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The federal trial for hip-hop mogul Sean “Diddy” Combs has officially entered week two. And the courtroom has become a battleground for both sides. The prosecution has presented a compelling case, featuring detailed testimonies from former associates like Casandra “Cassie” Ventura and Dawn Richard. These accounts have painted a picture of a pattern of control and manipulation. In contrast, the defense, led by seasoned attorney Marc Agnifilo, has acknowledged the existence of domestic violence but contends that the acts were mutual and not criminal.

Newsweek chief investigative reporter Joshua Rhett Miller told Showbiz Cheat Sheet that the prosecution does not have a “slam dunk” of a case against Combs. Here’s why.

Sean ‘Diddy’ Combs’ fate is not set in stone following Casandra ‘Cassie’ Ventura’s testimony

Casandra “Cassie” Ventura gave compelling testimony during week one of Sean “Diddy” Combs’ trial. As Combs’ former girlfriend, Ventura explained how Combs abused and controlled her throughout their relationship. “If I never had to have freak-offs, I would have agency and autonomy,” Ventura testified. “I wouldn’t have had to work so hard to get it back.”

Many might assume that Ventura’s testimony would be enough for a conviction. However, Newsweek chief investigative reporter Joshua Rhett Miller told Showbiz Cheat Sheet that the prosecution does not have a “slam dunk.”

“Combs has a top-notch legal team,” Miller explained. “He has a team of high-powered attorneys who are really good at what they do.” Miller noted that Anna Estevao, who cross-examined Ventura, “got what she needed to” and “didn’t appear too aggressive.”

“It’s kind of by the book in terms of what they’re doing,” Miller noted of the defense team. “They’re trying to show that she was a willing and able participant. … Two of his attorneys that he regularly consults with, Brian Steel and Mark Agnes Filo, that’s who he sat between, and those are his guys. He speaks to them the whole day. He is heavily involved with them, and Mr. Steel, as far as I’m concerned, is one of the best defense attorneys I’ve ever seen live. This guy is surgical, and he’s sweet … he is so, so good at what he does.”

Miller added that the prosecution has a “definite uphill battle … particularly as it pertains to the sex trafficking by abuse, threats, or coercion.”

Casandra ‘Cassie’ Ventura’s testimony might not prove to the jury that sex trafficking took place

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Sean “Diddy” Combs faces a sweeping federal indictment that portrays him as the orchestrator of a criminal enterprise spanning over a decade. The charges allege that Combs used his position in the entertainment industry to exploit women for his sexual gratification. According to the indictment, he organized “freak-offs,” elaborate sex performances involving drugs, that his employees facilitated. Combs is accused of coercing participation through threats, violence, and manipulation, including the use of incriminating videos to maintain control over the victims.

Newsweek chief investigative reporter Joshua Rhett Miller spoke about Ventura’s “compelling” testimony. However, he doesn’t know if it’s enough for a sex trafficking conviction.

“Cassie up on the stand, breaking down, saying that she felt heavily objectified by Mr. Combs by a bevy of escorts, that’s compelling. That’s powerful,” Miller said. “However, I don’t know if it meets the legal standards. That’s where the rubber’s going to meet the road, in this case.” Miller noted that while Combs’ bad behavior has been established in court, he’s uncertain whether the presence of sex trafficking has been proven.

The $10 million settlement ‘bombshell’ led to a shocked courtroom

During Casandra “Cassie” Ventura’s cross-examination, she revealed that she settled with the InterContinental Hotel in Los Angeles for $10 million. The hotel had recorded footage of Sean “Diddy” Combs abusing her in the hallway. Previously, Ventura also received a $20 million payout from Combs after she filed a lawsuit against him in November 2023.

Newsweek reporter Joshua Rhett Miller spoke about the moment the courtroom learned of the $10 million settlement. “There were gasps in the crowd,” he explained. “So, that was a bombshell, because our society, like it or love it, is based on the dollar. I’m just wondering the impact of her getting a combined $30 million settlement, basically, before this case started.”

How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area. 

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