Day 29 of the federal trial against Sean “Diddy” Combs brought intense focus on highly explicit video evidence and saw the presiding judge issue a sharp rebuke to attorneys on both sides over alleged leaks. Combs, facing charges including sex trafficking, racketeering conspiracy, and transportation to engage in prostitution, has pleaded not guilty to all counts.
Jury Watches Extensive ‘Freak-Off’ Videos
A central event of the day was the Manhattan jury’s extensive viewing of graphic videos depicting alleged drug-fueled sex parties. These recordings, referred to as “freak-offs” or “hotel nights,” are considered key evidence in the prosecution’s case. Wearing headphones and with their video monitors concealed from public view in the courtroom gallery, jurors watched lengthy clips that the prosecution alleges were created and saved by Combs.
While jurors had previously been shown brief excerpts and screenshots, Tuesday marked their first in-depth look at the footage. Special Agent DeLeassa Penland of U.S. Homeland Security Investigations, who presented the videos, reportedly appeared visibly uncomfortable during this segment of her testimony. Despite the sensitive nature of the content, sound from the audio feed reportedly bled through the courtroom gallery at times.
Prosecutors contend these videos were intended as blackmail material to silence women, citing former girlfriend Cassie Ventura’s testimony that she feared for her career and family if such videos were released. Ventura described the act as “horrible and disgusting.”
Combs’ defense team, however, presented the videos as powerful evidence against the prosecution’s claim of coercion. During cross-examination of Agent Penland, the defense showed longer excerpts and argued the footage demonstrates consensual participation by the women involved in these lengthy sessions. Defense attorney Teny Geragos has stated these videos are “powerful evidence that the sexual conduct in this case was consensual and not based on coercion.” Due to their explicit nature, the videos remain under seal, inaccessible to the public and media despite requests.
The Contentious Debate: Consent vs. Coercion
The viewing of the videos fueled the ongoing debate between the prosecution and defense over whether the sexual encounters were consensual or coerced.
The defense used their cross-examination of Agent Penland to highlight text messages they argue show Cassie Ventura’s enthusiastic involvement in “freak-offs.” Examples presented from late 2012 included texts from Ventura about buying “sexiest outfits for later,” being “really horny,” promising to be the “nastiest freak b,” and engaging in explicit role-play (“I am not Cassie and you are not Sean”). The defense maintains these messages directly contradict claims that Ventura was an unwilling participant merely texting what she thought Combs wanted to hear – an assertion Ventura herself made in prior testimony.
Conversely, during re-direct examination, the prosecution focused on messages sent after the widely publicized 2016 hotel attack on Ventura by Combs (captured on surveillance video shown earlier in the trial). Five days after the assault, Combs sent profusely apologetic texts, to which Ventura replied noting her “crazy bruising from Friday,” stating that “Nothing good comes out of (‘freak-offs’) anymore,” and starkly comparing Combs’ treatment of her to Ike Turner. Phone records immediately following the attack also showed Combs made numerous unanswered calls and demands for Ventura to contact him, including the false claim he was “about to be arrested.” Ventura’s single response at the time detailed her injuries (“black eye and a fat lip”) and her disbelief at his actions before a film premiere where her injuries would be visible.
Evidence related to the transportation charges was also discussed, including flight itineraries and payments for both Cassie Ventura and a male escort, identified by Ventura as “Jules Theodore,” with whom she was allegedly made to have sex as part of a “freak-off.” Texts and emails from 2009 regarding booking flights for Jules were presented.
Linking Business Empire to Alleged Crime
Prosecutors continued their efforts to demonstrate how Combs allegedly leveraged his extensive business empire to facilitate a criminal enterprise. Through Agent Penland’s testimony as a summary witness, financial records were introduced linking Bad Boy Entertainment accounts to expenses associated with the alleged “freak-offs.”
Evidence included:
A substantial $46,786 bill for damages to a penthouse suite at the InterContinental Hotel in New York in October 2012, booked under Combs’ alias “Frank Black.” This bill, part of a total $944,059 American Express statement for the month, was paid through multiple bank accounts controlled by Combs’ companies. Witnesses have alleged damages were often due to substances used during the parties.
Travel costs, including flights for Cassie Ventura and the alleged escort “Jules Theodore” in 2010, paid through a Signature Bank account held by Bad Boy Entertainment Worldwide.
- A charge for Diptyque candles, allegedly used during a “freak-off,” appearing on a large American Express statement paid by a Bad Boy Entertainment account.
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Prosecutors argue these records show how Combs intertwined his business and personal finances to orchestrate the alleged sex parties, using company funds to cover significant costs like travel, hotel damages, and potentially payments to escorts.
Aftermath of the 2016 Assault and Khorram’s Role
Beyond the financial links, text messages related to the 2016 assault video became a focal point, showing the alleged efforts by Combs and his staff to manage the fallout. Messages involving Kristine Khorram, Combs’ then-chief of staff, depicted her scrambling in 2016 to prevent the video from seeing the light of day. The video was later broadcast on CNN and has been repeatedly played during the trial.
After Ventura stopped responding to Combs following the incident, texts showed Khorram intervening, messaging Ventura to “Just talk to him” and stating she didn’t “want him to go back over there” (referring to the hotel). In a separate exchange, Khorram reportedly instructed an assistant to minimize the incident by saying they “had a fun drunk night try to get more info.” D-Roc, Combs’ bodyguard, also called Ventura multiple times and texted Combs that her face didn’t look bad.
While Khorram has not testified and is not charged, federal prosecutors have portrayed her as a key figure, describing her as an “agent and co-conspirator” in the alleged racketeering conspiracy. Khorram has publicly denied wrongdoing in response to civil lawsuits, stating she never condoned or aided sexual assault or drugging. A text from alleged victim “Jane” to Khorram expressing a desire for “no more hard-partying and no more hotel nights” was also introduced.
Judge’s Stern Warning and Juror Dismissal
The day began with U.S. District Judge Arun Subramanian issuing his most forceful warning yet to lawyers on both sides. Expressing clear frustration, the normally cool-headed judge threatened sanctions, including criminal or civil contempt charges, over alleged violations of the strict gag order imposed on the case.
Subramanian referenced a news article containing non-public information, though he did not specify the article or the leaked details. When attorneys pleaded ignorance, the judge directly stated, “Someone’s lying.” He vowed a swift investigation to “punish” the responsible party and warned lead counsel that the buck stopped with them, even threatening to compel attorneys to testify and allow examination of their electronic devices. “This is the only warning I will give,” he stated.
This warning coincided with a closed courtroom session to address an unresolved issue concerning a juror. Reports indicate Juror 6, a Black male, was dismissed due to a “lack of candor” regarding his residence after giving inconsistent answers, raising suspicions about his motivation for being on the panel. The defense argued that replacing him with a white male alternate disrupted jury diversity, but the judge dismissed this, stating race could not be a factor in such decisions.
Trial Nearing Conclusion
The prosecution is expected to rest its case by the end of the week, with plans to call two more witnesses on Wednesday: a former college basketball player-turned-personal assistant for Combs (reportedly Brendan Paul, who has immunity and may testify about obtaining drugs like GHB) and a final summary witness.
Defense lawyers informed the judge they plan to present a relatively brief case, anticipated to take between two and five court days, possibly even shorter. Their first witness is expected to be Vashta Dunlap, a former executive at Combs’ Bad Boy Records label. The judge indicated that a short defense case could allow for closing arguments as early as next week.
Combs remains in custody at Brooklyn’s Metropolitan Detention Center since his arrest in September 2024. If convicted on all counts, he faces the possibility of life in prison.
