With week five of the Diddy trial now in the books, Billboard is recapping the biggest moments you might have missed this week — from Jane’s blockbuster testimony to Kanye’s surprise appearance to the mysterious mention of an unnamed rapper.
The trial, expected to last until early July, will decide the fate of Sean “Diddy” Combs, who federal prosecutors say coerced ex-girlfriend Cassie Ventura and others to take part in freak-offs — drug-fueled sex marathons with male escorts for his entertainment. He has denied the charges; his attorneys say the events were consensual and part of a “swinger” lifestyle.
Combs is charged with five counts, including racketeering and sex trafficking, over those accusations. If convicted on all of the charges, he faces a potential sentence of life in prison.
If you weren’t following along for every moment this week, here are the five big developments you need to know.
Jane On The Stand
The week was dominated by testimony from “Jane,” an anonymous former girlfriend of Combs who says she was forced to participate in the freak-offs with male prostitutes.
Like Ventura, Jane told jurors about a complex romantic relationship, according to NPR — one that included real affection for the superstar, but also coercion and manipulation, including through promises of more time together or of financial support.
During cross-exam, defense attorneys tried to show Jane as a willing participant in the events, per The New York Times, by showing jurors a trove of text messages in which she appeared to have positive thoughts about the freak-offs. But she insisted she was simply telling Combs what he wanted to hear and was “putting on a show” during the events.
Mystery Rapper
At one point during her testimony, Jane described a night she allegedly spent with another famous rapper in January 2024 — setting off a debate between the legal teams over whether the mystery celebrity could be revealed.
On the night in question, per USA Today, Jane told jurors that she traveled to Las Vegas with the rapper and ended up watching what amounted to a freak-off — a male prostitute having sex with a woman — in the celebrity’s hotel room. She said the event later sparked rage in Combs, who demanded to know: “How could you go to another man’s freak-off?”
Prosecutors quickly urged the judge to bar any reveal of the rapper’s name, warning that it might threaten Jane’s anonymity if the name were divulged. Judge Arun Subramanian ultimately agreed to keep the name hidden, but defense attorneys gave clues — calling him an “icon in the music industry” and someone with a close relationship to Combs.
Jane v. Teny
Midway through cross-examination, Jane got into a heated exchange with Teny Geragos, one of Combs’ defense attorneys, over designer handbags.
According to TMZ, it started when Geragos asked if Jane, like another Combs girlfriend, received a Chanel bag from the rapper. Jane quickly shot back: “I only got trauma.” When Geragos then asked her what a Bottega bag was, Jane replied, “I’m sure you have one.”
“How much does it cost?” Geragos quickly asked her. “How much does my body cost?” Jane fired back.
The tense exchange highlighted Jane’s unusual position in the case. As reported by the Times, she dated Combs right up until his September arrest, didn’t participate in the criminal investigation until she was subpoenaed, and met with his defense attorneys repeatedly before the trial began. She also confirmed on the stand that he’s currently paying both her rent and her legal bills related to the case.
When she wrapped up her six days on the witness stand on Thursday, per CNN, Jane made an unusual move: She hugged the attorneys who had been questioning her, including prosecutor Maurene Comey and Geragos.
Ye Stops By
Ye, the rapper formerly known as Kanye West, dropped in on the trial on Friday (June 13), telling reporters he was there to support Combs.
Dressed in all white, Ye arrived at the courthouse late in the morning and spent about 40 minutes at the trial. Per the Associated Press, he didn’t make it into the main courtroom where the judge, jury and attorneys are arguing the case, instead watching testimony on a closed-circuit monitor in an overflow room.
Though hardly in the same kind of hot water as Combs, Ye has faced his own controversies in recent years — including posting antisemitic rants to social media, running Super Bowl ads for swastika t-shirts, and making outrageous claims about Jay-Z and Beyoncé’s children.
This wasn’t the first support Ye has shown for Combs, a longtime friend. In February, he posted to X (formerly Twitter) asking President Donald Trump to “please free my brother Puff.” And in March, he dropped a song called “Lonely Roads Still Go to Sunshine” that appeared to feature Combs’ voice on a phone-call recording.
When asked if he might testify on Combs’ behalf when the defense begins presenting its case, Ye didn’t respond.
Mistrial Denied
Early in the week, Judge Arun Subramanian denied a motion for mistrial filed by Combs’ lawyers over juicy testimony — a small but important moment.
Attorneys for the embattled hip-hop mogul had argued that prosecutors knowingly introduced false testimony by Bryana Bongolan, the witness who claimed that Combs dangled her from a 17-story balcony in 2016.
But at the start of Tuesday’s proceedings, Judge Subramanian said the alleged issue did not rise to the level of a trial-ending error: “This is not fodder for a mistrial. This is the adversarial process at work,” Subramanian said from the bench, according to ABC News.
