MANHATTAN (CN) – Howard Rubin, a retired financier accused of brutalizing and raping women in a BDSM dungeon in his Manhattan penthouse, asked an appeals court Monday to grant him bail after a federal judge rejected his multimillion-dollar bail package.
Rubin, 71, a former Bear Stearns trader, is being held in jail Metropolitan Detention Center in Brooklyn since his arrest last September at his home in Fairfield, Connecticut. Magistrates judges repeatedly denied his bail proposals, which started at $25 million with electronic monitoring and later rose to $75 million with armed guards stationed outside his residence.
Federal prosecutors charged Rubin with sex trafficking and transporting women across state lines for sexual acts. The 10-count indictment also accuses him of falsely telling a bank he was not involved in the lawsuit, despite facing a lawsuit filed by women who say he abused them. Rubin was previously ordered to pay $3.85 million in restitution to related victims civil dispute.
From 2009 to 2019, prosecutors accused Rubin and her personal assistant, Jennifer Powers, of recruiting 10 women to engage in sexual acts where “Rubin brutalized the women’s bodies, causing them to fear for their safety and/or resulting in significant pain or injury, which sometimes required the women to seek medical attention.”
Given the severity of the charges, Rubin’s wealth, ability to travel and history of obstruction of justice, prosecutors have strongly opposed his release. His attorney argued Monday before the Second Circuit that the lower court misapplied the parole reform law.
Defense attorney Michael Gilbert of Sheppard, Mullin, Richter & Hampton said the proposed release conditions would make it impossible for Rubin to obstruct justice or commit sex crimes.
“It’s not going to happen when he’s under 24/7 surveillance, armed guards, in his own home … it’s impossible for that activity to happen and therefore the standard is satisfied,” Gilbert told a three-judge panel, referring to the Probation Reform Act standards.
Prosecutors have pointed to several factors they say show Rubin is a flight risk, including his refusal to reveal his whereabouts. passport at the time of his arrest. Investigators also found at least seven cellphones in his home, including two still in their cases and another stored under a canopy. Prosecutors further noted that Rubin reported that an account in the Cayman Islands held $35 million, despite valuing it at $75 million on his 2024 tax return.
In Rubin’s arraignment, Assistant U.S. Attorney Tara McGrath argued, “It wouldn’t cause him any trouble at all to pick up and run to a country that doesn’t extradite.”
Gilbert dismissed the notion that Rubin would walk away without access to his assets. As for his client’s refusal to answer questions about the passport, Gilbert said Rubin was exercising his constitutional rights. “He had the right not to answer the question and he didn’t,” the lawyer said.
Gilbert faced questions from the panel, including U.S. District Judge Sarah AL Merriam’s inquiry into the standards for dangerousness and flight as opposed to the standards that would apply to a less serious offense, under which he could be detained if there is a serious risk of obstructing or threatening to obstruct justice.
If it were a case of bank fraud, for example, it would be “very easy” to meet that requirement, the judge said.
“The record is fraught with the risk of obstruction, I think,” said Merriam, a Joe Biden appointee.
Assistant US Attorney Kayla Bensing, arguing for Rubin’s continued detention, noted a history of “legal and financial coercion … to intimidate and persuade victims to report him.”
She focused on “Rubin’s access to the wealth … which is clearly what the magistrate judge was interested in,” noting that he initially claimed to have only one life insurance policy while taking millions of dollars from another policy he had access to.
There was also an incident, Bensing said, “that can only be characterized as an attempted bribery.” In a September 30, 2025 phone call, Howard Rubin told his wife, Mary Rubin, “There’s a guy here who can take me to a quiet floor, but it’s going to cost $800.” Mary Rubin then sent a payment to Zelle with a note for her husband’s floor replacement.
Earlier in his argument, Gilbert referred to that event himself, using it to bolster his argument that any third-party requests to change his client’s flooring would also be rendered impossible if the court grants his release.
Joining Merriam on the bench were Senior U.S. District Judge Guido Calabresi, a Bill Clinton appointee, and U.S. District Judge Steven Menashi, a Donald Trump appointee. The trial court reserved its decision.
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