Niederhoffer’s approach is eclectic. His funds, a friend says, appeal “to people like him: self-made people who have a maverick streak.” PHILIP BURKE

On a wall opposite Victor Niederhoffer’s desk is a large painting of the Essex, a Nantucket whaling ship that sank in the South Pacific in 1820, after being attacked by a giant sperm whale, and that later served as the inspiration for “Moby-Dick.” The Essex’s captain, George Pollard, Jr., survived, and persuaded his financial backers to give him another ship, but he sailed it for little more than a year before it foundered on a coral reef. Pollard was ruined, and he ended his days as a night watchman. The painting, which Niederhoffer, a sixty-three-year-old hedge-fund manager, acquired after losing all his clients’ money—and a good deal of his own—in the Thai stock market crash of 1997, serves as an admonition against the incaution to which he, a notorious risktaker, is prone, and as a reminder of the precariousness of his success.

Niederhoffer has been a professional investor for nearly three decades, during which he has made and lost several fortunes—typically by relying on methods that other traders consider reckless or unorthodox or both. In the nineteen-seventies, he wrote one of the first software programs to identify profitable trades. In the early eighties, he went into business with George Soros, then arguably the world’s most successful investor. A few years later, when prominent money managers were based almost exclusively in Manhattan, Niederhoffer moved his home and his trading room to Connecticut, to a twenty-thousand-square-foot neo-Tudor mansion crammed with books, manuscripts, silver jewelry, art work, and a collection of seashells. The walls of his vast living room, which has a ceiling about thirty feet high, are covered with more than two dozen paintings, many depicting industrial landscapes or Western shoot-’em-ups, and the floor is occupied by, among other objects, a large painted pony, a black-spotted wooden hound carrying three quail on its back, a seated pig, and two miniature black bears. Niederhoffer’s home is also frequently occupied by various of his children. (He has six daughters and an infant son, from two marriages and an extramarital relationship.)

After the 1997 Asian financial crisis, Niederhoffer was forced out of business for several years. Then, in his late fifties, he made a dramatic recovery. He founded three new hedge funds and launched a Web site, DailySpeculations.com, where he posts his idiosyncratic insights into the stock market—“What can we learn from shelled species about the markets?” he wrote in May—as well as opinions about sports, politics, and culture (“ ‘The Fantasticks,’ currently running as a revival on Broadway, is the perfect musical”). He has mentored dozens of successful traders, many of whom regard him as a guru. “Before I joined Victor, I used to trade for a Wall Street firm,” James Lackey, a self-employed Florida investor who placed trades for Niederhoffer from 2002 to 2006, told me. “But I quickly realized that I didn’t know very much. What he taught me was how to approach the market as a whole, and how to analyze it scientifically. He was just amazing at seeing what was happening and showing us how to make money.”

Niederhoffer, a former national squash champion who is considered one of the most talented Americans to have played the game, relishes the acclaim, but he knows that in his field circumstances can change quickly. By the end of August, his funds were in trouble, and on Wall Street rumors circulated that he would soon be out of business again. Niederhoffer had been worried all summer, but he tried to project a wry, self-deprecating humor. “If an event like 1997 occurred again, my dependents would be up the creek, and I would be a night watchman somewhere, just like Captain Pollard,” he said to me when I visited him at his home one morning in June. “In America, they give you a second chance but not a third.”

Tall and trim (he still looks like an athlete), with closely cropped white hair, olive skin, and a long, expressive face, Niederhoffer speaks softly, with a strong Brooklyn accent. He was wearing a yellow shirt, pink trousers, and white socks, but no shoes—he maintains a “no shoes” rule in the office, to reduce noise—and was sitting behind his desk, which is dominated by two Bloomberg screens, in a large room over the garage which he shares with his partner, Steve Wisdom, and several members of his company, Manchester Trading. (The trading operation fits into two rooms; the other one is over the kitchen.) In one hand, he was holding a telephone receiver, and his light-blue eyes were fixed on the computer screens. “The market’s way down today,” he said by way of greeting. Turning back to the telephone and addressing his broker at the Chicago Mercantile Exchange, he asked, “Can you repeat those quotes, please?” After a few seconds, he said, “I’ll sell two hundred red March at five hundred and ten. I’ll sell two hundred blue March at eleven ten.”

The Chicago Merc is a futures market, where people trade contracts that give them the right to purchase a particular commodity at a specified date in the future. Originally, the items traded on the exchange were physical commodities, such as eggs, butter, and pigs, and its main customers were farmers and food companies. In recent decades, futures trading has become more abstract; professional speculators now use the exchange to place bets on the prices of financial securities, such as stocks, bonds, and currencies—a development that Niederhoffer, a former math prodigy who has a Ph.D. in economics, has exploited. He likes to be at his desk well before the Chicago market opens, especially on days when he has big positions riding overnight. He is mainly a short-term operator—he bets on how prices will move in the subsequent few minutes, hours, or days—and most of his knowledge of current events comes from Bloomberg. (He doesn’t read newspapers or watch television.) When he arrives at his office, he turns on his computer and reads about developments in the Asian and European markets, which often foreshadow the day’s action in the United States.

At the end of the previous week, the yield on ten-year Treasury bonds had surged to almost five per cent, prompting Niederhoffer to turn uncharacteristically bearish on stocks. Once the bond yield reached five per cent, he had reasoned, some investors would move their money from stocks to bonds, which would depress stock prices. Accordingly, he had sold short more than a billion dollars’ worth of stock futures. (Selling short, a common tactic among speculators, involves selling something you don’t own with the intention of buying it back later, at a cheaper price. If the price of the security falls while you are “short,” you make a profit; if the price rises, you lose money.)

Even by Niederhoffer’s generous standards, going short a billion dollars of stock futures was a large bet, but it worked out well. Not long after the markets reopened on Monday, the bond yield climbed to five per cent, and stocks and stock futures tumbled. On Wednesday, the morning of my visit, shortly after the opening bell sounded on Wall Street, Niederhoffer repurchased the futures he had sold, making more than five million dollars.

He didn’t look pleased, though. During the morning, stocks had continued to fall, and he knew that if he had waited he could have made an even bigger profit. He says that in twenty-eight years as a professional investor he hasn’t had a single truly satisfactory trading day. At eleven o’clock, the Dow Jones Industrial Average had slipped about a hundred points and the S. & P. 500 Index was down about thirteen points. Niederhoffer stared morosely at his Bloomberg screens. “The score doesn’t look good,” he muttered. The screens were tracking the movements of various stock-market indices in Europe and Latin America, but I noticed that they weren’t displaying any American prices. Niederhoffer used to invest heavily overseas, but since his 1997 misadventure in Thai stocks he has confined his trading to the United States. He explained that when the U.S. market was falling he preferred to track the DAX, a German stock index that generally moves in synch with the American market. “You can see how much you are losing, but it doesn’t hurt as much as watching the S. & P.,” he said.