
'Jane,' ex-girlfriend of Diddy, testifies feeling financially threatened into 'freak offs'
This is a free article for Diddy on Trial newsletter subscribers. to get exclusive reporting and analysis throughout Sean Combs' federal trial.
A former girlfriend of Diddy's took the stand today under the pseudonym 'Jane' and testified that the music mogul pressured her to participate in drug-fueled sexual encounters known as 'freak offs.' At first, Jane said, she and Diddy shared a loving relationship beginning in 2021, giving each other the nicknames Bert and Ernie. But after her first 'freak off,' it became a 'Pandora's box' situation in which, she said, she had to oblige.
The sex sessions could last between 24 and 30 hours with no sleep, Jane said. Diddy would arrange the 'freak offs' around the world. As a single mother who came to depend on Diddy, 'I felt an obligation because I knew he was paying my rent,' she testified. Known as 'Victim-2' in the prosecution's indictment, Jane is expected to testify over multiple days, presumably building on allegations that Diddy used his business empire as a criminal enterprise to fulfill his desires.
Here's who else testified today:
Bryana Bongolan, the friend of Casandra Ventura 's who said she was dangled over a 17th-floor balcony in Los Angeles in 2016, was on the witness stand for a second day under cross-examination. Defense lawyer Nicole Westmoreland questioned that timeline of events and showed receipts that indicated Diddy was in New York. 'You came in here and lied to the jury, isn't that true?' Westmoreland asked, to which Bongolan replied, 'I can't agree with you.'
Enrique Santos, an investigative analyst for the U.S. attorney's office, briefly took the stand to talk about extracting data from cellphones. In one text message, Ventura informed a top Diddy aide about the alleged dangling incident.
By Adam Reiss, Chloe Melas, Jing Feng and Austin C. Mullen
In a striking moment for the otherwise mild-mannered Judge Arun Subramanian, he admonished the defense team after Diddy apparently flashed facial expressions at jurors during Bongolan's testimony. 'There was a line of questioning where your client was nodding vigorously and looking at the jury,' Subramanian said, warning that if Diddy didn't stop, 'it could result in the exclusion of your client from the courtroom.'
Diddy, in an oversize cream sweater and khaki pants, had been extremely engaged with his legal team all day, passing notes and conferring with his lawyers. In the morning, he waved and blew a kiss to his mother, Janice Combs, right after proceedings began. And when one of his lawyers made objections before the jury came in, he nodded in affirmation.
In other news: There were audible gasps and laughter in the courtroom overflow room with members of the public during the cross-examination of Bongolan, as Westmoreland got the witness to repeatedly say, 'I don't remember.' Westmoreland showed her legal chops again today in her exchanges with Bongolan.
Meanwhile, Jane's taking the stand drew obvious interest from the media and spectators in the overflow room, with some wondering how someone so close to Diddy became a witness for the prosecution.
👨⚖️ Analysis: Look not guilty
By Danny Cevallos
Diddy was reprimanded for trying to connect with jurors. Generally, it's OK for a defendant to react to testimony, but it should be subtle. A nod or a shake of the head is acceptable.
But it's also unwise.
Defendants should not be showing much emotion at the defense table. It seems counterintuitive, right? After all, if you are on trial, and you believe you are innocent, wouldn't you show emotion at all these 'lies' being told about you?
But for whatever reason, emotive defendants do not play well with juries. It's a paradox: The jury is constantly watching the defendant, but the defendant shouldn't actually do anything. A defense attorney once told me he advises his clients to 'just sit there and look not guilty.'
But what does that mean? What it doesn't mean is acting out. No muttering under the breath. No harrumphing. And, if Diddy is trying to make eye contact or otherwise connect with jurors, that's crossing the line.
It's another example of a defendant trying to engage in self-help. And that's almost always a bad idea.
Tomorrow: Jane is expected to return to the stand for more questioning from prosecutors.
PSA: Every night during Diddy's trial, NBC's 'Dateline' will drop special episodes of the 'True Crime Weekly' podcast to get you up to speed. 'Dateline' correspondent Andrea Canning chats with NBC News' Chloe Melas and special guests — right in front of the courthouse. Listen here. 🎧

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The Guardian
5 hours ago
- The Guardian
Another ex and alleged victim of Sean ‘Diddy' Combs testifies about ‘freak-offs'
The federal sex-trafficking and racketeering conspiracy trial of Sean 'Diddy' Combs resumed on Friday with testimony from a former girlfriend and alleged victim, identified as 'Jane'. The woman, described by prosecutors as a single mother who met Combs in 2020, testified on Friday that Combs denied requests that escorts wear condoms during the drug-fueled sexual encounters with male escorts at hotels known as 'freak-offs' or 'hotel nights', which she claims Combs orchestrated and watched as she took part. Jane told the court that she asked Combs at least twice if an escort could wear condoms, but said that Combs 'guilt-tripped me out of it … He didn't want to see a rubber while he was watching.' Combs, 55, was arrested in September 2024 and faces federal charges of sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He has pleaded not guilty to all charges. Jane began her testimony on Thursday and told the court that she began dating Combs in 2021, and that their relation ship was loving and passionate. However, she described a turning point in their relationship in May 2021, when Combs revealed his sexual fantasies involving other men and role-playing. She said that, wanting to please him, she agreed to go along with the idea and that within hours she was in a Miami hotel room watching Combs's assistants set up for a group sex encounter. 'That night really opened a Pandora's box for our relationship,' Jane testified. 'It set the tone for our relationship going forward … It was a door that I was unable to shut.' Jane testified that after that point, 90% of her sexual encounters with Combs included other men while Combs watched, masturbated and directed the sex acts. When the prosecutor asked if she wanted to have sex with the others, Jane replied: 'No … just Sean.' She said she repeatedly told Combs, in person and in writing, that she no longer wanted to participate in these sexual encounters, but he pressured her, and she felt 'obligated'. Jane told the court how she became financially dependent on Combs, who paid her rent and would send her money. She said that at times, when she voiced discomfort with the sexual encounters, he threatened to stop paying her rent. On Friday, Jane testified that she feared losing her home if she refused to participate in the so-called 'hotel nights' or 'freak-offs'. On the stand, she read aloud texts from 2023 in which she told Combs that it felt like the sexual encounters were 'the only reason you have me around and pay for the house', adding that she was 'doing things that make me disgusted with myself'. In other messages, Jane told Combs that she felt she had to perform for him and regretted ever participating in the encounters, writing: 'Ever since I opened Pandora's box, I haven't been able to close it.' Sign up to Headlines US Get the most important US headlines and highlights emailed direct to you every morning after newsletter promotion 'I don't want to keep feeling like that,' she wrote, telling Combs that she wanted them to 'talk like adults and figure out where we're going from here'. Combs replied: 'Girl, stop.' Jane recalled crying at least twice during the encounters with Combs and male escorts, and said that Combs appeared offended and 'disgusted' by her display of emotion. While Combs's lawyers have acknowledged his history of domestic violence, they argue that the women participated in the 'freak-offs' consensually and they maintain that Combs is not guilty of sex trafficking or racketeering, or of operating a criminal enterprise. So far, Jane's testimony has echoed that of Casandra 'Cassie' Ventura, who dated Combs on and off from 2007 to 2018 and testified last month. Ventura told jurors that she was subjected to years of physical and emotional abuse during the relationship. She alleged she was coerced, through violence and blackmail, into taking part in the so-called 'freak-offs', which she said were orchestrated and directed by Combs and involved drugs and male sex workers. During cross-examination, Combs's attorneys sought to portray Ventura as a willing participant in the 'freak-offs', framing the encounters as part of a 'swingers lifestyle'. If convicted on all counts, Combs could face life in prison. The Associated Press contributed reporting


BBC News
5 hours ago
- BBC News
Diddy ex-girlfriend 'Jane' testify for im sex-trafficking trial
For di fourth week of Diddy trial, we hia wetin one of im ex girlfriends "Jane" tok about dia relationship wey last from 2021 to 2024. She be di last woman wey di rapper, Sean "Diddy" Combs date bifor dem arrest am for 2024. According to di woman, dia relationship bin start for one girls trip wey she bin take go Miami. Di relationship come move from "head-over-heels" love enta relationship wey be say she must to dey sex prostitutes and even sef, e make am dey abuse drugs. Tori be say dis particular witness, fit take dis case enta Monday bifor even just di direct questioning sef go finish. She tell di court say di relationship bin start on wetin she call "exciting whirlwind" wia Diddy go carry am go holiday, and ogbonge restaurants dem. She later testify say Combs later ask am to do wetin prosecutors dey call "hotel nights". Dis na wen Combs go bring prostitute so e go fit to watch am dey nack anoda man. "Jane" tell di court say she bin reason say na just one time tin but e turn dia relationship to anoda tin. She tok say she do di oda hotel nights bicos she "really love am" and "bin wan make am happy". But she tok say she bin tell Combs say she bin no wan do again. She say Combs bin also give am drugs like ecstasy cocaine and ketamine from wen dia relationship bin first start. She also testify say she bin use di drugs wen she dey wit Combs and also for di hotel nights. Prosecutors bin show court text message from di both of dem for early in dia relationship wia "Jane" tok say she wan nack escort, but na bicos na Diddy fantasy. But later in dia relationship, around dat kain September 2023, she come dey message Combs say e be like di only reason wey e want am na for "hotel nights", say she no wan do am again but still feel like she need to do am so she go get house to live. Bicos by dat time, Combs don alreadi dey pay her $10,000 per month house rent for am for di past five months. Combs bin reply back say, "girl, stop." Wetin Jane say dey happun during di "hotel nights" "Jane" start to dey cry as she tell court how di mata of di "hotel nights" bin happun. Di jury even hear one recording wia Jane tok say she bin dey ask Combs weda she go fit use protection wit di prostitute. She tell di court say Combs bin dey disappointed wit dat question and na im bin dey control everytin wey bin dey happun for di "hotel nights". She say na Combs dey decide how many prostitutes go take part, how long e go last and wen she go finish. She also tok say sometimes, she go cry afta di marathon "hotel nights". She tok say she remember wen Combs call am make she come do one short one. Dat "short" one last for 18 hours. She say Combs bin give her drugs say, "I bin dey so high". She tell di court say Diddy look disgusted wen e see her as she dey cry and e bin wan comot but she beg am make e stay, as she explain am give court, "I bin just wan dey im arms". She tell di court say di longest "hotel night" bin last for three and half days. On a normal day, e fit last for 24 hours to 30 hours without any sleep. She tell court say na combination of drugs, caffeine and protein shakes. Jane tell court say her only rule na say make di prostitutes no take drugs bicos she bin no sure how e go affect dia control. But she tale am so di hotel nights go dey easier and feel less real. "Jane" remember say na just two times wey she decide say she no go do drugs to take do "hotel night". She tell court say na for October 2023, and she bin dey push Combs make e dey sober and healthier. E gree but say make dem do one last sobriety party wey last 12-18 hours. She say afta she run di "normal routine" wit two prostitutes, she go vomit for bathroom. Na so Combs go meet am for bathroom say e good say she don dey feel beta, from wia she don finish to dey throw up, e tell am say di third guy dey wait. As di testimony dey go on, Diddy just dey look "Jane" from im chair, sometimes e dey look di jury sha. "Jane" also tell di court tori of di network of employees wey Combs get wey dey help am get drugs. Dis dey come as one of di charges wey Combs dey face na racketeering. And prosecutors need to prove say e bin dey run criminal business and bin dey conspire to commit crimes. She say one time Combs Chief of Staff Kristina Khorram bin tell her to carry package of drugs form Los Angeles go Diddy mansion for Miami. She bin ask if e dey safe to which Khorram tell am say, "e dey fine, I dey do am all di time". "Jane" come tell court say na so she collect di package from one member of Comb security, carry am as check-in luggage go Miami, and na afta she land she find out say e bin dey full of ecstasy. "Jane" add for her testimony say she dey normally see Combs as e dey call im assistants and security say make dem carry drugs come di hotels wia she dey nack prostitutes.


Reuters
6 hours ago
- Reuters
Sean 'Diddy' Combs' ex-girlfriend testifies he rebuffed pleas that escorts wear condoms
NEW YORK, June 6 (Reuters) - Sean "Diddy" Combs twice rebuffed a former girlfriend's requests that male entertainers wear condoms when having sex with her as Combs watched, the woman said on Friday during often tearful testimony at the hip-hop mogul's sex trafficking trial. The woman, testifying under the pseudonym Jane to protect her privacy, said Combs would "guilt trip" her when she asked that the entertainers wear condoms during their frequent, lengthy sexual encounters. The sexual interactions resembled what another one of Combs' exes, Casandra Ventura, referred to as "Freak Offs" during her testimony last month. Jurors in the Manhattan federal court trial heard an audio recording in which Combs intervened after Jane asked a male entertainer named Don if he had a condom. As the recording was played, Combs rapidly tapped his fingers against his leg while seated at the defense table. "Why didn't you just insist that Don wear a condom?" prosecutor Maurene Comey asked. "Because I just didn't want to disappoint my lover," Jane responded, referring to Combs. Jane said she and Combs dated from 2021 through 2024. Combs, 55, has pleaded not guilty to five felony counts including racketeering conspiracy and sex trafficking. Prosecutors say he coerced women over two decades to take part in elaborate, drug-fueled sexual performances during Freak Offs over two decades. The Bad Boy Records founder's defense lawyers have acknowledged that Combs was occasionally abusive in domestic relationships, but say the women who took part in Freak Offs did so consensually. During the first day of her testimony on Thursday, Jane said she was "head over heels" for Combs and wanted to have a one-on-one relationship with him, but that starting five months into their relationship most of their time together involved sexual interactions with male escorts in hotels. Jane said that when she told Combs she wanted those encounters to stop, he threatened to stop paying her rent. On Friday, Jane frequently sobbed and dabbed her eyes with a tissue as she told jurors how Combs would encourage her to keep going even after she grew tired during the encounters, which she said often lasted 24 hours or more. She recounted one instance in which she broke down crying after Combs said he had to leave following an encounter with an entertainer, despite having promised Jane a one-on-one date night and that the entertainer would be there for "just a little bit." "I hung onto those words, just a little bit," Jane said. "I was feeling terrible that he was going to leave me alone." Combs' defense lawyers are expected to cross-examine Jane next week. They may focus on sexually explicit text messages that she sent Combs in between their encounters to show she was a willing participant in their relationship. Combs has been in federal lockup in Brooklyn since his September 2024 arrest. He could face life in prison if convicted on all counts.