The ongoing trial of music mogul Sean ‘Diddy’ Combs took a deeply personal turn Tuesday, as the court heard a series of graphic and intimate text messages.
The 55-year-old music artist is facing charges of racketeering, sex trafficking and transportation to engage in prostitution – he has denied all allegations against him.
The hearings kicked off last month in New York, with his ex-girlfriend, Cassie Ventura, and Kid Cudi among those who have taken the stand so far.
The messages shown in court yesterday were exchanged between Combs and his ex-girlfriend, identified in proceedings under the pseudonym ‘Jane.’
The texts, sent over nearly two years, offer a window into what prosecutors describe as a manipulative and coercive relationship masked by moments of affection and humor.
The earliest texts presented date back to November 7, 2021, when Combs joked about serving ‘orgasms and foodgasms’ over brunch, after apparently sending Jane an explicit photo.
The exchange began with Combs texting Jane: ‘Hey baby how are you?’.
After they discussed that Combs was preparing brunch, he sent an explicit photo to which she replied: ‘Sheesh you need to come with a warning signs (closed monkey face emojis).’
He wrote that brunch had gone well, before adding, ‘I’m serving orgasms and foodgasms,’ to which Jane replied, ‘That’s definitely the first time I’ve heard that.’
On April 7, 2022 , allegedly the day after one of Combs’ freak offs’ he checked in with Jane, texting: ‘Great. Checking on you adderall is the greatest lol.’
Jane responded warmly, saying she had enjoyed seeing him and included flirtatious emojis.
Later that same month, a more telling exchange took place. Combs texted Jane about having ‘crazy fantasies’ involving her and a male escort named Leo.
Jane responded, ‘Baby I wanna make love to you. I haven’t selfishly had you to myself for 5 months… I really just need you right now.’ Combs replied, ‘OK whatever you want,’ then asked whether Leo would be available after their one-on-one time.
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By May 2023, the tone of the messages had shifted.
Jane texted: ‘We didn’t film it, you forgot it, you promised you wouldn’t forget,’ referencing what prosecutors believe was another group sex encounter.
Jane has previously alleged that Combs threatened to release videos of her with male escorts, a threat she claims he followed up with a warning that he would show the tapes to her child’s father.
In a text thread from August 2023, Combs and Jane discussed a new male entertainer who was being considered for another ‘hotel night.’
Jane confirmed she’d ensure the man signed a non-disclosure agreement, a common practice in Combs’ circle, according to testimonies from former staff and partners.
‘He seems cool babe, hopefully he doesn’t know anybody we know lol,’ she texted.
While defense attorney Teny Geragos has argued that Jane was a willing participant in these encounters, prosecutors maintain that willingness was coerced under the weight of Combs’ fame, money, and threats.
Monday’s court session saw jurors viewing explicit videos involving Jane and other men, which were played privately using headsets.
Jane testified over six days, recounting what she described as a ‘sometimes loving’ relationship with Combs that became increasingly transactional and controlling.
When exchanging explicit messages in September 2023, Jane told Combs: ‘Love being kinky for you, love being wild.’
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In another message she spoke about shopping at a ‘freak store.’
Geragos, in her cross-examination, has tried to reframe Jane’s participation as consensual, even affectionate – underscored by texts in which Jane tells Combs she loves him and promises not to take him for granted.
But prosecutors argue those expressions are part of the psychological grip Combs maintained, citing Jane’s testimony that she ‘went along’ with his sexual requests because she wanted to please him.
Combs continues to deny all allegations, and the trial is expected to continue into July.
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