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DIDDY TRIAL HIGHLIGHTS: Orgies, drugs, baby oil, and beatdowns

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Jurors and courthouse habitues were treated to eight weeks of disturbing, occasionally titillating and deeply troubling testimony during the Sean “Diddy” Combs trial in New York City.

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On Wednesday, Combs, 55, was acquitted of the most serious charges, sex trafficking and racketeering but was convicted of prostitution. He insisted he was merely a swinger.

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HERE ARE SOME OF THE HIGHLIGHTS

THE HOTEL ATTACK

Jurors watched in silence as they were shown CCTV of Diddy assaulting his long-time girlfriend, Cassie Ventura in a Los Angeles hotel in 2016. In the video, he strikes her and throws her to the ground kicking her before dragging her back to their room. Jurors were also shown the damage to the hall. Diddy then tried to bribe a hotel security guard with a stack of $100s. He was rebuffed.

In this courtroom sketch, Sean Combs, seated right, looks at his attorney, Marc Agnifilo, left, as he delivers his bail argument as Combs’ family in the gallery, background, raise their hands indicating to Judge Tarnofsky that they are in attendance, to bolster the defense attorney’s bail argument, Tuesday, Sept. 17, 2024, in Manhattan Federal Court in New York. Photo by Elizabeth Williams /THE ASSOCIATED PRESS

FREAK OFFS

Me & U singer Cassie testified that Combs was a voyeur and dictated every aspect of sex events he dubbed “freak-offs.” Essentially, they were orgies and involved male and female sex workers, massive drug use and copious lubrication. Cassie said the sex parties, which often lasted days, were “his fantasy.” Typically, revellers would go through 10 large bottles of warmed baby oil.

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Cassie and Diddy
Sean Diddy Combs and Cassie Ventura attend the premiere of ‘The Perfect Match’ at the Arclight Theatre in Los Angeles on March 7, 2016. Photo by CHRIS DELMAS /AFP via Getty Images

THE CUCK

In addition to being asked to perform degrading and painful sex acts with male sex workers while Diddy watched, Cassie said the weekly “freak-offs” were her job for a decade. She felt compromised because of fears that videos of the raunchy antics would go public.

THE MALE STRIPPER

Stripper Daniel Phillip said he was paid to have sex with Cassie while Combs gave instructions. He testified that he once saw Combs drag Cassie by her hair as she screamed.

Singer Casandra Ventura also known as Cassie arrives for the screening of “Killing Them Softly” at the 65th international film festival, in Cannes, southern France, Tuesday, May 22, 2012.
Singer Casandra Ventura also known as Cassie arrives for the screening of Killing Them Softly at the 65th international film festival, in Cannes, southern France, Tuesday, May 22, 2012. Photo by Joel Ryan, File /AP Photo

COMPROMISED?

Combs’ legal eagles introduced messages that revealed a complicated relationship. They suggested that Cassie was an enthusiastic participant in the “freak-offs.” In one 2009 message, she wrote: “I’m always ready to freak off.” In a 2017 message, Cassie wrote to Diddy: “I love our FOs when we both want it.” She clarified that they were “just words at that point.”

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Dawn Richard arrives at the 66th annual Grammy Awards on Sunday, Feb. 4, 2024, in Los Angeles. Photo by Jordan Strauss /Jordan Strauss/Invision/AP

BEATDOWNS

Singer Dawn Richard ALSO recalled Combs beating Cassie on multiple occasions. Once, she testified, Combs tried to strike the singer with a heavy black skillet before dragging her up the stairs. “I was scared for her and scared to do anything,” Richard said. “I had never seen anything like that before.”

KEEPING IT CASUAL

The court reviewed text messages between Cassie and Combs discussing plans for “freak-offs.” The casual nature of their planning was likened to typical dinner reservations, highlighting the routine aspect of these gatherings.

THATS A LOT OF LUBE. US DOJ
THATS A LOT OF LUBE. US DOJ

HUH?

Homeland Security seized 900 bottles of Astroglide lubricant, 200 bottles of baby oil, and various firearms from Sean Combs’ Los Angeles home last March.

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Rival, Yung Miami. INSTAGRAM

JANE

Another ex-girlfriend, Jane, admitted she enjoyed the “freak-offs.” She also liked “movie nights” where the pair would stay in and watch sex tapes of themselves. Jane claimed she was jealous of Diddy’s secret girlfriend, Yung Miami.  Despite a financial arrangement for sex, including $10,000 monthly rent and additional funds for personal expenses, Jane expressed anger and frustration, questioning the value of her body compared to designer bags.  Jane, too, said she was forced to have sex with male sex workers while Diddy watched.

Rapper Kid Cudi, right, arrives at Federal Court for the trial of Sean “Diddy” Combs, in New York, Thursday, May 22, 2025. Photo by Richard Drew /AP

FIREBOMBING

Rapper Kid Cudi testified that Diddy broke into his home in 2011 after discovering Cudi was having sex with Cassie, and later suspected Combs was behind the firebombing of his car. Diddy denied involvement but apologized years later. His lawyers claimed Cassie was having sex with both men.

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EXTORTION

Cassie’s mom, Regina Ventura, testified she took out a $20,000 home equity loan in 2011 to prevent Diddy from releasing a sex tape starring her daughter.

SHARAY ‘THE PUNISHER’ HAYES

Male sex worker Sharay Hayes, a prosecution witness, unexpectedly aided the defence by stating he had sex with Cassie eight to 15 times, mostly unprotected, and noted that neither Cassie nor Combs seemed high or drunk. He added that Cassie appeared to enjoy the encounters.

BIG BUCKS

Cassie testified that the rapper bought the rights to her book for $20 million. She also won a $10 million out-of-court settlement with the L.A. hotel where her beating happened.

bhunter@postmedia.com

@HunterTOSun

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