We were back in the main courtroom today for Day 17 of the Sean “Diddy” Combs trial. Tension ran high inside the Southern District of New York courtroom as proceedings resumed with two key witnesses taking the stand: Bryana Bongolan, returning for continued cross-examination, and a woman identified only as “Jane,” whose testimony described a private and emotionally complex relationship with Combs.
Defence attorneys aimed to challenge the credibility and consistency of both accounts, while the prosecution sought to present a pattern of behaviour it alleges amounts to manipulation, abuse, and exploitation.
Defence Presses Bongolan on Alleged Inconsistencies
Bryana Bongolan returned to the stand today for a lengthy and at times tense cross-examination. The defence focused heavily on the origins of her sexual assault allegations, pointing out that the claims were first introduced by her former attorney, Tyrone Blackburn—who she later fired.
“Ma’am, isn’t it true that although your lawyer Mr. Tyrone started the story of sexual assault allegations that wasn’t true, you fired him but continued to repeat those same allegations?” the defence asked. She didn’t provide a direct answer. They followed that by questioning her legal intentions: “Do you believe that claiming Mr. Combs assaulted you was the only way to file a lawsuit?” Bongolan is currently seeking $10 million in damages through a separate civil suit.
One of the most contested points was her claim that Diddy physically assaulted her on September 26, 2016—allegedly entering a room, hanging her over a balcony, and causing visible injuries. But the defence presented hotel receipts from Trump Hotel in New York dated September 26–29 2016, charged to “Frank Black,” an alias prosecutors have confirmed is tied to Diddy. “Isn’t it true a person can’t be in two places at the same time?” the attorney asked. Bongolan didn’t offer a response.
The defence also pointed to contradictions in her earlier statements to the government, including her warning that a friend she said helped bandage her bruises wouldn’t be able to confirm that version of events. They brought up texts showing she asked her drug dealer—referred to in court as “Ray J”—to bring drugs to a private Diddy event. In addition, they also pointed out she continued her affiliation to Diddy even after the alleged assault, including a night where she admitted on the stand to having smoked a blunt with Diddy after being under the influence of ketamine for eight hours.
Remi Louis Harris / HipHopCanada
“Ma’am, isn’t it true you hung around Mr. Combs because he didn’t assault you?” one of Diddy’s defence lawyers Nicole Westmoreland asked. Bongolan did not directly answer. She consistently gave surface level answers stating that “she couldn’t recall” or “didn’t remember” key details—even when shown iOS metadata from a photo she had handed over to prosecutors that showed her injuries, which she had stated all occurred on the same day. When asked, “As you testify here today, you don’t want to say anything to mess up your lawsuit, correct?” she again could not give a clear answer.
As the defence’s cross-examination wrapped up, they closed with a sharp question: “Ma’am, you came in here and lied to the members of this jury, isn’t that true?” When asked again why she was testifying, Bongolan replied, “To seek justice.”
At that moment, at least two jurors appeared disengaged—one subtly shook their head, while another placed their hand on their face.
Digital Analyst Testifies to Deleted Messages
Later in the day, Enrique Santos—a digital forensic analyst from the U.S. Attorney’s Office for the Southern District of New York—testified about the forensic analysis of three iPhones, owned by Cassie Ventura.
He reported that approximately two-thirds of all messages on the phones had been deleted.
Santos explained that metadata from screenshots provided by prosecutors matched with the device data and timeline of events being investigated. However, the contents of some deleted conversations on the phones themselves were retrieved. Extraction tools such as Cellebrite Premium and GrayKey were used in the analysis.
Jane Testifies to a Private, Drug-Fueled Relationship with Combs
The day’s final testimony came from a witness identified only as “Jane,” who described a layered relationship with Sean “Diddy” Combs that she testified began in 2020 and continued until his arrest. According to Jane, their connection was passionate, secretive, and marked by constant drug use. She testified that she first met Diddy during a girls’ trip to Miami, while working as a brand ambassador.
At one point in their relationship, Jane said she told Diddy that her child’s father was someone he knew and was close to him. While she did not identify the individual publicly, she testified that this added another layer of complexity to their relationship. She also shared that one of her friends had initially been seeing Diddy, but after that friend got engaged and moved overseas, she and Diddy began seeing each other. Their first date, Jane said, lasted “five days.”
From the beginning, Jane said their encounters involved drugs—typically molly, cocaine, ketamine, and ecstasy—which she stated were often supplied by Diddy. “Every time I saw him, we would do drugs,” she told the court. She recalled one instance where she collapsed onto the sand after taking ecstasy at Diddy’s request and began convulsing.
Remi Louis Harris / HipHopCanada
According to her, she was placed into a lukewarm shower, which helped calm the episode. Despite those moments, she also testified that small doses made her feel “euphoric, good, and sexual,” adding that some nights would last 12 to 15 hours—sometimes even 24. Jane said Diddy would sometimes wire her $20,000 or give her money “just because,” and eventually began paying her rent, which was $10,000 per month. She testified that he told her early on they needed to keep the relationship private, and that while he made it clear he liked her, he was also seeing other women.
Their sexual relationship, according to Jane, was intense. She testified that they would often watch porn while high, and that Diddy liked having it playing in the background during sex. She told the court she “loved” their long sex sessions and described the early stages of the relationship as “passionate.”
In 2021, Combs allegedly initiated what Jane described as “fantasy conversations” of her having sex with other men while they were both high on ecstasy. These fantasies, she said, eventually turned into real-life scenarios. One specific encounter involved a man named “Don,” who she testified was from Cowboys and Angels.
Jane recalled that Diddy, while high, told her: “I can make that happen tonight.” When she asked, “Tonight?” and he said yes, she agreed.
She testified that she was high when she met Don, and that after having sex with him, she and Combs also had sex “because they were both in a good mood.” She admitted she initiated things by going to the room to “speed things up,” and claimed that Diddy didn’t want Don to wear a condom but eventually did so to keep her at ease.
Afterward, she said she felt “excited” and “happy” because she had done something “taboo” that made Diddy happy. However, she described the experience as emotionally complex, stating that the encounter opened a “Pandora’s box and a door she couldn’t shut.” Jane testified that following that night, she ended up having sex with other men in front of Diddy “90% of the time” she was with him.
She said that she didn’t want to continue doing that at the time but did so to keep him “happy”. At one point, she testified that she told Diddy—in writing—that she no longer wanted to be intimate with other men. According to her, Diddy responded by threatening to stop paying her rent, saying, “I’m not about to be paying rent for a woman I’m not seeing.” She said his words left her frustrated and emotionally torn.
She made it clear that her relationship with Diddy was complicated—marked by genuine feelings, alleged control, secrecy, and blurred boundaries. The defence did not get a chance to cross-examine Jane today as the prosecution has not finished their direct examination. Some jury members visibly appeared confused during some of Jane’s testimony but remained attentive overall.
For legal clarity: We here at HipHopCanada have determined and confirmed Jane’s identity. However, due to the judges order prohibiting press from publishing any identifying information, we will not be sharing her name at this time. The trial resumes tomorrow, with additional testimony from Jane. We will continue providing on-the-ground coverage from inside the courtroom as the Sean “Diddy” Combs trial unfolds. Stay with us for updates and exclusive reporting.
