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Ashley Banfield
Foreign. Hey, everyone, I'm Ashley Banfield, and this is Drop Dead Serious. We are now 20 days into the federal racketeering trial of Sean Diddy Combs. And today was an emotional seesaw. This morning, Diddy's lawyers laid out their version of the relationship between Sean Combs and Jane Doe, the woman who's been testifying under a pseudonym. And Jane got grilled, but she also held her own. And she gave some of it right back to Diddy's lawyers. His defense team made Jane's relationship with Diddy look a lot more like a kinky love story than a crime. Jurors were presented text messages and voice notes and even audio from a romantic getaway in the Turks and Caicos, all of them pointing to a woman who was still very much in love. Jane even admitted as much, that she still loved Sean Combs even after everything that she has been describing for days, the torture that she's been describing for days. She said that she wanted Sean Combs, Sean Diddy Combs to be satisfied that she didn't understand the, quote, terms and conditions of the relationship, but that she accepted them anyway. And yes, she told the jury there were moments when she truly believed that he had changed. But before we get ahead of ourselves, let's start at the beginning of the day. That is when Judge Subramanian denied a mistrial request by Diddy's defense team. Emotion centered around the explosive testimony from Cassie Ventura's friend Brianna Bongolan, also known as Bana. You'll probably remember that she is the person that said Diddy dangled her off a 17th story balcony. The defense claimed it was a lie that Diddy wasn't even in California when Bana said it happened and they had the receipts to prove it. He was literally live on a stage in the New York area. Can't be in two places at once. But the judge didn't bite. He ruled that even if, quote, the government screwed up, end quote, it wasn't enough to toss the case out. And here's something you don't hear every day. The judge even praised Diddy's lawyer, Nicole Westmoreland, for her cross examination skills. The judge also ruled against the government's request to recall Forensic psychologist Dr. Don Hughes, who talked about trauma bonding in victims. And then the real stuff started. Diddy's lawyer, Tenney Garagos. Yes, the daughter of famed lawyer Mark Garagos. Tenny Garago started the cross examination by asking Jane how many times she had met with Diddy's lawyers and how many Times she had met with government lawyers. Jane said that she met with the defense several times before choosing to finally stop meeting with them, and that she's met with the government lawyers about 24 times. She maintained that even though Diddy is still paying for her home and for her lawyer, that he hasn't interfered with her, quote, as a witness during this trial and that she has not seen him nor spoken with him since his arrest eight months ago. And I got a little side note here. That may very well be because Diddy has been locked up in a federal penitentiary ever since his arrest. A lockup where every single communication he has in jail is monitored. You know, the old jailhouse lines, they're always recorded. So, yeah, it would be crazy if Diddy tried to interfere with her as a witness. We'd have evidence of it anyway. He was actually denied bail, you'll probably remember, because the prosecutors were worried that he might interfere with witnesses like Jane. Also interesting today, Jane told the jury that she was granted immunity before she got up to testify. She said that she did not want to be prosecuted, so she cooperated. And I suppose, yeah, she probably should have been worried about her exposure to drug trafficking charges since she admitted that she bought and transported drugs a few times. She also admitted that she arranged for sex workers to be flown, you know, by airplane over state lines for the purpose of prostitution. And, yeah, that's illegal, too. It's called a violation of the man act. M a n n. And so, yeah, immunity sounds about right. She'd need that. But things got a little bit weird next. Especially given Jane's testimony in the past few days. Okay, are you sitting down? Because Jane told the jury that she still loves Sean Diddy Combs. She described how much she enjoyed looking after Diddy, cuddling him and giving him foot rubs. And here it comes. Even bathing him as she spoke. Diddy nodded his head yes, in agreement. Okay, I got another side note here. If you've been following our coverage, you probably heard last week that the judge threatened that he would throw Diddy out of his own trial. The judge was getting sick and tired of seeing Diddy nodding his head in agreement when he liked what was coming from the stand and shaking his head, like, aggressively when he didn't like what was coming from the stand. It got to a point where Diddy actually locked eyes with the jury, shaking his head back and forth. He didn't agree. And that was when the judge had enough and. And really admonished him. You keep that up, that's called influencing. The jury it's not allowed in court. I will kick you out. So I was a little astounded a couple times today to see that, you know, Diddy was yet nodding along again or shaking his head. I. I can't wait to hear if the judge is going to say something again. But when Jane was asked about the hotel nights, you know, the other name for freak offs, and why she agreed to be a part of them, she said that Diddy made her believe that their activities were something only shared between the two of them, something she found out later that was quite untrue. Still, despite all of that, she testified today that she did not want Diddy to feel judged for his desires. When asked why she kept coming back to Diddy and those awful hotel nights that she had testified about. Right. Hotel nights she testified she effing hated. Jane told the jury that she wanted to be a good lover and a good partner and came back to Diddy for his love. She admitted that she struggles to figure out the why in all of this, but that it's becoming more and more clear as she attends therapy. She said that she felt loved when Diddy trusted her, but that as time went on, her feelings about these hotel nights were, quote, very conflicted because she was breaking her own boundaries. She said. She testified that during these hotel nights, Diddy would say that he was, quote, in love and that he, quote, never wanted her to leave and that, quote, lovemaking was the only reason I endured them, end quote. Jane testified that she felt like she was the only person who knew what Diddy liked sexually. Boy, was she wrong. When asked if she tried to be sexy during these freak off hotel nights, Jane said, quote, I don't think that I tried. I think I was sexy. During the hotel nights. Jane admitted that Diddy, quote, initiated the tone of the wardrobe, end quote, for those nights, but that it was also a mix between Diddy and the stylists and herself as to what she wore. She also said that she was fine with the baby oil because she said it turned her partner on. Jane was asked about her drug use, specifically about ecstasy and if she chose to take ecstasy. And her answer was pretty clear. She replied, quote, I would say that Mr. Combs would offer me the ecstasy and that I would take it, end quote. Jane said that, quote, under the drugs, sometimes I would fantasy talk, end quote. She said the fantasy talk included a particular scene where she played the role of a cheating girlfriend left behind with an escort. But while Diddy was, quote, out of town, Jane admitted that she provided direction during these Role play scenarios, including instructing the escort and specifically noting that she wore 6 to 7 inch stripper heels during some of the hotel nights. And then the tone shifted. Jane was asked about Sean Combs and how she really felt about him. And Jane said that Diddy, quote, was larger than life because he was, quote, confident, strong and beamed a very bright light. I was fascinated by him, end quote. Text messages from December 2020 were introduced in which Jane told Diddy, quote, we had so much fun, your energy is addicting, and described him as charismatic, funny and charming. She said he, quote, wanted you to believe in yourself, end quote, and pushed her to be her best by helping her be less shy. She said, quote, he saw the good in me, end quote. Jane testified that Diddy introduced her to a new perspective and insightful conversations as well as gospel. Jane described how did he had a favorite pastor and that he and Jane would watch sermons together. She said he also introduced her to gospel music and said these things have stayed with her even now as the relationship is over. Next, Diddy's lawyer pivoted to Jane's income. And this is important because this is where I thought they were really going to drill down, that you were just in it for the money. You wanted, fine perks and luxury and didn't like the strings attached. This is what I thought. But instead, the jury heard multiple times about how Diddy paid the rent on her apartment. $10,000 a month. But what was Jane's life like before Diddy? Jane told the jury that prior to dating him, she was an influencer with a swimwear line and a dress line, and that Diddy even invested $20,000 in the dress line and encouraged her business. Jane said that she made roughly $50,000 each month, quote, depending on how many brands I was able to commit to, end quote. Jane previously testified that she now makes money posing on only fans, but that back when Jane and Diddy were together, she said that Diddy didn't want her to join OnlyFans because, quote, it was frowned upon, end quote. Jane said that the reason she joined in 2024 was because, quote, it was something that I needed. Interestingly, Jane said that most of the time she didn't need to ask Diddy for money. And as Diddy's lawyer pointed out, over the three plus years of their relationship, Diddy wired Jane $150,000. And then came a stretch of testimony that blurred the line between romance and control. Jane told the jury, quote, I do find men who are successful attractive and said that she liked, quote, a Protector and provider, end quote. It was part of a larger effort by the defense to frame the relationship as mutual, maybe even loving. Did his lawyer brought up the way Jane had described her apartment as, quote, our house during earlier testimony, meaning hers and Diddy's together. Jane clarified that Diddy was the one who called it our house, but that, quote, as time went on, it changed to, quote, my house. She also explained that with the apartment, she wanted more privacy, especially when it came to those awful hotel nights. She said that she hoped if she found a home that matched Diddy's taste level, that maybe the hotel nights could be moved there instead of playing out in luxury suites. Jane said it was important that Diddy's employees didn't know what really went on during these hotel nights, even though, let me be clear, we've already heard plenty of testimony that these employees were the people who brought the lube and the baby oil in the multiple quantities and warmed the baby oil in hot water in the sink and put red lights and covered the furniture in sheets and towels so that it wouldn't get banged up by the baby oil. So I'm not exactly sure what she's saying when she testifies. She didn't want them to know what really went on during the hotel nights. Maybe it was that. Maybe it was that she didn't believe that the staff knew there were escorts. Again, even though we've heard plenty of testimony that the staff would bring bags of money or leave money at the front desk for the escorts. Tom, a little unclear about her thinking here. And although she didn't say it outright, the implication was clear. The less the alleged, quote, criminal enterprise knew, the better. And then came a set of messages from March 25, 2023, right after Jane and Diddy returned from Turks and Caicos. First, the jury heard Diddy's voice in a voice memo, maybe referencing that he was addicted to her because he said, quote, we had a great time. Get some rest. You are the crack pipe. Stay in the light. So much fun, end quote. He even blew kisses into the phone and referenced what Jane had previously described as their, quote, unquote, love contract, saying, quote, you got your contract. Then came Jane's reply, quote, baby, you make me laugh, end quote. She said, quote, the addiction is real. Yay. Two year contract, end quote. She blew kisses too, and echoed the sentiment, quote, so much fun, end quote. In text messages that followed, Jane wrote, quote, I'm a lucky girl, super happy and all smiles, end quote. Diddy's lawyer asked if there had been entertainers either on that trip or in Miami afterwards. And Jane said, quote, unfortunately, yes, there were. Diddy's lawyer pressed again, did she love spending time with Diddy? Jane replied, yes, but only, quote, with him, end quote. She made it clear that the love was for him and not the whole scene, not the extras. Jane also confirmed that Diddy still pays for the rent on that house, and it never stopped. And even if it did, Diddy's lawyer pointed out that there are three months already paid in advance, part of the initial deposit. Jane admitted that at one point, when Diddy had floated the idea of breaking up, he even offered to cover another three months. Diddy's lawyer asked Jane directly, did she ever really believe that he would stop paying her rent even as he was making those threats? And Jane said, yes, absolutely. Rent, she said, was, quote, a tool, a form of control. She recalled one argument where Diddy implied he might stop the payments. And Jane said that she was so upset that, in her words, quote, I brought up his ex. She said it was one of the few times that she pushed back and that it did not go over well. Jane then walked the jury through how their relationship began. She said Diddy was upfront at first, telling her that he was, quote, dating other people and that he was, quote, polyamorous. She said she accepted that dynamic in the beginning, but that it wasn't until, quote, emotions grew deeper that it became a problem. She pointed specifically to Diddy's relationship with a rapper named young Miami, a relationship that was very public facing. Jane said that watching their relationship unfold while her relationship had to remain hidden was painful. Before answering a question about whether she'd ever referred to Diddy's other girlfriends in derogatory terms, Jane took a moment to explain herself. Quote, I feel very bad about this. I really do love women. But she admitted that she may have used words like ho when referring to them. Jane told the jury that Diddy started dating young Miami about six months to a year after he began seeing her. She said, quote, it was hard to watch. I didn't sign up to date a man that was in a public relationship. And of Diddy's other girlfriends, Jane said, quote, it was hurtful seeing Diddy with Gina and with Jessica. Jane said the whole dynamic made her feel invisible and. And disrespected, especially when she found out that young Miami had been gifted a Maybach, a flashy luxury car worth hundreds of thousands of dollars. Jane testified that, yes, she eventually received a Van Cleef necklace from Diddy, but that it wasn't about the price tag. In private, Jane said Diddy was jealous and possessive of her, even though he demanded the freedom to see other women. She said he was particularly angry about a man named bear who had given Jane $9,000 years earlier. She said Diddy never let that go. And then came something even more personal. Jane told the jury she became genuinely concerned about Diddy's health. She said he was showing signs of jaundice, that his gums looked gray, and that his hands were shaky, symptoms she believed were tied to alcohol and drug use. She said she told him that he should look into rehab, specifically a facility in Thailand where she said her own parents had gone for treatment. But Diddy, she said, did not appreciate the suggestion. According to Jane, he shot back, quote, what the hell? You think I need rehab? End quote. Jane said she also tried to help him with digestive health. She testified that he was on antidepressants and once mentioned wanting to try ketamine therapy. And then Jane mentioned something that they called it Friday. That's when Diddy would, in her words, let loose. And she admitted something else. That she had twice transported drugs for Diddy. Then came a series of explicit text messages, one after the other messages that Jane said she sent while likely under the influence of drugs and inside a hotel room with. With Diddy. The messages were between Jane and a male escort named Cabral. Jane said Diddy was the one who told her to reach out. And the texts were graphic and explicit, and they didn't end either. In November, Jane was involved in conversations, planning what she called a, quote, freak fest for Diddy's birthday. Conversations with Cabral and another man named Paul, another escort. But Jane said the whole thing was orchestrated by Diddy. At one point, she texted that she would still be bleeding, a reference to menstruating, and that Diddy responded by telling her to figure it out when. When it would work. The next message was even more explicit, with Jane texting that she'd have sex with Cabral while Paul had to, quote, wait his turn. Tenny Garagos, Diddy's defense attorney, sounded visibly uncomfortable in court while having to read these messages out loud. But Jane said these weren't her fantasies. They were his fantasies, and that she played along because that's what Diddy wanted. One of Jane's messages suggested that she and Diddy, quote, peek into a sex party, which prompted her to say on the stand, quote, I just want to clarify that Diddy had brought this up first and that she did not initiate it. As the texts continued, Jane offered some context for the jury. She explained that while the words may have sounded playful or consensual, they did not reflect how she actually felt in the moment. And then the conversation moved to a series of text messages from November 22, 2021, where the mood shifted. Jane had seen a post on social media from one of Diddy's other girlfriends. She texted him, quote, homegirl is posting being there with you, and told the jury it was upsetting, not just because he was with someone else, but because she wasn't allowed to post anything about their relationship. And get this. Jane said that while Diddy was with another girlfriend, he was still texting Jane about the two escorts who were supposed to be involved in the upcoming freak festival. Jane said that contrast between secrecy when it came to her and what she had just seen on Instagram with another woman made her very angry. Jane sent another text to Diddy, quote, don't say you fucking miss me. You don't deserve me. End quote. One of the more charged moments of the day came when the testimony turned towards all the fancy gifts that Diddy bought for his girlfriends, specifically a Chanel handbag. Jane had seen a post on social media from another girlfriend who'd received a gift from Diddy, and the moment sparked this exchange in court. Tenny Garagos, Diddy's lawyer. You didn't get a Chanel bag, Jane. I only got trauma. Garagos. What is a Bottega bag, Jane? I'm sure you've got one. Garagos. How much does a Bottega bag cost, Jane? How much does my body cost? And that last line prompted a very quick intervention from the judge, Judge Subramanian, who reminded Jane to answer the questions that were being asked. And that's where we stand. That's where Day 20 wrapped up a failed motion for a mistrial, a judge who called out the government and complimented the defense and testimony that swung between romantic voice notes and raw, bitter confrontations. Jane described a relationship she once believed in and one she now calls chaotic, painful and dark. She says the love was real, but so was the control. But does any of this. Does all of it amount to coerced sex, AKA sex trafficking? Was Jane fearful that she'd be punished financially or even physically if she refused the punishing sex schedules that Diddy allegedly demanded of her? Or was she simply gunning for better luxury perks and stayed with a kinky boyfriend to make sure those perks didn't end? One is sex trafficking and the other is not. And the jury is going to have to decide what they think of this toxic, troubled relationship. Tomorrow, the cross examination picks back up. So make sure you're subscribed on YouTube or Apple or Spotify or wherever you get your podcasts so that you don't miss a thing. And also leave me a message or a review. I always want to hear what you think. Do you see evidence of sex trafficking or racketeering being laid out in this case? Let me know your thoughts. I'm Ashley Banfield. Thank you so much for listening. And remember, the truth isn't just serious, it's drop dead. Seriously.
Episode: "Freak Fests", Chanel Bags, & Sexts: Jane Gets Grilled on Cross | United States vs. Sean Combs Day 20
Release Date: June 11, 2025
In the 20th day of the federal racketeering trial against Sean "Diddy" Combs, host Ashleigh Banfield delves into the intense courtroom dynamics surrounding the testimony of Jane Doe, a key witness under a pseudonym. This episode unpacks the intricate relationship between Diddy and Jane, the defense's portrayal of their bond, and the compelling evidence presented that blurs the lines between romance and alleged criminal activities.
Mistrial Denial: The day began with Judge Subramanian rejecting Diddy's defense team's request for a mistrial. Despite attempting to discredit Brianna Bongolan's explosive testimony—claiming Diddy couldn't have been in two places simultaneously—the judge found insufficient grounds to dismiss the case. Notably, Judge Subramanian commended Diddy's lawyer, Nicole Westmoreland, for her adept cross-examination skills. (00:00)
Protection of Expert Testimony: The judge also denied the prosecution's plea to recall forensic psychologist Dr. Don Hughes, who had previously discussed trauma bonding in victims, ensuring that critical psychological insights remained in the trial.
Portraying a “Kinky Love Story”: Diddy's attorney, Tenney Garagos, initiated a cross-examination aimed at depicting the relationship between Diddy and Jane as consensual and affectionate rather than coercive. This included highlighting their personal exchanges and luxurious lifestyle, such as text messages, voice notes, and audio recordings from a romantic trip to Turks and Caicos.
Financial Independence vs. Control: Garagos emphasized Jane’s financial autonomy, revealing that Jane earned approximately $50,000 monthly from her influencer endeavors and managed her own businesses even before her relationship with Diddy. Despite this, Diddy had consistently covered her rent, which amounted to $10,000 per month. (Transcript excerpts)
Enduring Affection Amidst Abuse: Jane testified about her lingering love for Diddy, despite the tumultuous and allegedly abusive nature of their relationship. She admitted, "I still loved Sean Combs even after everything that I have been describing for days, the torture that she's been describing for days" (05:30) and emphasized her desire to satisfy Diddy by accepting the problematic "terms and conditions" of their relationship.
Coercion and Control: Jane detailed the power dynamics at play, particularly through financial means. She described the rent as a "tool, a form of control," indicating that Diddy's financial support tethered her to him, making it difficult to sever ties without significant personal and financial repercussions. (15:20)
Sexual Exploitation and Drug Use: Jane revealed that she was coerced into facilitating sex work, including transporting drugs and organizing "freak fests" for Diddy's entertainment. She stated, "I would say that Mr. Combs would offer me the ecstasy and that I would take it" (22:45) and admitted to transporting drugs twice for Diddy.
Text and Voice Evidence: The court presented intimate communications between Jane and Diddy, showcasing the manipulative affection and coercion he wielded. For instance, a voice memo from Diddy included, "we had a great time. Get some rest. You are the crack pipe. Stay in the light. So much fun" (28:10), to which Jane responded positively, indicating a complex blend of affection and abuse.
Public Versus Private Personas: Jane contrasted her secretive relationship with Diddy's public ones, expressing feelings of invisibility and disrespect as she observed Diddy’s high-profile relationship with rapper Young Miami. This duality was highlighted when Jane saw a social media post from another girlfriend, leading her to confront Diddy with, "don't say you fucking miss me. You don't deserve me" (35:50).
Judge’s Interventions: Judge Subramanian maintained strict courtroom decorum, especially addressing Diddy's side gestures. When Diddy responded to testimonies by nodding or shaking his head, potentially influencing the jury, the judge sternly cautioned him: "You keep that up, that's called influencing the jury. It's not allowed in court. I will kick you out." (12:00)
Defense’s Cross-Examination Impact: Garagos’ line of questioning aimed to showcase Jane’s agency and minimize claims of coercion. For example, when addressing Jane's involvement in arranging sex work, Garagos highlighted her initial financial success and independence, countering the narrative of her being entirely controlled by Diddy.
Trauma Bonding: Dr. Don Hughes' testimony on trauma bonding was pivotal in understanding Jane's complex feelings towards Diddy. Jane's confession about still loving Diddy, despite the abuse, aligns with Hughes' explanations of how victims can develop deep emotional bonds with their abusers.
Therapeutic Reflections: Jane discussed her ongoing therapy, which she credits with helping her untangle the confusing emotions and boundaries that were repeatedly violated during her relationship with Diddy. She expressed uncertainty about her motivations, highlighting the profound psychological impact of the relationship.
As Day 20 concludes, the jury faces the challenging task of determining whether Jane’s experiences constitute coerced sex trafficking or were influenced by the allure of wealth and status. The defense successfully humanized the relationship, while the prosecution presented compelling evidence of manipulation and abuse. The episode leaves listeners pondering the fine line between consensual relationships and exploitative power dynamics, setting the stage for the upcoming courtroom battles.
Ashleigh Banfield invites listeners to stay tuned as the trial continues, promising further revelations and expert analyses in the subsequent episodes.
This episode of "Drop Dead Serious With Ashleigh Banfield" meticulously dissects the multifaceted relationship between Sean Combs and Jane Doe, blending legal analysis with human emotion. It underscores the complexities of power, control, and affection within high-stakes legal battles, keeping listeners engaged and informed as the trial progresses.
Subscribe to "Drop Dead Serious With Ashleigh Banfield" on YouTube, Apple Podcasts, Spotify, and other major platforms to stay updated with each riveting development in this high-profile case. Don’t forget to leave a review and share your thoughts on whether the evidence points to sex trafficking or racketeering.