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Day 17 of the Diddy Trial: Bryana Bongolan Cross-Examination and ‘Jane’s’ Stunning Testimony

  • June 5, 2025
  • Trent Lucas
the prosecution rests its case
Image Credit: Prince Williams / Contributor | Getty Images
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On the 17th day of Sean “Diddy” Combs’ federal trial, the courtroom again was on Bryana Bongolan‘s cross-examination, a critical part of the defense tactic to impeach testimony. Postponements had pushed the schedule later than usual, so jurors were informed to accept a shortened lunch when testimony in the high-profile proceeding continued. 

Bryana Bongolan Back on the Stand

Bongolan, who previously claimed that Combs held her over a Los Angeles balcony in 2016, was probed by defense attorney Nicole Westmoreland on why she remained with Combs’ and Cassie Ventura‘s companions after the reported incident. She admitted to getting high on drugs and visiting Ventura’s apartment a short while after the balcony incident. When asked if she was afraid of Combs, she paused and replied in a dazed tone as if she may not have been afraid.

The defense identified apparent inconsistencies in her memory. Bongolan had previously testified that Ventura had witnessed what occurred, but now could not recall seeing that. She described nightmares about what had happened, but was presented with ongoing contact with Combs, like smoking a blunt after the event.

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Text messages entered into court evidence showed that Bongolan had agreed to Ventura’s invitation for a night out at the very same apartment complex where the said incident happened. This, the defense argued, invalidated her claims of trauma or fright.

Shattering the 2016 Timeline

A lot of the defense was focused on discrediting Bongolan’s timeline. Westmoreland presented a receipt from a hotel that proved Combs to be in New York at the Trump International Hotel from September 24 through September 29 of 2016, the same period Bongolan said he was in Los Angeles and assailed him.

The defense blatantly accused Bongolan of fabrication, which she denied. She acknowledged some of the claims in a lawsuit she filed through her lawyer Tyrone Blackburn were false, including one for physical injury. However, Bongolan substantiated the main claim of being thrown over the balcony, saying she came forward for justice, although all details could not be recalled.

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Analyst Presents Cellphone Evidence

When Bongolan departed from the stand, federal prosecutors called Enrique Santos, a digital forensic specialist from the U.S. Attorney’s Office. Santos testified briefly on the undeletion of text messages on the phone of Cassie Ventura. Among the messages, it showed that Ventura told Combs Enterprises’ chief of staff Kristina Khorram, about the 2016 event.

Though Ventura acknowledged she did not witness it herself, the note suggested that she at least believed it took place, possibly lending legitimacy to Bongolan’s testimony and reaching potential liability on the part of Combs’ business, which prosecutors allege is connected to a broader racketeering conspiracy.

New Witness ‘Jane’ Takes the Stand

In the afternoon, another highly anticipated witness, testifying anonymously as “Jane,” testified. She told jurors she had dated Combs between 2021 and 2024. Judge Arun Subramanian warned jurors that while her real name would be known to them, it would not be made public for her protection.

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“Jane” described a loving beginning with Combs, recalling text messages in which they referred to each other as “Bert and Ernie.” Her testimony took a dark turn, however.

She recounted a 2020 Miami getaway in which Combs allegedly passed to women a pink powdery substance, and how she experimented with drug use with him on their early 2021 getaways, including one in which she convulsed after taking a pill from Combs. She said that Combs comforted her afterwards and promoted continued use of ecstasy, cocaine, and ketamine.

Shocking Details of Control and Coercion

What began as a consensual relationship quickly turned, according to “Jane.” She testified Combs arranged for her to engage in sex with another man while Combs watched, starting in May 2021. She had agreed initially, she explained, but that this was the starting point for repeated “freak offs” or “hotel nights”, terms prosecutors say are used to explain set-up group sex parties organized by Combs.

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“Jane” testified she didn’t wish to engage in sex with other men, but was forced to out of financial dependence on Combs, who was covering her rent. She characterized these nights as nightlong sessions of up to 30 hours, including extensive preparation such as music, lighting, liquor, and “two dozen or more bottles of baby oil.”

Prosecutors Build Racketeering Case

Jane’s testimony painted a picture of premeditated planning by Combs and his entourage, potentially helping prosecutors to strengthen their racketeering charge by framing the behavior as a component of an organized criminal enterprise. Her testimony suggested that Combs’ assistants, travel agency employees, and cargo handlers were all involved in the planning of trips and sex acts for Combs’ pleasure.

This is a dramatic change of pace in the trial, as federal prosecutors attempt to link Combs’ alleged abuse not just to him, but to a larger organizational theme involving his staff and company resources. 

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Moving Forward

The 17th day of trial saw some of the most salacious testimony to date, as well as Bryana Bongolan’s cross-examination coming under pressure from the defense finally coming to an end. While the prosecution presses on with witnesses like “Jane,” they hope to have their claims of manipulation, coercion, and organized abuse strengthened. With still more witnesses promised over the next few days, the courtroom remains deeply captivated by charges that are unfolding against Combs and what they could mean for his future in the courts.

The Bryana Bongolan cross-examination may be finished, but the effect continues as both sides build the grander story for jurors.

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