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)

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.

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)

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)

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)

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)

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.

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)

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

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.