A Complete Timeline of All the Allegations in the Diddy Trial: Freak Offs, Kid Cudi's Car and More

Yahoo

2 days ago

Since the trial of Sean 'Diddy' Combs kicked off at the Daniel Patrick Moynihan U.S. Courthouse in New York City on May 5, numerous witnesses have taken the stand to testify about their alleged interactions with the rapper.
Diddy was arrested in September 2024 and charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He has pleaded not guilty to all charges and denied all of the allegations against him.
The mogul's ex-girlfriend Cassie was a star witness for the prosecution, taking the stand on May 13 and testifying for four days about her relationship with Diddy, which lasted off and on from 2007 to 2018. During her testimony, Cassie revealed that she developed an off-and-on drug addiction during their relationship and said she started trauma therapy and went to rehab in 2023.
'I was spinning out,' she said on May 14, recalling an incident where she tried to walk into traffic. 'I didn't want to be alive anymore at that point.'
She said her husband, Alex Fine, stopped her, and the duo are currently expecting baby No. 3. The pair, who tied the knot in 2019, share daughters Frankie and Sunny, born in 2019 and 2021, respectively.
Keep scrolling for a complete timeline of all the allegations that have been mentioned during the Diddy trial:
Cassie Details Freak Offs in Testimony During Diddy Trial: 'Eventually It Became a Job for Me'
Capricorn Clark, who formerly worked as an assistant for Diddy, claimed the mogul and a bodyguard known as Uncle Paulie brought her to Central Park and threatened her after finding out she'd previously worked for Suge Knight. Diddy allegedly told her 'if anything happened [with Suge] he would have to kill me.'
That same year, Clark was allegedly accused of stealing jewelry from Jacob Arabo, a.k.a. Jacob the Jeweler. She claimed she was forced to undergo five days of lie detector testing about the incident.
Cassie (full name Casandra Ventura) testified that she met Diddy for the first time when she was 19. She soon signed a 10-album deal with his record label, Bad Boy.
Cassie's first and only album, which was self-titled, debuted in August. It spawned the hit single 'Me & U,' which peaked at No. 3 on the Billboard Hot 100. None of the other albums in the deal ever came out, which Cassie alleged was entirely Diddy's decision as she recorded 'hundreds' of songs.
The defense, meanwhile, tried to point out instances where Diddy was supportive of Cassie. 'Words were helpful,' Cassie said in response to a question about how her ex would build her up. 'He's got that energy, that inspiring energy.'
Clark, for her part, claimed Diddy got violent with her this year while she was staying with him at his home on Star Island in Miami Beach. 'He charged me,' she alleged, claiming he pushed her backward on her shoulders. She briefly stopped working for Bad Boy thereafter because 'that was crossing my boundary.'
During her May 14 testimony, Cassie alleged that her first kiss with Diddy happened at her 21st birthday party in Los Angeles. At that point he was her boss, but they were not yet dating. She told the court that she cried and ran away after the kiss because she wasn't used to an employer behaving in that way.
After the party, Cassie claimed Diddy began inviting her to meetings in hotel rooms, where she believed they would discuss her career. Instead, Diddy allegedly 'introduced' her to oral sex and 'made me feel crazy for not reciprocating' after he performed it on her for the first time. She added she was 'completely sexually inexperienced' at the time and dating someone else.
In response, the defense showed the jury texts between Cassie and ex-boyfriend Ryan Leslie in an attempt to prove that she was not sexually inexperienced when she met Diddy.
Cassie testified their romantic relationship began in earnest a few months after her birthday, during a trip to Miami where Diddy allegedly gave her a 'blue dolphin' ecstasy pill.
Cassie Recalls Diddy Hotel Assault in Day 2 of Her Testimony: Biggest Takeaways
Cassie alleged that Diddy physically assaulted her for the first time after she saw him flirting with someone else during an outing. When they got into his car after the event, she claimed he 'knocked me around and was just really mean,' hitting her in the side of the head in front of his driver and a security guard and knocking her to the floor. 'I was just shocked,' she told the court.
The defense has argued that Diddy's anger issues were caused by alcohol and drug use as well as opioid withdrawal. They also attempted to prove that Cassie was physically abusive to Diddy as well.
Cassie claimed that she participated in her first freak off when she was 22, alleging that Diddy arranged for a male dancer to have sex with her early in their relationship. She claimed they took ecstasy and drank alcohol during the encounter. While she felt 'dirty' afterward, she felt she couldn't say no to more freak offs, which she said happened almost weekly after the first time and continued through 2017 or 2018.
During cross-examination, the defense pointed to loving text messages Cassie sent to Diddy as evidence that she willingly participated in freak offs in order to please him. 'I'm always ready for a freak-off lolol,' she wrote to him at one point.
The same year of Cassie's first freak off, Diddy allegedly ordered his assistant David James and other members of his entourage to confront his rival Suge Knight in the parking lot of a diner. James claimed that his former boss had three handguns on his lap when he made the alleged request. 'I was really shook up by it,' James told the court. 'My life was in danger.'
Cassie testified that she witnessed this alleged incident as well, telling the jury that one of Diddy's security guards interrupted a freak off to tell him about Knight's location. She also claimed she was given a gun to put in her purse, and this 'terrified' her.
The defense questioned James about why he didn't object when Diddy asked him to look for Knight. 'Respectfully, sir, you have someone with three guns that close proximity, I didn't think I had the option to say something,' he told attorney Marc Agnifilo before agreeing with the lawyer's claim that the incident was 'a radical departure' from usual events during his time working for Diddy.
Cassie Recalls Diddy's Alleged Threat to Blow Up Then-Boyfriend Kid Cudi's Car: 'He Was Going to Hurt' Us
Danity Kane's Dawn Richard claimed in her May 16 testimony that she was once at Diddy's house when she saw him attempt to hit Cassie with a hot skillet that had just been used to cook eggs. 'He came downstairs screaming, belligerent, asking where his food was and continued to hit her in the head and kick her on the ground in front of us,' Richard alleged. 'He came downstairs angry and was saying, 'Where the f*** was his eggs' and he was telling Cassie she never gets anything right and where the f*** was his food. And he came over to the skillet with the eggs in it and tried to hit her over the head, and she fell to the ground.'
The singer went on to claim that Diddy kept beating Cassie while she was on the floor then 'proceeded to take his arm around her neck and dragged her by the hair up the stairs.' The following day, the mogul allegedly invited Richard and her Dirty Money bandmate Kalenna Harper to record with him in the studio, where he told them the attack they'd both seen was 'passion.' Richard further claimed he threatened them, saying, 'People who say something can end up missing.'
The defense questioned Richard about whether she was having a difficult time keeping her story 'straight,' but she replied that she didn't agree with that assessment. During cross-examination, Diddy's attorney Nicole Westmoreland claimed Richard's testimony didn't always match what she'd alleged in her own lawsuit against the rapper or what she'd told the government's investigators.
'Every day it gets easier to remember certain things,' Richard said during redirect questioning. 'I try my best to do it to the best of my ability.'
A woman testifying under the pseudonym 'Mia' began working as an assistant for Diddy and claimed that the first of several alleged sexual assaults occurred after his 40th birthday party, 'a few months' after she joined his company. Mia alleged that Diddy kissed her and put a hand up her dress. 'I was shocked and I froze,' she recalled. 'I didn't even process what was happening.'
During cross-examination, Diddy's lawyers asked why Mia never reported the alleged assaults or went public with her accusations. According to attorney Brian Steel, she didn't mention the allegations until June 2024 when speaking with the government about the case they were building against the rapper. Mia pushed back, denying the characterization that she was engaging in a 'money grab' by speaking out against Diddy. She also denied the implication that she was lying on the stand.
In her May 19 testimony, Richard claimed Usher was present on one occasion when Diddy allegedly punched Cassie in the stomach at a restaurant. 'She immediately bent over, [Diddy] told her to leave,' Richard alleged. 'No one intervened.'
The same year, Cassie's friend and makeup artist Mylah Morales testified that she was present during one of Diddy's attacks. She claimed she was napping on a couch in her hotel suite the weekend of the Grammys when Diddy barged in looking for Cassie, asking, 'Where the f*** is she?' Morales alleged Diddy then went into Cassie's room and said she heard 'yelling and screaming' before the rapper came back out. The makeup artist claimed Cassie left the room 'distraught' and had 'a swollen eye and a busted lip and knots on her head.'
Mia, for her part, claimed that Diddy allegedly raped her in 2010 while she was staying at his home in Los Angeles. She claimed she was sleeping in another room with the door unlocked (per Diddy's alleged house rules) when she woke up with 'the weight of a person' on top of her; she told the jury it was Diddy. 'I just froze. I didn't react,' she testified. 'It was very quick but it felt like forever.'
Mia went on to claim that other alleged sexual assaults occurred during her employment with Diddy, which ended in 2017, but she said she'd blocked out some of the memories. On cross-examination, the defense questioned why Mia never reported any of the alleged assaults. Mia maintained that she was still concerned about losing her job, noting that it was still 'devastating' when she stopped working for Diddy.
Cassie started dating rapper Kid Cudi during a break in her relationship from Diddy but soon ended the relationship because she feared for her and Cudi's safety. She claimed she was having a freak off with Diddy when he saw emails about her romance with the other rapper and lunged at her with a wine bottle opener. While she escaped unharmed, she noted that she communicated with Cudi (real name Scott Mescudi) using a burner phone.
The defense attempted to link Diddy's response to the Cudi romance as evidence of broader issues of infidelity and jealousy in Diddy and Cassie's relationship.
After Diddy found out Cassie was dating Cudi, he allegedly broke into Cudi's home in the Hollywood Hills. Cudi testified that he found presents unwrapped and his dog locked in the bathroom, but he noted during cross-examination that his home had been unlocked and nothing was damaged. He also agreed with the defense's assertion that he and Diddy were 'played' by Cassie, as neither man knew she was seeing them both at the same time.
Diddy allegedly threatened to release two explicit videos of Cassie as retaliation for her relationship with Cudi and attacked her at his home. When she returned to her hotel, she claimed, her room had been trashed, with urine and feces in the bathroom.
Around this time, Cassie also told her mother, Regina Ventura, about the abuse for the first time. In her own testimony, Regina claimed Diddy demanded $20,000 in exchange for a promise not to release the videos. Regina took out a home equity loan and wired him the money, but he allegedly returned it several days later.
Regina also took photos of Cassie's injuries from the alleged assault, noting she wanted to establish a record. 'She was bruised and I wanted to make sure we memorialize it,' she said. 'I was scared for my daughter's safety.'
Clark claimed that she was present during the alleged break-in and accused Diddy of kidnapping her and forcing her to go to Cudi's house with him. The defense, meanwhile, hinted that Clark willingly accompanied Diddy to stop him from doing 'something stupid,' but she pushed back on that idea. 'I did not want to go,' she said. 'It was not my choice.'
Clark further alleged that she witnessed Diddy beat Cassie after he found out about her relationship with Cudi and advised Cassie's mother to call the police.
Cassie Testifies Early Diddy Relationship Was 'Scary' in Day 1 of Cross-Examination
After finding out about Cassie and Cudi's relationship, Diddy allegedly threatened to blow up Cudi's car and said he wanted his friends to be there when it happened. Following their split, Cudi allegedly met with Cassie and Diddy, where they talked about the car. 'What about my vehicle?' Cassie recalled Cudi asking. Diddy allegedly replied, 'What vehicle?' Cassie then noted, 'And that was the end of the meeting.'
According to a police report obtained by Rolling Stone, Cudi's car was set on fire by an 'incendiary device' in January 2012.
Another witness, escort Sharay 'The Punisher' Evans, testified that his first freak off with Cassie and Diddy took place this year. He went on to participate in around a dozen freak offs with the pair and told the jury he did not initially know who they were, as Diddy allegedly wore a veil over his face and Cassie wore sunglasses and a wig.
While Evans said during direct testimony that he saw Cassie expressing hesitation at some of Diddy's freak off directives, he told the defense that he did not see any cues indicating she was experiencing discomfort.
That same year, Diddy allegedly overdosed on opioids while attending a party at the Playboy Mansion.
Cassie alleged Diddy threw her down at one point, which caused her to cut her eyebrow on the corner of a bed. She claimed his security brought her to a plastic surgeon's office to treat the injury, noting she texted him a photo of the cut 'so you can remember.' He allegedly replied, 'You. Don't know. When to. Stop. You [have] pushed IT Too far. And continue to push. Sad.' She said she has a permanent scar on her eyebrow from the incident.
During cross-examination, the defense referenced a statement Cassie made in May 2024 about the CNN video of Diddy assaulting her, where she wrote that domestic violence is 'THE issue.' The defense was seemingly trying to point out that domestic violence, while a crime, is not one of the charges that Diddy is facing.
Deonte Nash, a former stylist for Diddy and Cassie, claimed he witnessed the incident which led to the cut on Cassie's eyebrow. He testified that he tried to call the police but was told to hang up the phone. That same year, Diddy allegedly got violent with Nash during a music video shoot because he'd been going out to clubs with Cassie. On another occasion, Nash claimed he saw Diddy pulling Cassie by the hair and threatening to release explicit videos of her.
Cassie Gives Emotional Testimony About Sean 'Diddy' Combs Allegedly Raping Her
Cassie was hosting an event in Atlantic City, New Jersey, when someone she was working with told her they'd seen a sexually explicit video of her. 'Ask what the room looked like … girl you need to get this info,' Diddy allegedly texted her after the incident. 'You gotta tell him this is your life and this is serious. … This is crazy! Do not let him out of your [sight]. Wtf.'
During cross-examination, the defense played audio of Cassie threatening to 'kill' a DJ who claimed to have seen explicit videos of her.
In his own testimony, Nash claimed Diddy threatened him because of the way Cassie's hair looked at a Vanity Fair party, allegedly grabbing him by the jacket and lifting him up. Despite alleged incidents like this, Nash said he was still close to Diddy, telling the court, 'I don't hate him. It's just not in me.'
After one incident of alleged abuse, Cassie claimed Diddy told her to put on more makeup to cover her bruises so one of his sons, who was then staying at his house, wouldn't see them. Nash, for his part, claimed he saw Cassie with two black eyes during a FaceTime conversation with her.
The same year, she began dating actor Michael B. Jordan during another one of her breaks from Diddy. At the time, Diddy was allegedly dating another one of his on-off girlfriends, which Cassie said 'hurt' her.
One of Diddy's former assistants, George Kaplan, claimed he was on a plane with Diddy, Cassie and a few security guards when he heard glass shatter from behind him. He turned around and allegedly saw Diddy holding a cocktail glass over Cassie, who was lying on the ground. Kaplan claimed no one did anything, and after Diddy walked to the front of the plane, no one went to the back to check on Cassie.
That same year, Kaplan alleged he got a call on the intercom at Diddy's house to come to the bedroom, where he found Cassie on the bed 'clearly upset' with a bruised eyebrow and forehead.
Kaplan ultimately quit working for Diddy later that year after he allegedly saw his boss assaulting another girlfriend named Gina, saying that was 'the final straw' for him.
Sean 'Diddy' Combs and Ex-Girlfriend Cassie's Relationship Timeline
Diddy was captured on surveillance video physically assaulting Cassie on March 5 at the InterContinental Hotel in Los Angeles. (An edited version of the video was published by CNN in May 2024.) During her testimony, Cassie claimed Diddy was trying to drag her back to a freak off happening in a hotel room. After the assault, Cassie alleged, Diddy tried to contact her, but she texted him, 'Please stay far away from me.'
During cross-examination, the defense showed a text message Cassie sent in which she told Diddy she wanted to attend the freak off 'so bad' but was afraid of exhausting herself before a movie premiere happening two days later.
In September, Cassie allegedly witnessed Diddy dangling her friend Bryana 'Bana' Bongolan over a balcony and then threw her onto patio furniture. (Bongolan sued Diddy in 2024, and he denied her claims in a statement via his lawyer.)
That same year, Diddy allegedly took Cassie's phone when he believed she was dating a professional football player. Regina testified that she called the police and had a 'bitter argument' with Diddy outside her daughter's apartment building as she tried to get the phone back from the mogul while Cassie was inside.
Near the end of their relationship, Cassie had dinner with Diddy, and they returned to her home afterward. She alleged that he then raped her on her living room floor. 'I just remember crying and saying no, but it was very fast,' she recalled, adding that they had sex 'by choice' on September 27 one other time after the end of their relationship.
During cross-examination, the defense questioned the timeline of the alleged rape, noting that Cassie testified it happened in August while telling the prosecution it happened in September.
Prior to their split, Diddy allegedly attacked Cassie's friend Kerry Morgan with a wooden hanger in a fit of anger over another man Cassie was dating at the time. 'I had a concussion. I was dizzy. I vomited a few times,' Morgan testified, adding that the incident ended her friendship with Cassie. She went on to claim that Diddy and Cassie later asked to sign a $30,000 nondisclosure agreement after the alleged altercation. During her cross-examination, Morgan agreed with the defense's assertion that Diddy is a 'flawed person.'
Cassie Says She Doesn't Remember 'A Whole Lot' From Diddy Hotel Assault: Day 4 of Her Testimony
In March, months after their split, Diddy allegedly sent Cassie a message referring to 'iPads full of skeletons,' which she believed meant explicit videos he'd recorded. She also claimed he wanted to be reimbursed for personal training sessions he paid for when her now-husband had been training her.
If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673). If you or someone you know is experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support. If you or someone you know is a human trafficking victim, contact the National Human Trafficking Hotline at 1-888-373-7888. If you or someone you know is struggling or in crisis, help is available. Call or text 988 or chat at 988lifeline.org.