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A once high-flying Wall Street executive who admitted to drugging and raping multiple women in his swanky Manhattan apartment was forced back to court in cuffs and a prison jumpsuit this week in another humiliating fall from grace.

Edward Gene Smith, 50, was hauled into Manhattan Criminal Court on Wednesday to face separate gun-related charges - a week after he was slapped with a 30-year sentence for attacking his victims and keeping sickening notes documenting his predatory rampage.

Smith, a married former Citibank managing director currently serving out his hefty sentence in a federal prison, was given another two years after pleading guilty to attempted criminal possession of a weapon.

Sporting scruffy gray facial hair, Smith was silent as he was escorted to and from the courtroom with his hands and feet chained for the latest hearing.

The Harvard-educated bigwig's new prison look was a far cry from his suited up days at the height of his depraved crime spree.

Smith had earlier admitted to attacking the women at his luxury apartment opposite Central Park and would often keep chilling spreadsheets and planning notes on just how many drugs to give them.

He would then record some of the assaults to share with online groups who took pleasure in drugging their partners, according court documents.

‘The defendant is a serial rapist who used his money, access and affluence to drug and rape young women,' prosecutors said during his federal sentencing hearing late last month.

Edward Gene Smith, 50, was hauled into Manhattan Criminal Court on Wednesday to face separate gun-related charges after he was sentenced to 30 years in a federal prison

Smith, a married former Citibank managing director currently serving out his hefty sentence in a federal prison, was given another two years after pleading guilty to attempted criminal possession of a weapon

Smith admitted to drugging and raping multiple women after luring them to his Manhattan apartment. He is pictured above in one of the photos allegedly taken from his dating profile

'The women were young and many were from foreign countries or faraway states and had previous sexual trauma. They were not momentary lapses in judgment, these were well-thought-out crimes.

‘Why the defendant has done this is utterly unexplained.'

Smith's reign of terror came crashing down in late 2024 when he was arrested on a six-count indictment for drugging and assaulting various women.

He ended up pleading guilty to only four counts: drugging a victim with intent to rape her, enticing another victim to travel to New York for sex, receiving child pornography and obstruction of justice.

In one incident, he admitted to luring a victim to his luxury apartment at Central Park South in April 2023, where he laced her drink with the sedative Klonopin and then raped her while she was unconscious.

He recorded the attack and then shared the footage with an online group dedicated to sharing clips of incapacitated or unconscious women in sexually exploitative positions.

The moneyman also copped to repeatedly drugging and sexually assaulting a college student who he had convinced to relocate to New York City.

Once she arrived, Smith spent months controlling her finances and social life, as well as threatening her to ensure she complied with his demands, court filings show.

Sporting scruffy gray facial hair, Smith was silent as he was escorted to and from the courtroom with his hands and feet chained for the latest hearing

The Harvard-educated bigwig's new prison look was a far cry from his suited up days at the height of his depraved crime spree

In the federal case, Smith admitted to attacking the women at his luxury apartment opposite Central Park and would often keep chilling spreadsheets and planning notes on just how many drugs to give them

But prosecutors say his crimes were even more widespread - and that he allegedly confessed to preying on other victims too.

The 50-year-old admitted to drugging and raping multiple women in his upscale Manhattan apartment

Smith allegedly paid one victim $2,500 to spend two nights with him back in 2015. Years later, he drew up a chilling spreadsheet titled 'girl retrospective' that laid out a fresh plot to allegedly drug her all over again, according to court papers.

'Alcohol and drink kit: DRUGS!! 4 capsules full of dissolved k [Klonopin] 2mg,' his notes allegedly read, followed by a reminder to 'ask about other porn work she's done.'

In the fall of 2021, he allegedly targeted a 17-year-old victim on Seeking.com, telling her 'I want you to stay a virgin until you come up' as he waited for her to turn 18.

When she eventually arrived in New York, he spiked her Long Island Iced Tea and then sexually assaulted her, prosecutors alleged.

Smith once flew an 18-year-old girl to New York where he proceeded to spike her drink and then sexually assault her. The victim, who snapped the above photo of Smith, told the Daily Mail that she wasn't allowed to move inside his apartment while he was working

Smith married his wife, Heather, in 2012. The couple have a shared home in South Carolina

Unbeknownst to the teenager, Smith had allegedly posted her photos and contact information on a website advertising prostitution services.

Then, in a chilling escalation, the predatory banker allegedly drove her to a Manhattan apartment where she was forced to have sex with a man in his 50s, before Smith pocketed the cash himself, the court documents state.

Smith is also said to have allegedly encouraged her to recruit her own underage sister and friends for sexual encounters with him.

In addition, FBI investigators found Smith had collected more than 9,000 unique files of child sexual abuse material dating back to 2012 that had been organized across multiple devices.

Prosecutors said the Ivy League honcho, who was most recently a Citigroup managing director, hid ‘behind the façade of a well-educated bank executive’ to prey on and lure in his young victims.

Smith, who studied particle physics, built a two-decade career in high finance, working his way through Oliver Wyman, State Street, Santander and BlackRock.

He landed at Citigroup in 2021 as a managing director, earning a $400,000 base salary with a $1 million target bonus.

Investigators uncovered a note stored on his phone listing out packing items for a trip in 2023 with one of his victims, including 'klon'- a reference to the sedative Klonopin

In a note from 2024 that he stored on his phone, Smith made plans for an upcoming trip to Miami with a woman that specifically mentioned 'klon (fri night)' as well as various sex toys and a 'rope for tying legs'

The Harvard educated bigwig, who was most recently a Citigroup managing director, hid 'behind the façade of a well-educated bank executive' to prey on and lure in his young victims to his apartment opposite Central Park (pictured above), according to prosecutors

A Citi spokesman said Smith was fired as soon as the bank learned of the initial probe in 2024.

'We moved to terminate Mr Smith immediately upon learning about law enforcement’s initial investigation, well before the allegations of this depraved behavior came to light,' the spokesperson said.

'We cooperated with law enforcement as they sought justice for the victims of these heinous crimes.'

In his private life, Smith and his wife, Heather, married in 2012.

In pre-sentencing memos, his attorneys had begged for leniency on the basis that his wife, who has several children from a prior relationship, was planning to file for divorce once the court proceedings were over.

The couple had been spending large amounts of time apart ever since Heather relocated from New York in 2018.

The government has moved to seize and force the sale of the couple's shared home in South Carolina to help pay restitution to his victims.