Diddy’s trial timeline: Cassie, Kid Cudi headline witness list

(NewsNation) — Sean “Diddy” Combs is facing federal charges of racketeering conspiracy, sex trafficking by force, fraud or coercion and transportation to engage in prostitution.

On May 5, the former rapper’s trial started with jury selection. He has been held without bail since September 2024. Seven months before his arrest, two of his homes had been raided by federal investigators.

Prosecutors say Combs used the resources of his music empire to create “a criminal enterprise whose members and associates engaged in, and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice.”

His defense team said in court that the actions of their client were obscene and may amount to domestic violence but did not rise to the level of an orchestrated criminal enterprise that the prosecution has described.

Sean ‘Diddy’ Combs’ trial starts with jury selection

May 5, 2025

The federal sex trafficking trial against Combs started in New York City. The jury selection was briefly paused when Diddy claimed he was “a little nervous” and needed a bathroom break. There were three dozen potential jurors questioned by the judge regarding their answers on a questionnaire.

The potential jurors were given a brief description of the charges against Combs, saying that he had pleaded not guilty and was presumed innocent. By the end of the day, the jury pool was half the size it was, since some were excluded for personal reasons.

May 7, 2025

Wednesday marked the third day of jury selection in Combs’ case. On Tuesday, the prosecution and defense had secured 35 qualified potential jurors, but Judge Arun Subramanian said he wants at least 45. Right before 1 p.m. ET on Wednesday, the teams met that threshold.

From that pool, 12 jurors and six alternates were chosen. Lawyers questioned potential jurors on several topics, including their feelings on sexual abuse, knowledge of Combs’ case and whether they’ve seen the surveillance video of Combs allegedly dragging ex-girlfriend Casandra “Cassie” Ventura.

At least one juror was taken out on Tuesday after saying they had seen the surveillance video. Several potential jurors were also removed from the pool after watching news footage of the case. 

Diddy not treated differently because of race by prosecutors, judge rules

May 9, 2025

Subramanian ruled that prosecutors who brought charges against Combs have not treated him differently due to his race. This was in response to a request from the defense to dismiss some of Combs’ charges three days before opening statements.

Subramanian also refused to suppress evidence in Combs’ case in a separate written opinion. The lawyers had claimed that the prosecution was unprecedented because, “Most disturbingly, no white person has ever been the target of a remotely similar prosecution.”

“It’s the severity of what Combs allegedly did — not his race — that mattered,” Subramanian wrote. The judge also noted that Combs’ lawyers had alleged that the government sought to humiliate him through news releases, the way search warrants were executed, the refusal to let him surrender and alleged leaks to the media.

The judge wrote, “However, Combs doesn’t point to any evidence that racial bias played a role in the Government’s actions, that the prosecution team was responsible for any leaks to the press, or that the way Combs’s homes were searched bespeaks a discriminatory purpose.”

Male stripper testifies Diddy paid him to have sex with Cassie

May 12, 2025

Opening statements in Combs’ trial started on Monday. Prosecutors played the hotel video, originally obtained by CNN, that allegedly showed Combs beating ex-partner Ventura. Israel Florez, who is now a police officer, was a security guard during this incident.

He allegedly took video and photos of the damage to the hotel and was approached by Combs. According to Florez, Combs tried to hand him a stack of money, telling him that he didn’t see anything. Florez testified that he told Combs, “I don’t want your money. Just go back into your room.”

Daniel Phillip, a male stripper, also testified in Combs’ trial Monday, saying the rapper had paid him to have sex with Ventura while Combs watched. Phillip said this started in 2012, and Combs would provide instructions each time.

He said, on one occasion, “You need to rub more baby oil on each other. You don’t have enough on.” Phillip also claimed that he saw Combs assault Ventura in her apartment.

“I saw a liquor bottle fly across the room and hit the wall. Then Mr. Combs grabbed Cassie by her hair and started dragging her. … Mr. Combs pulled her into the bedroom. It sounded like him slapping her,” Phillip claimed during the trial.

Diddy’s ‘Freak Offs’ could last 4 days: Cassie

May 13, 2025

On Tuesday, Ventura, who is close to having her third child, took the stand in Combs’ trial. She testified that the sex parties that Combs would allegedly throw, called “Freak Offs,” could last up to four days.

Ventura told the jury, “The Freak Offs became a job.” She also claimed that they typically lasted 36 to 48 hours and would require frequent breaks due to drug use, alcohol use and dehydration. Ventura allegedly participated in these parties for around a decade, with her last one around 2017 or 2018.

She testified that, by the end of her participation, they were happening weekly.

“It was such a mess,” she said. “It was like, ‘What are we doing?’”

During her first “Freak Off,” Ventura said she was 22 years old and “confused, nervous, but also loved him very much.”

She told the jury that she couldn’t say no to Combs because she was afraid of violence and blackmail. She also said that Combs had threatened to post videos of her online if she didn’t follow instructions.

Cassie testifies that Diddy raped her, threatened to release sex videos

May 14, 2025

On Wednesday, Ventura testified that Diddy raped her when she ended their relationship that lasted a decade. Ventura claimed that Combs forced his way into her Los Angeles apartment and raped her on the living room floor after she said they were breaking up.

She also claimed that she didn’t feel like she could refuse his demands for her to have “hundreds” of encounters with male sex workers because he would make her “look like a slut” if he made any videos public.

“I feared for my career. I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” Ventura said during the trial.

Prosecutors showed five still images from the sex videos during the trial on Wednesday. Ventura claimed the images depicted her at various stages in Combs’ “Freak Offs.”

Trump hotel shooter claims he was ‘sex slave’ for Diddy, Cassie

May 14, 2025

Jonathan Oddi, who allegedly opened fire at President Donald Trump’s Florida resort and golf course, claimed in a video interrogation that he had been a sex slave for Diddy and Cassie.

He claimed, “I had sex with Cassie (Ventura) and Sean. Basically, he would masturbate and tell me what to do to Cassie. I had like 15 encounters, and I heard lots of business. … I was like a sex slave. For them, that’s what I was.” 

Oddi also claimed he settled a claim with Combs and turned over a video of his time with Combs and Ventura as part of the settlement. Oddi claimed that Combs was “scared I will expose him.”

“My settlement put me in a box. Basically, I couldn’t talk because I was going to be sued. They kept following me,” Oddi said.

Oddi told NewsNation he met Combs after the rapper called an agency that Oddi worked for and requested a show. Oddi’s comments to NewsNation were similar to those he told the police in 2018.

“I get dressed, and I’m (in) a police officer (costume). I stripped down and then, you know, they offer me some more money to do extra stuff,” Oddi claimed.

Cassie settled 2023 lawsuit against Diddy for $20M

May 14, 2025

Cassie told jurors during her second day of testimony that she settled a lawsuit in 2023 against Diddy for $20 million.

The lawsuit, in which Ventura claimed that Combs raped and abused her for years, was filed in November, 2023. It was resolved the next day.

When asked why she was testifying against Combs, she said she could no longer carry the shame of the abuse she reportedly suffered.

“I can’t carry the shame, the guilt,” she said Wednesday.

Cassie forced to read explicit messages with Diddy during trial

May 15, 2025

On Thursday, Ventura was pressed to read explicit messages between her and Combs out loud in court. This included texts that showed her expressing desire for the drug-fueled group sex she previously said left her traumatized, according to The Associated Press.

The messages were the focus of the fourth day of testimony, with defense attorney Anna Estevao reading what Combs’ texts said. Ventura had to recite her own messages about what she allegedly wanted to do during the “Freak Offs.”

One message exchange from August 2009 showed that Combs asked Ventura when she wanted the next encounter to be, and she replied, “I’m always ready to freak off.” Two days after that, she allegedly sent an explicit message that Combs replied to in eager anticipation.

She then responded, “Me too. I just want it to be comfortable.” However, later that year, Ventura sent messages to Combs about the state of their relationship, saying she needed more from him than sex.

Estevao also noted a text from July 2013 where Ventura wrote to Combs, “Wish we could’ve FO’d [Freak Offed] before you left.” In 2017, Cassie reportedly wrote, “I love our FOs when we both want it.” On the stand, Ventura explained that saying “loving FOs were just words at that point.”

She also complained during the trial that jurors weren’t hearing the full context of the text messages. She said, “There’s a lot we skipped over.”

Cassie takes witness stand while 9 months pregnant

May 16, 2025

On Friday, Combs’ defense team told the judge that their questioning of Ventura might not be finished until the end of the day. This would mean that prosecutors would need to use Monday to ask her follow-up questions.

The judge said that both sides had initially agreed that Ventura would be finished testifying by the end of the week. However, the defense said the prosecution interviewed two witnesses ahead of Ventura, which caused a delay in her taking the stand.

“That is why there is a sword that I must fall on,” Marc Agnifilo, one of Combs’ lawyers, told the judge. He also said that it seemed “strategic” that the prosecution called two witnesses before Cassie’s testimony.

Subramanian eventually told Combs’ team to finish up their questioning of Ventura on Friday morning to leave time for the prosecution to ask their questions.

By Friday afternoon, Ventura’s testimony had concluded. Her attorney, Douglas Wigdor, released a statement to reporters:

“This week has been extremely challenging, but also remarkably empowering and healing for me. I hope that my testimony has given strength and a voice to other survivors, and can help others who have suffered to speak up and also heal from the abuse and fear,” it read in part.

Diddy’s former protégé testifies in trial

May 19, 2025

On Monday, Combs’ trial started with testimony from Dawn Richard, who is his former protégé. Richard was a member of Danity Kane, a music group created by Combs on his reality show “Making the Band.”

Richard testified that Combs threatened her and another woman after they allegedly saw Combs attempt to assault Ventura with a skillet. Richard was then asked how many times she saw Combs allegedly assault Ventura.

She told prosecutors, “Frequently. He would punch her, choke her, drag her, slap her in the mouth. I saw him kick her, punch her in the stomach.”

Richard also testified that Combs did not need an impetus to attack Ventura. “It could be random. We wouldn’t even know where it came from,” Richard said. Richard sued Combs last year, accusing him of physical abuse, groping and psychological abuse when they worked together.

Diddy’s former personal assistant takes the stand

May 20, 2025

On Tuesday, Combs’ former personal assistant, David James, took the stand again. James worked for Combs from 2007 to 2009. On Monday, he testified, saying one of Combs’ staff members pointed to a photo of the rapper on the wall and said, “This is Mr. Combs’ kingdom. We’re all here to serve him.”

James also said Combs had described Ventura as “moldable” and said, “She’s good. I got her right where I want her. She’s young…” He also said that he told Ventura to leave Combs after seeing how he allegedly treated her.

Ventura allegedly said, “I can’t. I can’t get out. You know, Mr. Combs oversees so much of my life.”

Ventura’s former friend Kerry Morgan also testified, corroborating that Combs had engaged in violence with the singer. Morgan claimed she saw Combs assault Ventura twice — kicking her, pushing her and pulling her hair.

She also claimed she had heard Combs say he “owned” Ventura at one point. Morgan also told the court that she was choked by Combs in 2018 and then smashed on the head with a wooden hanger. This happened when Combs allegedly came to Ventura’s home in LA, furious because he thought she was with someone else.

The attack left her with a concussion, Morgan told jurors. Ventura allegedly made her sign a nondisclosure agreement in return for $30,000 to keep quiet about what happened.

Investigator who planned Diddy raid in Miami takes stand again

May 21, 2025

Special Agent Gerard Gannon of Homeland Security Investigations took the stand again Wednesday. He is one of the agents who helped plan the raid on Diddy’s home in Miami in 2024.

Gannon said the agents used an armored vehicle to get through Diddy’s security gate. They also had teams on boats, with a total of about 90 federal agents being deployed.

Agents found parts of two AR-15 rifles, among other items, on the rapper’s property. On Wednesday, Teny Geragos, one of Combs’ attorneys, questioned the measures that were taken during both raids on Diddy’s homes.

Geragos also asked, “So, HSI determined it would come in by land and by sea to secure the property?” Gannon said the search was conducted after Combs and his family left, and over 500 images were taken.

Gannon also said the federal investigation into Diddy started shortly after Ventura filed a civil lawsuit against the star.

Another Diddy assistant tells jurors he was strict, demanding

May 22, 2025

Another former assistant of Combs resumed his testimony Thursday. He told jurors Wednesday that Combs was strict and demanding.

George Kaplan worked for Combs from 2013 to 2015 and was initially going to plead the Fifth before striking a deal for immunity with prosecutors. Prosecutors said Kaplan could still be prosecuted for perjury if he lies.

Kaplan told jurors that he had purchased drugs for Combs two times when he worked for him. He also said, similar to Combs’ other assistant, that he would set up hotel rooms for Combs ahead of time. He said that included putting out baby oil and lubricant and helping clean up after.

On Thursday, Kaplan testified that Combs’ security staff gave him $50,000 to carry on a private jet. He also said he would go to Western Union and get thousands of dollars at a time on several occasions.

Former assistant says he saw Diddy assault Cassie on private plane

May 22, 2025

Kaplan told the jury he saw Combs assault Ventura on his private plane in 2015 on a trip to Los Angeles. He said he heard glass breaking, and when he turned around, he saw Combs with a whiskey glass in his hand.

“There was tremendous commotion and a scuffle, and then after the glass crashed, Cassie screamed: ‘Isn’t anybody seeing this?'” Kaplan claimed, and said that no one intervened. He then heard more glass crashing, and said Combs told Ventura to stay in the back of the plane while he came out to the front to sit.

Kaplan said that Combs appeared “even-keeled,” and no one checked on Ventura. When he was questioned on why he stood by and watched, he said he didn’t want to lose his job. He “couldn’t believe my good fortune to be working for such an icon.”

Kaplan allegedly gave his three-month notice after the incident, telling Combs it was due to his father being diagnosed with prostate cancer. He told the jury that, after the plane assault, he saw that Ventura had a black eye and Combs had sent him to get anti-inflammatory medicine for her.

“I had been a fan of his since I was a child. I keep lessons from him to this day,” Kaplan shared with the court.

Kid Cudi testifies in Diddy’s trial

May 22, 2025

Kid Cudi began his testimony in Combs’ trial Thursday and was escorted in by U.S. Marshals and Homeland Security agents.

Cudi told the jury that he had dated Ventura for a brief period in 2011 after meeting her in 2008. Prosecutor Emily Johnson asked Cudi if anyone else had been involved with Ventura when they dated, and he claimed that Combs was.

Diddy allegedly threatened to kill former assistant

May 27, 2025

Combs’ former assistant, Capricorn Clark, testified on Tuesday, kicking off the third week of his trial. She said that Combs had threatened her on the first day of the job, taking her to Central Park after dark with a security guard.

He was asking Clark about her former employment with music producer Suge Knight.

“He told me that he didn’t know that I had anything to do with Suge Knight and if anything happened, he would have to kill me,” Clark testified. When asked what she made of his’ remark, she said she believed he was “very serious.”

Clark is the third former assistant to testify against Combs. She worked for him from 2004 to 2012.

The Associated Press contributed to this report.