A wealthy woman from Manhattan made a notable appearance in court to back her estranged husband, a financier, who is facing charges related to trafficking women into a sex dungeon.

Mary Henry arrived at Brooklyn Federal Court on Monday morning, sporting a blue coat and maintaining a composed demeanor. Her husband, Howard Rubin, 71, is accused of enticing numerous women into a soundproofed sex chamber.

Jennifer Powers, 45, Rubin’s personal assistant, has also been indicted, accused of facilitating the transportation of women for sexual activities with Rubin.

Rubin, who has entered a plea of not guilty, was present at the federal court in Brooklyn on Monday, with his former wife, Mary Henry, showing her support.

Previously, Henry, 74, had penned a letter to the judge, lobbying for Rubin’s release and praising him as a committed family man.

She insisted that he was not a flight risk, a point strongly contested by prosecutors who also argued that he poses a societal threat. The couple initiated divorce proceedings in 2021.

The judge ultimately sided with the prosecution and at Monday’s hearing denied a $50 million bond package, The New York Post reported.

Rubin, who had waved to his ex as she entered the courtroom, reportedly blew Henry a kiss as he was being taken out of the courtroom after being ordered to remain in jail.

Mary Henry, 74, was in Brooklyn federal court Monday to support her former husband Howard Rubin as he was denied a $50 million bond package

Howard Rubin, 71, (left) is accused of luring dozens of women into a soundproofed ‘sex dungeon’ in his New York City penthouse to be assaulted. His personal assistant, Jennifer Powers, 45, (right) was also indicted for allegedly transporting women for sex acts with Rubin

Rubin has been in custody in Sunset Park’s Metropolitan Detention Center since his September 26 arrest, but last week his legal team requested he be released him on a $50 million bond.

The motion, which was almost 100 pages in length, included a letter from Henry.

‘I understand far too well the serious charges before the Court,’ Henry wrote in her letter to New York District Judge Brian Cogan.

‘I can only speak from my own experience when I say they do not represent the Howie Rubin I saw: a caring father, a loving son-in-law, and devoted grandfather known affectionately as ‘Pops.”

The couple married in 1985 and Henry filed for divorce in 2021, but the former couple still co-grandparent and attend family events together. 

She described Rubin as an intelligent, quick-witted, and kind family man whom she fell in love with while in graduate school. 

She also alleged that Rubin would ‘never’ abandon his family and believed that he wouldn’t flee if released on bond. 

It is unclear how Henry is feeling in wake of Rubin’s failed bid for bail. The Daily Mail’s calls and texts to Henry went unanswered.

Rubin, who has pled not guilty to the charges, reportedly blew Henry a kiss as he was being taken out of the courtroom. The pair (pictured in 2016) have been divorced since 2001

Rubin faces sex trafficking charges for allegedly coercing former Playboy models to his ‘sex dungeon’ in Manhattan, according to his indictment 

Prosecutors allege that Rubin, with the help of Powers, trafficked former Playboy models and other women to Manhattan from 2009 to 2019.

Rubin and Powers spent more than $1 million recruiting women to participate in sadomasochistic sex acts with Rubin in exchange for money, prosecutors said.

Once in New York, the women were encouraged to use drugs or alcohol to prepare for their sexual encounters, and sometimes engaged in conduct beyond the scope of their consent, according to the indictment. 

‘During many of these encounters, Rubin brutalized women’s bodies, causing them to fear for their safety and/or resulting in significant pain or injuries, which at times required women to seek medical attention,’ the court filing stated. 

Rubin allegedly gave the models a ‘safe word,’ but disregarded it when the acts continued and was allegedly violent with the women without their consent. 

After the encounters, Rubin and Powers allegedly paid the women $5,000 if he was ‘satisfied,’ through wire transfer, PayPal, or Venmo, according to the indictment. 

Prior to 2011, the commercial acts usually occurred at luxury hotels in Manhattan.

But from 2011 to 2017, the encounters typically took place at Rubin’s two-bedroom penthouse near Central Park, prosecutors wrote in a court filing.

Henry (pictured Monday) had previously written a letter to the judge advocating for Rubin’s release and hailing him as a dedicated family man. She maintained he was not a flight risk, a claim vehemently disputed by prosecutors who also argued he poses a danger to society

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.

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.

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.

The indictment paints a vastly different picture of Rubin than the letter written by his former wife. 

Henry depicted Rubin as a successful businessman and loving father who earned a reputation as a ‘nice’ trader on Wall Street.

She detailed the relationship Rubin had with her mother, noting that she wasn’t alive to see her ex’s shocking arrest.

‘I was shocked and angered by the news of Howie’s arrest just as I was by the news of his civil suit almost eight years ago,’ Henry continued.

Mary Henry said in her letter to the judge that even though she and her husband lived separate lives, they still co-parented their children and grandchildren 

Henry said that even though she understood the charges against her ex-husband, she believed that he wouldn’t abandon his family (pictured)

‘Although I realized my marriage was over many years ago, in both 2017 and 2025, my thoughts immediately turned to my children who I knew would be devastated by the news of their father whom they always loved and admired.’

Henry spoke of their three adopted children and how Rubin retired at the age of 44 to help raise them.

‘Howie was well known as a most devoted parent among teachers, family, adult friends, and the friends of his children,’ she added.

‘Through it all, the children always knew they were deeply loved and supported by their father. He has been a constant, unwavering presence in their lives.’