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Sean Combs Prosecutors Led with ‘Shock and Awe,’ Legal Experts Say

On the first day of Sean Combs’ sex trafficking and racketeering trial, jurors heard that the music mogul allegedly made a male escort urinate in his ex-girlfriend Casandra “Cassie” Ventura’s mouth, causing Ventura to feel like she was “choking.” Jurors also saw video of Combs kicking and dragging Ventura in a hotel hallway in 2016.

Prosecutors wasted no time introducing some of their most graphic and disturbing evidence. Experts say it was a clear tactical decision.

“It’s a shock and awe strategy,” Mark Chutkow, a former federal prosecutor in Detroit who specialized in human trafficking cases, tells Rolling Stone. He said when dealing with a high-profile celebrity defendant, prosecutors often try to dismantle any “positive feelings” as soon as possible.

“Here, [Combs] is handsome, charismatic, and well-known for many years in the New York area. They want to flip that narrative immediately, so any potential holdout jurors will be looking more skeptically at him,” Chutkow, now a trial attorney at Dykema Gossett, says. “They really want to create an impression about him right out of the gate.”

Chutkow and other experts tell Rolling Stone they expect prosecutors will focus on the hotel surveillance video as much as possible throughout the expected eight-week trial.

“The thing about video is you can’t really cross-examine video,” Chutkow says. “In the Derek Chauvin trial, they showed the video of him putting his knee against George Floyd’s neck in the beginning, middle and end of the case. It’s something the defense couldn’t really counter.” (Chauvin, a former Minneapolis police officer, was convicted of murdering Floyd, a 46-year-old Black man, on May 25, 2020.)

Prosecutors mentioned the video of the hotel assault during their opening statement Monday but called a former hotel security guard as their initial witness to play the entire video for jurors. The witness, Israel Florez, testified that he was called to the sixth floor of the InterContinental Hotel in Los Angeles on March 5, 2016 for a “woman in distress.” The guard not only described seeing Ventura with a visible injury, he also testified that Combs offered him a wad of cash to keep quiet. He said it “definitely” appeared to be a bribe.

“I think this was strategically thought-through,” former federal prosecutor Braid Bailey says of the decision to put Florez on the stand first. “He’s a non-involved witness in terms being just hotel security personnel. He’s not necessarily going to have any stake in any of this. It’s extremely helpful to the prosecution.”

Bailey says the mention of the alleged cash offer was important because according to Combs’ indictment, bribery is one of the predicate acts that prosecutors claim was part of Combs’ alleged pattern of racketeering. Bailey agrees the video’s introduction so early on was key. “When you can lead with a tangible example of force, it’s an extremely powerful way to start. It immediately casts Mr. Combs in an extremely negative light, which is going to be difficult for the jury to stop seeing him in. It’s not necessarily insurmountable, but that’s not an image you want in jurors’ minds,” he says.

Michelle Simpson Tuegel, a lawyer who represented multiple victims of disgraced USA Gymnastics national team doctor Larry Nassar, says she was struck Monday by the opening statement from Combs’ defense lawyer, Teny Geragos. In her address to the jury, Geragos said people might hear the evidence and determine Combs is a jerk, but they shouldn’t conclude that an incident of “domestic” violence caught on video is evidence of sex trafficking.

“I think their characterization of [Combs] as trying to accept responsibility, saying he’s a complicated man, and he may be guilty of domestic violence, but he’s not a sex trafficker – that’s a really dangerous position to take,” Simpson Tuegel says. “Saying domestic violence is completely separate from sexual violence, it’s just not the reality in most cases. There is an intersection with domestic violence and sex trafficking and sexual assault.”

Simpson Tuegel also notes prosecutors’ decision to call a male sex worker as the second witness in their case on Monday afternoon. She says it helped “set up the context of the full picture of this commercial sex that allegedly was going on.” The witness, Daniel Phillip, testified that he was paid to have commercial sex with Ventura and that he once witnessed an enraged Combs throw a bottle at Ventura before he pulled Ventura into another room and purportedly struck her.

“It sets the entire stage of the relationship being one of abuse, violence, and intimidation, which is important because the defense has tried to set it up [that] she chose to stay in this relationship,” Simpson Tuegel says. “I think that’s something jurors have a broader understanding of now – that there are people who remain in relationships who are victims, and that’s not fully a choice. It doesn’t feel like a choice to them in that moment, that they can leave. And the violence, the intimidation, and the threats are amplified with someone with the level of resources and power that Sean Combs had.”

The experts who spoke with Rolling Stone agree there’s plenty of time left for both sides to present additional evidence and score points with jurors. Much remains unknown. But if all goes according to plan, Ventura is expected to take the stand this week as the prosecution’s star witness.

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Combs, 55, was arrested and charged in September. He has pleaded not guilty. His initial indictment largely mirrored the bombshell sex-trafficking lawsuit filed by Ventura in November 2023. Prosecutors have since added additional charges of sex trafficking and transportation to engage in prostitution in connection with another alleged victim. Victim-2 was identified by prosecutors Monday using the pseudonym Jane.

The jury of eight men and four women ultimately must decide whether Combs was a “swinger” who indulged his eccentric appetites with other consenting adults, as the defense claims, or a serial sex predator who physically abused and forced women into drug-fueled sex marathons known as Freak Offs and Wild King Nights, as prosecutors allege.

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