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Sean 'Diddy' Combs' Trial Bombshell: Cassie Ventura Reveals Rapper's 'Swinger' Lifestyle During Cross-Examination

Photo of Cassie Ventura and Sean 'Diddy' Combs
Source: MEGA

Cassie Ventura exposed Diddy as a 'swinger.'

May 15 2025, Published 5:52 p.m. ET

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Cassie Ventura, the former girlfriend of Sean "Diddy" Combs, revealed intimate details about their relationship and the disgraced music mogul's involvement in what he claims is a "swinger's lifestyle."

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Cassie Ventura Details Sean 'Diddy' Combs Being a 'Swinger'

diddy trial cassie ventura swinger lifestyle cross examination
Source: MEGA

Cassie Ventura testified in Sean 'Diddy' Combs' trial.

Ventura's comments emerged as part of cross-examinations conducted by Combs' defense attorney Anna Estevao, who probed into the mogul's sexual preferences.

The singer confirmed that Diddy had openly discussed the "swinger's lifestyle" with her while they were together, leading to a string of shocking admissions.

She recounted accompanying Combs to s-- clubs, where she witnessed him engage in sexual acts with other women — not once, but multiple times. This contrasts with previous witness accounts detailing "freak-off" parties, where Diddy allegedly enjoyed watching Cassie in the company of male s-- workers.

When Estevao pressed Ventura about whether the freak-offs related to the swinger lifestyle, she candidly replied, “Related in a sexual way, yeah. But they're very different.”

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diddy trial cassie ventura swinger lifestyle cross examination
Source: MEGA

Diddy is on trial for s-- trafficking and racketeering.

This revelation about Diddy being a swinger is crucial to his defense.

The head of Combs' legal team, Marc Agnifilo, previously claimed that being a swinger is so prevalent in their circles that the rapper likely considered it a non-issue.

Adding fuel to the fire, Diddy's previous federal indictment highlighted these so-called "freak-off" parties, describing them as "elaborate and produced s-- performances that Combs arranged, directed, masturbated during, and often electronically recorded."

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diddy trial cassie ventura swinger lifestyle cross examination
Source: MEGA

Diddy and Cassie Ventura dated in the early 2000s.

From the witness stand, Ventura said the Bad Boy Records founder convinced her it would be “fun” to go to s-- clubs.

She also faced pushback from Combs’ defense for her accusation that he controlled her appearance.

“Would you send [Combs] photos of your clothes and your hair and ask him what he thought?” Estevao asked.

“Yeah,” Ventura said, later acknowledging that the dad-of-seven ran a fashion brand called Sean John and “had a big impact on fashion over many decades.”

Combs’ lawyers also asked Ventura about the fallen music producer’s alleged addictions.

“What was he addicted to?” Estevao asked.

“Success,” Ventura answered.

“What substances?” Estevao continued.

Ventura claimed it varied but that Combs at one point was addicted to opiates, and that she had witnessed him going through withdrawal from those drugs “more than once.”

Diddy Physically Abused Cassie Ventura

diddy trial cassie ventura swinger lifestyle cross examination
Source: MEGA

Cassie Ventura said Sean 'Diddy' Combs is addicted to success.

As OK! previously reported, before Ventura took the stand, the prosecution played an unedited version of the security footage of Combs beating his at-the-time girlfriend at a Los Angeles hotel.

The prosecution also displayed several photos in court showing the remains of a vase that broke after Combs threw it at Ventura in their room the same night the video was recorded.

When she was asked about that night, the singer told the court, "I just remember it coming towards me. I remember it hitting a wall."

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