Day 25: Hotel Wreckage, Escort Records, and “Freak Off” Footage—Inside the Government’s Final Strike Against Sean “Diddy” Combs
By Trinity Barnette
As the prosecution edges closer to resting its case, Day 25 of the Diddy trial delivered a cascade of damning receipts, from explicit videos and bruising texts to financial records tracing escort travel and hotel damages back to Combs’ American Express. Jurors were shown flight bookings for sex workers, luxury hotel invoices soaked in damage fees, and an avalanche of text messages—some affectionate, others obsessive—painted across timelines of violence, control, and so-called “Freak Offs.” Cassie Ventura’s 2016 assault took center stage again as prosecutors laid out a timeline of frantic calls, disturbing surveillance, and remorseful texts from Combs himself. Meanwhile, the defense tried poking holes in the government’s case with cross-examinations, selectively presented messages, and questions about Ventura’s willingness. But the weight of the evidence—video, voice, and vivid documentation—suggests a pattern that’s becoming harder and harder to spin.
Flights, Escorts, and Hotel Bills—Where the Money Led
Cassie Ventura sent flight info to Jules for his return trip.
The jury also reviewed extensive hotel damage fees:
$500 for drape/carpet damage (Beverly Hills, 2015)
$950 for linen damage
A whopping $46,786 for penthouse destruction at the InterContinental Times Square (2012), booked under the name Frank Black.
‘Freak Offs’ and Surveillance—Videos, Voices, and the Jury’s Reaction
Footage came from Ventura’s devices, recovered under a “Frank Black” user profile.
One clip, nearly four minutes long, included audio audible in court. A female voice was heard—prompting a courtroom officer to alert the judge.
Jurors’ visible discomfort was noted—five out of six had their chins in their hands.
March 2016—From Bruises to Breakdown
A timeline reconstructed events after the 2016 InterContinental hotel assault:
Photos showed Ventura’s swollen lip and sunglasses at 11:36 a.m.
Surveillance captured her sitting on the floor in distress.
Ventura eventually texted: “I have a black eye and a fat lip… I’m not a rag doll. I’m someone’s child.”
Staff Coordination and LAPD Involvement
Khorram and Elie Maroun exchanged texts on damage control.
“I’m going to ask just to cover damages.”
“Say they had a fun drunk night…”
“Lol no shot they aren’t playing nice,” Maroun replied.
Kerry Morgan (Ventura’s friend) texted Khorram a photo of an LAPD card.
Ventura reportedly asked her to help frame it as a domestic violence incident.
Police later asked for the InterContinental security guard’s name, but Maroun wouldn’t provide it.
Two photos were recovered the next day from Ventura’s device—showing two men and someone on a couch.
The $100K NDA and Exchange for Silence
The exchange involved a nondisclosure agreement, and Khorram photographed his license.
Garcia and Combs had multiple calls between March 7–25, including two that lasted over a minute.
Ventura texted on March 7: “I should have sued lol.”
Morgan replied: “Totally.”
The Defense Fights Back—Selective Messages and Gaps
Defense attorney Teny Geragos emphasized messages where Ventura appears to initiate or participate in “Freak Off” planning.
In one, she texted she was “always ready to Freak Off.”
Combs wrote in 2013: “Maybe one of those nights.” She replied: “Yesss.”
Geragos claimed Ventura’s tone changed over time and questioned why only parts of the messages were used in the government’s chart.
She pushed special agent Penland to admit she only included names when there was documented proof.
The defense also brought up a 2016-17 New Year’s meeting that Penland said had no supporting records.
The Final Blow—“I’m So Sorry”
Ventura responded:“I still have crazy bruising… You always want to show me that you have the power and you knock me around. I’m not a rag doll. I’m someone’s child.”
Penland is now off the stand, as the prosecution prepares to rest.
