Diddy’s former employee takes the stand in rapper’s trial after getting immunity deal

Sean “Diddy” Combs’ former employee George Kaplan testified that he often tidied up hotel rooms to protect the rapper’s public image.

Kaplan, who received immunity after the judge signed an order earlier Wednesday, told the jury about how he would sometimes travel with Combs or sometimes travel ahead.  Kaplan’s job was to set up the hotel rooms with clothes, speaker, candle, baby oil and Astroglide, he testified. He bought the supplies himself and paid using his corporate card. He claimed he was given a few hours notice to set up a hotel room.

Kaplan testified that he set up hotel rooms in Los Angeles at the InterContinental Hotel, New York at the Trump Hotel, and Miami at the SLS. The hotel rooms were always set up under the name “Frank Black,” he claimed.

Kaplan said it was his understanding Diddy would have “guests,” a female partner at the hotels. He explained Combs would stay anywhere from 12 hours to a few days.

Kaplan described things he would see in the hotel rooms. He told the jury he would see energy drinks, and lots of baby oil in the hotel rooms. He saw crystalized powder once on a counter in the bathroom, Kaplan testified.

Kaplan claimed he would tidy up the rooms to protect Diddy, to protect his public image. He said hotels would sell photos or videos to newspapers to try and embarrass celebrities and he wanted to avoid that. Kaplan claimed he did not see the rapper’s guests at these hotels.

Fox News' Maria Paronich contributed to this report.

George Kaplan (Getty Images)

George Kaplan told the court Wednesday that his former employer, Sean "Diddy" Combs, "threatened my job on occasion."

Kaplan, 34, testified to working for Combs Enterprises as Diddy's assistant beginning in 2014, and claimed he made $125,000 per year. He said he often worked 80-100 hours per week.

Diddy allegedly threatened his employment monthly, and would tell Kaplan he's only surrounded by the best.

Kaplan recalled the first time the "I'll Be Missing You" musician allegedly threatened him. He said he purchased 2.5 gallon water bottles instead of one gallon water bottles.

Diddy was allegedly angry and got in his face.

Fox News Maria Paronich contributed to this report.

George Kaplan arrives at Manhattan federal court (Getty Images)

George Kaplan, Sean "Diddy" Combs' former assistant, took the stand Wednesday in the disgraced music mogul's federal trial for sex crimes.

Kaplan, 34, testified that his first job was out of college working at Nickelodeon before moving to Combs Enterprises. He left the company in 2015.

He reported to Kristina Khorram while working for Diddy as his executive assistant in 2014.

"She essentially ran Mr. Combs' life," Kaplan testified. He worked out of Diddy's Los Angeles home, and carried a number of responsibilities, including carrying bags which contained phones, medicine, computers, iPads and food.

Kaplan claimed Diddy began trusting him more, and he soon was working late nights in the studio with the Bad Boy Records founder. He allegedly worked anywhere from 80-100 hours per week.

He claimed he was paid approximately $125,000.

Fox News Maria Paronich contributed to this report.

Dr. Dawn Hughes previously worked with Brian Steel. (Jane Rosenberg)

During Dr. Dawn Hughes’ re-direct examination, Assistant U.S. Attorney Mitzi Steiner asked if Hughes had been retained by defense attorneys. The clinical psychologist said yes and confirmed she had previously been retained by some of the defense attorneys on this case.

Hughes explained during re-cross examination that she worked for Diddy’s defense attorney Brian Steel who was defending a woman, a victim of domestic violence, and she was accused of shooting her husband. However, Steel did not end up calling Hughes to testify.

Fox News' Maria Paronich contributed to this report.

This image provided by Department of Justice shows a gun that was seized as evidence from the Miami home of Sean "Diddy" Combs. (SDNY)

The jury in Sean “Diddy” Combs’ sex-trafficking trial saw photos of evidence seized from the rapper’s Miami home.

Diddy’s homes in both Miami and Los Angeles were raided by Homeland Security on March 25, 2024. At the time, a U.S. official confirmed to Fox News Digital that the raids on Diddy's homes were connected to a federal human trafficking investigation.

On Wednesday, the prosecution in Diddy’s trial introduced evidence of a gun hidden inside a shoe box. The gun was found inside the disgraced music mogul’s home, former HSI agent Gerard Gannon testified.

Also visible in the photo were a few boxes of platform high heels, lingerie and toy handcuffs. Rope was visible in another box.

Fox News' Maria Paronich contributed to this report.

Dr. Dawn Hughes testifies in Sean "Diddy" Combs' trial. (Jane Rosenberg)

The clinical psychologist testifying in Sean “Diddy” Combs’ trial confirmed she’s never taken the stand in defense of a man accused of a sex crime.

“That’s correct…,” Dr. Dawn Hughes told Diddy’s attorney Jonathan Bach on Wednesday when questioned during cross-examination.

Hughes previously testified against R. Kelly in 2021. She also took the stand in NXIVM sex cult leader Keith Raniere’s case and testified against him.

In 2022, Hughes testified against Johnny Depp in his case against actress Amber Heard.

This year she will take the stand in Harvey Weinstein's rape re-trial, where she will testify against the former film producer.

Fox News' Maria Paronich contributed to this report.

Justin Combs and Christian Combs arrive at federal court in Manhattan, NY for the Sean "Diddy" Combs trial Wednesday, May 21, 2025. (Rashid Umar Abbasi for Fox News Digital)

Sean “Diddy” Combs’ sons continued to support their father in court Wednesday.

Justin Combs and Christian Combs were spotted outside the Manhattan courthouse as the jury heard from witnesses.

The jury in Diddy’s sex-trafficking trial heard from a former HSI agent earlier Wednesday. Gerard Gannon testified about the weapons and drugs seized from the disgraced music mogul’s home back in March 2024. Clinical psychologist Dr. Dawn Hughes has been testifying about abuse victims. She clarified that she has not examined Cassie or Combs before taking the stand and is only giving “blind testimony.”

During Tuesday’s testimony in Diddy’s sex-trafficking trial, the jury heard from a male escort nicknamed The Punisher and Cassie Ventura’s mom.

Fox News' Maria Paronich contributed to this post.

Diddy Miami home raid evidence (SDNY)

Evidence recovered from the scene of Sean "Diddy" Combs' Miami home during the raid on March 25, 2024 was introduced as evidence in the disgraced music mogul's federal trial.

Homeland Security Investigations officials recovered what appeared to be a white powder substance in a clear container, and showed a rolled up $100 bill nearby.

Detectives discovered a black Gucci bag on top of a dresser, and HSI agent Gerrard Gannon testified officers found an assortment of pills inside the bag, presumably narcotics and powder.

Authorities also recovered a number of weapons, including a handgun found inside a suitcase. Photo evidence from one of the rooms included images of AT-15's on a top shelf.

Gannon testified in court that he was personally in all the rooms of Diddy's Star Island mansion except the basement.

Dr. Dawn Hughes testified it’s not common for victims to disclose the abuse when she took the stand Wednesday. Victims will often wait years or months to come forward, she explained. 

She claimed they wait for fear of not being believed, fear of consequences and fear people will look negatively on them. Victims can also fear a change in economic situation or fear change in their network, according to Hughes.

The clinical psychologist said it’s very difficult for a victim to disclose abuse in the best of circumstances. Hughes testified that victims disclose when they are in a safe environment, when they get help and are able to put words to the abuse.

Abuse victims are most likely to disclose to trusted confidants, their mother or best friend, according to Dr. Hughes. She explained initial disclosure might be in pieces because different bits come out with different people at different times.

Hughes also testified that past threats affect disclosure in a very serious way. Sometimes victims will wait until other safety measures are in place before speaking up.

Fox News' Maria Paronich contributed to this report.

R. Kelly in court. (Getty Images)

Dr. Dawn Hughes has testified in other celebrity trials.

During Wednesday’s cross-examination, the clinical psychologist’s testimony in R. Kelly’s trial was brought up by Diddy’s defense attorney Jonathan Bach.

Bach asked if a psychologist can give an opinion on the psychological characteristics about an individual without evaluating them. Hughes claimed there is debate about that. Bach then pointed out that Hughes was asked the same question during the R. Kelly trial in the Eastern District of New York court and she agreed with it.

Hughes confirmed she did not do a comprehensive examination and claimed she has not gathered evidence about this case. The clinical psychologist explained she had seen a headline about Cassie, but did not evaluate her.

Bach called Hughes’ testimony “general background.” However, she called it “general subject matter.”

Hughes testified in R. Kelly’s trial in 2021. Before that, she took the stand in NXIVM sex cult leader Keith Raniere’s case. Both were convicted.

She also took the stand in the Johnny Depp-Amber Heard defamation trial.

Hughes will also appear in Harvey Weinstein’s on-going rape re-trial. Judge Curtis Farber ruled the clinical psychologist could testify about the traumatic and psychological effects of rape and sexual assault.

Fox News' Maria Paronich contributed to this report.

George Kaplan arrives at court. (Getty Images)

Sean “Diddy” Combs’ former employee, George Kaplan, invoked his 5th Amendment right not to incriminate himself on Wednesday.

Kaplan took the stand before the lunch break and explained he was there because of a subpoena. The former employee said “yes” when asked if he planned to invoke his 5th Amendment right.

The prosecution told Kaplan that if he is granted immunity, he will be forced to answer questions during Diddy’s trial. He said he understands.

An immunity order was then presented to Kaplan’s attorney for review.

Judge Arun Subramanian signed the immunity and it was entered as part of the record.

Fox News' Maria Paronich contributed to this report.

Sean "Diddy" Combs' defense lawyer, Marc Agnifilo, spoke about the on-going sex-trafficking trial outside of court Wednesday.

"It's a long trial and we're just getting started," Agnifilo told Fox News' CB Cotton on Wednesday morning. "And we have a lot of witnesses to go, we have a lot of weeks to go and as the summer gets hotter, I'm sure so will the trial."

Diddy's trial began with opening statements on May 12 after solidifying a jury panel. The trial is expected to last eight weeks and has already seen testimony from the rapper's ex-girlfriend, Cassie Ventura, Cassie's former best friend, the singer's mom along with former employees of Diddy and male escorts allegedy hired for "freak offs."

More celebrities are expected to take the stand. The jury already heard from former Danity Kane singer Dawn Richard and Kid Cudi should testify on Thursday.

Dawn Hughes, a clinical psychologist who testified on behalf of the government in the Sean "Diddy" Combs federal trial, told the court she uses multiple sources to confirm her information.

While on the stand Wednesday, Hughes admitted she approaches her forensic work for courts "with healthy skepticism."

She testified that in cases she will review police reports, medical records and educational background to perform a comprehensive evaluation.

Jonathan Bach, a lawyer on Diddy's legal team, asked Hughes about the concept of "malingering," which he claimed was a fancy way of fabricating the facts. Hughes said his terminology wasn't correct, and that it's fabricating an emotional response.

Hughes previously explained she does not have personal knowledge of this case and has not reviewed evidence or assessed anyone involved.

She confirmed she has not seen any details about what has happened in court. Her role today is to provide “blind testimony.”

Fox News' Maria Paronich contributed to this report.

Sean "Diddy" Combs court sketch. (Jane Rosenberg)

Clinical psychologist Dr. Dawn Hughes testified in Sean “Diddy” Combs’ sex-trafficking trial Wednesday.

According to Hughes, trauma affects memory. Trauma memories can be forgotten and recalled at a later time, she explained. Hughes claimed this occurs not just in domestic violence, but sexual abuse and combat.

Hughes testified memories can be fragmented. Fragmented memories, she testified, can be just as reliable, but not as complete. Coping mechanisms can also affect memory, according to the doctor. She explained sometimes victims deliberately try not to remember, which impacts the recall. Hughes said victims will try not to remember because it’s too painful.

According to Hughes, sometimes events start to blend together for abuse victims. Repeated events and routine of abuse can blend together, the doctor claimed. A victim can know they were punched a bunch of times, but can’t always place it in a timeline.

Hughes testified that connecting the memory to something else makes it more likely to be recalled.

Fox News' Maria Paronich contributed to this report.

Dr. Dawn Hughes testified that substance abuse can function as a coping mechanism within abusive relationships during court Wednesday.

Trauma survivors do drugs for a very trauma specific function, she said. Substance abuse can also be used as a preventative measure, according to Hughes. The clinical psychologist explained drugs can also sometimes be used to not feel or remember.

Cassie Ventura testified last week to using drugs, including ketamine and cocaine, as a way to disassociate during the "freak offs."

"For me, it was dissociative … I couldn’t imagine doing that without some sort of buffer," she previously told Assistant U.S. Attorney Emily Johnson. "I needed to remain high to stay present with the experience."

Cassie testified that she would almost always get sick from the drugs and often vomited. Diddy was allegedly aware that she was sick while engaged in a "freak off."

Fox News' Maria Paronich contributed to this report.

Sean "Diddy" Combs allegedly abused Cassie Ventura. (Getty Images)

Dr. Dawn Hughes testified Wednesday that victims will try to placate their abuser in order to stop the violence.

Hughes told the jury when you placate an abuser, you are trying to soothe the abuser and often apologize unnecessarily. The victim will try to do all the things to not get hit by their partner, according to the doctor. Hughes said placating can appear in all facets of a relationship - if you can’t say no to little things, it's hard to say no to something else.

Cassie testified on May 13 that she couldn’t say no to Diddy at times. Cassie recalled one instance when there was a blow up pool filled with oil she was told to get into. She explained she got in because “you couldn’t say no.” Cassie was concerned about Combs’ temper if she didn’t get in, the singer-songwriter told the jury.

Cassie also testified that Diddy was in control of every “freak off.”

“Every freak off was directed by Sean…,” she told Assistant U.S. Attorney Emily Johnson. Combs would tell her where she would be, what the lighting was, etc. During the first “freak off,” Cassie claimed she was wearing an outfit from a sex store, something with “really high platform shoes.” She also wore a masquerade mask.

Cassie told the jury she took ecstasy before the “freak off.” The singer said she was high “so there wasn’t too much feeling…a mixture of dirty and confusion…he’s happy with me, so I did something right…”

She claimed the next “freak off” occurred shortly after. Cassie testified she experienced the same nervousness, “What am I going to do. I can’t say no.” She “ultimately said yes.”

“I didn’t want to make him upset,” she told the assistant U.S. attorney. “I didn’t want to make him angry.”

Fox News' Maria Paronich contributed to this report.

Dr. Dawn Hughes arrives to court. (Getty Images)

Dr. Dawn Hughes told the jury about trauma bonds during her testimony Wednesday in Sean “Diddy” Combs’ sex-trafficking trial.

Hughes explained that because these relationships start with love, the victims continue to want that feeling. When they are shown that, they want it back, and it creates a psychological attachment called a trauma bond, according to Hughes. The victim loves their partner despite the violence and abuse. When times are good, that creates a very strong bond. Hughes claimed that because the acts are so private and often humiliating, the victim only turns to the abuser, creating a very powerful bond.

The clinical psychologist claimed a trauma bond has a sense of hopelessness and makes a victim feel they are unable to leave.

During cross-examination on May 15, Cassie admitted she kept the “freak offs” a secret from her mom and friends.

She also told Diddy’s defense lawyer, Anna Estevao, that Diddy trusted her with his secrets. The “Me & U” singer explained that she wanted to earn his trust.

Fox News' Maria Paronich contributed to this report.

Sean "Diddy" Combs and Cassie Ventura dated for 10 years. (Getty Images)

Dr. Dawn Hughes testified that financial dependence on an abuser is a factor affecting a victim’s ability to leave a relationship. It sabotages a victim’s independence, the clinical psychologist said.

Hughes explained when a victim doesn’t have financial dependence, they are kept on unstable footing.

Cassie Ventura told the jury Sean “Diddy” Combs controlled her entire lifestyle while testifying on May 13.

The singer-songwriter claimed that Combs paid for her entire lifestyle, which included cars, clothing and trips. In addition, the "Last Night" rapper would provide Cassie spending money.

According to Cassie, Diddy would "take things away if she wasn't doing what she was asked."

Fox News' Maria Paronich contributed to this report.

Sean "Diddy" Combs' sex-trafficking trial is expected to last eight weeks. (Elizabeth Williams via AP)

Dr. Dawn Hughes , who is being compensated $6,000 for her time, explained why victims stay in abusive relationships during her testimony Wednesday.

Victims will stay in abusive relationships because a lot of behaviors conspire to keep the victim trapped, according to Hughes. She also testified that in these relationships, there is almost always love, making it difficult for the victim to see their way out. She claimed psychological consequences from the abuse can also prevent a victim from leaving.

Hughes explained to the jury it’s about the power and control of the abuser, not just about the hitting. She continued saying when you are hit or beat up, you feel scared and it’s very hard to take that fear away. When in this high level of fear, Hughes claimed victims can’t take any other things into account – like leaving a relationship.

Hughes defined psychological abuse as the threat of physical violence. This can include intimidation.

Fox News' Maria Paronich contributed to this report.

Dawn Hughes arrives for the Sean "Diddy" Combs sex trafficking trial at Manhattan Federal Court on May 21, 2025 in New York City. (Michael M. Santiago/Getty Images)

After the jury heard from former HSI agent Gerard Gannon, Dr. Dawn Hughes took the stand.

Hughes is a doctor of clinical psychology. She explained to the jury the difference between clinical psychology and physical psychology.

Hughes testified she has treated people suffering from PTSD – including WWII veterans – rape and sexual abuse victims along with people suffering from trauma.

According to the doctor, she specializes in interpersonal violence and traumatic stress.

Hughes explained traumatic stress is the psychological outcome that comes from a traumatic event, like rape or sexual abuse. The clinical psychologist has practiced for 30 years and has treated thousands of victims of sexual abuse.

Hughes testified she is board certified and licensed in various jurisdictions including New York, New Jersey, Connecticut and North Carolina. The doctor has testified in court about 60 times.

Hughes explained she does not have personal knowledge of this case and has not reviewed evidence or assessed anyone involved. She confirmed she has not seen any details about what has happened in court. Her role today is to provide “blind testimony.”

Fox News' Maria Paronich contributed to this report.

HSI agent Gerard Gannon testified May 20 and May 21. (Jane Rosenberg)

HSI special agent Gerard Gannon testified that he did not personally conduct fingerprint analysis on the guns missing serial numbers found during the raid of Sean “Diddy” Combs’ Miami home.

During cross-examination, Diddy’s defense lawyer Teny Geragos asked about the ways law enforcement can identify the owner of a gun without a serial number. According to Gannon, you can dust for prints or test for hair and fibers.

Gannon confirmed you can get fingerprints off metals.

The special agent claimed he is not sure if HSI has Diddy’s DNA as he was not present for Combs’ arrest in September of 2024.

Gannon testified he did not personally conduct fingerprint analysis of the guns.

Fox News' Maria Paronich contributed to this report.

Police and Homeland Security officers are seen at the waterfront mansion of Sean Combs aka Diddy in Miami during a bi-coastal raid on March 25, 2024 in Miami Beach, Florida. (Photo by MEGA/GC Images)

Former HSI agent Gerard Gannon testified that at least one individual home at the time of the raids on Sean “Diddy” Combs’ property “wasn’t too happy” and wouldn’t cooperate.

According to Gannon, HSI knew Diddy would not be home the day they executed the search warrant. The special agent testified he was aware the rapper would be at the airport with his family. The plan was to execute the warrant after Combs left, but if plans changed, they would have to execute it with him present.

During the raid, Gannon testified there were six individuals on the property. They were handcuffed until they were identified, according to the special agent. He told the jury “there was one individual who wasn’t too happy” and who wasn’t cooperating when they searched him.

Fox News' Maria Paronich contributed to this report.

A photo of the handgun found inside Sean "Diddy" Combs' home. (SDNY)

Authorities seized a handgun found inside a suitcase from Sean “Diddy” Combs’ guest house during the raid on his Miami home. The jury was shown a 45-caliber and the gun pictured had a serial number.

Special agent Gerard Gannon testified that along with the gun, they found a magazine with ammo inside a bag. The agent showed the jury that the magazine had nine bullets in it. He held it up for the jury.

Gannon testified a box of 45-caliber bullets was also found. The prosecution showed a picture of a box of bullets. The former HSI agent then held up the box of bullets for the jury.

Assistant U.S. Attorney Madison Smyser asked Gannon to open the evidence bag containing the gun. He then walked the gun in front of the jury.

Fox News' Maria Paronich contributed to this report.

Photo of baby oil found inside Diddy's home in 2024. (SDNY)

Former HSI agent Gerard Gannon’s testimony turned to the master bathroom.

The special agent, who planned out the raid of Sean “Diddy” Combs’ home testified they discovered multiple bottles of baby oil and Astroglide in the closet outside the master bathroom. He testified they seized 25 bottles of baby oil and 31 bottles of Astroglide. The bags of the bottles were in the courtroom for the jury.

Gannon also testified they located a box with the inscription “Puffy” in the master bathroom. Inside was a bag with a clear pill and crystal rock-like substance.

Fox News' Maria Paronich contributed to this report.

Photo of drugs found at Diddy's residence during the HSI raid. (SDNY)

Court resumed Wednesday with testimony from HSI special agent Gerard Gannon. The agent helped plan the raid on Sean “Diddy” Combs’ home in 2024 and previously testified about the items they seized.

The jury was shown platform heels found inside Diddy’s home as Gannon testified they also found 12 other pairs of platform heels. The prosecution showed the jury various pairs of other shoes and boots. Inside one of the boots, Gannon claimed they found three cell phones.

They also found a black Gucci bag on top of the dresser. Gannon claimed inside the bag they found an assortment of pills, presumably narcotics, and powder.

Inside the bag were blue, pink, white, and yellow pills, plus a bag of pink pills, a bag of white powder and a container with a white substance inside. Photos of which were shown to the jury.

A $100 bill was also found inside the bag and tested positive for cocaine and ketamine.

Fox News' Maria Paronich contributed to this report.

Sharay Hayes on the stand. (Jane Rosenberg)

The jury in Sean "Diddy" Combs' sex-trafficking trial heard from male exotic dancer Sharay Hayes, who the rapper and Cassie allegedly paid for sex, during Tuesday's testimony.

During cross-examination, Hayes - also known as The Punisher - testified that sex with Cassie was consensual. Criminal defense attorney Duncan Levin explained this strategy is a "risky move."

"Diddy’s team is using Sharay Hayes to suggest that Cassie’s participation in the 'freak offs' was consensual, aiming to undermine her claims of coercion by presenting a third-party witness who described her as willing and engaged," the former defense attorney for Harvey Weinstein explained. "It’s a classic credibility attack -- trying to reframe disturbing power dynamics as mutual behavior -- but it’s a risky move."

"Even if Hayes didn’t see overt resistance, that doesn’t negate the potential for psychological coercion, especially given Cassie’s testimony about control and abuse," he continued. "Whether the jury buys it depends on how convincingly the prosecution reinforces the idea that consent under manipulation isn’t real consent."

Sean “Diddy” Combs appeared in court Wednesday as rapper Kid Cudi is expected to testify Wednesday or Thursday.

Diddy wore a light-colored sweater to listen to the eighth day of testimony. The rapper sat at the defense table while his lawyers, the prosecution and Judge Arun Subramanian discussed the upcoming testimony of Dr. Hughes.

During Tuesday’s testimony in Diddy’s sex-trafficking trial, the jury heard from a former HSI agent, a male escort nicknamed The Punisher and Cassie Ventura’s mom.

Male escort Sharay Hayes testified Tuesday that the sexual encounters he experienced with Cassie Ventura were "consensual." Hayes claimed he never witnessed Diddy or Cassie use drugs during their alleged "freak offs." His final "freak off" with the couple was in 2015, where he claimed to experience erectile dysfunction due to Diddy's aggressive nature.

Regina Ventura, Cassie's mother, testified that she “memorialized” her daughter’s bruises that she allegedly received from Diddy beatings. Regina testified that Cassie told her that Diddy beat the singer. The jury was then shown photo evidence of Cassie’s bruises.

Special agent Gerard Gannon will continue his testimony Wednesday. The HSI agent helped plan the raid on Diddy’s home in 2024 and has testified that they found weapons with the serial numbers missing.

Fox News' Maria Paronich and Fox News Digital's Tracy Wright contributed to this report.

Kid Cudi, photographed in 2011, will testify in Sean "Diddy" Combs' trial. (Getty Images)

Rapper Kid Cudi is set to testify in Sean “Diddy” Combs’ federal trial for sex crimes. The Grammy Award-winning artist, whose legal name is Scott Mescudi, was first mentioned in the trial during Cassie Ventura’s testimony. The two dated briefly in 2011, during a break in her relationship with Diddy.

During her testimony, Cassie claimed Diddy allegedly threatened to blow up Cudi’s car during her relationship with him, once he found out they were dating.

Cudi broke out onto the music scene with the release of his song, “Day ‘n Nite,” in 2007. He later released his debut album, “Man on the Moon: The End of Day,” in 2009, which included the song as his lead single.

The rapper has received six Grammy nominations throughout his career, going on to win two in 2012, for his collaboration with Kanye West, Rihanna and Fergie on the song, “All of the Lights.”

David James outside court. (REUTERS)

The conversation Sean "Diddy" Combs' former personal assistant , David James, recalled where the rapper allegedly told a business associate, “Cassie is good…I’ve got her right where I want her…,” could be a “window into his mind,” according to a legal expert.

"The jury may be led to believe Diddy intentionally targeted Cassie for abuse and manipulation by exploiting her relative age and immaturity to prey upon her. His statements that he got her where he wanted her is a window into his mind and perhaps intent to make Cassie his personal sex worker,” trial attorney Adanté Pointer told Fox News Digital. “It’s certainly worth noting that an off the cuff comment is not the best evidence as to a persons state of mind as they have to be placed in context of the circumstances surrounding them. Was Diddy intoxicated when made the comment, what was the subject of the conversation it was made in and whether the personal assistant has their own ax to grind against Diddy.”

Pointer, a partner with Lawyers for the People LLC, explained that James’ warning to Cassie to get out of the relationship could be seen “as proof that Cassie was made aware of the danger yet purposefully continued to pursue her romantic relationship with Diddy.”

“The jury may say this evidence is proof she was fully aware of what she was getting into yet continued the relationship clear eyed and purposefully,” he said. “The evidence tends to undercut the idea she was captive and engaged in the purported sex acts against her will. A jury can certainly relate in their own personal lives to being give a warning or seeing a red flag yet making the decision to move forward with a relationship, a job or behavior that can result in negative consequences. This is akin to knowing that driving your car faster than the speed limit can result in tickets, crashes and even death yet the person still decides to speed along the freeway, when a negative consequences takes place, the driver can’t then use ignorance as a shield when they’re busted for speeding."

While former Danity Kane singer Aubrey O’Day traveled to New York City amid Sean “Diddy” Combs’ sex-trafficking trial, the musician confirmed she is not testifying.

"No, I'm not here to testify for the Diddy trial, that I know of,” O’Day told T.J. Holmes and Amy Robach in an episode of the trio’s new podcast. The 41-year-old singer revealed she "was contacted by Homeland Security" and "did have a meeting with Homeland Security."

"I posted on my Instagram that I was here in New York and enjoying myself because I wanted to make it clear to everyone that I am not here testifying," O'Day added.

O’Day was referring to a video she shared to Instagram announcing she was in New York City.She posted a video on May 14 with the caption, “Hey New York!!! Where y’all think I should head first?” Opening statements began in Diddy's trial on May 12.

The musician, who appeared on Diddy’s “Making the Band,” added a weighing scale emoji – prompting online speculation she was testifying.

Cassie Ventura's mom and dad arrive at court. (Fox News Digital)

During Tuesday’s testimony, the jury heard from Cassie Ventura’s mom, Regina Ventura, who testified to the alleged abuse her daughter endured at the hands of Sean “Diddy” Combs.

Cassie's mom's testimony may prove to be a crucial component to the U.S. Attorney's Office's case against the disgraced music mogul, according to legal experts.

Los Angeles litigator John J. Perlstein exclusively told Fox News Digital that while “Generally speaking, relatives can be perceived as extremely biased witnesses,” the credibility of the testimony “is largely dependent on the demeanor of the individual.”

"It is irrelevant to the case whether Ventura’s mother spoke to Diddy or not, and would unlikely favor either side. What will be relevant is her testimony regarding the $20,000 payment exchange for keeping sex tapes from being released, which in my opinion, can be very damaging to the defendant as it shows what little value a man of great means placed upon this poor woman."

In addition to her testimony, the jury was shown emails sent from Cassie to her mom in 2011, alleging Diddy was threatening to release two sex tapes of her, with Regina claiming he also demanded “$20,000 to recoup the money he spent on Cassie.”

Fox News Digital’s Tracy Wright contributed to this report.

Evidence shared by the prosecution in Sean "Diddy" Combs' sex-trafficking trial. (SDNY)

Cassie’s mother, Regina Ventura, testified Sean “Diddy” Combs demanded $20K from the family in 2011. On Tuesday, the jury was shown an email from Cassie to her mother on Dec. 23, 2011.

The email read: "The threats that have been made towards me by Sean 'Puffy' Combs are that are that [sic] he is going to release 2 explicit sex tapes of me. One on Christmas Day, maybe before or right after and another one some time after that. He has also said that he will be having someone hurt me and Scott Mescudi physically (he made a point that it wouldn't be by his hands, he actually said he'd be out of the country when it happened)."

Regina testified Tuesday that she “was physically sick” and did not understand a lot of the email. She claimed the sex tapes threw her, but she understood that Diddy was allegedly going to hurt Cassie.

Regina explained she understood that the “Last Night” singer wanted $20K to recoup the money he spent on Cassie. At the time, Diddy was allegedly angry that Cassie was with another person. It was expected the money would come from Regina and her husband.

Regina claimed they took out a home equity loan to pay Diddy. When Regina received wiring instructions, she wired the money from her checking account to the Bad Boy account. About four to five days later, the money allegedly came back. Regina said she did not have any conversations with Diddy about the money and she does not have a copy of the wiring instructions.

“I was scared for my daughter’s safety,” Regina told Assistant U.S. Attorney Emily Johnson.

Fox News' Maria Paronich contributed to this report.