Inside Day 27 of the Sean “Diddy” Combs Federal Trial
The high-profile sex trafficking trial of Sean “Diddy” Combs continued in a New York federal courtroom, heading towards its conclusion as U.S. government prosecutors prepared to rest their case. Day 27, which took place on June 20, 2025, following a brief halt earlier in the week due to a sick juror and the Juneteenth holiday, featured compelling testimony from a former personal assistant and the presentation of revealing text messages.
Here’s a breakdown of the key developments from the courtroom:
Former Assistant Details Grueling Demands and Drug Procurement
Brendan Paul, who served as one of Combs’ personal assistants from late 2022 to March 2024, took the stand, painting a vivid picture of the demanding nature of the job. Earning a reported $100,000 annually, Paul described the role as “intense,” recounting instances where he worked without sleep for three consecutive days. He characterized working for Combs as requiring SEAL Team 6-level dedication, stating the music mogul “did not take ‘no’ for an answer.”
Paul testified under immunity, confirming he was instructed to purchase thousands of dollars’ worth of various drugs for Combs. He detailed procuring drugs from dealers using specific aliases, referring to hard drugs as “Gucci items” that he would place in a Gucci pouch. A text message shown in court included a dealer asking if drugs were for Paul or “Puff,” to which Paul replied they were for “Puff” but should be charged to him. He also confirmed procuring Cialis and Xanax for Combs, referencing specific text requests.
Paul’s testimony also touched on his March 2024 arrest for cocaine possession at a Miami airport while traveling with Combs. He stated the cocaine belonged to Combs but admitted he initially didn’t inform authorities out of “loyalty.” While acknowledging purchasing drugs, Paul’s attorney later issued a statement reiterating his client was “never a drug mule,” a point Paul also seemed to emphasize under cross-examination, agreeing it was a minor part of his duties.
Beyond drug runs, Paul testified about being directed by Combs’ chief of staff to arrange hotel rooms for events described as “Wild King Nights” involving Combs and an alleged victim referred to as “Jane.” His duties included extensive room preparation – ordering extra linens, bringing specific lighting, lubricants like AstroGlide and baby oil, and alcohol. He maintained a “running list” of supplies for these events. Paul indicated that a network of staff, including the chief of staff, property managers, security, and travel managers, were involved in facilitating these nights and obtaining drugs, which prosecutors suggest points to a structured criminal organization. Following these events, Paul testified he would clean the rooms, sometimes wearing gloves for sanitary reasons, and once photographed a disarrayed room to anticipate damage charges.
During cross-examination by defense attorney Brian Steel, Paul offered testimony that seemed to support the defense’s narrative regarding “Jane,” agreeing that she did not appear hesitant or apprehensive before or during sexual encounters (“freak offs”) and seemed to be a willing participant. This appeared to contradict “Jane’s” earlier testimony. Asked about his current feelings towards Combs as his testimony concluded, Paul offered a cryptic response: “It’s complicated,” acknowledging he learned a lot and felt “indebted” to Combs for the most part, despite the demanding work and noting Combs became “extremely creative” when using drugs.
Texts Reveal Allegations of Abuse and Conflicting Narratives
Prosecutors presented jurors with text messages exchanged between Sean Combs and his former long-term girlfriend, Cassie Ventura, highlighting conflicting dynamics in their relationship. In one powerful exchange, Ventura wrote to Combs, stating she didn’t deserve to be beaten by him and declaring, “That’s not love, that’s possession,” in an apparent reference to a recorded 2016 hotel assault.
Further texts from March and May 2017, a year after the reported incident, showed Ventura expressing being “scared” of Combs’ “rage” and not wanting to be “beat down for being defiant.” She wrote, “You hit me in my head two good times. That didn’t make me feel good.” Ventura also accused Combs of treating her “like a hooker,” recounting being hurt and dragged down the hall by her hair after he was “fed up.” She wrote of feeling “dead” at one point. Combs’ replies reportedly included accusations of her being unappreciative, acting like a “b,” wishing he hadn’t “wasted” time on her, stating she started it, and complaining she didn’t treat him “like the king.”
Conversely, the defense sought to portray some encounters as consensual, entering into evidence a March 2017 text message from Ventura that read: “I love our FO’s, when we both want it.” This text directly countered the prosecution’s narrative of non-consensual “freak offs.”
Digital Evidence Takes Center Stage
Special Agent Joseph Cerciello with the Department of Homeland Security testified as a government summary witness, corroborating charts compiled by prosecutors that linked thousands of pages of records, including text messages, travel data, and financial documents. Cerciello’s testimony included reviewing travel data related to Combs and “Jane” and presenting evidence of significant hotel damage fees charged to Combs following stays, including a $6,000 bill in 2021 and over $13,000 from two separate stays in 2023, with details citing damaged furniture, bodily fluids, and linens soaked in baby oil. He noted that while travel data showed numerous hotel stays for Combs and “Jane” before Ventura’s lawsuit in November 2023, records of such visits ceased afterward.
The analysis presented in court highlighted the critical role of digital evidence like text messages and financial records in modern federal trials. In this case, these documents serve as powerful, arguably “star witnesses,” allowing prosecutors to present the defendant’s own statements and patterns of behavior without him having to take the stand. While the defense can argue context, the sheer volume and detail of these records, meticulously compiled by agents and prosecutors, present a formidable challenge.
What’s Next in the Trial*
U.S. government prosecutors are expected to formally rest their case early the following week, likely on Monday. The defense team has indicated their presentation will be significantly shorter, potentially lasting only one or two days. Based on this timeline, closing arguments could commence as early as Thursday, potentially leading to jury deliberations shortly thereafter. Sean Combs faces serious charges including racketeering conspiracy, sex trafficking, and transportation to engage in prostitution, to which he has pleaded not guilty, with his defense arguing consensual encounters and that any violence did not constitute sex trafficking or racketeering.
