Diddy trial Day 2: Ex-girlfriend Cassie Ventura expected to take the stand

NOTE: The following article contains disturbing details and video footage. Please read at your own discretion.

As the sex trafficking trial for Sean “Diddy” Combs gets underway, the first witnesses took the stand Monday afternoon, sharing graphic testimony and setting the tone for what’s to be expected in the weeks-long trial.

Many expected Combs’ ex-girlfriend, Cassie Ventura, to take the stand Monday, but it became clear after calling two witnesses for their testimony and cross-examination, that Ventura would not appear Monday. She is expected to appear this week.

Ventura is considered a star witness for the prosecution and her testimony is particularly valuable. Combs was captured on security video violently assaulting Ventura in a hotel hallway in 2016.

The video was obtained and distributed by CNN in May 2024, and showed Combs launching a brutal physical assault on Ventura in which he grabbed her by the back of the neck and threw her to the floor, before kicking her twice while she lay on the ground.

Day 2

Male stripper Daniel Phillip continued to be questioned by one of Combs’ lawyers, Xavier R. Donaldson. Phillip testified on Monday that he was hired by Combs and his then-girlfriend — Ventura — to have sex with her while Combs watched. Sometimes, he said, the rapper would direct what should happen.

Day 1

Instead of Ventura, the jury heard from two other witnesses — a former security guard and a male stripper — to kick off the trial Monday.

Prosecutors used the trial’s first witness, Israel Florez, a former security officer at a Los Angeles hotel, to introduce recordings of Combs beating Ventura at the hotel in March 2016.

Florez said that when he responded to a call of woman in distress on the sixth floor of the hotel, he came across Combs, wearing only a towel and sitting on a chair “slouched down, like with a blank stare … like a devilish stare, just looking at me.”

He said he noticed that the hotel’s floor display was destroyed and told Combs it’ll be charged to the room. As he escorted Ventura and Combs to their room, he said Ventura indicated she wanted to leave and Combs told her: “You’re not going to leave.” Florez said he told Combs: “If she wants to leave, she’s going to leave.”

After Ventura left, Florez said, he was getting ready to leave their room when Combs called him back. Florez said he was holding a stack of money with a US$100 bill on top, telling him: “Don’t tell nobody.”

Florez said he considered it a bribe and told him: “I don’t want your money. Just go back into your room.”

In all, prosecutors showed the jury two cellphone videos and three hotel surveillance videos related to the attack by Combs on Ventura.

Florez testified that he recorded the hotel’s video of the attack on his cellphone because he wanted to describe what he saw to his wife and feared she wouldn’t believe him.

Following Florez, Daniel Phillip – a male stripper – took the stand, as prosecution dove straight into questions about Combs’ alleged violent streak.

He told the court that he was working as a stripper in 2012, when Ventura called him and requested that he meet her and Combs at the Gramercy Park Hotel.

Ventura, he said, told him she wanted to do something special for her boyfriend and asked Phillips to massage her with baby oil while Combs watched. She was wearing a red lack outfit, with dark sunglasses and high heels during the encounter.

He said that Combs was wearing a white robe and sat nearby, watching, while Phillips had sex with Ventura. He was paid a few thousand dollars for the encounter – but it wouldn’t be the only time he was solicited for sex work from the pair.

He said he stopped accepting money from the couple and ended their relationship when he saw Combs become violent toward Ventura one day.

He said Ventura was sitting at her computer when Combs called to her from the bedroom. When she replied to “hold a second,” he said, Combs came out of the room.

“Mr. Combs walked over to Cassie, grabbed her by her hair and started dragging her by her hair into the bedroom,” Phillip said.

He said he then heard what sounded like Combs slapping her as she screamed and said: “I’m sorry! I’m sorry!”

On direct questioning, Phillip had testified that he didn’t ask for money during his encounters with Cassie and sometimes he wasn’t paid, saying: “In my head, I was just excited I was in this world and happy to be involved with people of such notoriety.”

On cross-examination, defence lawyer Xavier Donaldson tried to attack Phillip’s credibility, mocking the slogan of the male review show company Phillip worked for and its slogan that it “provided the ultimate ladies night experience.”

Phillip testified that when he got to the door of the New York hotel room the first time he met Ventura, she told him that his boss had told her that she had to give him $200 upon his arrival. “And then she handed me $4,000.”

Trending Now

Opening statements

During opening statements on Monday morning, prosecutor Emily Johnson addressed Combs’ relationship with his ex-girlfriend, including a night that the mogul was allegedly “on the hunt” for the singer after learning she’d moved on.

“When he finally found her, he beat her brutally,” Johnson said, per NBC News, “kicking her in the back and flinging her around like a rag doll.”

Ventura sued Combs in 2023, accusing him of subjecting her to years of abuse, including beatings and rape. The lawsuit was settled within hours, but touched off a law enforcement investigation and was followed by dozens of lawsuits from people making similar claims.

Central to Combs’ sexual abuse, prosecutors say, were highly orchestrated, drug-fuelled sex parties he called “Freak Offs,” “Wild King Nights” or “Hotel Nights.”

Combs’ company paid for the parties, held in hotel rooms across the U.S. and overseas, and his employees staged the rooms with his preferred lighting, extra linens and lubricant, Johnson said.

Combs compelled women, including Ventura, to take drugs and engage in sexual activity with male escorts while he gratified himself and sometimes recorded them, she continued.

“To the public he was Puff Daddy or Diddy. A cultural icon. A businessman. Larger than life,” Johnson said. “But there was another side to him. A side that ran a criminal enterprise.”

“During this trial you are going to hear about 20 years of the defendant’s crimes. But he didn’t do it alone. He had an inner circle of bodyguards and high-ranking employees who helped him commit crimes and cover them up.”

Those crimes, she said, included kidnapping, arson, drugs, sex crimes, bribery and obstruction.

“The evidence is going to show you a very flawed individual, but it will not show you a racketeer, a sex trafficker or somebody transporting for prostitution,” she added.

Combs’ defence team argued Monday during their opening statement that many of his romantic relationships lasted for years. “These women were strong, capable, and they were in love with him,” Teny Geragos, one of Combs’ laywers, told the court.

Combs is charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. He has denied all the charges against him and rejected a last-minute plea deal earlier this month, choosing to go to trial instead.

If found guilty in the New York court, he could face life in prison.

—

Global News will be covering the Diddy trial in its entirety. Please check back for updates. 

— With files from Global News’ Katie Scott and The Associated Press

Curator Recommendations