Defense strategies for Sean ‘Diddy’ Combs in his sex crimes trial
A legal expert discusses strategies the defense attorneys for Sean “Diddy” Combs might use in his federal sex crimes trial.
Trials often are composed of careful building blocks. They start with mundane testimony that serve as a foundation for inevitable bombshell witness revelations that wrap the proceedings.
Not so the trial of the United States of America v. Sean Combs, a/k/a “Puff Daddy,” “P. Diddy,” “Diddy,” “PD,” “Love.”
The very first week of the drama unfolding in a lower Manhattan courthouse was marked by stunning and sordid details from arguably the trial’s star witness, Combs’ former girlfriend Casandra “Cassie” Ventura Fine. Her 2023 lawsuit against Combs, which was settled a day later for a now-revealed $20 million, opened legal floodgates that ultimately led to the government raiding various Combs properties and bringing charges against him.
The one-time R&B singer, now pregnant with her third child with husband Alex Fine, described in emotional detail numerous instances of physical, sexual and psychological abuse during her years with the mogul. Particularly gut-wrenching were her descriptions of “freak offs,” dayslong sex parties populated by drugs and alcohol where Ventura Fine inevitably had sex with numerous escorts while Combs pleasured himself nearby.
The prosecution wants the jury to view her saga as evidence that Combs is indeed guilty of sex trafficking and racketeering, for which Combs could potentially go to prison for life. But the defense is hoping to cast her recollections merely as sickening details in a deranged love story between two consenting and jealous adults.
Many observers have predicted that the trial will go on for another month or two. It may well, but it’s hard to imagine that we’ll see another week as packed with numbing and disturbing pictures from inside the world of Diddy. Here are some of the more critical moments in Ventura Fine’s testimony:
Cassie reveals Diddy once overdosed
On her third day of testimony, Ventura Fine revealed the extent of her and Combs’ drug use in their decade together. Combs was once hospitalized due to “a very strong” opiate, she told defense lawyers, revealing the incident occurred around the time Whitney Houston died.
After a “freak off,” the pair had gone to a sex club in San Bernardino, California, Ventura Fine said, then Combs went to a party at the Playboy Mansion in Los Angeles, but she went home. When he overdosed on painkillers later that night, she said took him to the hospital.
Cassie said Combs threatened to ‘blow up’ Kid Cudi’s car
During cross-examination, Ventura Fine was asked about her relationship with rapper Kid Cudi, whose real name is Scott Mescudi. The time the two spent together would cause Combs to fly into a jealous and even criminal rage.
Combs had introducted the two back in 2011, thinking that a musical collaboration with the rapper would be good for Ventura Fine’s career. At that time, Ventura Fine said she was on a break with Combs but didn’t want to tell him that she was seeing Mescudi. And yet she was concerned enough about Combs’ reaction that she obtained a burner phone for her communications with Mescudi.
Those fears appeared justified. The Ohio-born rapper was mentioned in Ventura Fine’s bombshell 2023 civil lawsuit against Combs, with Cassie citing an alleged incident in which Combs threatened to “blow up” Cudi’s vehicle, seemingly in retaliation for his relationship with Ventura Fine.
Cassie reveals how much Diddy paid to settle 2023 lawsuit
Months after Combs’ team first alluded to a “substantial eight-figure settlement” in for her 2023 lawsuit, Ventura Fine revealed on the stand that she had been paid $20 million by the record executive and his companies.
The revelation came as she delved into the years following her and Combs’ 2018 breakup, revealing she was involved in writing a book about her experiences while they were dating.
She wanted Combs to read it so he would understand what she went through in their decade-long relationship, she told the court. So she reached out to Combs through her lawyer and asked him to read the draft and offer her compensation.
Ventura Fine said she’d put a $30 million price tag on him acquiring the rights to her book, as this was an amount she thought would affect him. But after he allegedly failed to respond, she sued him, alleging he had trafficked, sexually assaulted and physically abused her.
Cassie breaks down crying while recalling ‘freak offs’
While discussing participating in the “freak offs,” Ventura Fine broke down and sobbed. “I just felt that’s all I was good for to him. I was humiliated and didn’t have anyone to talk to about it,” she told prosecutors, as she began to choke up.
“His eyes go black. The version I loved of him was no longer there,” she said of his anger, continuing to cry. Asked why she continued to participate in “freak offs” even when they made her uncomfortable, she said, “the one-on-one time.”
“When you really care about somebody and love them, you don’t want to disappoint them,” she said through tears. When she “gently” tried to broach the subject of no longer doing “freak offs,” Ventura Fine said Combs was “dismissive” and that it made her feel “unheard.”
“Doing this made me feel horrible. It made me feel worthless,” she said of the sometimes days-long sexual performances.
Ventura Fine’s testimony ended in sobs as the singer recounted the “agency and autonomy” she would have had in her life if she never participated in a “freak off.”
Cassie Ventura ‘Perfect Match’ premiere hid alleged Diddy hotel assault
After the now-infamous 2016 hotel hallway assault, Ventura Fine claimed Combs tried to break into her apartment, saying she heard “chaos outside the door,” with kicking, banging and Combs’ voice yelling.
The same night, Ventura Fine claimed she went to Diddy’s house to get fitted for the premiere of her movie “The Perfect Match.” The jury was shown a photo taken in Combs’ bedroom of her wearing her premiere gown and large sunglasses “to cover up my eye,” she said, explaining, “I got hit in the face.”
The jury was then shown a red carpet photo where a bruise was visible on Ventura Fine’s shoulder and another of her at the afterparty where, now in a shorter dress, a bruise on her right shin was visible.
If you or someone you know is struggling with mental and/or substance use disorders, you can call the Substance Abuse and Mental Health Services Administration‘s free and confidential treatment referral and information service at 1-800-662-HELP (4357). It’s available 24/7 in English and Spanish (TTY: 1-800-487-4889).
If you are a survivor of sexual assault, RAINN offers support through the National Sexual Assault Hotline at 800.656.HOPE (4673) and Hotline.RAINN.org and en Español RAINN.org/es.
Contributing: KiMi Robinson
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