Full timeline of Diddy's allegations from baby oil 'freak offs' to the Cassie video as rap mogul sits in squalid NYC jail
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Maybe he should have listened to his fated protege Biggie Smalls - 'Mo Money, Mo Problems.'
Heralded for decades as rap royalty, Sean 'Diddy' Combs now sits alone in an isolation cell in a notorious New York City jail - deemed too much of a 'threat to the community' by authorities to be let out even after offering a $50 million bond.
It's a stunning fall for the 'It's All About the Benjamins' rapper, who was once hip-hop's wealthiest and most influential mogul.
But if the feds' allegations are true it may be just be all the unlimited cash, unchecked power and the Hollywood privilege that goes along with it that landed Diddy where he now sits: facing a slew of racketeering conspiracy and sex trafficking charges that accuse him of presiding over a sordid empire of sexual crimes and physical abuse.
If convicted the 55-year-old could spend the rest of his life behind bars.
So how did we get here? Here is a look at the key events that have unfolded since prosecutors announced he was being investigated late last year.
November 16, 2023
Cassie says in a lawsuit that Combs subjected her to years of abuse, including beatings and rape.
Cassie, whose legal name is Cassandra Ventura, signed to Combs' label in 2005, and the two were on-again-off-again romantic partners for more than a decade starting in 2007.
The lawsuit filed in federal court says Combs was 'prone to uncontrollable rage' and subjected her to 'savage' beatings.
It says he plied her with drugs, forced her to have sex with other men, and raped her in her home as she was trying to end the relationship in 2018.
Combs, through his attorney, 'vehemently denies' the accusations.
November 17, 2023
With staggering speed, Ventura's lawsuit is settled the day after it is filed.
The terms of the agreement are kept confidential.
'We have decided to resolve this matter amicably,' Combs says in a statement. 'I wish Cassie and her family all the best. Love.'
Cassie Ventura (L) and Sean Combs attend the 'China: Through The Looking Glass' Costume Institute Benefit Gala at the Metropolitan Museum of Art on May 4, 2015 in New York City
Cassie, whose legal name is Cassandra Ventura, signed to Combs' label in 2005, and the two were on-again-off-again romantic partners for more than a decade starting in 2007
November 23, 2023
Two more women accuse Combs of sexual abuse in lawsuits filed on the eve of the expiration of the Adult Survivors Act, a New York law permitting victims of sexual abuse a one-year window to file civil action regardless of the statute of limitations.
The lawsuits, filed by Joi Dickerson and another woman who was not named, allege acts of sexual assault, beatings and forced drugging in the early 1990s by Combs, then a talent director, party promoter and rising figure in New York City's hip-hop community.
Combs' attorneys call the allegations false.
November 28, 2023
Combs temporarily steps down as chairman of his cable television network, Revolt, because of the wave of sexual abuse allegations.
It would be one of several business setbacks for Combs brought on by the lawsuits.
December 6, 2023
A woman alleges in another lawsuit that in 2003 when she was 17, Combs and two other men raped her.
The lawsuit filed in federal court in Manhattan says she was living in a Detroit suburb and was flown to a New York studio, where she was given drugs and alcohol that made her incapable of consenting to sex, and the men took turns raping her.
The same day, Combs posts a statement on Instagram broadly denying all the allegations in the mounting series of lawsuits.
'I did not do any of the awful things being alleged,' the post says.
'I will fight for my name, my family and for the truth.'
Sean 'P Diddy' Combs, Justin Bieber and Sean Kingston perform at the Help for Haiti benefit concert and telethon at AmericanAirlines Arena on February 5, 2010 in Miami, Florida
Sean 'Diddy' Combs is one of America's most famous rappers, record producer and record executives
February 26, 2024
A music producer files a lawsuit alleging Combs sexually assaulted him and forced him to have sex with prostitutes.
The lawsuit gives a long list of potentially illegal activities dealing with drugs and sex that the producer says he witnessed.
A lawyer for Combs calls the allegations 'pure fiction.'
March 25, 2024
Homeland Security Investigations serves search warrants in early morning raids on Combs' homes in Los Angeles and Miami in what officials declare is a sex-trafficking investigation.
Combs was at one of his homes in Miami at the time. His two sons, at his home in Los Angeles, were handcuffed during the search, Combs' attorneys said.
Officials did not say whether the raids were prompted by the civil lawsuits, but Combs' attorneys said they believed they were.
March 26, 2024
Combs' lawyer calls the raids 'a gross use of military-level force' and says Combs is 'innocent and will continue to fight' to clear his name.
The attorney, Aaron Dyer, says there is 'no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.'
Properties connected to rapper Sean 'Diddy' Combs were raided in March by federal agents
A picture from inside Diddy's Miami home shows how law enforcement agents conducted thorough searches
These aerial images taken in October 19, 2023, show the sprawling waterfront properties owned by the embattled rap mogul, real name Sean Combs, that were raided by federal agents
Homeland Security Investigations serves search warrants in early morning raids on Combs' homes in Los Angeles and Miami
April 4, 2024
A lawsuit that names Combs as a co-defendant alleges that his son Christian 'King' Combs sexually assaulted a woman working on a yacht chartered by his father.
The lawsuit filed in Los Angeles Superior Court says Sean Combs created the circumstances that led to the assault and paid to cover it up afterward.
An attorney for the two men calls the allegations 'outrageous.'
April 26, 2024
In the first major piece of legal pushback from Combs and his team, they file a motion to dismiss several elements of Dickerson's lawsuit because they were not illegal in 1991 when the alleged incidents occurred.
While the legal objections are procedural, the filing also slams the 'numerous false, offensive, and salacious accusations' in the lawsuit.
May 10, 2024
Combs asks a federal judge to dismiss the Dec. 6 lawsuit that alleged he and two co-defendants raped a 17-year-old girl from Michigan in a New York recording studio.
Again, the objections are procedural - alleging the lawsuit was filed too late under the law - but the court document calls its claims 'false and hideous.'
May 17, 2024
CNN airs video that shows Combs attacking Ventura in a hotel hallway in 2016.
The video closely mirrors an assault described in her lawsuit, which said Combs had already punched her that night, and she was trying to leave the InterContinental Hotel in Los Angeles when he woke and came after her.
In the footage, a man who appears to be Diddy, wearing only a towel, punches Ventura, kicks her, and throws her on to the floor.
The lawsuit alleges Combs paid $50,000 to take away the video at the time. Combs' representatives had no immediate comment.
The Los Angeles District Attorney's Office says it cannot prosecute Combs for the attack shown in the video due to statute of limitation, noting that no case had been presented to prosecutors.
CNN in May aired a leaked video that shows Combs attacking Ventura in a hotel hallway in 2016
This frame grab taken from hotel security camera video and aired by CNN shows Sean 'Diddy' Combs attacking singer Cassie in a Los Angeles hotel hallway in March 2016
Diddy, wearing only a towel, punches Ventura, kicks her, and throws her on to the floor
May 19, 2024
Combs posts a video on Instagram and Facebook apologizing for the assault on Ventura.
It's his first real acknowledgement of wrongdoing since the recent stream of allegations began.
'My behavior on that video is inexcusable,' Combs says, adding that he had hit 'rock bottom'.
'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. I'm so sorry.'
June 10, 2024
At the request of New York Mayor Eric Adams, Combs returns a key to the city.
Adams sent letters to Combs rescinding the honor as part of the fallout of the leak of the video of Combs beating Cassie.
Adams says he was 'deeply disturbed' by the video. Adams awarded Combs with the key at a ceremony in 2023.
A day earlier, Howard University announced it had rescinded an honorary degree given to Combs and disbanded a scholarship program in his name.
On May 19, Combs posted a video on Instagram and Facebook apologizing for the assault on Ventura. That was his first real acknowledgement of wrongdoing since the recent stream of allegations began
At the request of New York Mayor Eric Adams, Combs in June returned a key to the city
August 26, 2024
As part of a multi-faceted pushback against the lawsuits filed against him, Combs asks a federal judge to throw out the February lawsuit from the music producer.
His lawyers say the suit was overrun with 'tall tales,' 'lurid theatrics,' 'legally meaningless allegations' and 'blatant falsehoods' whose intent is only to 'generate media hype and exploit it to extract a settlement.'
September 11, 2024
Diddy is sued by singer Dawn Richard in a case describing years of psychological and physical abuse, including groping, that she says she suffered as he helped launch her career.
Richard, a member of the girl group Danity Kane and is well-known for appearing on the MTV reality show 'Making the Band,' alleges in the suit that she witnessed Combs abuse Cassie and was afraid of the mogul.
Diddy's representatives accuse Richard of making 'an attempt to rewrite history' by manufacturing 'a series of false claims all in the hopes of trying to get a pay day - conveniently timed to coincide with her album release and press tour.'
Combs poses for a selfie between a pair of fans ahead of his arrest on September 16
Authorities had planned on arresting Combs on Tuesday, 'but something happened that caused' federal officials to take him into custody earlier than planned, an official told the outlet
September 16, 2024
Combs is arrested on a Monday night in New York after a grand jury indictment. No details on the charges were made public, but federal officials say they will ask a judge to unseal the indictment a day later.
Combs' attorney calls it an unjust prosecution of an 'imperfect person' who is 'not a criminal.'
The rapper, clad in a long black coat over a black t-shirt with gray sweatpants and grey sneakers, was seen hours earlier flashing smiles and posing for selfies with several adoring fans as he wandered the streets of midtown Manhattan.
Christian, Combs' 26-year-old son who performs under the moniker 'King Combs', was also seen walking with his father before his arrest.
Earlier in the day, a video shared on social media showed Diddy flicking through his phone and enjoying the sunshine as he sat in Central Park, wearing a baggy black vest.
September 17, 2024
Combs was denied bail as he appeared in a Manhattan federal courtroom on shocking sex trafficking and racketeering charges that revealed a debauched lifestyle and serious allegations of sexual and physical abuse.
U.S. Attorney Damian Williams, in revealing what federal agents found during the March raid of Diddy's Miami residence, displayed graphics that showed off confiscated unmarked AR-15s, ammunition, as well as 1,000 bottles of baby oil and other lubricant.
'The indictment alleges that between at least 2008 and the present, Combs abused, threatened and coerced victims to fulfill his sexual desires, protect his reputation, and conceal his conduct,' Williams said.
'The indictment alleges that Combs used and exploited women and other people for years, and in a variety of ways. As alleged, Combs used force, threats of force, and coercion to cause victims to engage in extended sexual performances with male commercial sex workers, some of whom transported, or caused to be transported, over state lines.'
They also revealed evidence had been gathered of Combs' long-rumored sex parties — which he referred to as 'freak offs' — during their raids on his Los Angeles and Miami homes, finding, 'electronic devices that contain images and videos of the freak offs, with multiple victims.'
Diddy liked to plan and control the 'sex performances,' the feds alleged, that sometimes lasted 'days at a time,' and involved sex workers and a variety of narcotics such as ketamine, ecstasy, and GHB, 'which Combs distributed to the victims to keep them obedient and compliant.'
Diddy's legal team offered a $50 million package to secure his release from jail, including the rap mogul's Miami mansion, worth $48 million, as collateral.
It also includes the home of Diddy's mother, valued at $2 million.
September 24, 2024
Combs is sued by a woman who claims the rapper raped her and recorded the assault.
The alleged victim, Thalia Graves, says the music mogul, 54, and his head of security Joseph Sherman raped her the Bad Boy Records studios in New York back in 2001.
The alleged victim, Thalia Graves, says the music mogul, 55, and his head of security Joseph Sherman raped her the Bad Boy Records studios in New York back in 2001
Graves claims she was 25 and dating one of the rapper's employees when she was lured into a meeting by Diddy, who said he wanted to 'discuss her boyfriend's supposed performance issues.'
According to her lawsuit, Diddy and Sherman 'sequestered her' and gave her a drink that was 'likely laced with a drug that eventually caused her briefly to lose consciousness.'
In the lawsuit, obtained by DailyMail.com, Richard claims that she was 'manipulated' by Combs on promises that he would help her music career.
She also alleged that during the audition process for Making The Band, Sean had called female contestants various names, such as 'fat', 'ugly,' 'b****es' and also 'h***.'
In response, Erica Wolff, an attorney for Sean Diddy Combs, told DailyMail.com: 'Mr. Combs is shocked and disappointed by this lawsuit. In an attempt to rewrite history, Dawn Richard has now manufactured a series of false claims all in the hopes of trying to get a pay day — conveniently timed to coincide with her album release and press tour.'
September 27, 2024
Diddy is hit with a new lawsuit by a woman who claims he abused her for years and impregnated her.
The suit, filed under the name Jane Doe, was first reported by TMZ.
Jane Doe claims the rapper drugged and assaulted her over four years, and that she became pregnant during one of the encounters before suffering a miscarriage.
The alleged victim says she met Diddy in 2020, when she was invited to join him in an all-expenses paid trip.
The woman says Diddy's staff used 'coercive and harassing language' to force her to travel to see the music mogul.
Diddy allegedly inflicted physical injuries on the woman and forced her to take ketamine and other drugs, per the lawsuit.
The woman says she became pregnant in July of 2022 after she was allegedly drugged and assaulted.
She claims Diddy's associates harassed her to get an abortion before she miscarried.
October 2024
Diddy is hit with additional claims of abuse from 120 people - among them, an alleged victim who was nine-years-old when he says the rapper abused him.
The shocking new allegations were announced at by a lawyer who has taken on all of the cases, and intends to file them in various states.
Diddy's mother Janice Smalls Combs issued a statement in her son's defense.
'I come to you today as a mother that is devastated and profoundly saddened by the allegations made against my son, Sean Combs,' Janice, 84, told Dailymail.com in a statement through her lawyer Natlie G. Figgers. 'It is heartbreaking to see my son judged not for the truth, but for a narrative created out of lies.
'To bear witness what seems to be like a public lynching of my son before he has had the opportunity to prove his innocence is a pain too unbearable to put into words.'
Janice said claimed by rapidly settling Cassie's lawsuit suit late 2023 - a day after she filed it -her son opened himself up to litigation from others to go after him for financial gains.
November 2024
Combs is denied bail again after prosecutors alleged the rapper attempted to contact people he felt could testify in his favour as witnesses to influence public opinion before his trial began.
In a statement included in court documents, they said recorded jail calls made by Combs showed he urged family members to 'create narratives' to be picked up by a future jury.
Combs' legal team retorted that prosecutors made 'unsubstantiated claims of witness tampering'.
Sean 'Diddy' Combs, pictured with ex-girlfriend Cassie Ventura, is in the fight of his life as he faces decades behind bars in his ongoing federal trial
Kid Cudi sensationally revealed on the stand of Diddy's sex trafficking trial that his $140,000 Porsche was blown up after the hip hop mogul found out he had been seeing his girlfriend, Cassie Ventura
The disgraced rap mogul, 55, has been charged with two counts of sex trafficking, two counts of transportation to engage in prostitution and one count of racketeering
February 2025
Diddy's legal team say that the charge of 'transportation to engage in prostitution' should be struck off on grounds of racism.
Lawyers said their client was 'singled out because he is a powerful black man' and that 'no white person' has ever 'been the target of a remotely similar prosecution'.
April 2025
The indictment against Combs is updated with two new charges - another count of sex trafficking and another count of transportation to engage in prostitution.
Diddy pleads not guilty and applies for a delay to the trial scheduled to begin May 5.
The judge denied the request.
May 5, 2025
Jury selection began for Combs' trial.
May 12, 2025
A jury is selected and testimony begins in Combs' trial.
The disgraced rap mogul faces two counts of sex trafficking, two counts of transportation to engage in prostitution and one count of racketeering.
According to prosecutors, the rapper used his 'multi-faceted business empire' to carry out a 'criminal enterprise' for years, allegedly coercing victims into sexual 'freak off' marathons and threatening them into silence.
The racketeering and sex trafficking charges carry a minimum sentence of 15 years each, while transportation to engage in prostitution carries a maximum of 10 years behind bars.
The first weeks of the trial see Cassie, rapper Kid Cudi and male escorts testify against Diddy.
May 13, 2025
Cassie testified that she was left 'humiliated' by the marathon sex sessions explaining that she agreed to participate out of fear and a desire to please Combs.
The star witness in the federal sex trafficking and racketeering trial said she continued to participate in the freak-offs for years - sometimes on a nearly weekly basis - despite her discomfort.
May 27, 2024
A former employee testified that Combs threatened to kill rapper Kid Kudi.
Capricorn Clark, claimed Combs came to her apartment early one morning in December 2011, after he learned that Cassie had been dating the rapper Scott Mescudi, known as Kid Cudi.
Combs had a gun, Clark testified, and told her 'get dressed, we're going to go kill' Mescudi. 'I had never seen anything like this before,' Clark testified.
May 30, 2025
In the third week of the trial, the US President Donald Trump commented on the trial, saying that although no one had asked about a potential pardon, he would be open to looking 'at the facts' of the case.
During a news conference that served as a farewell for Elon Musk from the Oval Office, Trump was asked if he would consider pardoning Combs.
'Nobody's asked,' Trump said. 'But I know people are thinking about it. I know they're thinking about it. I think some people have been very close to asking.'
Noting that he hadn't been watching the case closely, Trump said, 'I would certainly look at the facts.'
June 13, 2025
Kanye West, legally known as Ye, made a brief appearance at Combs's trial to show support for Combs.
He was reportedly directed to an overflow room and left shortly after through the front entrance.
West was then seen getting into a car before driving away.
During the closing arguments, Ye released a song with one of Combs's sons titled Diddy Free.
Kanye West stunned the trial for Shawn 'Diddy' Combs as he showed up to support the disgraced rap mogul
West hugged Diddy's son Christian 'King' Combs as he made his surprise appearance at the trial
The day before his embrace with Kanye, Christian Combs, seen with Diddy's mother Janice, wore a t-shirt reading 'Free Combs' into the courtroom
June 16, 2025
Jurors at the Combs trial are shown video footage of the 'freak off' sexual encounters.
The clips, from 2012 and 2014, involved Cassie who earlier testified she had participated in the drug-fueled sex marathons out of fear of retribution from Combs, who reportedly physically abused her during their 11-year relationship.
The footage was not shown to the full courtroom, after the judge decided to conceal the material from reporters and members of the public who attended the trial.
Jurors watched the videos on screens that had been fitted with privacy guards and listened to the audio through headphones.
The videos were shown in a number of brief clips, around 30 seconds each.
Some footage was from an October 2012 stay at the Trump International Hotel in Manhattan, where two male escorts were invited to meet Cassie and Combs.
June 17, 2025
The judge dismissed a juror over conflicting residency claims.
The juror, identified as Juror 6, reportedly claimed during jury selection that he lived in the Bronx.
He later told court staff that he lived in New Jersey, making him ineligible for the New York jury.
'The record raised serious concerns as to the juror's candor and whether he shaded answers to get on and stay on the jury,' Judge Arun Subramanian said in court.
But Combs's legal team opposed the juror's removal. They argued that Combs would be 'severely prejudiced' if Juror 6, who they said was one of two Black men on the jury, were removed.
The alternate juror who replaced him was a white man from Westchester, New York.
June 24, 2025
After six weeks of letting his lawyers speak on his behalf, Combs addressed the court as he stood at the defence table out of the presence of jurors.
Asked by the judge, Arun Subramanian, how he was doing, Combs said: 'I'm doing great, how are you, your honor?' and quickly added: 'I wanted to tell you, thank you, you're doing an excellent job.'
June 27, 2025
Combs's lawyer made a final appeal to the jury, arguing that the government's evidence contradicted its case against the music mogul.
Lawyer Marc Agnifilo painted Combs out to be a flawed musician who had a drug problem and led a swinger's lifestyle but argued that the government's accusations that he was a sex trafficker or head of a racketeering organisation was 'badly exaggerated'.
'He did what he did,' Agnifilo said. 'But he's going to fight to the death to defend himself from what he didn't do.'
July 2, 2025
The verdict is in.
Combs was acquitted on Wednesday of sex trafficking and conspiracy charges, but convicted of transportation to engage in prostitution after the eight-week federal trial.
A jury in Manhattan found Combs not guilty to the most serious charges against him.
The result has been somewhat of a victory for the music mogul who faced life behind bars had he been convicted of other counts in the case.
He faces up to 20 years in prison on the two transportation for prostitution charges.
Each of the counts carries up to 10 years in prison, but the final sentence will be up to a judge.
