Diddy key witnesses could hurt prosecution's case despite explosive testimony: expert

During the first two weeks of Sean "Diddy" Combs' sex-trafficking trial, the jury heard from the rapper's ex-girlfriend Cassie Ventura, male escorts, ex-assistants and former Homeland Security Investigations (HSI) agents.

The prosecution has roughly six weeks to prove Diddy helmed a criminal enterprise used to sexually exploit women, including Cassie. Authorities charged Diddy with multiple counts of racketeering conspiracy, sex trafficking by force, fraud or coercion and transporting for prostitution in 2024.

"Week two of the Combs trial helped the prosecution corroborate Ventura’s testimony through independent witnesses and establish the elements of sex trafficking and racketeering," former federal prosecutor Neama Rahmani told Fox News Digital. "The defense scored some points on cross-examination, but I think they’re way behind."

However, other experts noted the defense is doing a "great job" using the prosecution's witnesses to bolster their arguments during cross-examination.

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"The defense is doing a great job at exploiting witness testimony to support their theory of the case and show that while Mr. Combs may be a ‘bad actor’ when it comes to domestic violence, etc. — something no one is condoning — the federal charges are unsubstantiated based on the testimony we have heard to date, in my opinion," attorney David S. Seltzer told Fox News Digital. "While we cannot hear the testimony in real time because we are in Federal Court, I think the Government is not meeting their burden to date."

Entertainment lawyer Tre Lovell noted that while the jury has heard "consistent" testimony from the witnesses, reasonable doubt "looms very heavy" after the first two weeks.

"To date, we have heard consistent testimony from several of the witnesses that Diddy was violent with Cassie Ventura, was controlling over her, instructed what to do in the ‘freak offs’ and was a jealous boyfriend, but none of this is sufficient to justify a criminal enterprise or a pattern of criminal conduct," Lovell, of The Lovell Firm, explained. "Cassie’s relationship can be as easily characterized as she was in love with Diddy, performed ‘freak offs’ because of her feelings for him and stayed with him for personal benefits such as furthering her career, developing connections, and being taken care of financially. Reasonable doubt looms very heavy in these first two weeks of trial. The prosecution will need to bring out additional victims that are not girlfriends of Diddy to separate a romantic, emotionally charged relationship from actual sex trafficking."

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On Thursday, the jury heard from rapper Kid Cudi — who testified that he had a romantic relationship with Diddy's ex, Cassie, in 2011. Kid Cudi testified that when Diddy found out about the relationship, he broke into the musician's home and later allegedly set fire to his car. However, there was no definitive evidence to prove Kid Cudi's claims.

"Ventura told Kid Cudi that Combs would hit and kick her, but Combs’ lawyers elicited testimony that Cassie never said anything about sexual abuse, which is important," Rahmani, founder of West Coast Trial Lawyers, said. "Kid Cudi broke up with Ventura because Combs was violent, and he was concerned for his own safety. He also said Ventura was playing both him and Combs. That’s a central theory for the defense: that Ventura is a strong, independent woman who made her own decisions, including willingly participating in the swingers lifestyle."

While there were flaws in the prosecution's presentation of Kid Cudi's testimony, it was still "important because arson is an underlying crime for a RICO conspiracy," Rahmani explained.

"That allows the prosecution to potentially get a racketeering conviction even if the jury believes the ‘freak offs’ were consensual and there was no sex trafficking," he added. "If the jury doesn’t find trafficking, they can still convict on racketeering if they find that Combs engaged in kidnapping, arson, extortion or prostitution."

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Male exotic dancer Sharay Hayes, also known as The Punisher, testified to having sex with Cassie at the request of Diddy and said that the encounters were always consensual. He told the jury that he didn’t get any cues of any discomfort from Cassie, and that if he had, he would have stopped. Diddy's defense lawyer doubled down, asking if Hayes ever did anything to Cassie that she didn’t want. Hayes replied no. He claimed it was consensual.

"The scenario I was there to create… was going well," he said during cross-examination.

Hayes spoke to Fox News Digital about his "nerve-wracking" experience testifying in the rapper's trial.

"Honestly, going into the courtroom… I thought I was prepared for it, but it was extremely nerve-wracking," he told Fox News Digital. "So I want to say, for almost the entire time of my testimony, I avoided eye contact. I avoided even looking in [Diddy's] direction. And then actually going into that environment, you can't really prepare yourself and I had no idea it was going to be that many people, that many rows and tables. So I wanna say, for about half of the testimony, I couldn't even locate where he was. It was a really intense atmosphere."

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Hayes also admitted that he "never truly understood what part of my testimony was valuable" to the prosecution. 

"I really thought my testimony — because there was nothing negative, nothing whatever — I really thought it was something that the defense would benefit them," he said.

"I'm not a legal analyst or anything, but sometimes I said, well, maybe the prosecution just wants to question me and have everything in case the defense calls me," Hayes added. "Because I really couldn't understand how I was significant to their case. But there's probably something there that I'm just unaware of."

According to Seltzer, The Punisher's testimony "did not help" the prosecution.

"The government is trying to put the pieces together for a RICO charge, but so far the testimony of The Punisher and Kid Cudi did not help them," he told Fox News Digital. "The Punisher, I believe, bolstered the defense position that all the activities were consensual, and that Cassie was a willing participant, stating he observed Ventura ‘sighing or wincing’ at Combs’ repeated directions, he interpreted it ‘as frustration’ with the situation rather than unwillingness to participate. Furthermore, stating he believed their experiences were ‘completely natural.’ Kid Cudi’s recount of decade-old allegations also assisted the defense, which was supported by the Judge sustaining an objection by the defense when it came to a speculative statement that Mr. Combs committed burglary and/or arson."

"The police in both those allegations could not connect Mr. Combs to the incidents, and the ‘apology’ by Mr. Combs years later, in my opinion, is not an admission to anything other than, sorry we had issues regarding Ms. Ventura," Seltzer added. "The government put on a Homeland Security agent to show all the items seized in Mr. Combs’ house. That tactic is a continuation of the government trying to paint Mr. Combs as a bad actor, someone the jury can convict because he is devious and reprehensible, but the testimony of the drugs, firearms and baby oil still do not support the charges."

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Cassie Ventura's mother Regina Ventura and former best friend Kerry Morgan were both called to the stand by the prosecution to testify against Diddy.

"Regina Ventura, Cassie’s mom, testified for only 15 minutes, but it was some of the most impactful testimony of the trial," Rahmani explained. "Regina also took pictures of Cassie’s bruises and they were shown to the jury. Combs was upset Cassie was in a relationship with Kid Cudi and Combs demanded that Cassie pay him $20,000. If Cassie refused, Combs said he would release two sex tapes of her and send someone to hurt her and Kid Cudi. Regina took out a home equity line to pay Combs the money.

"This testimony proved coercion, which is an element of sex trafficking, and extortion, which is a RICO predicate act. It also corroborates Cassie’s account that she was beaten and Combs used the freak off tapes as blackmail."

Morgan, who claimed she saw Diddy become physically abusive with Cassie on a handful of occasions, was one of the "best witnesses so far," according to Rahmani.

"She saw Combs punch and drag Ventura across the floor," he explained. "After the hotel attack, Combs came to Ventura’s apartment and banged on the door with a hammer. Combs controlled every aspect of Ventura’s life: her finances, her apartment, her car, and her career. This control explains the psychology of abuse and is evidence of coercion for the sex trafficking charges."

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The prosecution has also been presenting evidence of Diddy's alleged criminal enterprise with testimony in the past two weeks, according to Rahmani.

"David James, Combs’ former assistant, took the stand and told jurors that he got condoms, Astroglide and Percocet for Combs. This helps prove the criminal enterprise," he noted.

"One of Combs’ other assistants, George Kaplan, testified under a grant of immunity that he would pick up drugs for Combs and set up the hotel rooms with baby oil and Astroglide for the 'freak offs,' the attorney said. "He would also clean up the drugs and hotel rooms after the ‘freak offs.’ He also described a number of incidents where Combs was violent with Ventura: on his private jet with broken glass, and in his home with Ventura having bruising on her face. This was more evidence of the criminal enterprise, with Combs as the head."

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The jury has heard from at least one expert witness so far, Dr. Dawn Hughes. The clinical psychologist took the stand to provide "blind testimony" about why a person would stay in an abusive relationship.

"The psychology expert was helpful to the prosecution in answering a lingering question that every juror most certainly has: if Cassie was being trafficked and forced to do all these horrific things, why did she stay? The lay person would probably assume she stayed because she had feelings despite Diddy’s bad conduct," Lovell said. "The expert was able to provide an alternative reason emanating from abuse trauma where victims become controlled by the perpetrator and feel trapped and helpless."

"She testified it was about the power and control abusers have over the victim, which were the very buzz words the prosecution needs for the sex trafficking charge," he added. "She was helpful to the prosecution, both for providing a reason for Cassie staying other than she loved Combs, as well as the force and coercion elements necessary for sex trafficking."

Fox News Digital's Larry Fink contributed to this report.