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.

“The alleged conduct involves private activity between adults that concluded more than six years ago,” his attorneys wrote in the application.

Rubin once seemed ripped from the pages of Tom Wolfe’s “The Bonfire of the Vanities”—and was himself a character in Michael Lewis’s “Liar’s Poker”—but in the government’s telling appears to be more like Dr. Jekyll and Mr. Hyde.

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.

‘meet/greet/beat’

Much of the government’s criminal case against Rubin appears to be derived from two civil suits filed against him in 2017 and 2018.

Rubin was found liable and ordered to pay $3.8 million to six women as part of the primary civil case in April 2022. The second case also ended with a settlement.

In filings and subsequent testimony, several women told similar stories of what happened between 2009 and 2019. They were contacted over Instagram by a representative of Rubin’s about spending an evening with him. The women would be brought to New York and could receive $2,000 for a night—or up to $5,000 if he had a particularly good time. One woman said she was assured he was a “great guy.”

The evening might begin at the Russian Tea Room, located next door to the Metropolitan Tower, a skyscraper built in 1987 that one observer likened to a “glass-and-steel Godzilla looming ravenously” over the more elegant buildings nearby.

Inside Rubin’s penthouse was a safe that held a stack of blank nondisclosure agreements.

Some of the women said they were inebriated when they signed the form, which noted that the women had agreed, for payment, to engage in sexual acts “including Sadomasochistic (SM) activity that can be hazardous and on occasion cause injury,” read a form quoted by defense attorneys who argued it left little uncertainty about what the night might entail.

Breaking the contract would require paying $500,000 to Rubin.

The Russian Tea Room in Midtown Manhattan; a bear insignia above the restaurant’s entrance. Timothy Mulcare for WSJ

The women say a depraved side of Rubin emerged inside the dungeon, one that went far beyond the limits of BDSM (or bondage, discipline, sadism and masochism) role-play and aggression. It included electric shocks and severe beating.

Defense attorneys in the civil case argued that Rubin was clear with the women about the kind of evening that lay ahead, and noted that several met with Rubin many times, and even referred friends and associates to sessions in the dungeon.

One woman who sued Rubin alleged he gave her a safe word that would bring everything to a halt: “pineapples.” He then tied her wrists with ropes and lightly slapped her across the face.

She said he tightened the ropes and smacked her again—this time much harder.

“PINEAPPLES!” she yelled.

When she again asked him to stop, she said he only grew angrier, punching and smacking her as she remained restrained by ropes hanging from the ceiling. The assault continued and he raped her, she said.

Other times, women said, he gagged them so tightly they couldn’t speak the safe word when they tried.

Another woman alleged Rubin had beaten her chest so violently that one of her breast implants had flipped. After he ignored her use of a safe word, the abuse stopped when she had removed enough of the gag to bite him on the finger. (This was the same woman about whom Rubin said, “I don’t care if she screams,” according to court filings.)

Rubin paid for the implant to be repaired, according to the civil suit, which also references the incident. The woman said in the suit that Rubin requested she replace her saline implants with silicone, since that was a sturdier material.

Rubin’s attorneys in one of the civil trials submitted several dozen text messages that they argued showed an understanding among all parties of the BDSM practices expected inside the dungeon.

In a representative text message sent to one of the women in June 2014, Rubin said, “this is a real beating ur going to get.”

Several days before a session with two women in August 2016, Rubin texted them: “Its total BDSM. Most girls love it and come back for more, but I just like to be upfront about everything.”

The day before the women came to the Metropolitan Tower, Rubin texted again:

“Ladies, can’t wait to meet/greet/beat you tomorrow.”

“Sounds good to me,” one of the women replied.

The Metropolitan Tower on West 57th Street, where Rubin rented the penthouse. Timothy Mulcare for WSJ

Managing the logistics and soothing the distraught women, prosecutors allege, was Jennifer Powers, 45, a former model for Hawaiian Tropic and substitute teacher who was arrested along with Rubin.

“It got very rough jenn, we need to be VERY VERY VERY nice….” Rubin wrote to her after the encounter that injured the woman’s implant, according to court records.

“OK. I am being nice. I just hope you know what you’re doing,” she wrote back.

Powers has pleaded not guilty. She was also named in one of the civil suits against Rubin, but the claims against her were dismissed. Her attorneys didn’t respond to requests for comment.

Powers became Rubin’s full-time deputy in the trafficking operation in 2011, according to a government letter arguing against Rubin’s bail.

The following year, she married a professional DJ at the former Miami Beach mansion of fashion designer Gianni Versace, who was shot dead on its front steps in 1997. A photo from the event shows Rubin smiling in the crowd.

Powers filled many roles for her boss, prosecutors allege.

She was his logistics coordinator: booking flights to New York and letting Tower doormen know who was allowed up to the penthouse.

She was his good cop: telling the women that arnica cream might help soothe their bruises.

She was his accountant: paying the women in small disbursements that wouldn’t trip up bank rules.

She was his defender: explaining after the fact that the women shouldn’t have allowed Rubin to get drunk.

And she was his encourager: “I can only imagine what you did to her on that cross!!!” she wrote in a January 2015 text message included in court filings.

Rubin paid millions of dollars for her work, first in monthly wages and then by covering nearly all her expenses, including mortgage payments and private-school tuition. Rubin paid off annual credit-card expenses from Powers and her husband that exceeded $500,000 from 2018 to 2023—including after the two had been subject to the civil suits.

Jennifer Powers exited Brooklyn federal court after a hearing in October. Jeenah Moon/Reuters

It has been nearly a decade since details of their “enterprise,” as prosecutors have called it, began to spread in late 2016, after police were called to the penthouse. An argument had broken out between two women there over Rubin’s abuse. Rubin wasn’t there, and Powers told the women not to tell the police who leased the apartment.

She later warned Rubin the investigation could turn up other details: “drugs, sex, etcccc,” according to court documents.

One of the women began telling attorneys about the abuse. More women came forward, filing a civil case just as the #MeToo movement began to instigate a global reckoning over sexual abuse.

The women who formed the civil suits included freelance models and cocktail waitresses, many caring for younger siblings and kids of their own, and prosecutors say Rubin exploited that economic disparity.

In June 2014, shortly before he’d retire from Soros’s firm, Rubin contacted an associate, known only as Co-Conspirator-1, about a woman’s financial straits.

“She’s brokke and says she‘’ l l do anything!” he wrote in a text message, according to court documents in the criminal case.

“She hates it, but she’s soooo desperate! We’ve got to make her cry!!!” he added.

When the woman got in touch to say she was ready to meet, Rubin corrected her.

“Ur not, bbut ur desperate and thts good.”

Masters of the universe

Rubin grew up the middle son of three boys raised in the Boston suburbs. After his mother died when he was 13, “Howie” became a surrogate parent and role model to his younger sibling, his brother wrote in a letter of support for Rubin’s bail application.

He was the boy made good, having begun his professional life as a chemical engineer in New Jersey. But he eventually grew so bored that he moved to Las Vegas, where his card-counting skills made him fast money—and soon required him to wear disguises to slip past casino security.

He went on to Harvard Business School, and professionalized his knack for assessing risk and knowing when to bet. At Harvard, Rubin met Mary Henry, whom he would marry two days after Valentine’s Day 1985.

They were a Wall Street couple: She went to work at Merrill Lynch, while he started at Salomon Brothers alongside another new recruit, Michael Lewis, who would detail those heady years in his 1989 bestselling memoir, “Liar’s Poker.”

“You couldn’t always put your finger on losers, but you knew talent when you saw it,” Lewis wrote. “Howie Rubin had it.”

Mary Henry, Rubin’s estranged wife, leaving Brooklyn federal court after a hearing in October. jeenah moon/Reuters

Working together in 1980s Wall Street, Lewis and Rubin were crew mates on a rocket ship. The capital held by Wall Street’s securities firms would more than triple in Rubin’s first five years of employment. And the young bankers powering it all were the “masters of the universe,” so labeled by Tom Wolfe in his 1987 bestseller “The Bonfire of the Vanities,” a novel that he researched by spending a day on the Salomon Brothers trading floor.

Rubin’s skills, former colleagues say, included an encyclopedic recall, the ability to explain his bets in plain English and a high threshold for risk. After Merrill Lynch recruited him as a securities trader in 1986—with a guaranteed annual salary of $1 million—some of his new colleagues began to worry about just how risky he got.

Merrill was known as “the Thundering Herd,” but Rubin did not appear ready to run with the pack.

That became apparent on April 17, 1987—Good Friday—when Rubin called an executive at Merrill Lynch and admitted his reporting on recent mortgage trades hadn’t been accurate.

Rubin had been buying a significant amount of mortgage securities, hoping to take advantage of a market for mortgages that had risen 260% in 1986 alone.

But he hadn’t told the firm about the massive holding he’d accumulated, which meant other traders hadn’t hedged it and invested in securities that would rise in value if those mortgage securities fell.

When the rebound in mortgages never came, Rubin’s losses compounded to more than $250 million. At the time, it was believed to be the single-greatest loss in Wall Street history tied to one trader.

Merrill announced the loss and fired Rubin. The SEC launched an investigation, and Rubin ultimately settled charges that he had failed to keep accurate records, neither admitting nor denying guilt. He agreed to a nine-month suspension from the securities industry.

Rubin’s contemporaries from Wall Street today remember the $250 million loss as an ominous foreshadowing. Six months later, the Black Monday crash registered the largest one-day drop in the Dow’s history, wiping an estimated $1.7 trillion off the global market.

An April 30, 1987, article about Merrill Lynch’s losses. The Wall Street Journal

‘Superstar’

But Rubin was soon back to work. A month after Black Monday, he started at Bear Stearns.

“You hire good people when they become available,” Managing Director John Sites said at the time.

If Salomon Brothers had exemplified early ’80s excess, Bear Stearns embodied the conservatism that followed. The boss told employees to reuse paper clips and ordered Rubin to weekly “cold-sweat” meetings with the risk committee. By 1992, Rubin was collecting an annual bonus of $7 million, and oversaw an operation that generated $150 million in trading profit the following year.

“He’s a superstar,” Bear Stearns CEO James Cayne told The Wall Street Journal in 1993.

Employees were shocked when Rubin announced in 1999 that he was taking an early retirement at age 44 to spend more time with his wife and their three young children. The couple even converted their dining room into a kid’s gym, outfitted with mats and a mini-trampoline.

Rubin went back to work in 2008, this time as an investment adviser for billionaire George Soros’s Soros Fund Management.

He retired in 2015, and the U.S. Attorney’s Office indictment detailed criminal acts against Jane Does #1 through #10 that covered some of that time, from 2009 through 2019.

On the surface, Rubin’s life resembled the boom times. He posed for photos with Henry at galas raising money for child development and cancer research. In a 2018 deposition during the civil trial, Rubin estimated his net worth to be $50 million.

Colleagues and fellow parents at his kids’ private school say Rubin seemed like an ordinary guy who happened to be really, really smart. Once news broke of the lawsuits in 2017, though, Rubin disappeared from that social circuit.

Details of his depositions spread. His safe word became a recurring punchline among Rubin’s acquaintances at the time, appropriated by jokesters to mean “no.”

As in:

“Are you going to that dinner tonight?”

“Pineapple.”

The Metropolitan Detention Center in Brooklyn, where Rubin awaits trial. Timothy Mulcare for WSJ

Under arrest

When Rubin was arrested in September, he was living a quiet life in Connecticut. Powers was raising her family in Southlake, Texas. (Among other charges, they are accused of lying on a mortgage application that Rubin cosigned for her home.)

Powers was released on an $850,000 bail secured with the help of her parents. News of her arrest spread quickly through the wealthy Dallas suburb where she lives, especially since she has worked as a substitute teacher in a local school district.

Rubin has mounted a full campaign to also be granted bail, submitting letters of support from several people, including his niece, his business-school roommate and his granddaughter’s dance teacher. They largely portrayed Rubin as a retiree who dresses up as characters from “Frozen” to make his grandchildren laugh.

He has offered the court a $70 million bond cosigned by his wife and Annalee Rubin, his daughter.

“I am willing to risk losing a majority of my assets,” wrote Henry, who is in the process of divorcing Rubin.

It was a surprising show of support from a woman who is invoked by prosecutors to illustrate the extent of Rubin’s deceit.

In late 2014, he emailed Powers that he needed to tell his wife he was out of town, since there was a long night ahead of “rockettes, dinner and dungeon.”

Soon after, he told Powers he could probably see five women in one week—“Except the 16th is holiday and my anniversary!”

In her letter to the judge, Henry wrote that she understood “far too well the serious charges before the Court,” but added, “They do not represent the Howie Rubin I saw.”

In an email sent on January 17, Annalee Rubin defended her father, saying he “should be out on bail and home with his family. It is heartbreaking to not have my father by my family’s side.”

The government argued against bail, saying Rubin had behaved in suspicious ways that made him seem a flight risk. During his arrest, he said he didn’t know where his passport was, and was found to have eight cellphones and BlackBerry devices.

Rubin’s attorneys said many of those phones were old devices and that Rubin had merely forgotten where his passport was.

Details came up in the bail hearing that, in the judge’s view, undercut Rubin’s promise not to interfere in the criminal trial.

In 2019, he had sent a letter to another woman he learned was considering suing him, according to court filings. In that letter, he said he would characterize her as a “professional prostitute” if she continued the case.

The judge has now denied bail three times, leaving Rubin to await trial in the Brooklyn jail also housing ousted Venezuelan leader Nicolás Maduro and Luigi Mangione, the 27-year-old charged with killing UnitedHealthcare CEO Brian Thompson. He is next due in court on Jan. 27.

Before his arrest, Rubin had lived in a rented home in Fairfield, Conn., close to his daughter’s house. In a letter to the court, Rubin’s landlord said she lives across the street, and observes him babysitting his grandchildren, watching TV and reading the newspaper.

Through the house’s 20 windows, she noted, all she ever saw was “a man who is living a quiet, harmless, simple and respectful life.”