The trial of Sean “Diddy” Combs continued on Thursday, May 15, with more testimony from his ex-girlfriend Cassie.
Diddy, 55, 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 has denied all of the allegations against him.
Cassie, 38, took the stand for the third day in a row at the Daniel Patrick Moynihan U.S. Courthouse in New York City, where she was cross-examined by Diddy’s lawyer Anna Estevao. Estevao began by asking, “You and Sean Combs were in love for 11 years, right?” Cassie replied, “Yeah.”
Cassie went on to describe the early days of her relationship with Diddy, saying it moved fast and was “scary,” but she still found him “sweet” at times. “His real personality — or at least what I thought was his real personality — came out and I liked who he was,” she explained.
Estevao also asked about the parties known as “freak offs,” questioning Cassie about whether she “told” Diddy she wanted to participate in them to make him happy. “No,” Cassie said. “There’s a lot more to that.”
The defense showed evidence that included text messages between Cassie and Diddy sent near the beginning of their relationship. One text from 2009 from Cassie to her then-boyfriend read, “I’m always ready to freak off lolol.” (Cassie testified earlier this week that she was coerced into participating in freak offs.)
At one point, Cassie requested a break after the defense showed sexually explicit texts between her and Diddy, and the judge granted a 10-minute pause. When she returned, she was “clutching what appear[ed] to be a chain of beads with a tassel,” according to The New York Times.
Additional text messages allegedly showed Cassie and Diddy discussing logistics for freak off parties, including buying supplies, and in one exchange, Cassie asked her then-boyfriend whether he had any more pills. (She testified earlier this week that she was addicted to opioids off and on throughout their relationship.)
Further text messages attempted to bolster the defense’s argument that Cassie was hesitant to participate in freak offs not because she was coerced but because she was worried about Diddy not seeing her as his “full girlfriend.” In one message, she wrote, “When we used to freak off when we were so in love. There were no questions asked, it felt right, like it literally made sense for the next step in our sex life together. I get nervous that i’m just becoming the girlfriend that you get your fantasies off with and that’s it.”
As the defense read an email she sent Diddy in 2007, Cassie laughed in court, saying it made her “giggle” because it was from so long ago. She claimed that gushing love notes, however, were usually sent by her and not the other way around. “It was usually a one-way street,” she told the court of being open with her feelings for Diddy.
Explaining why she kept her identity a secret during freak offs, she said, “The encounter itself was pretty crazy. I didn’t want anyone to know.”
Estevao also asked about the idea that Diddy was leading a “swingers” lifestyle, and Cassie testified that she watched him have sex with another woman multiple times during their relationship. The defense also asked about Diddy’s work as a fashion executive with regard to Cassie’s previous testimony that her ex would comment on her appearance.
When Estevao asked about drug use, Cassie agreed with the attorney’s assertion that Diddy was at one point an “addict.” She claimed she saw him go through opioid withdrawal multiple times, which allegedly made him more irritable. Cassie further alleged that Diddy would get angry when he didn’t know her whereabouts “because he assumed I was cheating.”
After a lunch break, Estevao questioned Cassie about a text she sent that seemed to imply she enjoyed freak offs. “I would say that loving [freak offs] were just words at that point,” Cassie told the lawyer. When Estevao continued by asking about a text where Cassie was “excited” in 2017, she replied, “I probably would have been excited to see him and have fun with him.”
The defense then asked about Diddy’s late partner Kim Porter, who died in November 2018 at age 47. “I had some jealousy of Ms. Porter,” Cassie admitted before claiming that she and Diddy would often fight about infidelity. “It was a little scary,” she said of their arguments.
As discussion turned toward Cassie’s relationship with Kid Cudi, the singer reiterated her previous assertion that she used a burner phone to communicate with Cudi, now 41. Cassie confirmed that she continued to participate in freak offs with Diddy while dating Cudi, saying, “It was a job.” She noted that she didn’t tell Diddy about her romance with the “Day ‘n’ Nite” rapper because she “thought it would be way too dangerous.”
At one point, Cassie agreed with Estevao’s claim that Diddy was “irate” over her relationship with Cudi in part because he was also famous. According to Cassie, this issue came up multiple times while she was dating Cudi in 2011.
Four years later, Cassie said she was filming a movie in South Africa when she learned Diddy was dating someone else. She decided to cut off communication with him for a while and began dating Michael B. Jordan. According to Cassie, one of Diddy’s employees told her that the mogul knew about her relationship with Jordan, now 38.
Estevao also asked more questions about Diddy and Cassie’s drug use, asking Cassie to recall a 2017 incident when Diddy overdosed on opioids during a party at the Playboy Mansion. Cassie alleged that she and Diddy once obtained a “plant medicine” from Mexico that was illegal in the U.S. to try and help themselves detox, but it only worked temporarily. She told the defense that she and Diddy were dependent on drugs for most of their relationship, adding that he allegedly didn’t like it when she did drugs with other people. At one point, she claimed, he became “pretty explosive” upon finding out she’d done cocaine with a friend.
After prompting from Estevao, Cassie refuted a rumor that the baby oil used in the alleged freak offs was laced with date-rape drugs. According to Cassie, there was never any drugs in the baby oil she and Diddy used. Testimony ended for the day just as the defense began questioning Cassie about the 2016 surveillance video of Diddy assaulting her.
Since Diddy’s arrest last year, he and his team have repeatedly denied the charges as well as all additional allegations against him.
“We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office,” Diddy’s attorney Marc Agnifilo said in a September 2024 statement. “He is an imperfect person, but he is not a criminal. To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges. Please reserve your judgment until you have all the facts. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court.”
The arrest came nearly one year after Cassie filed a lawsuit accusing him of sexual and physical abuse throughout their relationship, which lasted off and on from 2007 to 2018. The rapper denied her claims in a statement shared by his attorney.
“Mr. Combs vehemently denies these offensive and outrageous allegations,” Diddy’s lawyer Ben Brafman said at the time.
One day after the suit was filed, Diddy and Cassie settled out of court. In May 2024, CNN published a hotel surveillance video of Diddy kicking and grabbing Cassie in 2016. He later apologized for his actions in a video shared via Instagram.
Cassie testified about the video on Wednesday, May 14, claiming that Diddy threw a vase of flowers at her that hit the wall. The video has no audio, so she attempted to remember what Diddy was saying to her. She claimed he was telling her that she “couldn’t” leave him as she was trying to exit the hotel.
The prosecution then displayed photos of Cassie in the aftermath of the assault, which showed her with a swollen lip. She told the court that she had a black eye under her sunglasses.
Cassie claimed Diddy tried to contact her after the assault, but she texted him, “Please stay far away from me.”
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.
