Sean ‘Diddy’ Combs trial dwell: Male escort offers graphic description of ‘freak-offs’ with Cassie Ventura

Related: Everything to know about Sean “Diddy” Combs’ trial

Two witnesses have testified following opening statements and the conclusion of jury selection in the high-profile trial of Sean “Diddy” Combs — including a male escort who gave a graphic description of the “freak offs” involving the rapper and his then-girlfriend, Cassie Ventura.

Twelve jurors and six alternates were finalized Monday before the roughly eight-week-long trial got underway in a Manhattan federal courtroom.

The first witness, LAPD Officer Israel Florez, was working security at the InterContinental Hotel in 2016 when Combs was seen on surveillance footage assaulting Ventura in the hotel’s hallway. He testified that Combs attempted to bribe him into staying quiet after, and prosecutors later showed the jury recordings taken from inside the hotel of the violent attack.

A second witness, male escort Daniel Phillip, testified that he was paid by Diddy to have sex with Ventura, with the rapper at least once directing him to apply more baby oil during the encounter.

Combs is facing sex trafficking, transportation to engage in prostitution, and racketeering conspiracy charges.

The music mogul was arrested in September 2024 as federal authorities alleged Combs and his associates threatened, abused, and coerced victims “to fulfill his sexual desires” between 2004 and 2024.

Diddy has denied any accusations of wrongdoing and has rejected the government’s plea deal offer.

Witness didn’t call cops because he felt Diddy had ‘unlimited power’

Maurene Comey, one of the prosecutors, asked male escort Daniel Phillip why he didn’t call the cops on Diddy.

“My thought was that this was someone with unlimited power,” he replied, according to The New York Times. “and chances are even if I did go to the police, that I might still end up losing my life.”

Isabel Keane 12 May 2025 21:23

Male escort says he believes Sean ‘Diddy’ Combs was ‘threatening’ him

Male escort Daniel Phillip testified that Cassie Ventura once appeared to be on drugs.

During one encounter, Sean Combs asked Phillip to see his ID for “insurance” before he had sex with Ventura, Inner City Press wrote on X.

When asked by the prosecutor how he interpreted that, Phillip said: “He was threatening me.”

Phillip said after the incident, during which Combs offered him Molly, he got high and handed out $100 bills.

After that incident, he stopped seeing Ventura and Combs, Phillip testified.

The final encounter also took place after Combs hit Ventura, Phillip said.

Ariana Baio, Isabel Keane 12 May 2025 20:56

Male escort testifies that Diddy instructed Cassie and him to use more baby oil

Male escort Daniel Phillip testified that while having sex with Cassie Ventura her then-boyfriend Sean “Diddy” Combs would instruct them to use more baby oil.

Diddy allegedly instructed male escort Daniel Phillip and his then-girlfriend Cassie Ventura while they were having sex.
Diddy allegedly instructed male escort Daniel Phillip and his then-girlfriend Cassie Ventura while they were having sex. (Reuters)

Diddy also allegedly instructed the two to role play, pretending they had just met at the airport.

Phillip later noted that they weren’t good at roleplaying and had to skip over it.

Isabel Keane12 May 2025 20:48

Second witness called to testify

Prosecutors called their second witness, Daniel Phillip, to testify.

Phillip, a male escort, was paid by Diddy to have sex with the rapper’s then-girlfriend, Cassie Ventura.

The trial of Sean “Diddy” Combs was underway Monday in Manhattan federal court.
The trial of Sean “Diddy” Combs was underway Monday in Manhattan federal court. (Reuters)

Phillip said he was hired under the pretense of stripping for women at a bachelorette party at the Gramercy Park Hotel.

He testified that Ventura gave him a few thousand dollars and would tip him at the end of the encounter, according to The New York Times.

He also said that after leaving an encounter at the hotel, Ventura texted him to return for more sex with her, with Combs masturbating in the corner of the room.

Phillip testified that he returned to have similar encounters with Ventura for the next year or two.

He also recalled Diddy giving him specific directions for how he should be having sex with Ventura, including instructions to apply more baby oil onto their bodies.

“Cassie was actually the one that asked me urinate on her…she asked me if I had ever done that before, she told me to do it, apparently I was doing it wrong, because they both told me,” Phillip testified, according to Courthouse News.

Ariana Baio 12 May 2025 20:42

Officer Israel Florez under cross-examination

Officer Israel Florez is now under cross-examination by Brian Steel.

Steel gained notoriety representing rapper Young Thug at his racketeering trial in Atlanta, Georgia.

Ariana Baio 12 May 2025 20:14

Prosecutors show hotel security footage

Following Israel Florez’s testimony, prosecutors showed jurors the hotel security camera footage from March 5, 2016.

The footage features Combs in a towel, hitting and dragging his then-girlfriend, Cassie Ventura, and hurling a vase in the elevator lobby.

Prosecutors played jurors hotel security footage of the March 2016 incident.
Prosecutors played jurors hotel security footage of the March 2016 incident.
Isabel Keane12 May 2025 19:26

Witness claims Diddy tried to bribe him to stay quiet about hotel incident

Florez testified that he responded to a report of a woman in distress on the sixth floor of the InterContinental Hotel on March 5, 2016.

He showed up and found Combs in a towel and his then-girlfriend, Cassie Ventura, on the floor.

Florez recalled Combs was only wearing a towel and was sitting on a chair “slouched down, like with a blank stare… like a devlish stare, just looking at me.”

Prosecutor Emily Johnson gave opening statements on behalf of the government.
Prosecutor Emily Johnson gave opening statements on behalf of the government. (Elizabeth Williams)

Florez said they were arguing and there was a broken vase, which he told them would be charged to their room.

Ventura had said she wanted to leave, which Combs denied. After she eventually left, Combs offered Florez a cash bribe to keep quiet, which Florez refused.

Florez said he told Combs, “I don’t want your money. Just go back into your room.”

Prosecutors were using Florez, the trial’s first witness, to introduce recordings of Combs beating Ventura in 2016.

Diddy’s defense had unsuccessfully tried to have the footage banned because a recording aired on CNN; however, prosecutors say they aren’t using that recording. Instead, they plan to show jurors recordings that were taken within the hotel.

With Associated Press contributions.

Ariana Baio, Isabel Keane 12 May 2025 19:20

New courtroom sketches show Diddy during his defense lawyer’s opening statements

New courtroom sketches showed Sean “Diddy” Combs sitting in court while his defense attorney Teny Geragos gave opening statements.

Combs was wearing a light gray or taupe colored shirt and glasses.

Sean “Diddy” Combs in court on Monday, May 12, during his sex trafficking trial in New York City.
Sean “Diddy” Combs in court on Monday, May 12, during his sex trafficking trial in New York City. (Reuters)
Combs, 55, stood while his defense attorney Teny Geragos gave their opening statement.
Combs, 55, stood while his defense attorney Teny Geragos gave their opening statement. (Reuters)
Isabel Keane12 May 2025 19:09

Trial resumes with first witness testimony

Following lunch, prosecutors called on their first witness, Los Angeles Police Department Officer Israel Florez.

Florez was a security guard at the InterContinental Hotel in 2016, where Combs was seen on surveillance footage assaulting Cassie Ventura in a hallway of the hotel.

Ariana Baio 12 May 2025 18:36

Dedicated Diddy fans show up to the trial

Roza Leonora, a longtime fan of Combs, showed up to federal court today to show support for the music mogul as his sex trafficking trial begins.

“I felt sad, sorry for him,” Leonora, 42, told The Independent when she saw the video feed of Combs in the courtroom from one of the several overflow rooms.

Combs’s hair has gone entirely grey, and he is noticeably thinner since being arrested and jailed at Metropolitan Detention Center.

A man wearing a “Free Puff” sweatshirt showed up outside Manhattan federal court last week during jury selection.
A man wearing a “Free Puff” sweatshirt showed up outside Manhattan federal court last week during jury selection. (Copyright 2025 The Associated Press. All rights reserved.)

Leonora thinks the charges against Combs are unfair and were brought wrongly. She said her “heart broke” when she first saw the video of Combs beating up Cassie Ventura in 2016, but she “never” believed the story about freaks offs that prosecutors say incited the incident.

“I’m hoping he walks,” Leonora said.

Ariana Baio 12 May 2025 18:32

Source: independent.co.uk