Judge denies $50 million bail for financier Howard Rubin amid flight risk concerns

 October 20, 2025, NEWS

Howard Rubin, a 70-year-old retired Wall Street titan, was ordered to remain behind bars Monday after a Brooklyn judge deemed even a $50 million bond insufficient to prevent his potential flight.

As reported by New York Post, Rubin, charged with sex trafficking alongside his assistant Jennifer Powers, faces allegations of luring numerous women to New York for abuse in a penthouse dungeon over a decade-long scheme.

Federal prosecutors argued Rubin poses a danger to the community, while his wealth, including a reported $74.4 million account in the Cayman Islands, raises doubts about whether any bail could tether him to face trial.

Judicial Skepticism Over Rubin’s Financial Ties

Magistrate Judge Brian James Cho, presiding over the hearing in Brooklyn federal court, expressed concern about Rubin’s vast resources, stating, “Fifty million dollars seems like a lot of money to a layperson, but it may not be a lot for this defendant and his family.”

That kind of cash might buy freedom for most, but when your bank statements read like a small nation’s GDP, it’s just pocket change. If prosecutors can’t even pin down Rubin’s full net worth, how can anyone trust he won’t vanish to some untraceable island?

Rubin’s attorney, Michael Gilbert, countered by pointing to his client’s age and recent health issues, including a stroke in July, arguing the allegations involve dated conduct.

Family Support Clashes With Grim Allegations

Despite ongoing divorce proceedings, Rubin’s estranged wife, Mary Henry, penned a heartfelt letter to the court, pleading for his release and describing him as “a caring father, a loving son-in-law, and devoted grandfather known affectionately as ‘Pops.’”

His daughter, Annalee Rubin, echoed this sentiment, painting a picture of a man who dressed as Frozen characters to delight his grandchildren. Yet, one wonders if such personal warmth can outweigh accusations of systemic brutality that span years.

Prosecutors swiftly dismantled these defenses in an Oct. 19 memo, noting, “It is unremarkable that he may have treated his family and friends with kindness, as most people do.”

Details of a Decade-Long Scheme Emerge

Federal authorities allege Rubin and Powers, 45, orchestrated a scheme to bring women to New York, where Rubin reportedly subjected them to violent BDSM encounters in a specially designed penthouse space over roughly ten years.

Additional charges complicate the case, with Rubin facing bank fraud accusations and Powers, along with her husband Steve, indicted for alleged tax fraud tied to unreported millions funneled by Rubin. This isn’t just a story of personal vice; it’s a tangled web of financial and moral decay.

Previous civil lawsuits over similar claims saw Rubin held liable, though Powers was not, adding a layer of legal history to the current criminal proceedings.

Courtroom Moments and Uncertain Future

In court, Rubin, clad in a tan jumpsuit and black glasses, blew a kiss to Henry and their daughter as he was led out, a gesture of defiance or perhaps desperation after waving to them upon entry.

Earlier that day, when asked about his condition in detention since his late September arrest, Rubin chuckled and replied with a wry “OK,” a response that hardly matches the gravity of his situation. With such nonchalance, it’s hard to see him grappling with the weight of what’s at stake.

As the judge’s gavel fell, denying bail, the reality set in that Rubin’s wealth and family support couldn’t buy his way out of custody, leaving his fate to be decided at trial amid a storm of disturbing allegations.

About Craig Barlow

Craig is a conservative observer of American political life. Their writing covers elections, governance, cultural conflict, and foreign affairs. The focus is on how decisions made in Washington and beyond shape the country in real terms.
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