Former lover of embattled hip-hop rapper and entrepreneur Sean “Diddy” Combs broke down in tears on Wednesday in the witness stand after she was made to read a burst of messages she had sent to Diddy in the past years while they were still together.

Teny Geragos, one of Diddy's defense attorneys and a founding partner at Agnifilo Intrater LLP, specializes in defending allegations of sexual misconduct.

During cross-examination, she appeared to reinforce the claim that the woman—who testified under the pseudonym 'Jane'—was a willing participant in the sometimes-weekly sex acts with male sex workers that Combs allegedly directed and watched for hours."

Geragos read aloud in the court, along with Jane read an avalanche of text messages exchanged between the former lovers during their 3-year-long relationship that began from 2021 until Combs was arrested last September 2024.

Among the messages read was one which Jane described as "one for the books". A remarkable night, she claimed, could not be forgotten, was with one male sex worker.

Also, there were messages which revealed Jane's knowledge of Diddy embarking on romantic vacations with other women. The message read “It’s not right how you’re treating me right now and how you’re doing me”.

At one point, Jane read a text saying she had “never had a man take care of me like you do” and professing her unending love for the entertainment icon — before Jane stopped reading and began sniffling, then dabbed tears from her eyes with a tissue.

However, prosecutors objected to some of the readings, leading to a sidebar conversation with the judge away from the jury.

Jane sat slumped in the witness chair, hair hanging over one side of her face. At the defence table, Combs was quietly reading from one of the TV monitors in front of him.

It was the fifth day of testimony for Jane, who has said she still loves Combs. She previously discussed gaining insight into her relationship with Combs after three months of therapy. Jane also said she never wanted to have sex with any man except Combs, but did so to please him.

At other points on Wednesday, Geragos elicited from Jane that she frequently became angry at Combs and wanted to end their relationship because she got upset that he was treating other girlfriends better.

In one instance, Jane acknowledged, the Bad Boy Records founder even bought another girlfriend jewellery that was a matching set to jewellery he had given Jane.

Meanwhile, Geragos said Jane’s cross-examination is expected to wrap up by the morning of Thursday, June 19.

Assistant U.S. Attorney Maurene Comey, who is leading the prosecution, said the government expects to rest its case as early as next Wednesday.

Defence attorney Marc Agnifilo would not outline what will occur when the defence gets its turn to call witnesses, saying that will depend on which witnesses the government still calls to the stand, but he said he was confident the trial will end by July 4.

Diddy is likely to end up in jail for life, considering the charges being leveled against him.

Prosecutors have charged Combs with racketeering, alleging that he operated a criminal enterprise that relied on violence, intimidation, and illegal activity to exert control.

A court document also mentions events called "Freak Offs," where victims were allegedly drugged and forced into long sexual encounters that could go on for days.

He is also accused of sex trafficking, with claims that he transported or coerced individuals into sexual exploitation across state lines.