Suppose you decided five years ago to give away $160 million of your net worth to charity. Would you be richer or poorer today?

Probably a lot poorer. Not so in the case of 78-year-old Robert Wilson, who was Wall Street’s premier short seller (a pro who bets stock prices will fall) between the 1960s and mid-1980s.

Starting in 2000, Mr. Wilson, a world traveler, lover of the arts, and former chairman of the New York City Opera, embarked on a program to give away $400 million to charity, principally in the areas of conservation, the environment, and education, including the New York Public Library. Currently sporting a net worth of about $600 million, he has around $260 million of charitable giving to go to fulfill his worthy goal.

Despite the huge sum he’s given away to charity, Mr. Wilson’s net worth, surprisingly, hasn’t declined very much. The reason: When he retired in 1986, he turned over his fortune to about a dozen money managers, most of whom, he tells me, have done better than the averages, especially over the last four years. “The money is coming in faster than it’s going out,” he said.

One of his managers figures Mr. Wilson – aptly described by one prominent Wall Streeter as a highly opinionated intellectual investor, often wrong, but never in doubt – would have probably gone broke during the Internet bubble had he been managing his own assets because of his propensity not only to short what he regarded as overpriced stocks, but to doggedly stick with his positions through thick and thin.

One example was a short sale he made in the late 1970s in Resorts International, an Atlantic City gaming operator, whose shares went through the roof after he placed his bet. At the time, Mr. Wilson was taking a sabbatical, a six-month vacation around the world. A partner at Neuberger & Berman, which is where he made the short bet, recalls he tried numerous times to reach Mr. Wilson while he was away, but was abruptly told: “Bob doesn’t want to be bothered while he’s on vacation. Wait till he’s back.” Whether the information would have swayed the short seller will never be known. Mr. Wilson eventually covered the short sale, in the process losing about $20 million.

In any event, if he were still managing his own money today, he would probably be more net-short than usual because, as he put it, he’s bearish. A lot of the good things have already happened, he said, pointing in particular to low interest rates, soaring earnings, and great productivity gains. He also argues that the huge amount of government and consumer spending, which stimulated the economy in recent years, simply can’t continue at the same pace.

“George Bush and Alan Greenspan engineered the great recovery, but that’s the past, not the future,” Mr. Wilson said.

He also feels the market is threatened by higher interest rates to deal with rising commodity prices, including food, and a falling dollar; renewed inflationary pressures, and a trade deficit which he characterizes as “sort of a Damocles sword hanging over the country and the economy.”

As for Iraq, a matter of considerable concern to many market players, a number of pros are taking a somewhat more positive view of the situation, given the recent elections there. Not so Mr. Wilson. His view: “People love to vote. I expected a high turnout. Iraq is a mini-Vietnam. We’ll leave the country in the midst of a civil war with our tail between our legs and we certainly won’t have won.”

Mr. Wilson figures stock prices will be at least 10% lower by year’s end; he also believes the market averages at the beginning of the first decade of 2000 will be roughly the same at the end of the decade. His reasoning: interest rates will go up and price/earnings multiples will go down to reflect the higher rates.

So how do you make money? That’s the wrong question, he replied. “Forget about what makes money,” he said. “The strategy now should be to keep it and to do it at an inflation-adjusted rate.” In this context, he rates TIPS (treasury inflation-protected securities) as today’s single best investment. (TIPS are a special type of marketable Treasury security whose interest and redemption are tied to the rate of inflation.)

Detroit-born Mr. Wilson, the son of a fire and casualty insurance agent, began his investment career in 1949 when he was 23 as a trainee at First Boston. In 1969, he started his own hedge fund, Robert Wilson Associates, and made the bulk of his fortune in the decade of the 1970s, a flat market period during which he increased his net worth about 30% a year. His secret to success: “I was always net long [meaning he owned more stocks than he was short] no matter how bearish I was since I never wanted to get up in the morning hoping things would be worse.”