Cassie, Kid Cudi and ‘The Punisher’ Take Stand: Five Key Moments From Diddy’s Ongoing Sex Trafficking Trial

Federal prosecutors on Tuesday will resume their case against Sean “Diddy” Combs, whose sex trafficking trial has included stirring and often lurid testimony throughout two sensational weeks.

Here’s a recap of five crucial moments from the courtroom in Lower Manhattan that may play an outsized role as the jury of eight men and four women weighs the fate of Combs, 55, who faces up to life in prison if found guilty.

Judge Arun Subramanian said Thursday he hopes the trial will conclude prior to the July Fourth holiday weekend.

‘Like Dirt’

Casandra Ventura, the star witness in the sex trafficking and racketeering conspiracy case against Combs, testified over four days last week — detailing instances of physical, sexual and psychological abuse during her 11-year relationship with the Bad Bay Records founder.

The 38-year-old R&B singer, who goes by Cassie professionally, is expecting her third child with husband Alex Fine in weeks. Heavily pregnant, she broke down on the stand while recalling the extended and sometimes violent drug-fueled sex sessions with escorts known as “freak offs.”

“How did you feel during the freak offs when Sean beat you?” prosecutor Emily Johnson asked Ventura, who began to get emotional.

“Worthless, like dirt,” she testified as jurors and Combs watched on intently. “Like I didn’t matter to him. Like I was nothing, absolutely nothing.”

Kid Cudi on the Stand

Rapper Kid Cudi, who briefly dated Ventura in 2011 while she was on a break with Combs, told jurors that Combs broke into his Los Angeles home late that year and then torched his black Porsche 911 weeks later in January 2012. Cudi testified that Combs was livid that the Grammy-winning rapper had been seeing Ventura romantically, even spending the holidays with her family in Connecticut.

No criminal charges were filed in either incident, although Cudi, 41, whose real name is Scott Mescudi, insisted in court that Combs “had something to do” with the Molotov cocktail placed inside his totaled Porsche. That testimony prompted an objection from Combs’ attorneys. Judge Subramanian sustained the objection, telling jurors to ignore the accusation.

The two rap stars then arranged a meeting after the car bombing at the Soho House hotel in Los Angeles, where Combs arrived first and stood near a window with his hands clasped behind his back “like a Marvel supervillain,” Cudi testified.

Combs and Cudi ultimately shook hands, although the tense meeting didn’t provide the answers Cudi sought, he told jurors.

“What are we going to do about my car?” Cudi recalled asking Combs.

“I don’t know what you’re talking about,” Combs replied, according to Cudi’s much-anticipated testimony.

‘The Punisher’ Speaks

Sharay Hayes, a male escort known as “The Punisher,” told jurors about the dozen “freak offs” he had with Combs and Ventura between 2012 and 2015, earning up to $2,000 per sessions at luxury locales in New York, including the Trump International Hotel overlooking Central Park.

Hayes, 51, said he was hired to create a “sexy scene” while doused in baby oil with Ventura as Combs masturbated nearby. The R&B singer paid him for the encounters, which included unprotected sex, he testified.

The hulking escort said he had trouble maintaining an erection as Combs demanded he and Ventura have intercourse during their final liaison in March 2015. But Hayes said he never sensed at the time that Ventura had been uncomfortable during their meetings.

“I did not get any cues that there was a discomfort with what was going on,” Hayes testified. “It seemed like it was consensual as far as I was concerned.”

A Once-Dutiful Employee

George Kaplan, 34, told jurors he worked up to 100 hours per week as Combs’ former executive assistant from late 2013 through 2015, often setting up hotel rooms in advance of drug-fueled romps in Los Angeles, New York and Miami.

Combs, who used an alias of “Frank Black,” would typically stay for as little as 12 hours or up to several days, leaving behind empty Gatorade bottles, baby oil and “brown crystalized powder” on one occasion, Kaplan testified.

Kaplan said he saw Combs get violent with Ventura during an incident on his private jet in 2015 and spotted the singer with bruises on her eyebrow and face during a visit to Combs’ home later that year.

Kaplan, who testified after being subpoenaed by federal prosecutors, said Combs’ “physical behavior” ultimately prompted him to leave his job.

“In my heart of hearts, I knew it was the right thing to do,” said Kaplan, who did not notify authorities in either alleged attack.

But Kaplan also spoke glowingly of his former boss, insisting Combs’ “infectious vibration” and intense work ethic had helped him grow as an aspiring executive.

“I’m a young man and this is a God among men talking to me,” Kaplan testified. “He not only pushed me to my depth, he pushed me to depths I didn’t even know I had.”

Agent Reveals Role in Raid

Gerard Gannon, a federal agent who searched Combs’ 20,000-square-foot Miami mansion in March 2024, testified that he was among 80 to 90 investigators who descended upon the property and found AR-15 components along with sex toys and dozens of bottles of baby oil and lubricant.

Agents from Homeland Security Investigations (HSI) also seized three cellphones found inside a Balenciaga boot, a Gucci pouch stuffed with ketamine and MDMA and a .45-caliber handgun discovered tucked away in a red suitcase.

The serial numbers on the disassembled AR-15 components had been defaced, but the high-powered weapons were not operable as found, Gannon said. He displayed the weapons to the jury, as well as one pair of seven-inch red heels found inside Combs’ closet. Twelve other pairs of similar stilettos were recovered in all, the agent testified.

Attorneys for Combs had previously characterized last year’s raid as a “gross overuse of military-level force,” but Teny Geragos tried a different tact during cross-examination of Gannon on Tuesday — asking the agent if he owns a gun as a resident of Florida.

Gannon, who confirmed he did as part of his federal role, responded to Geragos’ questioning as two of Combs’ sons entered the courtroom. Combs and his family, meanwhile, were not present at the Star Island mansion during the raid. Gannon said agents waited until the mogul departed for a trip with his relatives prior to executing the search warrant.

Case Far From Slam Dunk

Despite nearly two weeks of lurid testimony, in which the defense even acknowledged their client as a domestic abuser, the prosecution’s top charge of sex trafficking has not yet been proven beyond a reasonable doubt, according to legal analysts who spoke with Newsweek. That is largely due to contemporaneous texts between Ventura and Combs shown in court, which suggest she was a willing participant in the “freak offs” at the time, the analysts said.

To that argument, Dr. Dawn Hughes, a forensic psychologist, testified as a prosecution witness, explaining to jurors why some victims stay in abusive relationships, including psychological bonds or deep-rooted love for their partner.

“They experience a tremendous amount of shame, humiliation, degradation,” Hughes said of sexual abuse victims. “They don’t want to talk about it. They don’t even want to think about it in their own brain.”

Hughes, who provided testimony as a so-called “blind expert,” had not interviewed Combs or the alleged victims in the case, she acknowledged.

Former Combs’ employee Capricorn Clark is scheduled testify next when the case resumes on Tuesday, followed by Los Angeles police and fire officials.