in 2008. She allegedly flew out to meet him in New York City and was given “copious amounts of drugs and alcohol” before the men forced themselves on her, according to court docs obtained by Us.

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Diddy declared that “ENOUGH IS ENOUGH,” in a statement to Us at the time, adding, “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.”

Diddy’s Ups and Downs Over the Years: Name Changes, Lawsuits, Home Raid and More

February 2024

Diddy once again denied any wrongdoing after being accused of sexual assault in another lawsuit, this one filed by music producer Rodney “Lil Rod” Jones. Jones alleged that during his time living and traveling with Diddy from September 2022 to November 2023, he witnessed and recorded Diddy and his staff “engaging in serious illegal activity.” Jones claimed he was sexually assaulted by Diddy in more than one of the rapper’s homes, as well as on a yacht rented by Diddy.

Diddy called Jones — who was seeking $30 million in damages — “a liar” in a statement through his attorney Shawn Holley. “We have overwhelming, indisputable proof that his claims are complete lies. We will address these outlandish allegations in court and take all appropriate action against those who make them,” Holley added.

A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests

March 2024

Diddy’s Los Angeles and Miami homes were raided in connection with a federal sex trafficking investigation by Homeland Security. Diddy was not present at his homes at the time of the raids but was later found boarding a private jet at a Miami airport. Two of his sons were reportedly detained in the raid on his L.A. property but were released without charges.

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“Yesterday, there was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences,” Diddy’s attorney Aaron Dyer said in a statement to Us, denying that any of his family members had been arrested. “There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.”

Following the raids, it was revealed that Diddy’s eldest son, Justin Combs, was named in an amended complaint filed by Jones. In the court docs, obtained by Us, the phrase “sex trafficking” was mentioned 50 times. Reps for Justin said in a statement that he “categorically denies these absurd allegations,” per NBC News.

The Most Eyebrow-Raising Quotes About Diddy’s Alleged Behavior Over the Years

April 2024

Diddy’s youngest son, Christian “King” Combs, was accused of sexually assaulting a woman who worked on a yacht Diddy chartered for a 2022 trip in a Los Angeles County Superior Court lawsuit. The woman, Grace O’Marcaigh, also accused King of sexual harassment and emotional distress and Diddy for aiding and abetting.

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Diddy’s attorney Dyer slammed the lawsuit in a statement to Us. “We have not seen this woman’s claim but I’m sure we can expect the same kind of manufactured lies ... just as we saw in Rodney Jones’ lawsuit — which has yet to be served.”

Later that month, news broke that Diddy’s alleged drug mule, Brendan Paul, was arrested for cocaine and marijuana possession. Paul was later charged with one felony count of drug possession. (Paul avoided jail time but was ordered to enter a six-month drug diversion program the following month.)

A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
Sean 'Diddy' Combs and Cassie.

May 2024

Less than a week after Diddy filed a motion to dismiss Jane Doe’s December 2023 lawsuit against him, CNN released security footage from 2016 allegedly showing Diddy physically assaulting Cassie in a now-closed Los Angeles hotel. In the clip, Diddy was shown allegedly hitting and kicking Cassie, as well as throwing an object at her.

The Los Angeles District Attorney’s office explained in a statement that Diddy could not be charged for the security footage “as the conduct would have occurred beyond the timeline where a crime of assault can be prosecuted.”

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Diddy addressed the footage in an Instagram video, telling fans, “My behavior on that video is inexcusable. I take full responsibility for my actions in that video. I’m disgusted.” Though he didn’t mention Cassie by name, he captioned the post, “I’m sorry.”

A member of Cassie’s legal team, Meredith Firetog, criticized Diddy’s apology video in a statement to Us. “When Cassie and multiple other women came forward, he denied everything and suggested that his victims were looking for a payday,” she said. “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.”

Cassie addressed the security video in a lengthy social media statement, writing, “Thank you to everyone that has taken the time to take this matter seriously. My only ask is that EVERYONE open you hear to believing victims the first time. It takes a lot of heart to tell the truth out of a situation that you were powerless in.”

Everything Diddy Has Been Dropped From Following Sexual Assault Allegations

May 2024

Diddy continued to face more allegations after a woman named April Lampros accused him of drugging and sexually assaulting her several times in a new lawsuit. The alleged abuse took place after she met Diddy in NYC in 1995 during her time as a student at the Fashion Institute of Technology.

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Lampros’ lawsuit alleged that she was once forced by Diddy to have sex with his late ex-girlfriend, Kim Porter, as he watched and that the music mogul recorded one of their sexual encounters without her knowledge.

Diddy moved to dismiss Lampros’ case in August 2024, arguing that some of her claims were time barred and did not apply to New York allowing previous sex offenses to be prosecuted. Lampros filed a cross-motion one month later, asking for permission to add additional details to her case regarding the alleged time barred claims.

Diddy was also accused of sexual assault by model Crystal McKinney for an alleged incident that took place in 2003. In her lawsuit, McKinney claimed that Diddy forced her to perform oral sex despite denying his advancement and that she was subsequently blackballed from the modeling industry. (Diddy’s team did not respond to Us’ request for comment for either lawsuit at the time.)

McKinney, Dickerson-Neal and Jane Doe came forward about their experiences in a Rolling Stone report. “It isn’t about money,” Dickerson-Neal told the outlet of their respective lawsuits against Diddy. “It’s about making sure the world sees that this man who rose to the level of an ‘icon’ is actually sick and has left so many victims in [the wake of his] unpunished disgusting behavior for years.”

A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests
A Timeline of Diddy Legal Troubles and Accusations From Cassie Lawsuit to Multiple Arrests

August 2024

Adria English filed a criminal complaint against Diddy after accusing him of sex trafficking her from 2004 to 2009 in a July 2024 lawsuit.

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“Ms. English is very excited and cautiously optimistic about her journey to justice starting with the filing of her civil lawsuit on July 3, 2024, and now with the filing of a criminal complaint with the Miami Beach Police Department,” Ariel E. Mitchell told Us in a statement. “Ms. English hopes to file an additional criminal complaint in New York but has been precluded to this point as New York requires an individual to be in person in order to file a criminal complaint.”

Diddy’s attorney Jonathan Davis called English’s accusations “baseless” in a statement to Entertainment Weekly one month prior, adding, “No matter how many lawsuits are filed, it won't change the fact that Mr. Combs has never sexually assaulted or sex trafficked anyone. We live in a world where anyone can file a lawsuit for any reason and without any proof. Fortunately, a fair and impartial judicial process exists to find the truth and Mr. Combs is confident he will prevail against these and other baseless claims in court.”

Diddy’s Family Guide: Meet the Rapper’s Children and Their Mothers

September 2024

Former Danity Kane member Dawn Richard filed a lawsuit against Diddy accusing him of sexual abuse, manipulation and terrorizing her. She also alleged that she witnessed Diddy abuse Cassie and Porter in front of her, and claimed Diddy promised to advance her singing career if she gave into his sexual demands following her time on MTV’s Making The Band.

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Another of Diddy’s attorneys Erica Wolff noted that he was “shocked and disappointed” by the lawsuit in a statement at the time. “It’s unfortunate that Ms. Richard has cast their 20-year friendship aside to try and get money from him, but Mr. Combs is confidently standing on truth and looks forward to proving that in court,” she added.

Later that month, Diddy was ordered to pay a $100 million default judgment for a civil lawsuit filed by a Michigan inmate who accused him of sexual assault. The default judgment was ordered after Diddy failed to appear in a virtual hearing. Derrick Lee Cardello-Smith accused the rapper of drugging and sexually assaulting him at a 1997 party in Detroit. Diddy proceeded to challenge the ruling by filing an emergency motion to vacate the default judgment. He also filed to dissolve a preliminary injunction and temporary restraining order.

With authorities apparently armed with necessary evidence to move forward, Diddy was arrested in NYC on September 16 after a grand jury indicted him on charges of sex trafficking and racketeering. The indictment accuses Diddy of abusing and threatening women to “to fulfill his sexual desires, protect his reputation and conceal his conduct,” with some incidents dating back to 2009, according to new documents.

Diddy’s Celebrity Connections Through the Years: From Friends to Collaborators

“To do so, Combs relied on the employees, resources and influence of the multifaceted business empire that he led and controlled — creating a criminal enterprise whose members and associates engaged in, and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice,” the indictment stated.

Diddy plead not guilty to the sex trafficking and racketeering charges at the time.

“We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office,” his attorney Marc Agnifilo told Us in a statement.

He added: “He is an imperfect person, but he is not a criminal. … Please reserve your judgment until you have all the facts. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court.”

Diddy pleaded not guilty to charges before he was denied bail and remanded to the Metropolitan Detention Center in Brooklyn until his trial. Multiple reports surfaced that Diddy was subsequently placed on suicide watch.

Diddy’s lawyer, however, denied the reports in a statement to Us. According to Agnifilo, it is standard protocol for “new, high-profile inmates,” but Diddy is “not at all suicidal” and is “strong, healthy, confident and focused on his defense.”

Later that month, The New York Times obtained a new court letter that laid out Diddy’s alleged plan to blow up a car. While the letter did not identify the targeted person, the details aligned with claims laid out by Cassie in her November 2023 lawsuit against Diddy. She alleged that Diddy had been “angry” when she started dating Kid Cudi after one of their splits and threatened to firebomb the rapper’s vehicle in retaliation. (Diddy did not specifically address the firebomb allegations at the time but issued a broad statement denying all of Cassie’s claims.)

“In the early morning hours of December 22, 2011, the defendant [Diddy] and a co-conspirator kidnapped an individual at gunpoint to facilitate breaking into and entering the residence of another,” the court documents read. “Multiple witnesses would testify at trial to the events surrounding the kidnapping and break-in, the latter of which is corroborated by police reports and other records.”

According to the letter, Diddy’s “co-conspirators” allegedly “set fire” to the car “by slicing open the car’s convertible top and dropping a Molotov cocktail inside the interior.”

“Police and fire department records extensively document the arson and conclude that the fire was intentionally set,” the letter continues.

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673). If you or someone you know are experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support.

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