Warning: This story contains details of sexual abuse and domestic violence.
This time last year, Sean “Diddy” Combs had just released his fifth studio album, The Love Album: Off The Grid. It featured everyone from Justin Bieber to John Legend and snagged a Grammy nomination.
To much of the public, he was — as his lawyer Marc Agnifilo phrased it — “a music icon” and “self-made entrepreneur” who had spent “the last 30 years building an empire”.
But a civil suit alleging sexual and physical violence from ex-partner Casandra Ventura, known professionally as Cassie, would be the start of his downfall.
Cassie’s lawsuit was the first of multiple similar civil cases levelled against Combs, the most recent filed on September 25.
In less than 12 months, Combs has gone from a rap mogul/business entrepreneur/actor to being under lock and key in one of New York City’s most notorious prisons facing charges of sex trafficking and racketeering.
So, how did it come to this?
We break down who Sean Combs is, his rise to fame and where this could go from here.
The Past
Who is Diddy?
Sean “Diddy” Combs — who has gone by the names Puff Daddy, P Diddy and Love — is an American rapper, actor and entrepreneur who founded an entertainment empire, including Bad Boy Records, the clothing label Sean John and Revolt TV, which has since announced a new ownership structure. Combs was also the face of alcohol brand Cîroc Vodka, in a deal that ended acrimoniously.
Born in Harlem in New York City, Combs was just three years old when his father Melvin Combs was murdered after being mistaken for an informant during a drug deal gone wrong.
“My father was a hustler, he was a drug dealer,” Combs told Revolt.
“So, I learned early in life there was only two ways out of that, dead or in jail.”
He said that, despite taking a different path, he had his father’s DNA.
“I have his hustler’s mentality,” he said.
Combs with Uptown records founder Andre Harrell in a New York City nightclub in 1994. (Getty Images: Al Pereira)
Combs was nicknamed Puffy in his youth due to his habit of huffing and puffing whenever he was angry. (He changed his middle name from John to Love in 2021.)
Combs dropped out of Howard University in 1990 to pursue an internship at Uptown Records.
It would be a rapid rise at Uptown; before long, he was promoted to an A&R executive and later, vice-president.
How did Diddy build his empire?
Uptown has been home to artists such as Mary J Blige, Heavy D & The Boyz, and then Combs is said to have discovered the Notorious BIG, aka Biggie Smalls (real name was Christopher Wallace).
But Combs was fired from Uptown Records in 1993 by its founder, Andre Harrell.
“I got fired because there can’t be two kings in one castle,” Combs explained to talk show host Oprah Winfrey, saying getting fired was one of the best things that could have happened to him.
Sean Combs, singer Aaliyah (born Aaliyah Haughton, 1979 – 2001), and rapper the Notorious BIG (born Christopher Wallace, 1972 – 1997) pose together during a 1994 event. (Getty Images: Nitro)
He turned his attention to starting his own record label, Bad Boy Entertainment, taking Biggie with him.
In 1995, Biggie dominated the charts, making him Bad Boy’s premier star.
But on March 9, 1997, Biggie was murdered in an unsolved case amid an East Coast-West Coast feud. He was 24 years old.
A few months later, Combs released his debut album No Way Out under the moniker Puff Daddy. The album included the Grammy-Award-winning single I’ll Be Missing You, a tribute to Biggie, which featured his widow Faith Evans and sampled Every Breath You Take by The Police.
No Way Out won Best Rap Album at the Grammys, and Combs snagged Best Rap Performance by a Duo or Group for I’ll Be Missing You.
Combs with his award for Best Rap Performance by a Duo or Group at the 46th Annual Grammys. (Getty Images: Chris Polk)
He also dabbled in the silver screen at times: he played a death row inmate in 2001’s Monster’s Ball, starring Oscar-winner Halle Berry; a record executive in the comedy Get Him to the Greek in 2010 opposite Russell Brand; and he was a sports agent in the 2014 football drama Draft Day.
The Present
What happened with the Cassie lawsuit?
In November 2023, singer, Casandra “Cassie” Ventura filed a lawsuit against Combs, her former partner.
A day later, the lawsuit was settled.
Cassie states that she was 19 years old when she met Combs, who was 37, in 2005. She was signed to Bad Boy Records and lured “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”.
Cassie alleges, among other things, that Combs raped her, as well as punched, beat, kicked and stomped on her. She also alleges he forced her into sex trafficking, and demanded she carry his firearm in her purse.
Combs denied all allegations, but when CCTV was broadcast by CNN depicting Combs assaulting Cassie in a hotel corridor, he apologised for his behaviour in the footage.
What are “freak offs”?
Cassie alleges in her lawsuit that, within a few months of their romantic relationship, Combs told her he wanted to engage in a fantasy of his called “voyeurism”, and that it would turn him on to see her “with another dick”.
In an encounter that lasted multiple days, she says Combs hired a man who he directed Cassie to perform sexual acts on while he watched and masturbated.
Cassie Ventura and Sean Combs at the 2018 Met Gala in New York City. (Getty: John Shearer)
The lawsuit states that Combs referred to the arrangement as a “Freak Off” or “FO”. She says he would repeatedly tell her at random moments that he wanted to engage in one, and that she was expected to facilitate the location and hiring of the sex workers.
The lawsuit states: “He treated the forced encounter as a personal art project, adjusting the candles he used for lighting to frame the videos he took.”
From raid to arrest
In March 2024, US authorities raided Combs’ properties in Los Angeles and Miami as a part of an ongoing sex-trafficking investigation by federal authorities in New York.
Combs’ LA home was raided in March by federal law enforcement agents. (Getty Images)
Combs’ lawyers said the raids were “a gross use of military-level force“.
It would be another six months before Combs was arrested in New York, on September 16.
What is Diddy charged with?
Combs has been charged with racketeering conspiracy, sex trafficking by force, fraud or coercion and transportation to engage with prostitution, according to his unsealed indictment.
In a press conference, Damian Williams, the US attorney for the Southern District of New York, said the charges dated from 2008 to the present.
“The indictment alleges that … Combs abused, threatened and coerced victims to fulfil his sexual desires, protect his reputation, and conceal his conduct,” Williams said.
Williams announcing the federal indictment of Sean Combs
“As alleged in the indictment, to carry out this conduct, Sean Combs led and participated in racketeering conspiracy that used the business empire he controlled to carry out criminal activity, including sex trafficking, forced labour, kidnapping, arson, bribery and the obstruction of justice.”
The federal charges against Combs also include details about the alleged “freak offs” that Cassie mentioned in her lawsuit. Williams said victims were allegedly given illegal narcotics to keep them compliant, that the sessions were frequently recorded without the victims’ knowledge, and those recordings were used to silence victims.
The indictment also alleges that IV fluids were often administered to victims after “freak offs” to help recover from exertion and drug use.
What is racketeering?
Racketeering essentially means engaging in a criminal enterprise.
During the press conference, Williams explained how they applied in this case.
“Combs did not do this all on his own. He used his business and employees of that business and other close associates to get his way,” Williams said.
“They booked the hotel rooms and stocked them with the supplies … When the hotel rooms got damaged, they helped clean it up.
“They arranged for victims and commercial sex workers to travel for the freak-offs, and they delivered large quantities of cash to Combs to pay for the commercial sex workers.”
He also alleges that Combs used his associates to conceal his crimes by monitoring victims and preventing them from leaving locations.
What did the police find in the raids?
During the press conference, Williams revealed that firearms and ammunition were seized at Combs’ property during the March raids.
US Attorney Damian Williams stands next to a chart showing some of the items seized from Mr Combs’ properties. (Reuters: Shannon Stapleton)
This included three “defaced” AR-15 machine guns and a “large-capacity drum magazine”.
Evidence of the “freak offs” were also seized, including “electronic devices that contain images and videos of the freak offs with multiple victims” and more than 1,000 bottles of baby oil.
The Future
Will Diddy get out on bail?
Combs has been denied bail twice.
His legal team offered up $US50 million, the equity on his mother’s Florida home and the passports of his daughters (his own passport was taken in April) as security, but it was not accepted.
Sean Combs and his defence lawyers Marc Agnifilo and Teny Geragos seated during a bail hearing in federal court in Manhattan. (Reuters: Jane Rosenberg)
Part of the reason bail was refused was because Combs allegedly has a history of intimidating victims and witnesses, including brandishing firearms to “intimidate or threaten others”.
Court filings detail other intimidation incidents allegedly carried out by Combs and his associates, including kidnapping one person at gunpoint and slicing open a car’s convertible top to drop a Molotov cocktail inside, causing the car to explode.
