Tragic Details About Cassie Ventura & Diddy's Toxic Relationship

The following article includes allegations of domestic abuse and sexual assault.

Cassie Ventura's long-standing relationship with disgraced rapper Sean "Diddy" Combs brought her a tremendous amount of emotional turmoil. According to the singer's 2023 civil lawsuit, Ventura's path first crossed with Diddy's in 2005, when she was 19 and he was around 37. The following year, Ventura made her mark on the music industry by releasing her debut album under Diddy's legendary label, Bad Boy Records. Rumors of a romance between the two didn't blossom until 2007, once Kim Porter and Diddy broke up for good after being in an on-again-off-again relationship for years. 

Although Combs and Ventura didn't officially address their relationship at the time, the rumored couple was spotted in public together several times. In August 2012, the "Me & U" hitmaker shared a photo of her nails while sporting a diamond ring, naturally leading people to speculate that they were engaged. However, a rep clarified to E! News that Combs hadn't popped the question. As E! News noted, in February 2014, Diddy posted a pic of Ventura showing off a diamond ring and captioned it: "Baby do you like it? I just want to get you wat you Like ! I just wanna Mk you smile :) #takeDat. !." 

Once again, though, a spokesperson shot down any talk of an engagement. Then, in October 2018, a representative for Ventura informed LoveBScott.com that the couple had parted ways a couple of months prior. Shortly afterward, the "Kiss Me" singer found her match in Alex Fine, and Diddy even publicly congratulated the happy couple after news of her pregnancy broke. However, in November 2023, Ventura filed a civil lawsuit against her former partner, accusing him of sexual assault and abuse.

According to court documents obtained by People, in Cassie Ventura's civil lawsuit against Sean "Diddy" Combs, she claimed that he essentially took over the reins of her life and career once the singer signed onto his record label as a 19-year-old. According to Ventura's account, he started to relentlessly pursue her in 2007, and she only agreed to date him because she was afraid of the reaction a rejection might bring. Ventura alleged that Combs had physically assaulted her numerous times during their relationship and frequently displayed "uncontrollable rage."

The singer also claimed that after she finally ended things with Combs in 2018, he entered her home without her consent and sexually assaulted her. "She has required intensive medical and psychological care to recover from the trauma she lived through," the filings detailed. In addition to a myriad of other disturbing revelations, Ventura also alleged that her former partner had plied her with excessive amounts of drugs. Shortly afterward, Diddy's lawyer Ben Brafman told NBC News that he "vehemently denies these offensive and outrageous allegations." 

Additionally, the rapper's legal representative pointed out that Ventura threatened to write a book about her relationship with Diddy if he didn't pay her $30 million. "Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs' reputation and seeking a pay day," the statement continued. Meanwhile, Ventura's lawyer, Douglas Wigdor, asserted that although Combs had tried to buy her silence with tens of millions of dollars, she stood her ground in sharing her story with the world. The lawsuit was notably settled privately just a day after the initial filing.

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

In May 2024, CNN released disturbing security footage from March 2016 that showed Sean "Diddy" Combs violently assaulting Cassie Ventura in a hotel hallway. In the R&B singer's lawsuit, she claimed that Combs was highly inebriated at the time and the attack left her with a black eye. Ventura also alleged that she had tried sneaking out of the room after the rapper fell asleep, but he awoke and launched glass vases at her as she walked down the hallway and screamed at her (the surveillance footage did indeed appear to show Diddy throwing a vase at her). 

Shortly afterward, the disgraced music producer shared an Instagram apology video where he took "full responsibility for [his] actions" after acknowledging that the shocking video showed the lowest point in his life. "I was disgusted then when I did it. I'm disgusted now," Diddy added. He also claimed that his actions from that time had prompted him to attend therapy and rehab. Although Combs apologized numerous times throughout the video, he still concluded by saying that he wasn't expecting people to forgive him and had resolved to better himself every day.

Meanwhile, Ventura released a powerful statement expressing her gratitude for the outpouring of support she had received. "Domestic Violence is THE issue," she wrote. "It broke me down to someone I never thought I would become. With a lot of hard work, I am better today, but I will always be recovering from my past." Additionally, she urged people to believe anyone who opened up about their trauma as soon as they spoke about it.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

In May 2025, Cassie Ventura took the stand in Sean "Diddy" Combs' sex-trafficking trial. Some of the most disturbing details from Ventura's testimony during the Diddy trial revolved around the infamous so-called "freak-offs" he hosted. The "Me & U" hitmaker testified that Combs had first asked her to join one of the controversial parties when she was 22. Although Ventura found the idea incredibly nerve-wracking, she went through with it because she was unsure what kind of reaction a refusal would bring. According to the singer, the freak-offs could last anywhere from 36 hours to four whole days. 

She allegedly endured these parties for years, and they would sometimes happen every week. During this period, Ventura would take copious amounts of drugs to stay awake and "dissociate" from the fact that she had no desire to perform any of the sexual acts that Combs wanted her to do with male escorts, per the BBC. Additionally, the R&B star claimed that Diddy made her do a variety of "humiliating" sexual acts with other men purely for his gratification. To make matters worse, Combs sometimes made her select these men herself because his busy schedule didn't leave him much time for the task.

Assistant U.S. Attorney Emily Johnson also stated that Combs had recorded some of his partner's humiliating sexual encounters with male escorts and subsequently used them to blackmail Ventura when she got into a relationship with someone else. The singer started visibly tearing up as she reflected on her feelings about the freak-offs, confessing, "I felt pretty horrible about myself." Ventura sadly added, "It made me feel worthless." 

During Cassie Ventura's second day of testimony, she disclosed how Sean "Diddy" Combs threatened to release her "freak-off" videos when she refused to attend one of the parties because she wanted to spend some time with her loved ones instead. As The Guardian reported, the singer made it clear that she had no desire to be recorded during these humiliating moments, detailing the emotional strain that the recordings brought. "I feared for my career, my family [...] It is horrible and disgusting, no one should do that to anyone," she explained. "It could ruin everything I worked for, make me look like a s**t [...] I wasn't supposed to be on those videos." 

Meanwhile, during the first day of her testimony, she owned up to the fact that her love for Combs had been a major factor in her decision to stay with him for about 11 years in total. However, during the defense's opening statements, one of Combs' lawyers, Teny Geragos, argued that Ventura had chosen to stick by Combs' side for over a decade because "that was the better choice," (via People). 

Further, Geragos also dragged Ventura's husband, Alex Fine, into it by claiming that she ended things with the disgraced music producer and "ran into the arms of another man — a physical trainer Combs had hired to train her." The trial also appeared to have become a tragic detail of Ventura's husband's life because he looked visibly shaken in videos of Fine leaving the courtroom after the first day of the trial. Meanwhile, Diddy's behavior on day one of the sex trafficking trial didn't have anyone fooled.

During Sean "Diddy" Combs' May 2025 sex trafficking trial, Cassie Ventura opened up about why she chose to align herself with his label Bad Boy Records as a 19-year-old in the first place. According to The Washington Post, Ventura recalled, "I wanted to be around Sean for the same reasons as everyone else at the time — this exciting, entertaining, fun guy who also happened to have my career in his hands." She continued, "It felt special because not a lot of people got that time with him." 

During their 11-year union, the talented singer recorded enough songs to fill nine albums, but sadly none ever saw the light of day. As Ventura explained, she was never paid for the music she created and her career subsequently suffered. Elsewhere in her testimony, Ventura noted that as their relationship progressed, she started to feel that her career revolved around Combs' sexual gratification rather than her artistic expression.

Ventura also acknowledged that she had an uncomfortable age gap with her ex Diddy since he was 17 years her senior. However, that didn't stop the then-38-year-old from kissing her on her 21st birthday. Ventura had no desire to be kissed by Combs at the time, and she even teared up afterwards. As ABC News reported, their age gap was also a sticking point when Ventura divulged how she couldn't come up with a nickname for Combs. The confusion led the disgraced music producer to question what name she had given her grandfather, and he disturbingly decided to go with "Pop Pop" as a result.