EXCLUSIVEDiddys ex-girlfriend Cassie Ventura seen with bruise marks around her eye in unearthed photos - years before shocking caught-on-video hotel assault

DailyMail.com has unearthed a disturbing cache of photographs showing Diddy’s ex-girlfriend Cassie Ventura with what appear to be bruises on her forehead and a black eye.

The pictures, which were taken in 2013 while the pair were dating, show the disgraced rapper, 54, and Ventura, 38, arriving at a party in Kingston, Jamaica, in January that year.

Ventura can be seen wearing a pair of dark glasses with a glimpse of what looks like bruising beneath them while a small dark mark is visible on the side of her head.

Sean Diddy Combs attended a party in 2013 with his then girlfriend, Cassie Ventura, in Kingston, Jamaica 

Ventura was pictured with what appears to be dark bruising hidden behind her sunglasses which she wore despite the party starting at night

Ventura was also pictured with a small dark spot on the side of her head, believed to be another bruise 

She is also sporting white nail polish which, she revealed in court papers filed late last year, was a shade chosen by Combs because the hue stood out during his infamous ‘freak off’ orgies.

Combs, meanwhile, is seen clutching Ventura’s hand as the ex-couple headed into the Jamaican capital’s Lime Light Entertainment complex for a party following his performance at that year’s Bad Boys Sound Clash.

The couple split in 2018 with Ventura filing a civil case against the billionaire rapper in November 2023 accusing him of subjecting her to a decade of beatings and other abuse.

In the civil case, which was settled shortly after it was filed, Ventura described how she had been forced to participate in the weekly ‘freak offs’, which included her being made to have sex with black male prostitutes and plied with drugs.

Among the orgies detailed in the papers was a particularly wild 2013 event – the same year DailyMail.com’s photos were taken – that caused tens of thousands of dollars’ worth of damage to a luxury hotel room.

The papers read: ‘On one occasion around 2013, Mr. Combs had an FO set up at the InterContinental Hotel in New York City, after which he was charged with tens of thousands of dollars in damages by the hotel.

‘Upon information and belief, Mr. Combs’s Chief of Staff Toni Fletcher paid the invoice charged by the hotel.

The lawsuit also notes that the white polish was chosen because it stood out against the gigolos’ dark skin.

The filing says: ‘Mr Combs insisted she wear white nail polish to contrast with the skin of the black men he hired to have sex with her’.

Although Diddy had repeatedly denied Ventura’s allegations about his physical abuse, the publication of the video by CNN forced him into a groveling public apology where he described his behavior as ‘inexcusable’

Ventura was captured with her nails painted white. Her lawsuit against Combs claimed she was forced to wear the color during his freak offs 

According to Ventura, her enforced participation in freak offs began in 2007, shortly after the pair began dating, and routinely included her being plied with narcotics while Combs filmed the encounters

Combs and Ventura began dating in 2007 and were together on and off for eleven years. She claims she was forced to participate in the freak offs

According to Ventura, her enforced participation in freak offs began in 2007, shortly after the pair began dating, and routinely included her being plied with narcotics while Combs filmed the encounters.

Ventura says she was frequently made to search escort websites for ‘large black penises’ and was expected to ‘dress up in lingerie’ for the events.

She also endured years of physical abuse which the rapper denied until a harrowing video showing him beating her at the now-closed InterContinental Hotel in Beverly Hills emerged earlier this year.

The surveillance footage, shot in March 2016, shows Combs who was wearing nothing but a white towel rushing up behind Ventura and grabbing her by the neck before shoving her to the ground.

Combs is then seen kicking the mom-of-one several times as she lies motionless on the ground before dragging her by her sweatshirt back towards their hotel room.

Combs, who was wearing nothing but a white towel, could be seen on camera rushing up behind Ventura and grabbing her by the neck before shoving her to the ground

Ventura was seen being beaten by Combs before dragged away by her sweatshirt towards their hotel room

Although Diddy had repeatedly denied Ventura’s allegations about his physical abuse, the publication of the video by CNN forced him into a groveling public apology where he described his behavior as ‘inexcusable’, adding: ‘I was disgusted then when I did it. I’m disgusted now.’

His public mea culpa was not enough to shield him from the attention of law enforcement, however, and he has since been hit with federal charges of sex trafficking, racketeering and transportation to engage in prostitution.

The indictment, seen by DailyMail.com, echoes Ventura’s civil lawsuit and also sees Combs accused of involvement in kidnapping, forced labor, bribery and intimidation.

The documents also shed further light on his penchant for orgies, with prosecutors referring to multiple victims and describing how raids on his LA and Miami mansions earlier this year yielded videos of the events, as well as ‘supplies’ including 1,000 bottles of baby oil and illegal drugs. 

The federal indictment against Combs accuses the rap mogul of being involved in kidnapping, forced labor, bribery and intimidation as well as sexual offenses involving his freak offs

 Prosecutors say Combs used ‘threats, force and coercion’ to make his lovers, Ventura among them, ‘engage in extended sex acts with male prostitutes’.

The indictment added: ‘freak offs occurred regularly, sometimes lasted multiple days, and often included multiple commercial sex workers.

‘During freak offs, Combs distributed a variety of controlled substances to victims, in part to keep the victims obedient and compliant.’

Combs was arrested in Manhattan last month and is currently banged up at the Metropolitan Detention Center in Brooklyn.

On Thursday, he appeared in a New York court room for a status conference in leg chains and was once again denied bail.

He is now scheduled to face trial in May and will return to court next month.