NEW YORK (AP) — A retired Wall Street financier was arrested Friday on charges that he lured dozens of women, including former Playboy models, to be sexually and physically assaulted during encounters in his Central Park penthouse in a soundproofed room described in court papers as “The Dungeon.”

Howard Rubin, 70, was arrested Friday at his rental home in Fairfield, Connecticut, authorities said. He pleaded not guilty at a federal court in Brooklyn. His former personal assistant, Jennifer Powers was also arrested at her home in Southlake, Texas, and is expected to appear in court in Texas on Monday, authorities said.

The wealthy former financier was ordered to remain detained, despite efforts by his lawyers to have him freed on a $25 million bond. Messages for comment were sent to multiple lawyers for both Rubin and Powers.

During a three-decade career, Rubin worked at various financial firms, including Merrill Lynch, Bear Stearns and Soros Fund Management.

Prosecutors said Rubin, with the help of Powers, abused the women between 2009 and 2019 after recruiting them to fly to New York to engage in sadomasochistic sex acts with Rubin in exchange for money.

They said Rubin and Powers spent more than $1 million recruiting women to participate in paid sex acts involving bondage and submission, including victims who had previously been sexually abused, were financially desperate or who suffered from addiction. Once they were in New York, the women were encouraged to use drugs or alcohol to prepare for their sexual encounters, and they sometimes engaged in conduct beyond the scope of their consent, prosecutors said.

During the encounters, women suffered significant pain, including bruises and psychological trauma, and sometimes required medical treatment, according to prosecutors.

Prior to 2011, the commercial acts usually occurred at luxury hotels in Manhattan, but from 2011 to 2017, the encounters usually occurred in a two-bedroom penthouse near Central Park, prosecutors wrote in a court filing.

The penthouse contained “The Dungeon,” a soundproofed room painted red that had a lock on the door and was outfitted with bondage and discipline instruments, prosecutors said.

They said Powers maintained the dungeon, cleaned it between uses and restocked the equipment, while also recruiting women, arranging their flights and managing fallout from complaints about the sessions with Rubin.

Rubin and Powers required the women to sign nondisclosure agreements and pledge that they were not under the influence of drugs or alcohol when they signed the agreements, prosecutors said.

According to court papers, Rubin has funded virtually all aspects of Powers and her family’s lifestyle since 2012, including rent on their Manhattan apartment; her children’s private school tuition; and the down payment and mortgage on their Texas-based home after the Powers moved to Texas in 2020.

Some of the alleged victims sued Rubin and Powers in 2017. A jury found at trial that only Rubin was liable and awarded the women $3.9 million. He is currently appealing the verdict.

If convicted of all charges, Rubin and Powers each face a sentence of at least 15 years in prison.

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This story corrects that Rubin was found liable in a 2017 sex trafficking case. Only Powers was found not liable in that case.