A Timeline of Sean “Diddy” Combs’ Recent Legal Troubles, From Cassie’s Lawsuit to His Arrest

While Sean “Diddy” Combs became a definitive figure in hip hop — as his career spread from music to fashion, spirits and more, climbing to the top echelons of these industries — reports over the past year have made clear that rumors of his conduct behind closed doors persisted for years. The first crack in the dam came in November, when accusations in a legal complaint from his ex-girlfriend, “Me & U” singer Cassie, opened the door to what’s now mounted to 10 legal complaints against the mogul. On Sept. 17, he was arrested in Manhattan on charges that included sex trafficking, forced labor, coercion to engage in prostitution and narcotics distribution.

Combs entered a not guilty plea on these charges and, in a statement after his arrest, his attorney Marc Agnifilo said the U.S. Attorney’s Office is pursuing an “unjust prosecution,” adding that Combs has cooperated in the investigation. 

“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,” Agnifilo, a former federal and state prosecutor, said. “He is an imperfect person, but he is not a criminal.”

Here is a look at the accusations that have emerged over the past 10 months involving Combs.

Nov. 16, 2023: Cassandra Ventura, also known as the singer Cassie, filed a legal complaint alleging years of sexual abuse, harassment and rape during the relationship she entered in with Combs and remained in for years. Cassie also alleged in the suit that Combs made a threat to blow up Kid Cudi’s car; later, the rapper’s car exploded and Cudi confirmed the version of events detailed in her suit. Her case was filed under New York’s Adult Survivors Act and just one day after it was filed, the lawsuit was settled out of court for an undisclosed sum.

Nov. 23, 2023: A week later, under the wire before the cutoff date for filing under the Adult Survivors Act, Combs was hit with two more lawsuits. Joi Dickerson-Neal accused him of misconduct in the 1990s after the two went on a date when she was 19. The case alleges that Combs drugged and raped the teenager while videotaping the attack, while another anonymous lawsuit alleged Combs is accused along with singer Aaron Hall of sexually assaulting a female and then beating her days later.

Dec. 6, 2023: Combs is accused of involvement in a gang rape in 2003 where he allegedly drugged the accuser, who was 17 years old at the time; two other men have been accused in the alleged assault, which the alleged victim says took place in a recording studio in 2003. The backlash against Combs after this accusation is palpable and he steps down as chairman of Revolt TV; several brands also decide to cut ties with his business​. Combs takes to Instagram and denies all the allegations in the lawsuits he now was drowning in: “I did not do any of the awful things being alleged,” he wrote. “I will fight for my name, my family, and for the truth.”

Feb. 26, 2024: The famous Lil’ Rod lawsuit drops, accusing Combs of sexual assault and forcing the upstart producer to engage with prostitutes, ingest drugs and engage in various uncouth activities. The complaint details elements of Rodney “Lil’ Rod” Jones’ 14-month odyssey living and working with Combs; in the complaint, the 38-year-old says he was sexually assaulted, allegedly forced by Combs to engage in sex acts, made to solicit sex workers, drugged, humiliated and repeatedly groped — and in what his attorneys say is the real motivation behind the suit, Jones alleges he was stiffed by Diddy for his work on the mogul’s 2023 album. Combs’ legal team cries foul on all of the details of the suit, calling them “pure fiction” and denying Jones completed the work he claims he produced for 2023’s Grammy-nominated The Love Album: Off the Grid.

March 25, 2024: The Combs case escalates, with massive attention on his dealings after authorities raided his properties in New York, Los Angeles and Miami as part of a broad investigation into sex trafficking allegations. That this all came as the Lil Rod lawsuit was raising eyebrows about the mogul’s behavior did no favors for Combs and soon, he was a daily subject of gossip and conspiracy theories across the web. Combs’ then-attorney, Aaron Dyer, called the raids a “gross overuse of military level force” and said the “unprecedented ambush [was] paired with an advanced, coordinated media presence.”

April 4, 2024: A lawsuit implicated Christian Combs, the rap mogul’s son, in a sexual assault that allegedly involved a staff member on a yacht that had been chartered by the beleaguered rapper. In the suit, Combs is accused of facilitating the environment that allowed the assault to take place.

April 26, 2024: At this point, Combs’ legal team goes on the offensive when they file motions to dismiss key elements of the lawsuits. Their argument? Some of the claims, like those relating to revenge porn and human trafficking, were not illegal in 1991, which is when they allegedly occurred​. This specifically relates to Dickerson’s lawsuit, which involved footage of the alleged rape being circulated. In the filing, they also slam the “numerous false, offensive, and salacious accusations” made.

May 10, 2024: Combs’ legal team again pushes back on claims against their client, this time alleging the lawsuit from the Detroit woman alleging Combs raped her with two others in a studio in 2003 was filed too late and that the claims around Combs’ alleged behavior are “false and hideous.”

May 17, 2024: Combs’ reputation is dealt a massive blow after CNN obtained a video of the mogul wearing a robe and walking into a hotel hallway where he then brutally assaulted his former romantic partner, Cassie, in 2016. The shocking video is blanketed across the media and leads Combs to issue a public apology. “My behavior on that video is inexcusable. I take full responsibility for my actions in that video,” he said in a video statement posted on his Instagram page.

June 9-10, 2024: Howard University revokes an honorary degree it handed to Combs; the rapper returns a key to New York City at the request of Mayor Eric Adams.

June 10, 2024: Longtime rap game rival of Combs, Suge Knight, who ran Death Row Records on the West Coast while Diddy was at the helm of Bad Boy, dropped a theory from prison that the mogul is working with the FBI as an informant. This is why, Knight claimed, Combs had been able to act as he did with impunity. “It shouldn’t be a gray area when it comes to doing something right, doing something positive, or doing something for the community,” Knight said on an episode of his Collect Call with Suge Knight podcast. “That being said, naturally, Puffy has been an FBI informant forever, as they would say. That’s why it’s different when it comes to him.”

Aug. 26, 2024: Combs’ attorneys issue a motion to dismiss Lil Rod’s explosive case, saying that his accusations were exaggerated and some even fabricated. They accused Jones of aiming only to exploit his fame for media attention and a potentially large settlement​. They also mention that his initial gripe with Combs had to do with nonpayment and that it was only when he teamed up with his attorney, Tyrone Blackburn, that he began to make the salacious claims in his complaint, which includes the assertion that Combs was using kompromat as leverage to gain power and control over others.

“Mr. Combs possesses compromising footage of every person that has attended his ‘freak off’ parties, and his house parties,” the complaint said, referring to alleged days-long sex parties the mogul is said to have thrown. “Upon information and belief, due to this treasure trove of evidence he has in his possession, Mr. Combs believes that he is above the law and is untouchable.”

Sept. 11, 2024: Singer Dawn Richard filed what is now the 10th lawsuit against Combs since the cascade of litigation began in November. In 2003, Richard formed the girl group Danity Kane, which Combs mentored as part of his role in MTV’s Making the Band. She alleges that Combs, as they worked together, subjected her to years of psychological and physical abuse, which included groping. 

Sept. 15, 2024: Combs had returned to New York in anticipation of his arrest. He was spotted around Manhattan multiple times and reports indicate the beleaguered near-billionaire seemed to be in good spirits. On the Sunday before he was taken into custody, Combs was spotted mingling among fans in Central Park and is seen in a photo obtained by News Nation sitting on a bench with his attorney; that night, he was photographed walking around town with his son, Christian Combs.

Sept. 16, 2024: Combs is arrested in Manhattan and an indictment, unsealed the following day, accuses the fallen mogul of crimes related to an alleged decades-long pattern of physical and sexual violence against women. Federal prosecutors charged him with sex trafficking and racketeering for directing a vast criminal enterprise through which he assaulted and trafficked women with the help of his various businesses from at least 2008. He pleaded not guilty and fought for a $60 million bond, but the judge decided he would be detained until his trial.