The Journal. - A Wall Street Legend and His Penthouse Sex Dungeon

Episode Date: January 29, 2026

Howard Rubin is a Wall Street legend, famous in the 1980s and ‘90s for being a risk-loving star trader. He also allegedly was involved in secret sex trafficking for years, hidden in a midtown penthouse. WSJ’s Erich Schwartzel traces the saga and explains the allegations of abuse that ultimately led to Rubin’s arrest. Ryan Knutson hosts. Further Listening: - The High Pressure Tactics Gloria Allred Uses On Her Own Clients - Behind the Scenes at Davos, Claims of a Toxic Boss Sign up for WSJ’s free What’s News newsletter. Learn more about your ad choices. Visit megaphone.fm/adchoices

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. 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. 90s. 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. When I talked to folks who worked with him at the time, they would tell me that, you know, frankly, Howie, as they all call him, 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. But something that not many people knew was that Ruben had a dark side. 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.

How would you describe who Howard Rubin is? The answer to that question in 1985 would have been Howard Rubin is a star trader at Solomon 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. 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 is very dark secret. 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.

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. 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 you the story of how Howard Rubin rose to power on Wall Street? So Howard Rubin, who's now in his 70s, he was born and raised outside of Boston. He was 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. After that stint in Vegas,

Ruben 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. Now, 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, 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.

At what point did he start appearing in the Wall Street Journal? 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 wanted to assemble the right team. And so Merrill Lynch brings Rubin in from Solomon Brothers, and it's seen as this, this, like, massive poaching and this massive get on their part. It wasn't long, however, before stories in the Wall Street Journal about Rubin's success turned into stories about his failure.

In April of 1987, Rubin bought up a massive trove of mortgage securities. 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. Hedge it, meaning that if he's wrong, there's no safety net that they're building underneath him.

No safety net. And then mortgages did fall in value. And Rubin's investment became this $250 million loss. Wow. At 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, 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. It was such a big deal that Merrill Lynch had to publicly announce the loss to investors and that Howard Rubin was responsible.

And he sort of became, he went from being rather famous on Wall Street to being infamous for this $250 million trade. Did he face any consequences for this other than getting fired? 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. But even the $250 million loss didn't slow him down. 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 trade. who were talented but a little toxic.

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? So we're not exactly sure, but the cases against him have ever... and stories that date back to 2009. And who are the women he allegedly targeted? 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 Rubens 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? 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. When you read the cases, it sounds like, Jennifer Powers filled many roles in this operation. She was Ruben's good cop.

Sometimes she would be his banker. She would send the women money. I came to think of her as like the C-O-O of this enterprise. Oftentimes finding the women, making first contact with them, and then sort of maintaining the relationship throughout. Those allegations sound sort of like the relationship between Galane Maxwell and Jefferner. Epstein. Yes, and when I would talk to folks, they would make that connection. 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. 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. Powers would tell the women she recruited

that Ruben 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 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. That room in the apartment, the so-called sex dungeon, was soundproofed, according to prosecutors. The room was painted red, and Rubin had it filled with ropes, whips, and sex toys. And the stories that are included in these complaints do show what the women perceived 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. man they see inside the dungeon. Say more about that. What would they see? This might include everything from

punching, slapping, abusing in all kinds of ways. While some of these women knew to expect aggressive sex like BDSM, victims say Ruben took it much further than that. The encounter is often tipped into torture. Ruben did give the women a safe word, but several said he ignored it.

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.

Multiple women accused Ruben of rape. The women were told to sign an NDA, and if they broke it, they would have to pay Rubin $500,000. So there was a safe in the penthouse that held a stack of blank nondisclosure 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 an exchange. 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 entities. NDAs as part of their defense, saying that the language of the NDA bolstered their case, that this was a consensual agreement and that there was no sort of confusion or there shouldn't have been any confusion. And then what would happen after all of this was over? Well, this is, 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 Rubin 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. 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, but According to court records, Rubin himself wasn't there, but a fight broke out between two women. We believe over what exactly had happened and transpired in the dungeon. One woman saying that she had been misled into how intense the evening would get.

The fight breaks out and the police are called. After the police got to the apartment, one of the women texted powers. It 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. After that day, the women started comparing stories. And as the women are talking and the case 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 2016. And that is when it kind of all spills into the open. This is what would ultimately form the basis of two civil cases and later a criminal investigation. What did Ruben and Powers do when they found out that these women were coming together to sue them? 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 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 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. 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. 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 and his wife would be photographed at charity gala's.

And then after these suits were filed, they said, you just never saw Rubin anywhere. And as the details really started to spread, they became these, like, punchlines. I mean, specifically, 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 person who knew Rubin through these social circles, and he said that eventually Pineapple became synonymous with no. 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. 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. What do we know about how his family reacted when these allegations came out? 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. Ruben'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. 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 Rubin in this bail package, ranging from his wife, his daughter, his daughter's partner, his daughter's partner, his grandkids. 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. 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 Nicholas Maduro and Luigi Mangione. If convicted, Rubin could face life in prison. 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 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. 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. tomorrow.