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Sex dungeon perv Howard Rubin copied ‘Fifty Shades of Grey’ for kinky encounters: court papers

sex-dungeon-perv-howard-rubin-copied-‘fifty-shades-of-grey’-for-kinky-encounters:-court-papers
Sex dungeon perv Howard Rubin copied ‘Fifty Shades of Grey’ for kinky encounters: court papers

Twisted financier Howard Rubin has a “fixation” with “Fifty Shades of Grey” — and even based his notorious “dungeon room” on the movie.

The retired banker, deemed to be worth over $50 million in court papers, converted a room in his Central Park penthouse to be entirely red and filled with sex toys, just like the 2015 Jamie Dornan and Dakota Fanning erotic thriller, based on the novel by writer EL James.

That room is where he is said by prosecutors to have enticed models “with promises of cash, fancy dinners, and first-class airline tickets,” before allegedly subjecting them to sadistic sexual abuse and torture — leading to the federal charges he is now in jail awaiting trial on.

Howie Rubin and Mary Henry attend the Center for Comprehensive Health Practice- Early Childhood Development Center Gala.

Howard Rubin and his former wife, Mary Henry, at a 2013 gala. Patrick McMullan via Getty Images

A street scene featuring the large glass-fronted 146 West 57th Street building next to a brick skyscraper, a white building with

146 West 57th St., where Rubin kept a penthouse with his sex dungeon, just a few minutes walk from the home he shared with his family. James Messerschmidt

“Borne out of his fixation with the movie ‘Fifty Shades of Grey’ some of the plaintiffs referred to the dungeon as the ‘red room’ because Rubin painted the walls of the room red,” court papers from a separate civil case against Rubin stated.

“Rubin adorned the walls of his dungeon with whips, chains, ropes, dildos, and sexual devices, including a large X-shaped machine … and a restraint device to which a woman could be affixed on all fours,” the papers added.

In the “Fifty Shades of Grey” movie and its sequels — which are works of fiction — Johson plays character Anastasia Steele, a college graduate seduced by powerful business Christian Grey, played by Dornan, who introduces her to his fetishistic desires, carried out in his own “red room.”

Rubin and his assistant, Jennier Powers, are both charged with sex trafficking and transporting women to engage in commercial sex acts between 2009 and 2019. Both have pleaded not guilty, and Rubin has been denied bail as he is deemed a flight risk.

View from a skyscraper overlooking Central Park in New York City.

A view from inside Rubin’s penthouse, taken by one of his alleged victims. Provided to NY Post

New York Post front page with headline

The Post’s front page story on Rubin from Sept. 27, 2025.

The civil trial finally concluded last week with a judge ruling Rubin has to pay $3.85 million to six plaintiffs, all anonymously listed as Jane Does in the court proceedings.

One of the victims said she “broke down in tears” at the verdict and added in a statement to The Post: “It was as if a weight I’ve carried for so many years was finally lifted. This ruling gives me hope that I can finally start to find peace and healing … it reassures me that my voice continues to be heard.”

Some of the plaintiffs in the civil case are also believed to be involved in the criminal case.

Rubin does not deny that he had contracts and BDSM sexual relations with numerous women, but the criminal case against him centers on how the things he allegedly did to them, including inflicting lasting physical harm, went far beyond what they had consented to.

Jennifer Powers in Brooklyn Federal Court, wearing a black NY baseball cap and sunglasses.

Jennifer Powers was Rubin’s personal assistant and is accused of recruiting women for him who he later tortured and abused. She has pleaded not guilty. Paul Martinka

Photos of women and DVDs on a dark wooden dresser.

Rubin kept pictures of beautiful women and sexual material all over his sadistic penthouse. Provided to NY Post

Lawyers for Rubin did not immediately return a request for comment.

He is also accused of “threatening the women with legal consequences and public shaming if they sought legal recourse,” according to the indictment against him.

Lawyers for Rubin did not immediately return a request for comment.

The civil case also sheds light on some of the things likely to be included at Rubin and Powers’ trial.

Many of the details are too graphic to publish, but describe a pattern of extreme abusive behavior.

Howard Rubin lying on the floor next to a baby, playing with toys.

Howard Rubin’s daughter Annalee Rubin sent a letter to the court pushing for his release, which included this photo of him allegedly being a model grandpa. BklynFedCt.

Howard Rubin smiles at the 19th Annual Samuel Waxman Cancer Research Foundation Collaboration For A Cure Benefit Dinner.

Rubin sports a black eye in a photo, which sparked conspiracy theories about whether he got it in a sex game. Sylvain Gaboury/PMC

In one instance, Rubin — a father of three — hired one woman to accompany him and his friends to a strip club. There, he rented a private room, handcuffed the woman and verbally berated her, then started to “beat her with his fists and then began penetrating her,” causing them both to be thrown out, according to the court records.

The civil trial detailed how Rubin “actively recruited women who were uneducated, financially dependent, and victims of childhood abuse,” and supplied cocaine, alcohol, Vicodin, Percocet, and oxycodone to them, then subjected them to significant psychological and physical abuse.

The jury found Rubin escalated his depraved sexual behavior “only after plaintiffs grew comfortable and financially dependent upon him” and although they had agreed to certain “commercial sex encounters,” they “did not engage in this later conduct voluntarily.”

In one text message, which was part of the civil trial, Rubin boasted about his paid conquests.

He claimed: “I’ve been with a lot of girls, including two Playmate centerfolds, Penthouse pet, Playboy lingerie cover girl, Maxim model of the year, Hustler cover girl, and Maxim and Playgirl and FHM models.”

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