Wall Street Millionaire Busted for Penthouse “Sex Dungeon” Allegedly Used to Abuse Playboy Models

Howard Rubin, once a high-flying Wall Street financier, now faces the fight of his life. The 70-year-old retired investor—who made his fortune at George Soros’ hedge fund—was arrested Friday morning in Fairfield, Connecticut, on federal sex trafficking charges.

Rubin’s longtime assistant, Jennifer Powers, 45, was also taken into custody in Texas. Together, prosecutors say, they ran a secret sex network that lured dozens of women—many of them former Playboy models—into a Manhattan penthouse turned “dungeon in the sky.”

A newly unsealed 10-count indictment accuses Rubin and Powers of creating a red-painted, soundproof sex room inside a luxury West 57th Street apartment on “Billionaires’ Row,” one of the most exclusive stretches of real estate in the world.

“During many of these encounters, Rubin brutalized women’s bodies,” prosecutors wrote, adding that he spent more than $1 million to finance the operation between 2009 and 2019.

According to the indictment, Rubin often pressured women to drink or take drugs before sessions, then ignored their “safe words” when they begged him to stop. One victim’s breast implant was flipped upside down and required surgery. Others reported injuries so severe they couldn’t return to work.

Prosecutors say Rubin and Powers misled women about the nature of the encounters, handing them non-disclosure agreements after they were intoxicated. None of the women ever received copies of the NDAs.

When victims complained to Powers about being injured, she allegedly told them Rubin was drunk—or worse, blamed the women themselves.

“These weren’t consensual arrangements,” one law enforcement official familiar with the case said. “This was about power, money, and deception.”

This isn’t Rubin’s first scandal. In 2017, two Playboy models and a Florida woman accused him of beating and raping them in Manhattan. A Brooklyn federal jury later ordered him to pay roughly $4 million in damages after finding him liable for trafficking in a civil case.

Rubin made millions in finance, working at Soros Fund Management before retiring. His fortune, prosecutors allege, helped bankroll the private sex ring.

Rubin and Powers appeared in Brooklyn federal court Friday before Magistrate Judge Peggy Kuo. If convicted, they face a mandatory minimum of 15 years in prison and could spend the rest of their lives behind bars.

“This case shows the lengths some will go to exploit women for profit and pleasure,” prosecutors said in a statement.

The once-celebrated financier now stands accused of running one of New York’s darkest underground operations—just blocks from Central Park and the world’s most expensive apartments.