analysis

Diddy’s trial reveals the more, the murkier, freak off parties with excess of depravity

Monica Hesse
The Washington Post
The Washington Post: Diddy’s mind-boggling trial has revealed an excess of depravity at the rapper’s ‘freaky-deaky’ parties
The Washington Post: Diddy’s mind-boggling trial has revealed an excess of depravity at the rapper’s ‘freaky-deaky’ parties Credit: Scott Gries/Getty

There is a reason that the most gawked-over detail from Sean “Diddy” Combs’s 2024 criminal indictment was the allegation that law enforcement had seized, from his residences, more than 1000 bottles of baby oil and lubricant.

The reason is that this number is insane. A professional massage therapist couldn’t get through that oil supply in five years. A typical human couldn’t get through it in a lifetime.

That figure, taken as a discrete fact, proved nothing about the criminality of Diddy’s bedroom predilections, but by God did it reveal something about the excess.

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Combs’s trial began this month, the goal of which is to determine whether he is guilty of sex trafficking and racketeering. Was he, as his defence team suggests, merely a polyamorous mogul with some freaky-deaky tastes and the money to satiate them? Or was he, as the prosecution proffers, illegally plying women and male escorts with drugs that obliterated their consent before making them perform degrading acts in expensive hotels?

In the early days of a trial expected to last at least eight weeks, it might be too soon to responsibly offer guilt-or-innocence judgments out loud. (Though, man, once you’ve seen the surveillance footage of Combs slamming Cassie Ventura to the ground and kicking her while she cowered, you might need to repeat “innocent until proven guilty” with the fervour of a nun clasping rosary beads to keep the judicial faith.) But it’s not too early to remark upon the unfathomably stage-managed excess.

Both the prosecution and the defence agree that there was sex in hotel rooms. Sometimes between Combs and women he was dating, often between those women and male escorts who were paid to be there.

Paris Hilton with the host at one of the White parties
Paris Hilton with the host at one of the White parties Credit: Jon Furniss/WireImage for MAC Cosmetics

The sex parties were called “freak-offs.” There were, we have heard in the trial, a specific brand of candles, so many candles. A specific brand of lubricant, so much lubricant.

There were piles of cash so large that one recipient testified he couldn’t even begin to quantify the value.

“It was just 100-dollar bill on the top, and then the rest were just — it was just a stack of money,” Daniel Phillip, a sex worker hired to sleep with Ms Ventura, told the jury. He was then asked how big the stack was. “I don’t know,” he said. “If you extend your thumb to your pinkie.”

Thermostats were always set to Combs’s preference, as was lighting. Ms Ventura testified that Combs required her nails to be not only manicured but “white or French-tip.”

She testified that he dictated her entire life, from the terms of her career, to the way she dressed, to whom she spoke with, and that when she did not do exactly what he wanted exactly when he wanted it, he would often respond with violence: “knots in my forehead, busted lips, swollen lips, black eyes, the whites of my eyes would be red, bruises all over my body.” (Combs’s defence team does not deny that he was physically abusive but has said that Ms Ventura was also abusive, and that none of the acts in the relationship constitute sex trafficking.)

She testified that he asked her what she’d called her grandfather (“Pop-pop”) and then told her that this is what she would now call him. She testified that she had been young and inexperienced when they met — that she didn’t even understand the “vocabulary” he was using when he described the things he wanted her to do, and then she had to do those things all the time.

Her testimony was intimate, revealing and horrible. There were details that were probably important for a jury to hear but that I cannot bring myself to repeat here.

“He knew specifically where he wanted everyone to be, the lighting and such,” she told the jury. She said that every freak-off was “directed by Sean”.

You cannot read the trial transcripts without remembering that we are talking about the same man whose White Parties were the star-studded social event of the 2000s and late ’90s.

The man who not only curated a guest list but also demanded an aesthetic, inviting Paris Hilton and Moby and Leonardo DiCaprio and Lil’ Kim out to the Hamptons to sit on his lawn while requiring them to wear the colour of clothing most impractical for sitting on lawns. The kind of concept that could have only been created by the kind of man whose exacting vision was met by his exorbitant bankroll.

After being shown images from a Freak Off (not shown to the public), jurors are shown images of what Casandra "Cassie" Ventura described as bruises from Sean "Diddy" Combs
After being shown images from a Freak Off (not shown to the public), jurors are shown images of what Casandra "Cassie" Ventura described as bruises from Sean "Diddy" Combs Credit: Jane Rosenberg/REUTERS

Mr Phillip testified that he would be at the freak-offs for up to 10 hours as Combs obsessively barked out orders and instructions regarding the kinds of intimate acts he wanted to see enacted in front of him.

Ms Ventura testified the longest freak-off she participated in lasted four days. Previous court documents have alleged that the sessions would sometimes go for such a long time that when they finally ended, a depleted Ms Ventura required IV fluids

In the footage of Combs attacking Ms Ventura in the elevator bay as she tried to leave after a freak-off, you can see the sun shining outside; a security guard testified that it would have been around 11am, and in all of the monstrous things we have learned in the trial, this detail keeps absurdly standing out to me. 11am! The indignity of being forced to continue a sex marathon performance when you should be folding laundry or visiting the dentist.

Each sexual abuse scandal that has come to light in recent years — starting with Harvey Weinstein; Weinstein is always case zero — has brought with it its own unique rot, its own necrosis of the soul. For Weinstein: the worst manifestation of the casting couch, actress after actress trying to fight off a man who could end their careers with a casual phone call.

For Bill Cosby: the roofies, the disorientation, the perversion of America’s dad into a monster. For Louis CK: the confusing conflation of a man and his art. Onstage, he made jokes about being the kind of man gross enough to do the things he was actually doing in real life.

As I have followed the mind-boggling case of Combs, the word that kept coming to mind was “more”. More sex, more women, more money, more ego, more carelessness, more cruelty. Everything was expensive and everyone was expendable.

Ms Ventura testified that the freak-offs happened more and more frequently, weekly, and that she used ecstasy and “molly’ to get through them, and eventually she used cocaine. Mr Phillip testified that, after Combs had given him the drug Molly, Mr Phillip wandered out of the hotel and started passing out gobs of cash to passersby.

“But how did the Molly make you feel?” the prosecutor asked, and Mr Phillip responded, “It made me feel like a jackass that wanted to go out in the middle of Times Square and hand out $100 bills to every person he saw.”

And the money and the drugs and the baby oil kept flowing, and Combs, who during the course of his career had renamed himself Puffy, Puff, Puff Daddy and P. Diddy, allegedly also went searching for a more fitting name for his elaborate private events. They went from being called freak-offs, the prosecution said, to “wild king nights” or “hotel nights”.

Into that linguistic transmogrification, you can read all kinds of things. Did Combs first decide that “freak-offs” sounded too pedestrian? Was the banal “hotel nights” meant to sanitise the activities in his own mind, or was it just a subversive wink? Has there ever been a more desperate-sounding name than “wild king nights?”

Whatever elaborate production Combs was trying to stage, did he get there? Did it ever look just as he’d imagined?

Not long into this sordid, seedy trial, it doesn’t look like a case of power and money corrupting; this looks like a case of power and money dementing — a circumstance where power causes the person who possesses it to cease seeing those around him as people at all.

Where he sees them instead as life-size Barbies, existing only to be positioned, propositioned, beckoned, cast out, dragged back, flung around and ultimately discarded when they got too decrepit to be of use.

Where no matter what happens, he still wants more.

Casandra Ventura, a singer known as Cassie, is the star witness against Sean "Diddy" Combs.
Casandra Ventura, a singer known as Cassie, is the star witness against Sean "Diddy" Combs. Credit: AAP

The freak-offs “became a job where there was no space to do anything but to recover and just try to feel normal again,” Ms Ventura testified. They made her feel dirty and they made her feel confused and eventually they consumed her entire life.

“Y’all need to rub more baby oil on each other,” Mr Phillip recalled Combs instructing, the very first night Mr Phillip showed up at the mogul’s hotel suite, when Mr Phillip had expected to merely dance for a bachelorette party and instead found himself embroiled in a situation that would alternately enthral, disgust, terrify and sadden him, a situation that would last for years.

“He would say, you’re too dry,” Ms Ventura testified, saying that the baby oil was supposed to be reapplied every five minutes. “You need to put on more oil. You need to be glistening. You need to be shining.”

One time there was a small blow-up swimming pool, she said, at a hotel in Beverly Hills that she thought might have been L’Ermitage, and it was filled with oil. Bottles and bottles and bottles of oil.

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The Nightly cover for 16-05-2025

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DIDDY’S WORLD OF DEPRAVITY: 1000 bottles of baby oil. Stacks of cash. Booze and drugs.