Insider Trading

Phone taps, FBI surveillance, confidential informants — it's the stuff of major mafia investigations and Law & Order reruns. But they're also the tactics used by federal authorities against a slew of dark-suited desk jockeys accused in Wall Street's largest insider-trading scandal in decades. Authorities say billionaire hedge-fund manager Raj Rajaratnam, founder of the Galleon Group, and 19 others illegally used secret information about public companies to inform investments that yielded some $60 million in profits over the past several years. The defendants, who also include traders, lawyers and executives at firms such as IBM and McKinsey & Co., now face hefty fines and years behind bars. (Read "Arrests Open a Window on Hedge-Fund Culture.")

It requires only a kindergartner's sense of justice to understand why insider trading is a Wall Street no-no: it's unfair. Simply put, insider trading means buying or selling stocks, bonds or other securities based on significant information that's not available to the general public. Besides creating an uneven playing field that disadvantages regular investors, insider trading by corporate officials also violates their responsibility to operate in the best interests of shareholders.

Insider trading hasn't always been a crime. On the contrary, it was once considered logical and efficient to let any competitive advantage inform decision-making in the free market — a position many economic libertarians continue to embrace today. What some consider to be America's first insider-trading scandal took place shortly after the nation's birth; a former Assistant Treasury Secretary named William Duer capitalized on his government connections to make bets on the country's debt. His investments eventually soured, however, and Duer's bankruptcy brought down much of New York's economy in 1792; he died a few years later in debtors' prison. (The charter members of the Buttonwood Group, the predecessor of the New York Stock Exchange, first assembled to formulate a response to that market crash.) Nineteenth century railroad magnate Jay Gould didn't try to hide his flagrant insider trading; profits from buying and selling stock in his own companies helped make him one of the wealthiest men in U.S. history.

The first real crackdown against the practice came in 1909, when the U.S. Supreme Court ruled that that a director of the Philippine Sugar Estates Development Company committed fraud when he bought stock in his company without sharing information with the seller that soon boosted its value. But it wasn't until after the 1929 stock-market crash that Congress passed laws to limit such trading (although it didn't move to ban it outright) and created the Securities and Exchange Commission to enhance market oversight. As the stock market expanded in the 1960s, the SEC grew more aggressive in fighting insider trading, relying on a general prohibition against securities fraud. In 1987, the Supreme Court ruled that a former Wall Street Journal reporter, R. Foster Winans, and two associates were guilty of mail and wire fraud for trading on names mentioned in upcoming editions of the newspaper's "Heard on the Street" columns. Winans was sentenced to 18 months in prison, although the court split on whether his actions also constituted illegal insider trading. (Read "What's Still Wrong with Wall Street.")

The 1980s were a monument to Wall Street excess, witnessing some of the most notorious insider-trading prosecutions in history. Corporate raider Ivan Boesky — said to be an inspiration for the fictional Gordon ("Greed ... is good") Gekko, villain of the Oliver Stone film Wall Street — was sentenced to 3½ years in prison and fined $100 million in 1986 for insider trading. Financier Michael Milken, the "junk-bond king" who famously earned $550 million in 1987, avoided prosecution on similar charges by pleading guilty to other criminal counts. But the largest insider-trading conviction came two decades later, in 2007, when former Qwest Communications head Joseph Nacchio was convicted of selling $52 million in company stock while knowing the company was headed for trouble. He was sentenced to six years in prison, though an appeals court later ordered his sentence reduced.

These days, you don't have to work on Wall Street to get entangled in an insider-trading scandal — just ask Martha Stewart. The homemaking guru spent five months in prison in 2004 after a series of events triggered by her sale of $228,000 in shares of biomedical firm ImClone Systems, the day before its value plunged 15%. Thanks to a 1997 Supreme Court ruling, even those who lack a connection to a company cannot trade on inside information if they know it is meant to remain confidential. (ImClone was run by Stewart's friend, Sam Waksal.) Ultimately, Stewart was not convicted of insider trading, but of lying to authorities and obstructing justice during the investigation. (Read "How Washington's Bailout Will Boost Wall Street Bonuses.")

Meanwhile, a mastermind of one of the most elaborate insider-trading schemes in recent history remains on the lam. David Pajcin, a former Goldman Sachs analyst, pleaded guilty in 2006 of running a $6.7 million scam that authorities first detected when a retired underwear seamstress in Croatia earned $2 million in profit from a suspicious, two-day investment in Reebok. The 63-year-old, who did not own a computer, was Pajcin's aunt; he traded stocks in her name and in the name of an exotic dancer he was dating to escape scrutiny. In one ploy to glean inside information, Pajcin and an accomplice, former Goldman colleague Eugene Plotkin, hired workers in the Wisconsin printing plant where BusinessWeek was published to filch copies of the magazine straight from the press to discover which companies would be mentioned. Plotkin pleaded guilty and was sentenced to nearly five years in prison. Pajcin served two years before being released, and promptly disappeared — possibly leaving the country. Once he's tracked down, he faces more jail time for violating his probation.

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