By Elizabeth Wagmeister, Kara Scannell, Eric Levenson, Josh Campbell and Elizabeth Wolfe, CNN
(CNN) — Sean “Diddy” Combs had just released a new album and was granted the key to New York City when he was accused of abuse and violence in a startling 2023 civil lawsuit from his former girlfriend.
Combs denied the allegations, and the lawsuit was settled a day after it was filed. But the person behind that lawsuit, Cassie Ventura, is expected to soon be a key witness for the prosecution in his federal criminal trial.
In nearly two years since Ventura’s lawsuit, much has happened: Dozens of men and women have alleged Combs committed serious wrongdoing, CNN published a 2016 hotel surveillance video showing him physically assaulting Ventura, federal authorities conducted searches on his homes, and he was arrested and faces serious criminal charges.
Now comes his criminal trial in a federal courtroom in Manhattan.
It all marks a sharp downfall for Combs, 55, who founded the music label Bad Boy in 1993 and has gone by the stage names Puff Daddy and Diddy. Over his illustrious decades-long career, he earned three Grammy wins and 14 nominations, and he successfully expanded from rap into the wider culture, with forays into fashion, alcohol sales, reality TV and acting.
Combs has pleaded not guilty to five counts, including one count of racketeering conspiracy, two counts of sex trafficking and two counts of transportation to engage in prostitution. If convicted, he could face a sentence of up to life in prison.
To better understand what led to this moment, here’s a timeline of the key events and allegations against Diddy in recent years.
From mogul to defendant
September 15, 2023: Diddy released “The Love Album: Off the Grid,” his fifth studio album, featuring appearances by a who’s who of the music industry, including Justin Bieber, the Weeknd and Mary J. Blige.
To celebrate, New York City Mayor Eric Adams gave Diddy a symbolic key to the city.
“The Bad Boy of Entertainment is getting the key to the city from the Bad Boy of Politics,” Adams said.
November 16, 2023: Combs’ former girlfriend, Casandra “Cassie” Ventura, filed a lawsuit against the producer claiming he raped and physically abused her. She also claimed Combs inflicted years of emotional abuse on her and sought to control all aspects of her personal life, according to the filing in federal court in New York.
The lawsuit accused Combs and other defendants of sex trafficking, human trafficking, sexual assault, gender-motivated violence, sexual harassment, gender discrimination and a hostile work environment. In particular, the suit described an altercation in a hotel hallway in March 2016 in which Combs “grabbed at her,” beat her and threw glass vases at her.
Ventura filed the suit days ahead of the November 23 expiration of the New York’s Adult Survivor Act, which created a one-year window for adult survivors of sexual abuse to sue their abusers, regardless of the statute of limitations.
Combs’ attorney at the time, Ben Brafman, said in a statement that “Mr. Combs vehemently denies these offensive and outrageous allegations” and that the suit was “riddled with baseless and outrageous lies.”
November 17, 2023: Just a day later, Combs and Ventura agreed to settle the lawsuit.
Both musical artists released statements saying the matter was resolved “amicably.” Combs’ attorney, Brafman, said the settlement was “in no way an admission of wrongdoing.”
November 23, 2023: Two more women, Joi Dickerson-Neal and Liza Gardner, accused Combs of sexual assault in lawsuits filed in New York Supreme Court on the eve of the expiration of the state’s Adult Survivors Act.
Combs denied the accusations.
December 6, 2023: After more accusers came forward, Combs wrote in an Instagram post:
“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,” he wrote. “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.”
That post has since been removed from his Instagram feed. Only seven posts remain on his account page, most of which are photos of his children.
March 25, 2024: Heavily armed teams of federal agents – some in armored vehicles and tactical gear – executed searches of Combs’ homes in Los Angeles and the Miami area. The searches were carried out by Homeland Security Investigations as part of an ongoing sex trafficking investigation, a law enforcement source told CNN at the time.
March 26, 2024: Aaron Dyer, then an attorney for Combs, criticized the raids as a “gross overuse of military-level force.”
May 17, 2024: CNN published hotel surveillance video from 2016 that showed Combs kicking and dragging Ventura.
The video, taken at the now-closed InterContinental Hotel in Century City, Los Angeles, shows Combs running down a hallway after Ventura with a towel wrapped around his waist. He grabs Ventura by the back of the neck, throws her to the floor and kicks her, video shows. The video goes on to show Combs dragging Ventura on the floor and throwing an object at her.
Ventura declined to comment on the video.
Wigdor, an attorney for Ventura, told CNN: “The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs. Words cannot express the courage and fortitude that Ms. Ventura has shown in coming forward to bring this to light.”
May 19, 2024: Combs released a video statement apologizing for physically assaulting Ventura in the hotel surveillance video published by CNN.
“My behavior on that video is inexcusable. I take full responsibility for my actions in that video,” he said.
“I was disgusted then when I did it. I’m disgusted now,” he added. “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. 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.”
The apology video has since been removed from Combs’ Instagram.
May 29, 2024: CNN reported federal investigators were preparing to bring Combs’ accusers before a grand jury, citing two sources familiar with the probe. Additional sources told CNN that most of the plaintiffs who had filed civil lawsuits against Combs had been interviewed by federal investigators. Some were handing over evidence they believed could assist investigators, one source said.
June 10, 2024: Combs returned his symbolic key to New York City after Mayor Eric Adams sent a letter to him requesting he do so. Adams wrote that he was “deeply disturbed” by the hotel surveillance video published by CNN.
September 11, 2024: Singer Dawn Richard, a former member of the musical group Danity Kane, filed a suit accusing Combs of sexual battery, sexual harassment and false imprisonment, among other allegations. She also claims to have seen Combs “brutally beat” Ventura while the pair were dating in the 2000s.
Erica Wolff, Combs’ attorney, denied the allegations in a statement to CNN.
Arrest and criminal charges
September 16, 2024: Combs was arrested in New York City after a grand jury voted to indict him on charges of racketeering conspiracy, sex trafficking and transportation to engage in prostitution in incidents dating back to 2008.
Combs had relocated to New York several days before the arrest in anticipation of the charges, his attorney said. Negotiations for his surrender had been ongoing, according to a source familiar with the talks.
September 17, 2024: A wide-ranging indictment against Combs was unsealed and accused him of creating a “criminal enterprise” whose members and associates engaged in and attempted to engage in sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice.
Prosecutors alleged Combs perpetrated decades of abuse and coercion against women and others in his network to “fulfill his sexual desires, protect his reputation, and conceal his conduct,” the indictment states. In addition to allegations of physical abuse against women, prosecutors accused Combs of orchestrating extended, drug-fueled sex performances called “Freak Offs” between victims and sex workers.
The indictment stated law enforcement seized guns, ammo, drugs and more than 1,000 bottles of baby oil and lubricant during searches of Combs’ homes in Miami and Los Angeles in March.
Combs appeared in court and pleaded not guilty. He was denied bail and Judge Robyn Tarnofsky ruled he will remain in custody as the case plays out, a decision that Combs’ attorneys appealed.
September 18, 2024: In a hearing appealing his detention, prosecutors asked the judge to keep Combs behind bars, telling the court he has attempted to tamper with witnesses. His defense asked the judge to release him until trial and submitted a bail package that included a $50 million bond.
Judge Andrew Carter, who later recused himself from the case, sided with prosecutors and agreed to detain Combs ahead of trial. “My bigger concern deals with the danger of obstruction of justice and the danger of witness tampering,” Carter said.
He has been held in a federal detention facility in Brooklyn, New York, ever since.
January 30, 2025: Federal prosecutors filed a superseding indictment against Combs, expanding the racketeering conspiracy allegations to include two new female victims. The new indictment alleged the criminal conduct goes as far back as 2004, four years earlier than the initial indictment said.
March 14, 2025: A gray-haired Combs appeared in court and pleaded not guilty to the superseding indictment.
April 4, 2025: In another superseding indictment, federal prosecutors added two new counts of sex trafficking and transportation to engage in prostitution related to “Victim-2” that they allege occurred between 2021 and 2024.
April 14, 2025: Combs pleaded not guilty to the two new counts.
April 25, 2025: Federal judge Arun Subramanian ruled footage of Combs physically assaulting his ex-girlfriend, Cassie Ventura, will be shown to the jury at his trial. In addition, a prosecutor informed the judge that Combs had rejected a plea deal, though there were no further details on what it entailed.
May 5, 2025: Jury selection began in Combs’ federal trial in a Manhattan courtroom. The trial is expected to last several weeks.
The-CNN-Wire
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CNN’s Lauren del Valle, Nicki Brown, John Miller, Alli Rosenbloom, Kristina Sgueglia, Lisa Respers France and Sandra Gonzalez contributed to this report.
