All old abodes have their ghosts, and Wall Street has been well lived-in since the Dutch erected a wooden stockade to guard against attack in the 17th century. With hundreds of years during which fortunes have been won, lost, lamented and despaired over, there is no shortage of restless spirits from the past. Let's look at three gory tales let loose from Wall Street's crypt.

Wall Street's Unholy Trio
During the second half of the 19th century, Jay Gould, Jim Fisk and Daniel Drew provided the archetypes for Wall Street greed and corruption. The men came from different backgrounds but shared the goal of making their fortunes on Wall Street. By pooling their capital and talents for ruthlessness, the three became hostile-takeover specialists, attacking everything from tanneries to railroads.

Between the three of them, they committed every imaginable financial atrocity upon the markets and, far from being brotherly, even turned against each other. Their most famous battles were with "Commodore" Cornelius Vanderbilt over the Erie Railroad, one of the few railroads competing against Vanderbilt's growing transport empire. During the struggle for control, Vanderbilt bought up vast numbers of shares, unaware that the trio was watering stock - literally printing additional (and illegal) stock certificates with a press in the basement.

This glut of shares devastated the company's shareholders, but buying up the endless supply proved too costly for even Vanderbilt, and he threw in his hat. While the outcome was still in doubt, Drew held secret talks with Vanderbilt in hopes of striking a private deal that would have been to Fisk's and Gould's misfortune. Alas, in retaliation, Fisk and Gould negatively manipulated the stocks in Drew's fortune and ultimately ruined him. Gould's and Fisk's victory earned them a considerable reputation, as they were the only people to tangle with Vanderbilt and come out on top.

Gould and Fisk did not stop there. With Gould now at the helm, the two gathered a group of speculators and tried to corner the gold market, resulting in the Black Friday of 1869. Duping both the short sellers and the U.S. Treasury, Gould and Fisk pushed up prices rapidly. Discovering the ruse, the government opened its vault and the price of gold plummeted within minutes, ruining everyone but Gould, who had been tipped off and failed to tell his partners.

Fisk, his fortune diminished from the drubbing of Black Friday, was eventually gunned down in a quarrel over a woman (not his wife) in 1872. Jay Gould got away with it all, and his fortune was still intact when he eventually died of natural causes. Gould's defeat of Vanderbilt and the financial havoc he wreaked during his life earned him the title of the "Mephistopheles of Wall Street."

Boesky and Siegel
As if channeling the long-dead spirits of Gould and Fisk, Martin Siegel and Ivan Boesky teamed up to become the center of one of the largest insider trading scandals to rock Wall Street. The 1980s were already a time of black knights, vulture funds and dawn raids, as the leveraged buyout (LBO) revolutionized Wall Street. To take advantage of the LBO madness, arbitrageur Boesky needed an edge. He found it in Siegel, an investment banker in the mergers-and-acquisitions side of Kidder, Peabody & Co., which became defunct in 1994. Boesky wanted tip-offs about upcoming mergers and takeovers. To that end, he sent Siegel a briefcase with $150,000 in $100 bills and the two began a "professional" relationship.

The tips were well worth the money, because Boesky made millions by buying up pre-takeover shares and unloading them after the market learned about the deals. The takeover of Carnation by Nestle (OTC:NSRGY) alone netted Boesky $28 million and, for that reason, alerted the Securities and Exchange Commission (SEC) to his activities. Siegel's firm also came under scrutiny, and Boesky and Siegel parted ways, with Siegel receiving a final pay-off from Boesky of $400,000 dropped at a phone booth. The net was already cast, however, and the SEC reeled in Siegel and Boesky along with other big criminal names, such as Michael Milken.

Siegel became a witness for the government and was let off easy with a two-month sentence and a fine, while Boesky was given three years and fined $100 million for his involvement in the scheme.

Bram Stoker's Broker
Less high profile, but all the more chilling for it, is a tale of a dishonest broker and a wealthy client. L.R. Castelein was a Belgian investor with $12.5 million that he wanted to invest in U.S.Treasury bonds. In 1997, he met with a Corporate Securities Group (CSG) broker named Douglas Reid, who promised Castelein that he would set up an account at Bear Stearns - which later suffered its own financial misfortune in 2008 - that would return 7% interest. The account was set up at CSG, not Bear Stearns, in the first of many abuses that Castelein would suffer.

After receiving the money from Castelein, Reid forged Castelein's signature to route all the account information through Reid's own office and began actively trading in the account. By churning the account for commissions and paying out large management fees to himself and a fellow banker, Reid quickly bled the account dry.

For three months, Castelein tried to obtain clear information about the profits on his money and made several fruitless visits to Reid's offices, during which Castelein was given fabricated account statements. Forcing disclosure, Castelein discovered that his $12.5 million had been churned to a zero balance in the mere three months since opening his account. Castelein immediately began legal proceedings and sued the corporations involved. CSG had been purchased by Wachovia (NYSE:WB). He won $17.8 million in damages, but no doubt lost his faith in brokers.

The Bottom Line
It's impossible to air out all the skeletons in Wall Street's well-stocked closet. Familiar names like Boesky and Siegel still strike a raw nerve with investors, and vaguely remembered figures like Fisk and Gould wrote he book that modern fraudsters still study. It is unlikely that Wall Street will ever be free of people in positions of power getting involved in all manner of devilry. Money is at the root of many terrible crimes, and Wall Street is the junction through which much of the world's wealth passes. As a result, it will continue to attract fresh hordes of ghoulish people committing the same old crimes.

Related Articles
  1. Insurance

    Top 9 Vacation Destinations For Wall Street Geeks

    Indulge your inner geek with one of these financial-themed holiday getaways.
  2. Personal Finance

    The History Of Capitalism: From Feudalism To Wall Street

    Find out how the economic system we now use was created.
  3. Bonds & Fixed Income

    Dragons, Samurai Warriors And Sushi On Wall Street

    From samurai to sushi, there's no denying the East Asian influence on investing terminology.
  4. Options & Futures

    Terrorism's Effects On Wall Street

    Terrorist activity tends to have a negative impact on the markets. Find out how to take cover.
  5. Insurance

    A Nightmare On Wall Street

    These tales of banking terror sent shivers down the spines of even the most steadfast bankers.
  6. Professionals

    10 Must Watch Documentaries For Finance Professionals

    Find out about some of the best documentaries that finance professionals can watch to gain a better understanding of their industry.
  7. Savings

    Is It Safe to Send Money Through Facebook?

    Learn how Facebook employs strong measures to keep your information safe when sending money, but understand the rare threats that still exist.
  8. Investing

    How Shackling Offshore Banks Will Impact You

    FATCA regulations have cast a wide net on offshore banking activities, and many innocent account holders might get caught in its tangle.
  9. Investing Basics

    Toshiba's Accounting Scandal: How It Happened

    Learn how Toshiba's corporate culture and lax internal controls led to an accounting scandal that ended with the resignation of the company's CEO.
  10. Professionals

    Is Your Financial Advisor Looking Out for You?

    Financial advisors sometimes aren't looking out for clients' best interests. Regulators are scrutinizing their practices; investors should too.
  1. What are some high-profile examples of wash trading schemes?

    In 2012, the Royal Bank of Canada (RBC) was accused of a complex wash trading scheme to profit from a Canadian tax provision, ... Read Full Answer >>
  2. What are examples of inherent risk?

    Inherent risk is the risk imposed by complex transactions that require significant estimation in assessing the impact on ... Read Full Answer >>
  3. What is the difference between wash trading and insider trading?

    Wash trading is an illegal trading activity that artificially pumps up trading volume in a stock without the stock ever changing ... Read Full Answer >>
  4. What impact did the Sarbanes-Oxley Act have on corporate governance in the United ...

    After a prolonged period of corporate scandals involving large public companies from 2000 to 2002, the Sarbanes-Oxley Act ... Read Full Answer >>
  5. Who are the most famous people convicted of insider trading?

    In finance, insider trading refers to the buying and selling of security by a person who has access to material non-public ... Read Full Answer >>
  6. What's the difference between insider trading and insider information?

    Insider information is the knowledge of nonpublic material about a publicly traded company that may affect the stock's price. ... Read Full Answer >>

You May Also Like

Hot Definitions
  1. Section 1231 Property

    A tax term relating to depreciable business property that has been held for over a year. Section 1231 property includes buildings, ...
  2. Term Deposit

    A deposit held at a financial institution that has a fixed term, and guarantees return of principal.
  3. Zero-Sum Game

    A situation in which one person’s gain is equivalent to another’s loss, so that the net change in wealth or benefit is zero. ...
  4. Capitalization Rate

    The rate of return on a real estate investment property based on the income that the property is expected to generate.
  5. Gross Profit

    A company's total revenue (equivalent to total sales) minus the cost of goods sold. Gross profit is the profit a company ...
  6. Revenue

    The amount of money that a company actually receives during a specific period, including discounts and deductions for returned ...
Trading Center
You are using adblocking software

Want access to all of Investopedia? Add us to your “whitelist”
so you'll never miss a feature!