New court filings and reporting by The Wall Street Journal have revealed additional details in the criminal and civil cases against millionaire financier Howard Rubin, who is accused of orchestrating a long-running pattern of abuse against women inside a soundproof room in his Manhattan apartment.
According to the report, Rubin allegedly paid women between $2,000 and $5,000 to participate in violent sexual encounters at his Midtown residence. Prosecutors and civil plaintiffs say the room—described in court documents as a “dungeon”—was designed to prevent sound from escaping and was equipped with restraints and other sadomasochistic devices.
In one incident detailed in court filings, Rubin allegedly struck a woman’s chest repeatedly, even after she attempted to stop the encounter by using a designated safe word. The alleged assault was so severe that it caused her saline breast implant to shift. The woman later sought medical treatment, which Rubin allegedly paid for, while suggesting she replace the implant with a silicone version that he described as more durable, according to the civil suit cited by the Journal.
Text messages reviewed by investigators and referenced in court records further describe Rubin allegedly expressing an intent to inflict pain during encounters. Although a safe word—“pineapples”—was provided, multiple women allege that invoking it either failed to stop the abuse or led to increased violence. In some instances, plaintiffs claim they were restrained or gagged to the point that they could not speak.
Several women have also alleged they were asked to sign consent agreements while intoxicated. The documents reportedly included clauses imposing penalties of up to $500,000 if they disclosed what occurred, according to the Journal.
Rubin, 70, is currently being held in a Brooklyn federal detention facility while awaiting trial on sex trafficking and related charges. In prior civil proceedings, he has been ordered to pay a total of $3.8 million to women who accused him of abuse. He has pleaded not guilty to all criminal charges, and his attorneys maintain that the encounters, which allegedly occurred between 2009 and 2019, were consensual.
Prosecutors dispute that characterization, arguing that the conduct amounted to coercion and abuse. They further allege that Rubin relied on his personal assistant, Jennifer Powers, to help recruit women for the encounters. Powers, a former model, has also pleaded not guilty to the charges against her. According to prosecutors, she coordinated meetings with women, including models and others experiencing financial hardship.
Court records state that the room in question was remodeled around 2012 inside Rubin’s luxury apartment at Metropolitan Towers in Midtown Manhattan. The space was allegedly painted red and outfitted with whips, chains, restraints, and a large X-shaped structure commonly associated with sadomasochistic practices.
Rubin, a Harvard Business School graduate, built his fortune after transitioning from professional card counting in Las Vegas to a successful career in finance, including work at major Wall Street firms. His legal troubles began to surface publicly following civil lawsuits filed several years ago, some of which were settled before criminal charges were brought.
The case remains pending as Rubin awaits trial in federal court.
