New details in Sean 'Diddy' Combs’ trial: Messages, 'hotel nights' and explicit videos presented to jury

The sex trafficking and racketeering trial against hip-hop mogul Sean "Diddy" Combs continued Monday in New York, with the jury reviewing a series of text messages, records and videos that shed light on the allegations against him.

The day, marked by key testimony and evidence presented by the prosecution, delved into the dynamics of so-called "hotel nights" and interactions between Combs, his ex-girlfriend Cassie Ventura, his former chief of staff Kristina Khorram and other team members.

Text messages revealing the planning of the "hotel nights"

The jury examined text messages detailing how Combs' staff arranged hotel rendezvous for him and Cassie Ventura. In a March 2016 exchange, Khorram and other assistants discussed the logistics of adding an escort's name to a hotel room reservation and bringing $4,000 in cash to the location.

In one message, Khorram warned an attendee, Dave Shirley, that Combs was "about to do wild king tonight," to which Shirley responded with a comment about restocking on “baby oil and shit.” Another message showed Khorram informing Ventura that "Dave is at your door with the green," suggesting the delivery of money.

In November 2021, the jury saw texts between Combs and Khorram coordinating another "hotel night." Combs asked that the room be ready and that the hotel not know his identity to avoid "unneeded charges.”

Khorram instructed him to wait until Jane (who dated Combs from 2021 to 2024) and an assistant named Joey arrived. Later, Khorram reported that "Paul," a man previously mentioned by Jane as a participant on these nights, would be coming to the room.

High hotel damage costs

The prosecution presented messages from February 2022 between Khorram, Jane and Combs discussing high charges for damage to a hotel room. Khorram commented that “damage charges on the one hotel are always high,” and asked Jane to order 15 bath towels. Jane, in turn, asked if the security team could carry between $5,000 and $10,000 in cash, to which Khorram replied that the money was in Combs' safe.

Drug purchases

The text messages also revealed discussions about drug purchases. In December 2021, Combs and Khorram discussed a package delivered by a dealer named "Guido."

In another exchange, Combs' head of security, Faheem Muhammad, obtained approval to pay thousands of dollars for drugs, including "flower" (marijuana). In April 2023, Combs explicitly requested “Molly, 15 pills" through messages with Khorram and Muhammad, who also confirmed giving $5,000 to an assistant for hotel expenses.

More messages from Cassie Ventura

Cassie Ventura, a central figure in the case, appeared in May 2017 messages with Khorram, where she expressed her distress after an incident with Combs.

“No one deserves being dragged by their hair,” Ventura wrote, adding that she had locked the door for her safety and did not have her belongings or money. Khorram offered to talk to Combs about how to resolve the situation.

Jane, another key witness, recounted being threatened by Combs with "sex tapes" following Ventura's November 2023 lawsuit.

In messages recovered from Khorram's devices, Jane expressed feeling “exploited, heartbroken and manipulated” for three years.

In a subsequent communication, Jane informed Khorram that Combs had threatened to send those videos to her son's father.

The explicit videos presented to the jury

For the first time, the jury viewed explicit videos of so-called "Freak Offs," sexual encounters arranged by Combs. The clips, recorded between 2012 and 2014, lasted just over two minutes and were shown only to jurors, the judge and the parties with headphones, with no access to the public. Some jurors showed discomfort.

Interactions with staff and key witnesses

Special Agent DeLeassa Penland and paralegal specialist Ananya Sankar, summary witness, guided the jury through records and messages.

Penland presented evidence of travel and hotels from 2009 and 2012, including a meeting at the London Hotel in New York with Combs, Ventura and a companion, paid for with Combs' card. Sankar showed charts summarizing previously undisputed messages, such as those of Combs attempting to contact his former assistant "Mia" in 2024, whom he alleged had sexually assaulted between 2009 and 2017.

Defense challenges evidence

Defense attorney Teny Geragos cross-examined Sankar, highlighting messages that could suggest consent, such as one from Jane in 2022, in which she expressed being “excited to surprise” Combs with a room decorated for Valentine's Day.

Geragos also pointed to a message from Jane in 2023 in which she resisted Khorram's pressure to make plans, saying, “my answer to him is no and it is still no.” In addition, the defense stressed that there were no records of Combs contacting Mia after learning she was out of the country.

The trial

The case, which has been going on for six weeks, centers on allegations of sex trafficking, prostitution, kidnapping and more against Combs.

Key witnesses such as Ventura, Jane, and the ex-assistant, Mia, have provided testimony about abuse, coercion and the "Freak Offs."

The prosecution has presented more than 30 witnesses, while the defense seeks to argue that the encounters were consensual.

The presence of Combs' mother in court added a personal element to the day.