A Wall Street Legend and His Penthouse Sex Dungeon

Summary

Podcast Summary: The Journal.

Episode: A Wall Street Legend and His Penthouse Sex Dungeon
Date: January 29, 2026
Hosts: Ryan Knudsen & Eric Schwartzel (The Wall Street Journal)

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Main Theme & Purpose

This episode investigates the dramatic double life of Howard Rubin: a once-celebrated Wall Street trader whose success stories were frequently featured in the Wall Street Journal, and who is now facing severe allegations of running a sex trafficking and abuse operation out of a Manhattan penthouse. Through reporting, interviews, and court records, the show explores Rubin’s rise in finance, the collapse of his public reputation, and the disturbing details of the alleged crimes, highlighting themes of power, secrecy, and the duality of public personas.

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Key Discussion Points & Insights

1. Howard Rubin’s Early Life and Wall Street Career

• Background: Rubin was raised near Boston, the middle of three sons, and began his career as a chemical engineer before shifting to professional gambling and later to finance.
  • “He moved to Vegas and he started gambling. And he was a card counter…had to soon start wearing a disguise because casino security would recognize him.” (Eric Schwartzel, 04:25)
• Financial Success:
  • Started at Salomon Brothers in the 1980s, gaining a reputation as a high-risk, highly successful trader.
  • Was "poached" by Merrill Lynch in 1987 amid a Wall Street focus on star talent—described as analogous to an NBA-level trade.
    • “He was seen as like, almost in a way that like you might trade an NBA player…” (Eric Schwartzel, 05:54)
• Infamy: In April 1987, Rubin's risky decisions backfired, resulting in a $250 million loss—the largest tied to a single trade at the time.
  • “Imagine telling your boss you lost $25,000 for the company. Now imagine telling him you lost 250 million.” (Eric Schwartzel, 07:17)
  • Was investigated by the SEC, who suspended him from the securities industry for nine months, but he quickly landed another role at Bear Stearns, a firm known for hiring “talented but a little toxic” traders. (08:17)

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2. Rubin’s Secret Penthouse Life

• Location: Metropolitan Tower, Midtown Manhattan, a building emblematic of both the mundane and the fantastical sides of New York. Rubin secretly rented a penthouse there, converting one bedroom into a soundproofed "sex dungeon" outfitted with BDSM equipment. (03:21, 13:06)
• The Double Life:
  • To public acquaintances and Wall Street colleagues, Rubin was a “family man” and not seen as the hard-partying type.
  • "The literary comparison that would often come up is Jekyll and Hyde." (Eric Schwartzel, 01:22)

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3. Alleged Sex Trafficking Operation

• Recruitment of Women:
  • Starting as early as 2009, women (often Playboy models, waitresses, freelancers) were recruited—many struggling financially—by Jennifer Powers, Rubin’s associate.
  • Powers’ role included making contact, arranging travel, and maintaining relationships with the women. She was described as the “COO” of the operation and was heavily financially compensated. (11:08)
    • “I came to think of her as, like, the COO of this enterprise.” (Eric Schwartzel, 11:08)
  • Payment ranged from $2,000–$5,000 per night, with premium rates for encounters Rubin enjoyed more; sometimes expenses like travel and accommodations were covered. (12:33)
• Experience of the Women:
  • Dinners or drinks at the Russian Tea Room (next door to the penthouse) were often followed by time in the dungeon.
  • Encounters, while advertised as consensual BDSM, frequently escalated to violence and torture, according to multiple lawsuit allegations.
    • Women claimed Rubin ignored safewords (notably “pineapples”) and continued abuse; some were gagged so tightly they could not speak the safeword. (14:02)
      • “Whenever she shouted the word pineapples, he continued to ignore her, and the evening ended in raping her.” (Eric Schwartzel, 14:02)
  • All women were required to sign Non-Disclosure Agreements (NDAs)—sometimes while inebriated—under threat of $500,000 penalties, further intimidating victims. Rubin’s legal team used these NDAs as evidence of consent. (14:50)

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4. The Operation Unravels

• Turning Point:
  • In 2016, a fight broke out among several women present at the penthouse (while Rubin wasn’t there). Police were called, leading victims to begin comparing their experiences and seeking legal counsel. (17:11)
  • “After the police got to the apartment, one of the women texted Powers and [Powers said,] ‘Don’t tell them who rents this place. Hide any incriminating evidence.’” (Ryan Knudsen & Eric Schwartzel, 17:27)
  • This culminated in a high-profile civil suit in 2017 by a group of women, leading to further legal scrutiny and ultimately criminal prosecution. (18:11)

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5. Aftermath, Legal Consequences, and Public Fall

• Rubin was found liable in civil court, ordered to pay $3.8 million to six women, with subsequent cases settled confidentially. He disappeared from social life; gossip about the “pineapples” safeword and his secret dungeon became notorious within certain social circles. (19:13, 19:30)
  • “Pineapple became synonymous with no.” (Upper East Side resident via Eric Schwartzel, 20:16)
• Arrest and Current Status (as of 2026):
  • Arrested in September 2025, living in Connecticut at the time.
  • His wife is divorcing him but remains supportive publicly, even signing bail applications; his daughter calls for his release home.
    • “It is heartbreaking not to have my father by my family’s side.” (Rubin’s daughter’s email, 21:11)
  • All bail requests have been denied due to flight risk; Rubin is jailed in Brooklyn, alongside high-profile inmates like Nicolas Maduro.
• If convicted, Rubin faces life in prison.

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Notable Quotes & Memorable Moments (with Timestamps)

• On Career and Reputation:
  • “He was seen as like, almost in a way that like you might trade an NBA player…”
    (Eric Schwartzel, 05:54)
  • “Imagine telling your boss you lost $25,000 for the company. Now imagine telling him you lost 250 million.”
    (Eric Schwartzel, 07:17)
• On the Double Life:
  • “The literary comparison that would often come up is Jekyll and Hyde.”
    (Eric Schwartzel, 01:22)
• On the Abuse:
  • “One woman said that she was gagged too tightly to even say the safe word.”
    (Eric Schwartzel, 14:02)
  • “Whenever she shouted the word pineapples, he continued to ignore her, and the evening ended in raping her.”
    (Eric Schwartzel, 14:02)
• On the Social Fallout:
  • “I was talking to one person who knew Rubin through these social circles, and he said that eventually pineapple became synonymous with no.”
    (Eric Schwartzel, 20:16)
• On Rubin's Multiple Public Faces:
  • “It’s hard to imagine one person containing as many different identities depending on the person looking at him, as Howard Rubin.”
    (Eric Schwartzel, 22:43)

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Timeline of Important Segments

• 00:05 – Introduction to Howard Rubin and the Journal’s investigation
• 03:21 – Rubin’s secret penthouse and the Metropolitan Tower details
• 04:25 – Rubin’s career rise and reputation as a risk-taker
• 07:17 – The $250 million loss story and consequences
• 09:31 – Alleged sex trafficking operation and recruitment methodology
• 13:06 – Description of the penthouse “sex dungeon”
• 14:02 – Accounts of abuse and ignoring safewords
• 17:11 – The 2016 incident that led to legal exposure
• 19:13 – Rubin’s social exile and the spread of the “pineapple” story
• 20:16 – Bail situation, family reactions, and Rubin’s current status
• 22:43 – Reflection on Rubin’s life of contradictions

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Conclusion

This episode of The Journal provides a harrowing, well-reported look into how a man can wield finance-world power, privilege, and social invisibility to hide predatory abuse for years. Through the lens of Howard Rubin’s rise, fall, and criminal exposure, the podcast explores themes of wealth protecting secrecy, the vulnerability of those less powerful, and society’s tendency to overlook monsters in high places—until they can no longer be ignored.

Transcript

[Ryan Knudsen]

Not too long ago, a short story in the Wall Street Journal caught the attention of our colleague Eric Schwartzel. It was a story about a man named Howard Rubin who'd been arrested on sex trafficking charges. He pleaded not guilty.

[Eric Schwartzel]

I had never heard of Howard Rubin before. And when I started to learn more about his biography and realized that he had been a pretty regular feature of the Wall street journal in the 1980s and the 1990s.

[Ryan Knudsen]

Rubin was a star trader on Wall street who made millions and whose successes and failures over the years got written up in our newspaper in the Wall Street Journal. Along with his reputation as a big shot trader, he was also known as a family man.

[Eric Schwartzel]

When I talked to folks who worked with him at the time, they would tell me that, you know, frankly, Howie, as they wasn't necessarily the hard partying type. He was seen as someone who was just pretty normal guy and he had the trappings of a pretty domestic life.

[Ryan Knudsen]

But something that not many people knew was that Ruben had a dark side.

[Eric Schwartzel]

The literary comparison that would often come up is Jekyll and Hyde. This question of like someone who appeared to be one person in the daytime and another person behind closed doors.

[Ryan Knudsen]

How would you describe who Howard Rubin is?

[Eric Schwartzel]

The answer to that question in 1985 would have been, howard Rubin is a star trader at Salomon Brothers on Wall Street. The answer in 1987 would be, Howard Rubin is a disgraced trader at Merrill lynch on Wall Street. The answer in late 1987 would be, Howard Rubin is a star trader at Bear Stearns on Wall Street. And the answer in 2017, according to prosecutors, would be, Howard Rubin is a sex trafficker presiding over a ring of abuse and torture at a sex dungeon in midtown Manhattan.

[Ryan Knudsen]

Welcome to the Journal, our show about money, business and power. I'm Ryan knudsen. It's Thursday, January 29th. Coming up on the show, a Wall street titan and his very dark secret. Hey, it's Ryan. Thanks for being a listener to our show. If you're looking for more deeply reported stories like the ones we share every day, consider becoming a subscriber to the Wall street journal. Visit subscribe.WSJ.com thejournal to subscribe now. South of Central park in Manhattan, there's a building called the Metropolitan Tower. It was built in 1987. It's 68 stories tall, and the outside is all glass.

[Eric Schwartzel]

It's a skyscraper. And it looms over this block that I kind of came to see as like a quintessential midtown Manhattan block. It's on the same block as Carnegie hall, but there's also a small grocery store and a place where you can buy eyeglasses and the Russian Tea Room. So it is this block that has that Manhattan combination of the mundane and the fantastical. And it is where Howard Rubin secretly rented a penthouse apartment, where he converted one of its bedrooms into what he called his sex dungeon.

[Ryan Knudsen]

This room in this apartment would be the center of the alleged sex trafficking. Since being arrested for this and other crimes this past September, Rubin has pleaded not guilty. His lawyers have argued that the encounters were consensual. Before news of the alleged sex trafficking broke, Rubin had built a decades long reputation on Wall street as a smart and risk loving trader. Can you tell me the story of how Howard Rubin rose to power on Wall Street?

[Eric Schwartzel]

So Howard Rubin, who's Now in his 70s, he was born and raised outside of Boston, one of three boys. His father worked at Polaroid and he was the middle son. And he started his career as a chemical engineer and quickly grew bored of that. And he was a really smart guy, very good with numbers. And he moved to Vegas and he started gambling. And he was a card counter and he was so good at card counting, he had to soon start wearing a disguise because casino security would recognize him.

[Ryan Knudsen]

After that stint in Vegas, Rubin went to Harvard Business School, then moved to New York to start a career as a financial trader in the 1980s. But he never lost that gambler mentality.

[Eric Schwartzel]

Now he, he joins a financial industry that is just on a rocket ship. He joins these firms that are seeing their holdings and their assets just grow exponentially in those years when he's a trader and he's working at Solomon Brothers, which is seen at the time as sort of being the premier, a class of traders. And Howard Rubin was seen as a star. He was someone who would take big bets, take on massive amounts of risk, but also often be proven right and make a ton of money for the firm.

[Ryan Knudsen]

At what point did he start appearing in the Wall Street Journal?

[Eric Schwartzel]

He started appearing in not just the Wall Street Journal, but all over the world in 1987 because Merrill lynch poached Rubin from Solomon Brothers, paid him this big salary. And it was really also, it was explained to me that like, this was also a time when Wall street was starting to recognize individual talent. Like he was seen as like, almost in a way that like you might trade an NBA player like you, you wanted to assemble the right team. And so Merrill lynch brings Ruben in from Solomon Brothers and it's seen as this, this like massive poaching and this massive get on their part.

[Ryan Knudsen]

It wasn't long, however, before stories in the Wall Street Journal about Rubin's success turned into stories about his failure.

[Eric Schwartzel]

In April of 1987, Rubin bought up a massive trove of mortgage securities. Mortgage mortgage activity at the time was skyrocketing, and it seemed like it was going to go up and up and up and up and up. And so Rubin had bought a bunch of mortgage securities, but he hadn't told his bosses just how many he had purchased, which meant the firm couldn't hedge it.

[Ryan Knudsen]

Hedge it, Meaning that if he's wrong, there's no safety net that they're building underneath him.

[Eric Schwartzel]

No safety net. And then mortgages did fall in value, and Rubin's investment became this $250 million loss.

[Ryan Knudsen]

Wow.

[Eric Schwartzel]

The time, it was believed to be the single greatest loss tied to a single trade. And the stories at the time that were written, I mean, it's a lot of them are written as kind of like every employee's worst nightmare. Like, there's one that's like, imagine telling your Boss you lost $25,000 for the company. Now imagine telling him you lost 250 million.

[Ryan Knudsen]

It was such a big deal that Merrill lynch had to publicly announce the loss to investors and that Howard Rubin was responsible.

[Eric Schwartzel]

And he sort of became. He went from being rather famous on Wall street to being infamous for. For this $250 million trade.

[Ryan Knudsen]

Did he face any consequences for this other than getting fired?

[Eric Schwartzel]

The SEC launched an investigation, and Rubin would settle with them. He didn't admit or deny guilt. He just said he had failed to keep accurate records and agreed to take nine months off from the securities industry.

[Ryan Knudsen]

But even the $250 million loss didn't slow him down.

[Eric Schwartzel]

I had to check and make sure I had the dates right, because that was in April of 87. And before the end of the year, Rubin was back on Wall Street. He was hired by Bear Stearns to start trading for them. And at the time, Bear Stearns had a reputation for hiring the traders who were talented but a little toxic.

[Ryan Knudsen]

Over time, Rubin's trading exploits faded from the pages of the Wall Street Journal. But now Rubin is back in the news, but under very different circumstances. Details about Rubin's alleged abuse first started to emerge in 2017 when a group of women sued him. Another lawsuit followed a year later, and eventually a criminal prosecution. Through court records, Eric was able to put together a picture of what allegedly happened. Before we go on, I should say that we're going to describe allegations of sexual Assault and abuse, which for some listeners, might be difficult to hear. What do we know about when the alleged sex abuse started?

[Eric Schwartzel]

So we're not exactly sure, but the cases against him have evidence and stories that date back to 2009.

[Ryan Knudsen]

And who are the women he allegedly targeted?

[Eric Schwartzel]

So several of the women have very similar stories. The details might be different, but the broad outlines are the same, which is that many of them were not necessarily living in New York. They were working, some as models, some as waitresses. More than a few had been models for Playboy at one time or another. And these women would be contacted, often by an associate of Howard Rubin's, who would explain that they worked for a man in New York who was interested in meeting them. He would pay them for sex. He would pay them possibly to take their photos. He might pay them for what they would often refer to as light fetish activity. And would they be interested in doing that?

[Ryan Knudsen]

The women who formed the civil suits included freelance models and cocktail waitresses. Prosecutors say that many of them were caring for younger siblings or kids of their own, and that Rubin exploited that economic disparity. According to court documents, in a 2014 text message, Rubin wrote that one woman was, quote, broke and says she'll do anything. Typically, Rubin didn't make first contact with these women. One person who allegedly did that for him was named Jennifer Powers.

[Eric Schwartzel]

When you read the cases, it sounds like Jennifer Powers filled many roles in this operation. She was Reuben's good cop. Sometimes she would be his banker. She would send the women money. I came to think of her as, like, the COO of this enterprise.

[Ryan Knudsen]

Hmm.

[Eric Schwartzel]

Oftentimes, finding the women, making first contact with them, and then sort of maintaining the relationship throughout.

[Ryan Knudsen]

Those allegations sound sort of like the relationship between Ghislaine Maxwell and Jeffrey Epstein.

[Eric Schwartzel]

Yes. And when I would talk to folks, they would make that connection.

[Ryan Knudsen]

Powers has pleaded not guilty to charges of sex trafficking and transporting women over state lines for sex. Her attorneys did not respond to requests for comment.

[Eric Schwartzel]

For this work, it seems as though she was subsidized quite nicely. She was paid a lot of money, and it came in different forms, too. There was a time where she was paid almost kind of like a monthly stipend. But then for several years, Rubin just subsidized her entire life. He paid for all the credit card bills that she and her husband accumulated, and they would rack up, like, half a million dollars in credit card bills a year, and he would just pay them off. He was paying for their house in Texas. He was paying for private school for their Children. I mean, he was really just covering, it seems, nearly every expense they could have had.

[Ryan Knudsen]

Powers would tell the women she recruited that Rubin would pay $2,000 for a night, or up to $5,000 if Rubin had a particularly good time. Many of them came from out of.

[Eric Schwartzel]

State, and they would be flown to New York. And once they were there, they might go to dinner or get a drink, often at the Russian Tea Room, which is located right next door to this tower on 57th Street. And then at some point, Howard would escort them up to the penthouse apartment that he rented and take them into one of the bedrooms, which had been outfitted into this sex dungeon.

[Ryan Knudsen]

That room in the apartment, the so called sex dungeon, was soundproofed. According to prosecutors, the room was painted red, and Reuben had it filled with ropes, whips, and sex toys.

[Eric Schwartzel]

And the stories that are included in these complaints do show what the women perceive to be a kind of noticeable shift in his behavior and demeanor, especially when it comes to, you know, the man they met at the Russian Tea Room is behaving very differently than the man they see inside the dungeon.

[Ryan Knudsen]

Say more about that. What would they see?

[Eric Schwartzel]

This might include everything from, you know, punching, slapping, abusing in all kinds of ways.

[Ryan Knudsen]

While some of these women knew to expect aggressive sex, like bdsm, victims say Rubin took it much further than that and that the encounter is often tipped into torture. Rubin did give the women a safe word, but several said he ignored it.

[Eric Schwartzel]

One woman said that she was gagged too tightly to even say the safe word. Another time, a woman claimed that the safe word was pineapples, and that after she thought Ruben was getting too rough, she said pineapples, and he ignored her. In fact, he only grew angrier and more aggressive, and that whenever she shouted the word pineapples, he continued to ignore her, and the evening ended in raping her.

[Ryan Knudsen]

Multiple women accused Rubin of rape. The women were told to sign an NDA, and if they broke it, they would have to pay Reuben $500,000.

[Eric Schwartzel]

So there was a safe in the penthouse that held a stack of blank non disclosure agreements that the women were told they had to sign before proceeding. And some of the women say that they were inebriated when they signed the form, but the language of it says that they have agreed that in exchange for payment, they've agreed to engage in sexual acts that, quote, including sadomasochistic activity that can be hazardous and on occasion, cause injury. And a safe full of blank NDAs in a penthouse that houses a sex dungeon certainly conjures a Pretty intense image. It was interesting that Rubin's attorneys actually cited these NDAs as part of their defense, saying that the language of the NDA bolstered their case, that this was a consensual agreement, that. And that there was no sort of confusion, or there shouldn't have been any confusion.

[Ryan Knudsen]

And then what would happen after all of this was over?

[Eric Schwartzel]

Well, this is, again, the kind of the Jekyll Hyde impression that you get reading these stories is that sometimes it would seem as though the spell was broken after the dungeon activities had ended. And Ruben might, you know, thank them for a pleasurable evening and say that he had to get going because he was meeting his wife and kids for dinner.

[Ryan Knudsen]

Howard Rubin's secret would eventually get exposed. How that happened is next. Howard Rubin and Jennifer Powers alleged sex trafficking enterprise began to fall apart in 2016. It started with a group of women who were at Rubin's apartment at the same time. According to court records, Rubin himself wasn't there. But a fight broke out between two.

[Eric Schwartzel]

Women, we believe, over what exactly had happened and transpired in the dungeon. One woman saying that she had been misled into being how intense the evening would get. The fight breaks out, and the police are called.

[Ryan Knudsen]

After the police got to the apartment, one of the women texted Powers and.

[Eric Schwartzel]

Says, you know, what do we do? The police are here. And the women claim that Jennifer said, you know, don't tell them who rents this place. You know, hide any incriminating evidence.

[Ryan Knudsen]

After that day, the women started comparing stories.

[Eric Schwartzel]

And as the women are talking in the case of over this fight is developing, they start talking to lawyers about what happens in the dungeon, and they form a group who come together and collectively Sue Rubin in 2017. And that is when it kind of all spills into the open.

[Ryan Knudsen]

This is what would ultimately form the basis of two civil cases and later a criminal investigation. What did Rubin and Powers do when they found out that these women were coming together to sue them?

[Eric Schwartzel]

It seems as though there was a flurry of activity to try to figure out what to do, whether it was try and offer payments to settle the cases or to get the women to drop charges. And then once it went to court and once the charges were filed, it was described to me as. As almost comical. The number of attorneys Rubin and Powers had at their disposal, just sort of sitting behind them to try to counter these claims and really pretty aggressively go after these. These charges and argue that these were consensual arrangements and that the women were either out to get a payout or out to Ruin his reputation seeking revenge. Any host of motivations there.

[Ryan Knudsen]

Rubin was found liable and ordered to pay $3.8 million in total to six women as part of the first case. The second case also ended with a settlement. Afterwards, Rubin disappeared from public life.

[Eric Schwartzel]

I mean, he was like a pretty regular guy on the Upper east side social circuit. I mean, people whose kids had gone to the same private school that his kids went to said that he'd be around. You know, he was. He and his wife would be photographed at charity galas. And then after these suits were filed, they said, you just never saw Ruben anywhere. And as the details really started to spread, they became these, like, punchlines. I mean, specifically this. This story about the safe word being pineapples just started to float all through the Upper east side. And so I was talking to one. One person who knew Reuben through these social circles, and he said that eventually pineapple became synonymous with no.

[Ryan Knudsen]

In September of last year, Rubin was arrested. Eight years after that group of women filed the first civil lawsuit against him. At the time, he was living in Connecticut near his daughter and grandchildren.

[Eric Schwartzel]

And one thing that I kept asking everyone is, you know, why did it take so long for these charges to be filed? And I don't have a firm answer, but several things that have come up are, you know, one of the civil suits was appealed. There was also delays related to Covid.

[Ryan Knudsen]

What do we know about how his family reacted when these allegations came out?

[Eric Schwartzel]

Well, you know, his wife is in the process of divorcing him, and a lot of people have kind of marveled at her presence that she's willing to sort of be the star defender. She's coming forward and saying, I will basically back his effort to be released on bail.

[Ryan Knudsen]

Rubin's daughter has also come to his defense, saying in an email that he should come home. Quote, it is heartbreaking not to have my father by my family's side. Rubin's lawyers have applied for his bail three times. They said in the application that, quote, the alleged conduct involves private activity between adults. That concluded more than six years ago.

[Eric Schwartzel]

The main argument that his defense attorneys have made is that he was living this very kind of docile, harmless life as a grandfather in bucolic Connecticut. And there are more than a dozen letters of support for Ruben in this bail package, ranging from his wife, his daughter, his daughter's partner, his granddaughter's dance teacher, his granddaughter's swim coach. Really drawing as stark a contrast as you can imagine, to the stories these women have of being gagged and having to bite his finger. To get him to stop, you know, hurting them and abusing them.

[Ryan Knudsen]

A judge rejected all three of Rubin's requests for bail after the government argued that Rubin could use his money and resources to flee. Jennifer Powers, who was arrested at her home in Dallas, was released on bail last year. Rubin is now sitting in jail in Brooklyn, the same jail that houses Nicolas Maduro and Luigi Mangione. If convicted, Rubin could face life in prison.

[Eric Schwartzel]

I think the story of Howard Rubin is one of those kind of special cases where in one life, you have several different worlds. You have one Wall street, then you have a very different Wall Street. You have a man who was once considered a master of the universe, but who now shares prison space with Nicholas Maduro. You have a neighbor who was seen as a family man, maybe even a boring family man, but who for, you know, nearly a dozen women was seen as an abuser and a torturer. I mean, it's hard to imagine one person containing as many different identities depending on the person looking at him, as Howard Rubin.

[Ryan Knudsen]

That's all for today. Thursday, January 29th. The Journal is a co production of Spotify and the Wall Street Journal. If you like our show, follow us on Spotify or wherever you get your podcasts. We're out every weekday afternoon. Thanks for listening. See you tomorrow.