What it was like covering both Diddy trials
Business Insider's Senior Legal Correspondent Laura Italiano breaks down what it's been like reporting on both Diddy trials.
Business Insider's Senior Legal Correspondent Laura Italiano breaks down what it's been like reporting on both Diddy trials.
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Before Sean Combs, also known as Diddy, was sued by more than a dozen people, alleging sexual misconduct among other things, he was a powerful music tastemaker, creating his own record label.
Diddy founded Bad Boy Records in 1993 and went on to sign major musicians such as The Notorious BIG, Mase, and Faith Evans. It's impossible to think of '90s and '00s rap without also thinking of Bad Boy, which released 13 No. 1 albums from 1997 to 2022.
Over the years, Bad Boy and its founder gained a reputation for being difficult to work with, highlighted by multiple public instances of friction between artists and the label.
In a statement provided to Business Insider, a representative for Combs said, "It's easy to reduce a 30-year legacy to a few negative statements, but that doesn't capture the full story."
"Sean Combs and Bad Boy Records were more than just a label β they were a cultural movement that shaped music, launched careers, and produced iconic hits," they said. "Focusing only on grievances distorts the narrative. The label's contributions remain an essential part of music history."
Before Diddy was arrested in September 2024, he had begun the process of reverting the publishing rights of many of Bad Boy's most famous songs to their original artists, provided they signed agreements, as reported by Billboard.
On Wednesday, a Manhattan jury found Diddy not guilty of sex trafficking and racketeering, but convicted him of two lesser charges: two counts of transportation to engage in prostitution.
"It's a great victory for Sean Combs. It's a great victory for the jury system," Diddy's lawyer Mark Agnifilo said, NBC reported.
Diddy, who remains in custody, is facing up to 20 years in prison, but experts say it's unlikely he'll serve for that long. His sentencing is scheduled for October. At this point, it's unclear what will happen to Diddy and his career.
Bad Boy is still in existence today and remains one source of Diddy's wealth. Here are 15 of the biggest acts that have released albums through Bad Boy since its inception.
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Biggie was one of the first artists signed to Bad Boy, and his two studio albums ("Ready to Die" in 1994 and "Life After Death," which was released 16 days after his death in 1997) were released through Bad Boy.
Publicly, the two appeared to be close friends, and Diddy released "I'll Be Missing You" with Biggie's wife, Faith Evans, in 1997.
However, their relationship had become strained. Rolling Stone reported the "Juicy" rapper was preparing to leave Bad Boy. He "was absolutely about to leave Puff" before he was shot, fellow rapper Babs Bunny told the publication.
In the decades since his death, Biggie's mother Violetta Wallace (before her death in February 2025), negotiated with Diddy to gain control of her son's music, per Variety. In February 2025, his estate partnered with Primary Wave Music to handle his music in the future.
Primary Wave did not respond to a request for comment.
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Evans, who was married to The Notorious BIG from 1994 until he died in 1997, was also signed to Bad Boy Records.
Her first three albums, 1995's "Faith," 1998's "Keep the Faith," and 2001's "Faithfully," were put out through Bad Boy. She then moved to Capitol Records.
"In my heart, I really wanted to try and leave Bad Boy after Big died. I mean, after I came back to any type of reality, any clear thinking. I just was so distraught," Evans told XXL in 2014.
Evans said she left Bad Boy because she felt Diddy and the label were paying more attention to other artists, but she emphasized that there was no bad blood.
Evans did not respond to a request for comment.
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Mase released his first two albums, "Harlem World" and "Double Up" through Bad Boy, and was also known as Diddy's hype man through the '90s.
Their partnership collapsed after he released his third album, "Welcome Back," in 2004, also with Bad Boy.
Mase said he felt like his contract was too constricting, leading him to crash a Diddy interview on V103 in Atlanta and demand that Diddy sign paperwork allowing him to feature on other artists' songs.
Things simmered down until 2022, when Mase once again criticized Diddy's business practices in a now-deleted Instagram post.
"Your past business practices knowingly has continued purposely starved your artist and been extremely unfair to the very same artist that helped u obtain that Icon Award on the iconic Badboy label," he wrote.
Mase added that he had offered Diddy $2 million to buy his songs back and was refused. "This is not black excellence at all," he wrote.
Diddy responded during an interview on the syndicated iHeartRadio show "The Breakfast Club" and said that Mase actually owed him $3 million after failing to deliver an album.
In 2023, on another "Breakfast Club" appearance, Diddy said they were "brothers" and that he had "unconditional love" for Mase.
Mase's rights were returned to him when Diddy allowed songs from Bad Boy to revert back to artists that year.
In 2024, Mase called Diddy's arrest "the big payback" and added that "reparations is getting closer and closer" on an episode of the podcast he cohosts with Cam'ron, "It Is What It Is."
During the trial, Mase wondered aloud if he should attend Diddy's trial on his podcast, but it doesn't appear that he ever went.
Mase did not respond to Business Insider's request for comment.
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The R&B group 112's first four albums were released through Bad Boy from 1996 to 2003. Most famously, they were featured alongside Diddy and Faith Evans on the song "I'll Be Missing You."
As MTV reported, 112 said that they left Bad Boy for Def Jam because of a "lack of money and attention." They added that they also left because their contract was "doo-doo."
"We still work with [Diddy] as far as getting ideas. We got three joints from his camp. It's no bad blood, it's no love lost," said member Mike in 2003.
"It's unfortunate what happened with Diddy," 112 member Slim said while appearing on "Ryan Cameron Uncensored" after the verdict was announced on Wednesday. "That's somebody people looked up to, and there was no win for any of the victims or anybody involved in the situation. It's more like you learn something from this."
112 did not respond to a request for comment.
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Cassie started publicly dating Diddy shortly after her debut album, "Cassie," was released in 2006 through Bad Boy. They dated until 2018.
In November 2023, Cassie sued Diddy and accused him of rape, abuse, and blowing up Kid Cudi's car after Diddy found out the rapper was interested in Cassie. The suit was settled the same month for an undisclosed amount, The New York Times reported.
In May 2024, CNN published a 2016 video that appeared to show Diddy dragging and kicking Cassie through the halls of a California hotel.Β Diddy apologizedΒ in a since-deleted Instagram post and said he was "disgusted" by his behavior in the video.
In an Instagram post, Cassie thanked fans for their support after the video was made public. "The outpouring of love has created a place for my younger self to settle and feel safe now, but this is only the beginning," she wrote. "Domestic Violence is THE issue."
Cassie was one of the witnesses called during Diddy's trial, taking the stand for four days. "I hope that people still see what Cassie did and think that she really made a difference," her lawyer, Douglas H. Wigdor, told ABC News after the verdict announcement.
"She was pleased that he's been found guilty and held responsible to federal crimes, something that he's never been held responsible [for] in his entire life," Wigdor said outside the courthouse.
Cassie Ventura had no comment on the lawsuit when reached by Business Insider.
Samir Hussein/Getty Images for Sean Diddy Combs
In December 1999, Diddy, his then-girlfriend Jennifer Lopez, and his protΓ©gΓ©, Shyne, were arrested after a nightclub shooting, but Shyne was the only one who went to prison.
He was later convicted of assault and sentenced to 10 years in prison, reports The New York Times.
Bad Boy released his self-titled debut album in September 2000, while he was in prison.
In 2012, Shyne, who served almost nine years, told MTV that he and Diddy made amends.
"As far as Puff is concerned, that's been a long time coming," he said. "He had reached out to me twice while I was in the pen, but I just wasn't ready for it."
In 2024, he spoke about Diddy's legal troubles. He told journalists soon after Diddy's arrest, "Let us not forget what the cold facts are. This is someone who destroyed my life."
A Hulu documentary following Shyne, "The Honorable Shyne," is set to be released on November 18. In the trailer, he said he believed he was set up to be the fall guy for the shooting.
In December, he told People, "We live in a world, in democracies at least, where the rule of law is tantamount. Everyone is innocent until proven guilty. I pray for justice, I pray for the victims. I pray for Diddy."
Shyne did not respond to a request for comment.
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The Lox released their first album, 1998's "Money, Power & Respect," via Bad Boy before the trio β Sheek Louch, Styles P, and Jadakiss β left for Ruff Ryders and Interscope.
That wasn't without its drama. The Lox said they had to plead with Diddy to get off Bad Boy and started a grassroots campaign to "Free The Lox," as they felt they weren't receiving a fair publishing deal.
This culminated in a 2005 appearance on Hot 97 in which Styles P threw a chair at Diddy, per Billboard.
"We made one record with you, 'Money Power & Respect.' It's 10 years later, and you still got half of our publishing. And you can't make it justifiable that you deserve half of our publishing," Styles P is heard saying in the recording.
According to AllHipHop, a deal was struck soon after the altercation.
In 2023, Jadakiss appeared on an episode of the podcast "I Am Athlete," saying how he appreciated how Diddy handled the situation: "He could've played much harder ball than he played."
The Lox did not respond to a request for comment.
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MonΓ‘e is one of the remaining artists signed to Bad Boy who isn't Diddy or his family members.
All four of MonΓ‘e's albums have been released through Bad Boy, including the 2019 album of the year nominee "Dirty Computer" and her most recent album, 2023's "The Age of Pleasure" (though both were also co-released by Atlantic Records).
"I got to say, I was scared to be partnering with a major label after a few years of being independent. I met Puff at a time I had decided to live frugally," MonΓ‘e told Billboard in 2018.
"But when I spoke to him, his words were, 'I love what you and Wondaland are doing," she continued, referencing the indie record label she had founded. "I don't want to be creatively involved. I just want people to know who you are and what you guys are doing.'"
"It was so humbling and beautiful. We're still close," she added.
MonΓ‘e did not respond to a request for comment.
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Dream, a girl group, was formed in 1998 and then signed to Bad Boy as its first white act.
Their first album, "It Was All a Dream," was released in 2001 and debuted at No. 6 on the Billboard 200. Their second album, 2003's "Reality," failed to chart at all, and they were dropped from Bad Boy and broke up.
"There were some shady people who maybe didn't have the best intentions for children. And there were some people who maybe were just doing business," Ashley Poole, a former member, told Complex in 2016.
"There was a big disconnect from Puff and us because we were from such different worlds," continued Poole. "Puff was straight business. He didn't care if feelings were hurt. He said what he needed to say. He would tell us we needed to lose weight."
One of Dream's former members, Alex Chester-Iwata, told Business Insider that working with Bad Boy was "a nightmare," saying they "pitted each of us against each other."
Another group member, Holly Restani, told Business Insider what she thought of the verdict.
"Sean Combs, the same as all individuals, should be held accountable for his wrongdoings, namely his abuses of power, coercion, manipulation, violence, and harm of others in positions beneath him," she said.
"Many of these are well documented and known to many to have occurred. He was acquitted of the charges the prosecution brought in his trial. He is not free of accountability, nor is he innocent," she continued.
The other members of Dream did not respond to a request for comment.
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Yung Joc was one of the biggest musicians signed to Bad Boy South, another offshoot of Bad Boy, this time focusing on rappers out of cities like Atlanta.
Both of the rapper's albums (2006's "New Joc City" and 2007's "Hustlenomics") were released by Bad Boy South.
Two years later, it went south: In 2009, Yung Joc told Billboard he was planning to sue Bad Boy and Block Entertainment, his original record label that partnered with Bad Boy, for "failure to pay royalties and advances for his first two albums and charging 'outrageous clearance fees' for his collaborations with other artists."
"Diddy said he's got to stay out of it because it's between me and Block Entertainment," he said, adding, "I feel like [Bad Boy] isn't doing anything to try to intervene and help the situation."
It's unclear if he ever filed the suit.
He hasn't released an album since, though he has put out singles and EPs independently.
In 2014, Yung Joc told The Grio, "Diddy and I are great. We made a lot of money together. Every time we've crossed paths since, it was love."
Yung Joc did not respond to a request for comment.
Johnny Nunez/Getty Images for BET
All four of French Montana's albums have been Bad Boy releases, most recently 2021's "They Got Amnesia."
"The deal [with Diddy] just felt right and it felt like it was the right thing to do. I felt like I can make a change with this for the music culture that I came from," Montana told Billboard in 2011.
In April 2024, during an episode of "Vlad TV," he confirmed he had left Bad Boy.
"I fulfilled everything. I make sure everybody got their money. I made sure, you know, Rozay got his money," he said, referring to rapper Rick Ross, who also owns a record label. "I made sure Puff got his money, made sure Epic got their money."
French added that he left Bad Boy on good terms with Diddy.
Montana did not respond to a request for comment.
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After an eight-year hiatus, New EditionΒ teamed up with Bad BoyΒ for their first album, "One Love." ItΒ was released in 2004 and is their last album to date.
The band's members said there were lots of disagreements about the future of the band with Diddy and his label. In a 2005 radio interview, they opened up about the problems.
"Diddy, when we didn't agree with him on certain songs, we would get sent home for like six, seven months. You know, it would just be nothing being done," said member Ricky Bell.
The final straw, they said, came when a song that none of the members liked appeared on the album instead of a song they worked on together with their longtime producers, Jimmy Jam and Terry Lewis.
"On top of that, Puffy paid himself $50,000, on top of that put a song on it that we didn't like, and we just felt like that was just a slap in the face. No respect," Bell added.
New Edition did not respond to a request for comment.
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Pitbull released two albums via Bad Boy: 2006's "El Mariel" and 2007's "The Boatlift."
Pitbull was one of the first acts signed to Bad Boy Latino, an offshoot founded by Diddy and Emilio Estefan in 2005, per Billboard. He was also a partner in the venture and had an A&R role.
It didn't last long. Before "The Boatlift" was announced, Pitbull said he was leaving the label. Pitbull was dissatisfied with his role, a 2006 New York Post report said.
"I told him, 'Yo, I want a piece. If I'm gonna get in the bed with you, I want a piece,'" he said. "I got a whole lot to bring to the table, which [he] is gonna definitely capitalize off of."
Pitbull did not respond to a request for comment.
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From 2012 to 2022, Machine Gun Kelly's six albums and three EPs were released through Bad Boy. His most recent EP, "Genre: Sadboy," was released in March through Interscope.
The "Wild Boy" rapper was first signed in 2011, as Diddy noted in a now-deleted Instagram post in August 2019.
"When I first signed @machinegunkelly I knew he was going to be a star. I didn't know how exactly we'd get there but I knew it would happen," he wrote. "'I'm so proud of the artist he is becoming, he's shown all the traits of an artist that will stand the test of time."
Kelly did not respond to a request for comment.
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Both of B5's albums β 2005's "B5" and 2007's "Don't Talk Just Listen" β were released by Bad Boy. They were a departure from Bad Boy's roster, as the group was primarily a boy band that also appeared on Radio Disney.
During an interview with The Shade Room in 2023, the brothers said they didn't regret leaving Bad Boy. "We just couldn't see eye to eye so we decided to split," said Patrick Breeding.
They added that after Diddy announced his intentions to revert publishing to the original musicians, they hadn't heard anything from him.
"We didn't hear anything. We didn't get no calls or nothing like that from them," said Carnell Breeding.
Dustin Breeding added, "Puff, Diddy, yeah, we all want our publishing too. We were so young at the time, we didn't understand the business of it. But looking back now, damn, why our names wasn't on the credit?"
B5 did not respond to a request for comment.
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A final sexual assault witness testified on Thursday that agreeing to have sex with male escorts while Sean "Diddy" Combs watched and directed their actions opened up a "Pandora's box" she could not close.
"It was just a door I was unable to shut," said the witness, testifying under the pseudonym "Jane."
"It was so much of it," she said of the drug-fueled, dayslong sexual performances that she and Combs called "hotel nights."
"It was too much of it," she told the jury.
Jane is due to testify this week and next at Combs' federal trial in Manhattan, with her testimony meant to bolster the two top charges of sex trafficking and racketeering.
Her testimony follows that of R&B singer and sex-trafficking witness Cassie Ventura, who said Combs coerced her into humiliating sex with male escorts in the 10 years ending in 2018. Former Combs employee "Mia" has also testified and said he sexually assaulted her at least four times between 2009 and 2017.
Jane is the millionaire music and lifestyle mogul's last victim before his arrest, according to the indictment.
Prosecutors say Combs sex-trafficked Jane βmeaning forced her to cross state lines to engage in sex with paid male escorts β between 2021 and 2024, the year he was arrested at the Park Hyatt, a Manhattan luxury hotel.
Inside Combs' hotel room, investigators recovered bags of ketamine and ecstasy powder, a blue party light, and more than a dozen bottles of baby oil and sexual lubricants, a Department of Homeland Security investigator testified during the trial's first week.
Prosecutors have previously described these items as the ingredients for freak offs, the dayslong sexual performances at the center of the sex trafficking case. Prosecutors have suggested that Jane will testify to having participated in Combs' final freak off β or "hotel night," as she called them β at that hotel.
On Thursday, Jane told the jury that she agreed to the first encounter in 2021 because she loved Combs and wanted to make him happy. She conceded on the stand that she felt "exhilarated" afterward.
Still, "I didn't think that we would be doing that again," she told the jury. "I figured it was something we did that one time, and maybe on a random night we might do it again."
She said she soon realized that participating was the only way Combs would agree to have sex with her.
But when she would tell him she wanted to stop having the encounters, which jurors have also heard were called "freak offs" and "king nights," Combs would abruptly brush her off.
"I could just feel the tension was building," she said. Combs would tell her, "We don't have to," and "That's fine," she said, and then quickly changed the subject.
Ultimately, she said, "We would just do it" again.
Prosecutors have also said that Combs could be violent with Jane. In openings last month, they described Combs chasing her through the rooms of the house he paid for her to live in in Los Angeles, breaking down doors as she tried to escape.
Jane Rosenberg/REUTERS
Jane's testimony may be key to proving not just sex trafficking, but racketeering as well. Racketeering requires proof that Combs, through his business empire, committed at least two underlying crimes.
Those potential underlying crimes include sex trafficking. They also include bribery and obstruction of justice, two crimes that prosecutors have alleged that Jane witnessed.
During her May 12 opening statements, Emily Johnson, an assistant US attorney, told the jury that Combs and his family members repeatedly reached out to Jane in an attempt to influence her testimony against him.
"You will hear him try to manipulate Jane into saying she wanted freak offs," Johnson said in her opening, describing a recorded phone call she promised the jury would hear.
"You will hear him interrupt Jane when she pushes back," the prosecutor added.
Prosecutors say Combs made sure that Jane would continue to receive housing payments from him after his arrest, something they may describe as a bribe.
Combs, 55, has pleaded not guilty to the indictment, through which he risks a maximum potential sentence of life in prison.
His lawyers have insisted that all sexual contact in the indictment was consensual, and they have described his business activities as legitimate and not constituting a criminal "racket."
The trial may continue into early July, depending on the length of the defense case, which is expected to begin in mid-June.
This story has been updated with additional detail from Jane's testimony.
Gilbert Flores/Variety/Getty Images/Shareif Ziyadat/Getty Images
Sean "Diddy" Combs' long-running feud with rapper 50 Cent was spotlighted in testimony given at the hip-hop mogul's criminal sex-trafficking trial this week.
50 Cent later took an online jab at Combs over the Tuesday testimony from Combs' former personal assistant and top executive, Capricorn Clark.
While on the witness stand in Manhattan federal court, Clark was asked by prosecutor Mitzi Steiner whether Clark ever heard Combs discuss guns during her stint working for the music tycoon.
Clark responded "once" and then went on to describe a time following an MTV press event that involved 50 Cent, whose real name is Curtis Jackson III.
Following the event, which both Combs and Jackson attended, Clark told the jury that Combs mentioned the rappers' beef to late music manager Chris Lighty, who at the time represented both men.
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Lighty, who also managed artists like Missy Elliott, Busta Rhymes, and Mariah Carey, was found dead from a gunshot wound in his Bronx apartment in 2012. His death was later ruled a suicide by the New York City medical examiner.
Combs "was doing MTV press with 50 Cent and after the interview wrapped up, myself, Puff, and Chris Lighty got in the elevator," Clark said, referring to Combs as "Puff."
Clark testified that while in the elevator, "Puff told Chris, because they were having some sort of issue, like, 'I really don't like all the back and forth, I don't do that, I like guns.'"
"And what's the issue, with an individual?" the prosecutor asked.
"He had an issue with 50 Cent," Clark said.
Clark β who also testified that Combs kidnapped her at gunpoint in 2011 and made threats against her life β said Combs' demeanor was "very serious" when he brought up his fondness for guns.
Following the testimony, Jackson took the opportunity to troll Combs on Instagram writing in a caption: "Wait a minute PUFFY's got a gun, I can't believe this I don't feel safe πLOL."
Jackson has been working on a documentary for Netflix about the sex assault allegations against Combs.
The feud publicly erupted when Jackson released a 2006 diss track accusing Combs of knowing who killed rapper Notorious B.I.G. in 1997.
Combs' trial is now in its third week.
Prosecutors allege that for two decades, the one-time near-billionaire led a criminal enterprise that involved the sex trafficking of his ex-girlfriend, R&B singer Cassie Ventura, and another woman.
If convicted of the sex trafficking and racketeering charges against him, Combs could face up to life in prison.
Lloyd Mitchell for BI
From the start of Sean "Diddy" Combs' sex-trafficking trial, everyone was waiting for Cassie Ventura to appear. She was the star witness.
I expected Ventura's testimony to be explosive. But it turned out to be more graphic than I ever imagined.
In the courtroom, I noticed the distress on the face of Ventura's husband. His wife, who is eight months pregnant, was telling her alleged abuser and a room full of strangers about some of the worst moments in her life.
In September, federal prosecutors in Manhattan accused Combs of racketeering and sex trafficking. They say he used the vast power and resources of his record label and other businesses to arrange drug-fueled and baby oil-lubricated sexual encounters called "freak offs" with Ventura, other victims, and male escorts.
Combs pleaded not guilty and denies the sex-trafficking allegations, but he hasn't quite denied all wrongdoing. His legal team said he participated in "mutual abuse" with Ventura, and that the two frequently fought physically. This was a domestic violence case, they argued β ugly, but not criminal sex trafficking.
In her testimony, Ventura talked about a messy, 11-year relationship during which she fought for scraps of Combs' attention. He was often busy with other women and his various businesses, she said. Ventura participated in the freak offs out of love for Combs, she said, but they were never something she wanted.
The hip-hop mogul introduced her to the idea of freak offs about six months into their relationship, when she was 22 and owed him another nine albums as part of a record label deal, Ventura said. Combs would watch as Ventura would have sex with other men, who were paid thousands of dollars in cash, according to court testimony.
In text messages and emails shown as trial evidence, Ventura talked about arranging the freak offs, which required dropping by a Duane Reade to pick up baby oil, lubricant, candles, and condoms.
The freak offs could last up to four days, requiring drugs to maintain stamina, she said. They typically required up to 10 large bottles of baby oil, she testified. Everyone "had to be glistening," as she described it. At one point, the judge stepped in to ask prosecutors to pull back from the deluge of baby oil questions.
The disturbing nature of the testimony was only heightened by Ventura's appearance. She is due to have a baby in June and was visibly pregnant. One courtroom marshal said he was prepared to deliver her baby if the stress of testifying induced labor. I wasn't sure if he was joking. One of the prosecutors urged the judge to require Combs' lawyers to wrap up cross-examination. "We are afraid she could have the baby over the weekend," she said.
Over the years, I've reported on about a dozen trials and countless more court hearings. There were the uncomfortable benches of Donald Trump's criminal trial. The rowdy fans at the R. Kelly Trial. The cold December mornings when I lined up for the Ghislaine Maxwell trial. The ultracompetitive Sam Bankman-Fried trial, where getting in line at 4 a.m. still wasn't early enough to get inside the courtroom.
But nothing in my experience has compared to the Combs trial, which began Monday morning after a week of jury selection and is supposed to last two months.
Lloyd Mitchell for BI
Ever since Ventura accused Combs of sexual abuse in November 2023, Combs' legal quagmire has been one of the biggest stories in the country. Combs paid Ventura $20 million to settle her case, but a flood of other accusers filed additional civil lawsuits against him. When prosecutors brought the criminal case against Combs, it was put on the fast track.
No longer the image of a pop star, Combs dresses for court like an office drone, wearing thin crewneck sweaters over white button-down shirts. He rarely betrays any emotion, occasionally nodding during his lawyers' arguments or huddling with the attorneys beside him.
His large family, including his mother and seven children, has been in the courtroom to show their support. Every day, Combs flashes them heart symbols with his hands. Their expressions, during trial proceedings, have remained neutral. The gravity of the situation β Combs could spend the rest of his life in prison if convicted of all charges β is obvious.
Lloyd Mitchell for BI
On the other side of the courtroom aisle are Ventura's support group, which includes her husband, Alex Fine, and several relatives. At some of the more raw moments of Ventura's testimony, Fine's face looked visibly pained. When her texts with Combs about the freak offs were shown to the jury, he broke his gaze and looked at his lap.
As Ventura testified in graphic detail, the courtroom was rapt. She spoke in a faint, dispassionate voice.
The grim atmosphere made the otherwise unbelievable details of the trial feel upsetting rather than dramatic. On social media, these details fly by as jokes. For Ventura, they left scars. In February of 2023, years after she left Combs, Ventura couldn't sleep, she testified.
"I couldn't take the pain that I was in anymore, and so I just tried to walk out the front door into traffic," she told the jury. "And my husband would not let me."
On Monday, for opening statements, the line outside the lower Manhattan courthouse began the previous afternoon. Same Old Line Dudes, the standard-bearer line-sitting company for New York trials, declined to disclose the precise time their clients booked because "it's very competitive," a receptionist told me.
During lunch breaks, live-streamers went outside and updated their followers on what unfolded indoors. Christine Cornell, a courtroom sketch artist, took photos of her illustrations in natural sunlight to share them with the media. Vicky Perez, who had come to New York City from Connecticut to watch the trial's opening day, said she's a fan of Ventura, having purchased her first album when she was in the fifth grade. Perez wanted her to "get justice," she said.
"I want to see his downfall," she said of Combs.
Lloyd Mitchell for BI
The scene overwhelmed even Dennis Byron, the editor in chief of the Hip-Hop Enquirer, who said he's reported on the hip-hop scene for 35 years. He covered Comb's career since he was an up-and-coming artist.
"I've been to a Diddy party," he said.
"Not one of those parties," he quickly clarified.
Byron β who wore a tweed vest and trousers in the May afternoon heat β said he's attended and photographed Combs' extravagant "White Parties," where he took photos of the likes of Combs, Ventura, Kim Porter, and Jay-Z.
Lloyd Mitchell for BI
These parties took on a new meaning following the indictment against Combs, where they've been widely re-interpreted as sex parties (virtually every single celebrity who has been asked about this denies they were sex parties). But celebrities have been having orgies forever, Byron said. He remembers hearing about them in the 1980s. Flying in escorts β as prosecutors said Combs did for freak offs β wasn't anything new either, Byron said.
"Well, I never stayed for those," Byron said. "I never stayed for those orgies. But I'm sure they happen. But I never seen them."
Combs' White Parties were meant to show off his power as "a tastemaker," Byron said. Combs accrued cultural capital β something prosecutors later said he used to coerce his victims.
"Remember, that party was a regular party," he said as I wrapped up our conversation. "Ain't no party like a regular Diddy party."
Combs' trial was taking place in the same 26th-floor courtroom that saw the trials of Sam Bankman-Fried and two of E. Jean Carroll's lawsuits against Trump. (Bankman-Fried and Combs share a jail unit together; Trump is in the White House.) As with all federal court cases, there's no broadcast or livestream.
Karen Agnifilo-Friedman, Luigi Mangione's lead defense lawyer and the husband of Combs' lead lawyer Mark Agnifilo, often showed up to watch. The court staff had also set up three overflow rooms for journalists and members of the public to watch the trial on a closed-circuit camera feed, plus two rooms for members of the in-house press like me.
Several people I spoke to said they were willing to keep an open mind, but believed it would be hard to shake the memory of watching the video of Combs beating Ventura and dragging her through a hotel hallway.
"I'm going to try to give him a fair shake, said Oota Ongo, a YouTuber who livestreamed himself walking around the courthouse after watching opening statements. "We all saw the Cassie tape. That Cassie tape is just something that I can't get out of my head."
Lloyd Mitchell for BI
Depending on the day, I alternated between the courtroom itself and a press room. When I checked out an overflow room one day, I spotted a prominent federal prosecutor who had put Bankman-Fried behind bars. He was paying close attention to Combs' lawyer, Teny Gregagaros, giving Combs' side of the story in an opening statement.
While Combs may have been an unpleasant, angry, jealous, and violent man β especially when drunk or high β he was not guilty of sex trafficking, Gregagos insisted. At most, he was responsible for domestic violence, she conceded.
"He is not charged with being mean," Gregaros told the jurors. "He is not charged with being a jerk."
The first witness was a security guard at the Intercontinental Hotel, who testified about the infamous video where Combs assaulted Ventura (Combs just wanted to get his phone back from her, his defense lawyers said).
Next, before Ventura, was a male dancer who said he acted as an escort. He testified about being asked to carefully urinate during sex.
"Apparently, I was doing it wrong because they both stopped me and told me that I was supposed to let a little out at a time and not go full, like, take a leak on her," he said, in a quote that perhaps best encapsulated both the graphic nature of the trial testimony and how prosecutors say Combs intimately choreographed people around him to satisfy his own desires.
During Ventura's cross-examination, Combs' lawyers pulled up texts in which Ventura indicated she enjoyed the freak offs.
But Ventura, in her testimony earlier, said she just wanted to make Combs happy. She loved him. But she never wanted the freak offs, she said.
"It made me feel worthless," Ventura testified. "Like I didn't have anything else to offer him."
Jane Rosenberg/REUTERS
The prosecution has rested after 6 Β½ weeks of testimony in Sean "Diddy" Combs' sex-trafficking and racketeering trial.
A federal jury in Manhattan has heard R&B singer Cassie Ventura β Combs' ex-girlfriend and the catalyst for his public downfall β tearfully testify about the humiliating "freak offs" she says she endured throughout their 11-year relationship.
A second sex-assault accuser, who testified as "Mia," described four times she says Combs attacked her, and a third accuser. The third accuser, "Jane," testified about the alleged violence underlying what prosecutors say were her three years as Combs' sex-trafficking victim.
Along the way, there have been numerous celebrity mentions, including pop icon Britney Spears, actor Michael B. Jordan, rapper Kid Cudi, and late music legend Prince.
Combs was arrested in September on charges of racketeering conspiracy, sex trafficking, and transportation to engage in prostitution β the culmination of months of lawsuits and public accusations of sexual assault and other misconduct.
The music tycoon is arguing through his defense team that all sexual encounters were consensual, including the alleged drug-fueled freak offs at the trial's center β and that any violence fell short of sex trafficking.
Here are some of the most striking moments from the trial so far.
AP Photo/Larry Neumeister
Ye, the rapper formerly known as Kanye West, has been given special access to attend his pal Combs' trial.
The "Jesus Walks" rapper has been added to Combs' friends and family trial guest list, according to two sources with knowledge of the document.
Ye showed up to court to support Combs during the trial's fifth week, but was denied entry to the Manhattan courtroom.
"He did not wait in line like everybody else from the public," a court source previously told BI. "No one gets special treatment."
Ye was instead seated in an overflow room on the courthouse's 23rd floor β three floors below where Combs' trial is unfolding β and left after listening to about half an hour of testimony.
It's not clear whether Ye will be back to support Combs at his trial, but if he does, he will have a seat available alongside Combs' family members in the courtroom.
Jane Rosenberg/REUTERS
In May 2024, shortly after CNN aired hotel surveillance video showing Combs dragging Ventura down a hallway and beating her, the rapper posted an apology on Instagram.
On video, Combs told his followers that his behavior that day was "inexcusable" β and that he began therapy soon after the 2016 hotel incident.
"I take full responsibility for my actions in that video. I'm disgusted. I was disgusted then when I did it. I'm disgusted now," he said in his Instagram video.
On June 9, however, Combs' ex testified that exactly one month after he posted that apology, he abused her, leaving her face covered in bruises.
After the abuse, she said, Combs leaned close to her and asked her: "Is this coercion?"
The woman, who testified under the pseudonym "Jane," said he then demanded she put on makeup, pop an ecstasy pill, and have sex with a male escort.
"Take this fucking pill. You're not going to ruin my fucking night," Jane said Combs demanded as she screamed, "I don't want to! I don't want to!"
Prosecutors say Combs sex trafficked Ventura and Jane by means of false promises, violence, and coercion.
Jane's and other trial witnesses' testimony contradicts the story she says Combs told people close to him after the CNN video was released.
Jane testified that when the news broke, Combs "huddled" with his team and his family.
"He said that that was the only time that they had physical violence like that," Jane said of the abuse between Combs and Ventura. "He said that she was a hitter and she would hit.
At trial, the jury has heard testimony from multiple witnesses describing more than a dozen times they said Combs physically abused Ventura between 2008 and 2018.
Jane Rosenberg/REUTERS
A former security guard described Combs personally pulling $100,000 out of a paper bag and counting it, painting an image that's both surprising and legally significant.
The guard said Combs hoped the cash β prosecutors call it a bribe β would bury forever a 15-minute video showing him beating Ventura in the hallway of the InterContinental Hotel in Los Angeles in March, 2016.
Combs fed "stacks of $10,000 at a time" into a money-counting machine, then stuffed it back in the paper bag, according to the ex-guard, Eddy Garcia.
The ex-guard said Combs then handed him the bag as payment for a USB thumb drive containing what both men believed was the only copy of the incriminating footage.
"Eddy, my angel," the guard said Combs called him after the transaction.
"Something like this would ruin him," he said Combs told him.
Eight years later, a surviving copy of the video was first made public by CNN. Now, it's the single most important piece of evidence in the trial, both sides say.
Prosecutors say the video shows Combs in the very act of sex-trafficking Ventura, meaning coercing her through physical force into engaging in sex at the hotel with a male sex worker known only as "Jewels."
The first charge in Combs' indictment accused him of racketeering, a charge that requires proof of at least two underlying crimes. Prosecutors may argue that the video alone is proof of three underlying crimes: sex trafficking, bribery, and obstruction of justice.
Prosecutors hope the video will also clinch the second charge in Combs' indictment, which accuses him of sex trafficking Ventura. Both racketeering and sex trafficking carry maximum sentences of life in prison.
US Attorney's Office, Southern District of New York
One of Combs' former personal assistants testified under the pseudonym "Mia," telling jurors he sexually attacked her four times between 2009 and 2017, when she was in her mid-20s and early 30s.
She said that two of the attacks were at the sprawling glass and concrete mansion he rented in Beverly Hills, including a rape in the staff bedroom. She described waking to feeling Combs on top of her. "Be quiet," she said he told her.
"I knew his power and I knew his control over me," she told the jury, her voice hushed and halting.
"And I didn't want to lose everything that I worked so hard for β or this, like, this world that was the only thing I had anymore."
BERTRAND GUAY/AFP via Getty Images
Combs once attacked Ventura during a party thrown by music icon Prince, the former personal assistant also testified.
The ex-PA, who used the pseudonym "Mia," told the jury she and Ventura had snuck out to Prince's Los Angeles home after learning he would be performing for a small gathering β a "once-in-a-lifetime" experience, as Ventura described it on the stand.
Prince did not disappoint. Mia said that as he played music, they danced atop his backyard pool, which was backlit and covered in purple plexiglas.
Then Combs showed up, she said.
"I saw his bucket hat come through the entrance and then made eye contact with him," Mia said of Combs. "Me and Cass just booked it."
They ran through Prince's house and into the woods out front, where "Puff caught Cass," and started beating her, Mia said, until Prince's security intervened.
Later that night, Ventura testified that Combs continued to beat her back at her hotel, leaving her with "bruising on my face, knots on my head."
Adam Gray/Getty Images
Capricorn Clark, another former personal assistant and one who became one of his top marketing executives, kicked off week three of the trial by telling jurors that he once kidnapped her at gunpoint.
It was December 2011, after Combs learned of rapper Kid Cudi's brief relationship with Ventura, Clark testified on May 27.
Combs was "furious" with Clark for keeping him in the dark about Ventura's romance with the "Pursuit of Happiness" rapper, she said.
Clark told the jury that Combs, armed with a gun, went to her house in a rage and banged on the door.
"He just said, 'Get dressed, we're going to go kill'" him, Clark testified that Combs told her, using the N-word to refer to Kid Cudi.
Combs then took Clark to Kid Cudi's Los Angeles home, she told the jury, describing it as being "kidnapped."
"The way he was acting, I just felt like anything could happen," a tearful Clark testified.
Getty Images/Giulio Marcocchi
In the first week of trial testimony, Ventura told jurors that starting in late 2008, she was coerced by Combs into a decade's worth of near-weekly "freak offs" β dayslong sex performances, usually at luxury hotels, involving male escorts, Glade candles, and numerous bottles of baby oil.
Clark told jurors that in the years she was Combs personal assistant, from 2004 until 2006, she would set up and clean up the hotel rooms where Combs took another longterm girlfriend, model Kim Porter, the mother of four of Combs' children.
During those years, Combs and Porter would stay for days at luxury hotels in Atlanta, Los Angeles, and New York. Clark said, as a personal assistant, she made sure Combs' suite was stocked with ecstasy, baby oil, and pricey Diptyque candles.
Cleanup was tricky, Clark told jurors, who mentioned "handprints left in oil on the, like, ultra-suede wall" as a particular problem. "It was just a lot of baby oil. It was just everywhere."
These were not "freak offs," Porter's former family attorney, Suzanne Kimberly Bracker, told Business Insider.
"He was madly in love with Kim," said Bracker, who helped negotiate Combs' child support settlement and who said that Porter had two children with Combs at the time.
"There is absolutely no way that he would share her with another man," she said. "He would tell her 'I'm not gonna pay for an apartment with my kids in one room while you're with another guy in the other bedroom.'"
Jane Rosenberg/REUTERS
Kid Cudi took the witness stand in Combs' trial on May 22, telling jurors that in December 2011, the music tycoon broke into his Hollywood Hills home, enraged after finding out about the rival rapper's short-lived romance with Ventura.
Kid Cudi, given name Scott Mescudi, told the jury that he returned home after the break-in to find the Christmas gifts he'd planned to give his family unwrapped and opened. His dog, he said, had been shut in the bathroom.
"Motherfucker, you in my house?" Mescudi recalled telling Combs over the phone as he raced home to confront him.
Combs was gone by the time he arrived, Mescudi said.
Mescudi also told the jury that some two weeks later, his Porsche was firebombed while in his driveway.
The Porsche "arson" is a specific element in the racketeering charges against Combs. Prosecutors alleged in court papers that Combs ordered his underlings to torch a vehicle "by slicing open the car's convertible top and dropping a Molotov cocktail inside the interior."
Kylie Cooper/REUTERS
Regina Ventura corroborated her daughter's testimony, telling jurors she witnessed the aftermath of two of Combs' violent, jealous rages over romantic rivals.
The first was in 2011. The mom said Cassie Ventura came home to Connecticut for the Christmas holidays with a large bruise on her back.
Cassie Ventura had told jurors the week before that the bruise was from being kicked to the ground by Combs during a fight over Mescudi.
Regina Ventura also confirmed a 2016 incident from shortly before the younger Ventura's 30th birthday. Combs had swiped her cellphone, Cassie Ventura testified, after learning about her affair with an unnamed professional NFL player.
When she returned to her Los Angeles apartment without her phone, her mother, who was visiting, called the police and confronted Combs outside the building as her daughter remained upstairs, the elder Ventura testified.
"I was yelling and screaming and trying to hit him," the mom told jurors. "He did give it back," she told jurors of the missing phone.
Jane Rosenberg/REUTERS
A former Combs personal assistant described watching β and doing nothing β as his boss brutally attacked a cowering Ventura in the bedroom of the rapper's private jet.
George Kaplan, 34, said the attack happened on a crowded flight to Las Vegas in the latter half of 2015. Kaplan said he heard the sound of screams and shattering glass coming from the jet's bedroom.
He said he turned to see Combs standing over Ventura with a "whiskey rock glass" in his hand, as she cowered on the bed.
"After the glass crashed, Ventura screamed, 'Isn't anybody seeing this?'" Kaplan told the jury.
"Did you look away?" asked a federal prosecutor, Assistant US Attorney Maurene Comey. Kaplan said he did.
"And after you looked away, what did you hear?" the prosecutor asked.
"Further glass crashing and chaos."
When the prosecutor asked what, if anything, the Combs security staff did in response, Kaplan answered, "Nothing."
No one, he said, went back to check on Ventura after Combs left the bedroom to rejoin his employees.
"I was 23 years old," Kaplan said in explanation of his own inaction. "All I wanted to do was have a great job in the entertainment industry."
Ultimately, he told the jury, this and similar domestic violence incidents drove him to quit.
John Lamparski/Getty Images
Combs' former personal assistant spent two days on the witness stand, and in his most dramatic testimony, described how a 2008 run for cheeseburgers at an all-night diner nearly escalated the East Coast-West Coast rap wars.
It started at 4 a.m. in the parking lot at Mel's Drive-In in Los Angeles, the ex-assistant, David James, testified.
Combs' trusted security guard, Damian "D-Roc" Butler, noticed that Suge Knight, cofounder of rival recording studio Death Row Records, was sitting in an Escalade just a few parking spots away.
James, Combs' personal assistant from 2007 to 2009, testified that he was at the wheel of Combs' silver Lincoln Navigator when Knight and D-Roc faced off.
"What are you doing in my city?" James, according to his testimony, remembered hearing Knight asking Combs' security guard, who had introduced himself as "D-Roc, Biggie's boy," a reference to the rapper Notorious B.I.G.
Within moments, James and the bodyguard saw someone pass a gun to Knight and watched as four SUVs pulled up into different corners of the parking lot, he told jurors.
James testified that he was ordered by D-Roc to speed back to Combs' Hollywood Hills estate. There was no mention of whether they drove back with or without the cheeseburgers.
Once back home, and as Ventura protested in tears, Combs grabbed three guns for the ten-minute drive with D-Roc back to Mel's, testified James, who said he was still the driver.
Knight was nowhere to be found upon their return, James said.
"It was the first time I realized my life was in danger," the former PA testified, telling jurors that he sent in his resignation soon after.
Gareth Cattermole/Getty Images for MTV
Danity Kane singer Dawn Richard was the fifth prosecution witness, and her testimony on May 16 alleged that in 2009, Combs brutally beat Ventura after she took too long to cook him dinner.
"Where's my fucking egg?" Richard recounted to the jury Combs shouting in 2009, as he stormed into the kitchen of his rented Los Angeles mansion.
"He took the skillet with the eggs in it and tried to hit her in the head, and she fell to the ground," Richard testified.
Ventura cowered on the floor "in a fetal position" as Combs punched her and kicked her, she testified. Then he dragged her upstairs by her hair, she said, adding that she then heard the sound of screaming and breaking glass from the third floor.
The next day, Combs called Ventura and Richard into the mansion's first-floor recording studio, she said.
"He said that what we saw was passion, and it was what lovers in a relationship do," Richard said.
She said Combs told the two women that "he was trying to take us to the top, and that, where he comes from, people go missing if they say things like that, like, if people talk. And then he gave us flowers."
While back on the stand on May 19, Richard re-emphasized that she felt this was a threat to her life.
The details in the testimony came as a surprise to Combs' lead defense attorney Marc Agnifilo, who called it prejudicial and "just a drop dead lie."
"It didn't happen," the lawyer complained to the judge. "And the reason we know it didn't happen is that Ms. Ventura didn't talk about it" during her four days on the witness stand.
On cross-examination on May 19, Richard agreed that she only recalled the alleged death threat in speaking with prosecutors earlier this month. It had gone unmentioned, she agreed, during a half-dozen prior interviews with prosecutors.
Gilbert Flores/Variety via Getty Images; Johnny Nunez/WireImage
Ventura was beaten by Combs for the most minor of perceived infractions, including taking too long in the bathroom, prosecutor Emily Johnson said in her opening statement.
"He beat her when she didn't answer the phone when he called. He beat her when she left a freak off without his permission," Johnson said.
Ventura's ex-best friend, Kerry Morgan, was called to the witness stand on May 19 and told jurors about two attacks on Ventura she witnessed, including one while on vacation in Jamaica in 2013.
Morgan said Ventura at one point went to the bathroom at the residence where they were staying, and Combs said, "She's taking too long."
"A few minutes later, I heard her screaming β like guttural. Terrifying," Morgan said. "He was dragging her by her hair on the floor."
Morgan told jurors that she saw Combs push Ventura to the ground, causing her to hit her head on the paving bricks.
"She didn't move. She fell on her side," Morgan said, adding, "I thought she was knocked out."
Ventura, too, had testified that arguments with Combs would regularly result in physical abuse.
Ventura βwho dated Combs on and off from 2007 to 2018 β described six separate times when Combs' attacks left her with injuries, with the most severe beating occurring in Los Angeles in 2009 following a party Combs had hosted at a club called Ace of Diamonds.
Ventura said she punched Combs in the face after he called her a "slut or a bitch" for talking to a record producer. Combs retaliated in the back seat of a chauffeured luxury vehicle by punching and kicking Ventura throughout a ten-minute ride to the rapper's rented mansion, she said.
She said she hid under the back seat to escape the attack. Combs demanded she stay hidden in a hotel for a week so her bruises could heal, she said.
Richard Shotwell/Invision/AP
The prosecution's fourth witness took the witness stand briefly on May 16 to detail what she and other Homeland Security investigators say they found inside Combs' suite at Manhattan's Park Hyatt New York after his September arrest.
Combs had checked into the luxury Midtown hotel, his lawyers have said, in case federal prosecutors in Manhattan had asked him to surrender voluntarily.
Special Agent Yasin Binda told the Combs jury she photographed what her colleagues found inside the room.
Those items included a clear plastic bag of baby oil bottles found inside a duffle bag. There were three more bottles of baby oil in his bathtub, alongside two bottles of personal lubricant.
Two more bottles of lubricant were recovered from a nightstand drawer, next to a prescription pill bottle she said held two small baggies containing a pink powder.
On the living room floor was a large blue party light of the kind Ventura testified were used to illuminate freak offs.
Similar bags of pink powder have previously been seized from Combs and tested positive for ecstasy and other drugs, a prosecutor had said in court the day after Combs was arrested.
Jane Rosenberg/REUTERS
In some of her final moments on the witness stand, Ventura was asked by the defense about a legal settlement that she said she is on the verge of receiving from the InterContinental Hotel in Century City, Los Angeles.
"I think it was $10 million," Ventura said of the settlement, hesitating when asked for the total amount agreed to.
The InterContinental is where security cameras captured Combs beating Ventura in a hallway in 2016, as she tried to flee what prosecutors say was one of Combs' freak offs.
The jury was shown the infamous footage at the beginning of the trial.
Johnson, the prosecutor, said in her opening statements that at the time of the attack, Combs paid a security guard at the hotel $100,000 in a brown paper envelope in exchange for the footage.
Combs apologized for his actions in the video after CNN published the footage last year.
It was the second big-money settlement revealed in Ventura's testimony.
Earlier in her testimony, Ventura told jurors that Combs paid her $20 million to settle her civil suit against him in 2023.
Christopher Polk via Getty Images
Pop icon Britney Spears and actor Michael B. Jordan were both name-dropped on May 15, on Ventura's third day of testimony.
During a cross-examination, Ventura was asked to tell the jury about the 21st birthday party Combs threw for her in 2007, at a club in Las Vegas.
The party was a significant moment in the Combs-Ventura story. Ventura testified that Combs, who recently signed her to his record label, gave her an uninvited kiss in a bathroom, sparking their relationship.
"I believe there were other celebrities there in attendance?" defense attorney Anna Estevao asked Ventura, who answered yes, there were.
"Sean was there, and he brought Dallas Austin, he brought Britney Spears," Ventura said, referring to the "Oops!β¦ I Did It Again" singer and the record producer. "I think those were the two people that stand out to me," Ventura added.
Asked how a 21-year-old of limited fame was able to attract such big names to her party, Ventura credited Combs, saying, "That was all him."
Jordan's name came up as the cross-examination focused on 2015, when Combs became suspicious that she was having an affair with the actor.
"Is Michael B. Jordan a celebrity?" Estevao asked.
"I would say so," Ventura answered, sounding surprised.
Emma McIntyre/Getty Images
Ventura testified on May 13 that she was initially nervous, but felt a sense of responsibility to participate in Combs' freak offs.
"I was just in love and wanted to make him happy," Ventura told the jury.
Ventura testified that in 2007, Combs first proposed "this sexual encounter that he called voyeurism, where he would watch me have a sexual encounter with a third man, specifically another man."
"I didn't want to upset him if I said it scared me or if I said anything aside from, 'OK, let's try it,'" she said.
Johnson said in her opening statements that Combs eventually made it Ventura's job to find and book escorts to participate in the sex encounters.
While on the stand, Ventura described in detail what went on during freak offs. Prosecutors say Combs arranged, directed, and often electronically recorded the sex performances.
Ventura testified that Combs would urinate and ask escorts to urinate on her during the freak offs.
"It was disgusting. It was too much. It was overwhelming," she said. "I choked."
Nicholas Hunt/Getty Images
Cassie burst onto the music scene in 2006 with an irresistible blend of pop and R&B.
Although the singer, whose legal name is Casandra Ventura, withdrew from the spotlight in the ensuing years, she's still beloved by fans of 2000s club jams.
In 2023, she filed a lawsuit against Sean "Diddy" Combs, alleging abuse throughout their relationship, including rape. An attorney for Combs denied the allegations to Business Insider. Cassie is now a key accuser in Combs' criminal sex-trafficking and racketeering trial, which began on May 12.
Here's everything to know about Cassie's career, her connection to Diddy, and what her life is like today.
Before launching her music career, Cassie had done some modeling for brands like Delia's.
In 2006, when she was 19 years old, she released her debut single "Me & U." It became her first hit, reaching No. 1 on Billboard's Hot R&B/Hip-Hop Songs chart and No. 3 on the Hot 100.
"Me & U" set the tone for her self-titled debut album, which was praised by critics for its "hypnotic groove" and "flippant playfulness." Rolling Stone later described the album as "the most brilliantly minimalist R&B album of its era."
In a positive review for Slant, Sal Cinquemani also said, "'Me & U' has single-handedly revived his ailing Bad Boy imprint," referring to Combs, then known as Diddy.
John Shearer/Invision/AP
An archived feature from 2008 said that Combs heard "Me & U" in a club and felt inspired to help Cassie's career.
Combs teamed up with Ryan Leslie, who wrote and produced the song, to record Cassie's album.
In 2008, she announced her plans to release her sophomore album.
"I guess I grew up a lot but I'm still in essence the same person," Cassie, then 21, told Billboard. "Lots has changed in my life, stuff that has made me think about things differently. I'm more vulnerable and you can hear my vocals better this time around. There's real emotion and a much realer connection with my fans."
At the time, Combs praised Cassie's musical development, which he said was reflected in the album.
"We pulled out, we took our time, we developed her for like, a year-and-a-half," he told Billboard in a 2008 interview. "People are just going to see her there and be like, 'Wow, she's really cocooned into a butterfly.'"
However, the album was delayed several times. She didn't release new music until 2012, when she surprise-dropped a set of three mixtapes. She continued releasing singles sporadically in the years following.
Cassie played Sophie in the 2008 film "Step Up 2: The Streets," and has also appeared in "The Perfect Match" and on several episodes of "Empire."
Additionally, she appeared in the 2022 TV movie "Hip Hop Family Christmas Wedding."
Charles Sykes/Invision/AP
Prior to her lawsuit, gossip news sites reported that Cassie and Combs maintained an on-again, off-again relationship. They reportedly started dating in 2007 and broke up in 2018.
Cassie's 2023 civil lawsuit accused Combs of serious allegations, painting the music mogul as an extremely violent and angry ex-partner.
It details several instances when the music mogul physically and mentally abused Cassie, as well as used intimidation tactics to keep her in the relationship. Combs quickly settled the suit shortly after it was filed.
Combs has been accused of sexual assault, rape, drugging, and other forms of violence in more than 50 civil lawsuits. He was arrested in September following a grand jury indictment and has denied the charges against him and all other allegations of sex abuse.
Combs' criminal sex-trafficking and racketeering trial began on Monday. Cassie, the prosecution's key witness in the case, took the stand on Tuesday and Wednesday to testify against Combs.
Paul Morigi/Getty Images
Following her split from Combs in 2018, Cassie began a relationship with Alex Fine, a professional bull rider, model, and personal trainer.
In June 2019, the singer revealed that she and Fine were expecting their first child together. The couple tied the knot in a small, surprise wedding in September of that year in Malibu, California. Their daughter, Frankie Stone, was born in early December.
Cassie and Fine welcomed their second child, a baby girl named Sunny Cinco, in March 2021.
In February 2025, Cassie revealed that she was pregnant with their third child, a son. While testifying Wednesday, Cassie's stylist, Deonte Nash, said he called Cassie to congratulate her on the birth of the baby, born Tuesday, about two weeks after Cassie testified against Combs.
Additional reporting by Laura Italiano.
Libby Torres contributed to an earlier version of this story.
REUTERS/Jane Rosenberg/File Photo
Prosecutors want to make sure the public doesn't see the "freak off" videos made by Sean "Diddy" Combs, which they say they'll present as exhibits in his upcoming criminal sex-trafficking trial.
Even the audio from those videos shouldn't reach the ears of the public and the press, argued Assistant US Attorney Madison Smyser in a court conference on Friday.
"These are extremely sensitive videos, they are going to involve videos of 'freak offs,'" Smyser said. "They involve other parties, victims, and, in some videos, Mr. Combs."
Smyser said prosecutors and defense lawyers were working out a way so that only jurors would be able to see and hear the videos when they're presented in court.
The indictment, brought by federal prosecutors in Manhattan, accuses Combs of sex trafficking and racketeering.
The primary victim prosecutors identified is Cassie Ventura, who was in a romantic relationship with Combs for 10 years. According to prosecutors, Combs sexually abused Ventura through "freak offs," which they described as elaborate and lengthy sexual performances that Combs staged, masturbated during, and often recorded.
Prosecutors have identified another four accusers who are expected to testify as victims in the trial. The judge has also allowed one "propensity witness," a yet-identified former romantic partner who is set to testify by name about alleged prior abuse, but who is not considered a victim in the criminal charges. Some of the witnesses are also expected to include sex workers who were recruited for the "freak offs."
Combs was attentive during Friday's court conference, the penultimate one before jury selection begins on May 5.
The hip-hop artist wore khaki jail garb and what appeared to be laceless Vans slip-on shoes.
Before the start of the hearing, Combs hugged his three female attorneys and then shook hands with one of his male lawyers. Throughout the conference, he sipped water from an unusually small plastic cup on the defense table before him.
US District Judge Arun Subramanian, who is overseeing Combs' criminal case, asked prosecutors to provide legal justifications for sealing the "freak off" videos, which would become court records if they were to be entered into evidence.
Prosecutors said they'd file a letter providing examples where similar procedures were followed in other cases. In R. Kelly's trial in Brooklyn, the court had jurors watch videos of sexual abuse on small screens in front of their jury seats while wearing earphones, while journalists and members of the public were kept out of the courtroom.
During Friday's hearing, prosecutors also said they wanted an accuser to testify about a "medical procedure" that they said was a result of a "freak off."
Combs's defense attorneys argued that the procedure wasn't sufficiently related to the conduct described in the indictment, and that the accuser shouldn't be able to testify about the experience.
Submaranian ultimately concluded that he'd wait and see what else the victim would testify about before deciding if prosecutors could ask questions about the purported medical procedure.
The judge also issued a ruling narrowing the scope of what Dawn Hughes, an expert on interpersonal relationships, would be allowed to testify about. Hughes, who previously testified in the trial between Johnny Depp and Amber Heard, and is expected to testify in Harvey Weinstein's ongoing trial, is expected to testify on behalf of Combs. Combs's lawyers have said she would partly testify about the "swingers" lifestyle the singer participated in.
Subramanian previously resolved most of the other legal issues ahead of the trial, which is set to take place in the same lower Manhattan courtroom where Combs's jailmate Sam Bankman-Fried had his trial.
The judge allowed Combs's team to obtain drafts of Ventura's memoir for cross-examination, but did not allow them to obtain other notes, emails, or bank records they had requested.
Mark Von Holden/Invision/AP, File
Subramanian also forced Warner Bros. to give Combs' lawyers interview footage with two accusers taken for a Max documentary, "The Fall of Diddy." An attorney for Combs said in Friday's hearing that they expected to receive the footage next week.
The contents of Ventura's memoir have never been made public, and little information about it is known.
Combs's lawyer Marc Agnifilo discussed the memoir in a September court hearing, where he unsuccessfully asked a judge to allow Combs to stay out of jail ahead of the criminal trial.
Agnifilo said Combs and Ventura had a consensual, if complicated, 10-year relationship, and that she essentially tried to extort him with the memoir draft after it ended. In November 2023, Combs settled a civil sexual abuse lawsuit that Ventura brought against him.
"'My client has written a book, and she is going to publish it, but if you want to buy the rights, then you will have the exclusive rights, and she won't be able to publish it.'" Agnifilo said, characterizing an offer from one of Ventura's previous lawyers. "'And you know what, you can buy the rights for $30 million.'"
Later, Ventura retained a different lawyer and sued Combs under New York's Adult Survivors Act, alleging sexual abuse,
"'I am not really here to embarrass you anymore to the tune of $30 million; I am going to bring this civil sex claim against you,'" Agnifilo said, purportedly quoting Ventura's other attorney.
Agnifilo's arguments were not successful. Combs has been detained in Brooklyn's Metropolitan Detention Center since September.