Overview of "A Wall Street Legend and His Penthouse Sex Dungeon"
This episode of The Journal (Wall Street Journal & Spotify Studios), hosted by Ryan Knudsen, profiles Howard (Howie) Rubin — once a celebrated Wall Street trader — and the criminal allegations that later engulfed him. The episode traces Rubin’s rise and fall in finance, the discovery of a Midtown Manhattan penthouse “sex dungeon,” the civil suits and criminal charges accusing him of sex trafficking, and how a network of power, money and secrecy allegedly enabled abuse for years.
Key facts & timeline
- Early life: Born outside Boston; began as a chemical engineer, became a skilled card-counter in Las Vegas, then attended Harvard Business School.
- 1980s finance career: Star trader at Salomon Brothers; recruited by Merrill Lynch in 1987 in a high-profile hire.
- April 1987: Rubin amassed mortgage securities that fell in value — a trade that produced a roughly $250 million loss and national headlines. He settled with the SEC (no admission of guilt) and was barred briefly from the industry.
- Late 1987 onward: Hired by Bear Stearns; remained active in finance for years.
- Alleged abuse timeline: Complaints and evidence go back to roughly 2009. Civil suits began in 2017 after a 2016 incident at Rubin’s penthouse sparked women to compare stories.
- Legal outcomes to date: Civil suits resulted in settlements and Rubin being found liable in one case (ordered to pay millions). Rubin was arrested (in September of the prior year referenced in the episode), pleaded not guilty to sex trafficking and related charges; bail requests denied; currently detained in Brooklyn. Jennifer Powers, alleged recruiter/organizer, was arrested, has pleaded not guilty and was released on bail.
Rubin’s Wall Street profile
- Reputation: A risk-taking “star” trader known for big, often profitable bets. Portrayed in the 1980s media as a top talent.
- Notable failure: The 1987 mortgage securities trade — characterized as the largest single-trade loss at the time (~$250M) — led to public disgrace but did not end his career.
- Hiring culture: Firms like Merrill Lynch and Bear Stearns at times poached high-performing traders, even after controversies.
Allegations and the alleged operation
- Location: A penthouse at the Metropolitan Tower (57th Street, Midtown Manhattan) allegedly had a soundproofed, red-painted bedroom outfitted with ropes, whips, and sex toys — described as a “sex dungeon.”
- Recruiting: Women (models, cocktail waitresses, some former Playboy models) were allegedly recruited — often by Jennifer Powers — with promises of pay for sexual encounters, photos, or fetish activities. Payments ranged from about $2,000 to $5,000 per night.
- Coercion and abuse: Plaintiffs allege the encounters frequently crossed into nonconsensual and torturous acts (slaps, punches, gagging, ignored safe words such as “pineapples,” rape allegations). NDAs were presented and signed (sometimes while women were intoxicated); NDAs allegedly carried $500,000 penalties.
- Financial leverage: Prosecutors say Rubin exploited women’s economic vulnerability; Powers allegedly received sustained financial support from Rubin (paying credit card bills, mortgage, private school, etc.), effectively subsidizing the recruitment operation.
How the alleged enterprise unraveled
- Tipping point: A dispute among women present at the penthouse in 2016 led police to be called. Afterward, the women compared experiences and consulted lawyers.
- Civil action: A group of women filed civil suits in 2017; these suits produced public details and helped lead to subsequent civil settlements and later criminal investigation.
- Criminal charges: Authorities eventually filed sex trafficking and related criminal charges; Rubin arrested and detained. Delays in prosecution were attributed to appeals, procedural issues and COVID-related slowdowns.
Defense, family response, and legal posture
- Rubin’s plea: Not guilty to criminal charges.
- Defense arguments: Lawyers argue encounters were consensual, point to NDAs and adult private activity that ended years earlier; assert Rubin’s present life is harmless (grandfather, Connecticut residency). They have repeatedly applied for bail.
- Family support: Despite divorce proceedings, Rubin’s wife and daughter have submitted bail-support letters describing him as a family man and seeking his release — a contrast to accusers’ accounts.
- Court rulings: Multiple bail requests denied due to prosecution’s argument that Rubin could flee using his resources. Powers released on bail; Rubin remains jailed. If convicted, Rubin faces severe penalties, potentially life.
Main takeaways and implications
- Dual identities: The episode spotlights the stark contrast between Rubin’s public Wall Street persona and the alleged private life of abuse — a modern Jekyll-and-Hyde narrative.
- Power, money and exploitation: The case exemplifies how financial resources and influence can be used to recruit, coerce, silence (via NDAs) and sustain alleged trafficking operations.
- Collective action matters: The women’s comparison of experiences and collective civil suits were pivotal in exposing the alleged pattern and moving the matter toward criminal prosecution.
- Legal complexity: NDAs, consent claims, delays, appeals, and the passage of time complicate prosecutions of historical sexual abuse — particularly where powerful defendants are involved.
Notable quotes & details
- “Jekyll and Hyde” — common literary comparison used to describe Rubin’s different public and private personas.
- The 1987 mortgage trade resulted in “a $250 million loss” described as the single greatest loss tied to a single trade at the time.
- Safe word allegedly ignored: “Pineapples” — became a widely circulated anecdote.
- NDAs with $500,000 penalties were kept in a safe in the penthouse, according to complaints.
Where this leaves the listener
- Rubin’s criminal case remains active; the episode provides background, alleged patterns, and courtroom context rather than a final legal resolution.
- The story raises broader questions about accountability, the limits of NDAs in cases of alleged criminal acts, and how social and financial influence can delay exposure and prosecution.
If you want a fuller legal timeline or case documents, the episode references court filings and civil suits beginning in 2017 that provide detailed allegations and settlement outcomes.