NEW YORK—The penthouse atop the Metropolitan Tower on West 57th Street offers proximity to Central Park and has two bedrooms.
In the summer of 2012, prosecutors say, one of those bedrooms was soundproofed.
It was painted red and outfitted with an inventory of ropes, whips and sex toys labeled A to Z. A “St. Andrew’s cross,” an X-shaped contraption named for the martyred apostle, was equipped with four cuffs—two for the ankles, and two for the wrists.
The equipment was assembled for Wall Street legend Howard Rubin, the discreet renter of the penthouse—and for years, prosecutors allege, he lured women into what he called his sex “dungeon,” where he abused and tortured them high above the Manhattan skyline.
“I want to hurt her,” Rubin texted about a woman who would be joining him at the penthouse, according to court documents. “I don’t care if she screams.”
He then added an emoji of a laughing face.
For much of his life, and for much of his day, Rubin was a mythic figure of business, famous and infamous for rising, falling and rising again as a star trader on 1980s Wall Street. In a career that began at Salomon Brothers and ended with George Soros, he embodied the excessive wealth and excessive risk of a gunslinger era in finance, most notably when he was blamed by Merrill Lynch for an unauthorized trade that cost the firm some $250 million in 1987.
“Howie,” as he was called by colleagues, was a former card-counter who brought the risk tolerance of Las Vegas to the financial world. He maintained the trappings of a New York success story: the five-bedroom apartment on the Upper East Side, the Hamptons estate, the charity galas, a wife and three kids.
According to legal filings, archival materials and interviews with associates from several chapters of his life, Rubin was also a Wall Street titan who rose to the upper echelons of the finance industry despite a history of not following the rules.
Since being arrested for sex trafficking and other crimes in September, today the 70-year-old Rubin lives in a Brooklyn jail cell. He has pleaded not guilty. His attorneys, allies and even his estranged wife say he is a retiree living a quiet life, whose most important job is shuttling his granddaughter to dance classes.
In previous cases and in an unsuccessful application for bail, Rubin’s lawyers have argued that the women were aware of what the encounters involved and were willing participants.
Prosecutors have outlined an operation of recruitment and sexual torture against 10 victims, with alleged sourcing methods and coercion reminiscent of the approach taken by Jeffrey Epstein and Ghislaine Maxwell.
Rubin allegedly worked with a former romantic partner to recruit women, often approaching former Playboy playmates who thought they were agreeing to sex-for-hire and light fetish play. The evenings often ended up including NDAs, beatings and advice on treating the bruises, court records show.
After beating and raping a woman one November evening, he offered her a drink and thanked her for a “pleasurable experience,” according to a separate civil suit filed against Rubin. He then told her she had to leave the apartment. He was going to meet his wife and kids for dinner.
If convicted, Rubin could receive a sentence of life imprisonment.
