Robert Wilson doesn’t do small philanthropy. Whether it’s $22 million to the Nature Conservancy in 2005 or $22.5 million to the New York Roman Catholic Archdiocese in 2007, the retired hedge fund manager has no compunction about giving away gigantic sums. “My aim is to give away 70 percent of my net worth before I die,” he says. All told, his foundations gave away more money than those of any other Wall Street professional, mostly to environmental causes. Considered one of the greatest short-sellers of all time, Wilson sat down with Condé Nast Portfolio’s Duff McDonald to share his thoughts on how, why, and to whom he gives.

What’s your main focus in terms of giving?
My primary interest has been conservation—the idea that but for my money, this building or piece of land or that animal would be gone. To that end, I have been a substantial donor to the World Monuments Fund, which preserves old buildings around the world. I have also given to the Nature Conservancy, which acquires land around the world, and the Wildlife Conservation Society, which is trying to save animals. I’ve given to the Environmental Defense Fund too, though that’s more of an advocacy organization. It doesn’t collect and conserve properties; it’s just trying to save the world so these properties that I am spending money acquiring will be around.

Your donations to the Nature Conservancy ($22 million) and the Wildlife Conservation Society ($13.6 million) in the past year are huge by any standard. Why so big?
Because my aim is to give away 70 percent of my net worth before I die. That’s my strategic plan. We all know there’s no strategic plan that actually works, but you’ve got to have one anyway. By that I mean I don’t know when I will die. Most of my rich friends will probably end up fobbing off their wealth on a foundation that will be run by people who are not nearly as smart as they are and who won’t do what they want them to do. About 10 years ago, I decided that I would like to give away a lot of my money aggressively while I was still alive and not rely on others to do it after I died.

But you did set up a foundation. Why not just write checks to the organizations you support?
The main reason for setting up a foundation is that there are certain tax advantages to giving to a foundation instead of directly to a charity. These are tax wrinkles. The foundation, as such, is a product of the Internal Revenue Code. I also have a trust. The trust is to avoid probate when I die. It can be an expensive thing to die, especially if you live in New York State. All the rich people I know now have trusts rather than regular estates if they live in New York.

Why not just leave the money to your heirs?
Honestly, if I could take it with me, I probably wouldn’t give a dime to anybody. I don’t have any children, but I’m not sure that would be a controlling factor, in any case. I think I would agree with the general feeling among the rich today, which is that it’s acceptable to give enough to their children to make them modestly rich but not so much that they’re filthy rich.

As for giving itself, it seems to me than many of my peers fob that problem off on their surviving spouse or children. They do that because giving money away is much more boring than making it. A lot of rich Wall Streeters really can’t be bothered with thinking about giving it away when there are so many opportunities to make it. But I’m 80 years old, and I haven’t been active in the market for 20 years. I don’t have that distraction of making money anymore. I have other people who are making money for me, but I myself am not making it. So I can concentrate on this.

There are exceptions. George Soros is a renowned exception, someone who has seriously given money away—big money—while he has been making money. Julian Robertson is too, although on a smaller scale. He hasn’t given as flamboyantly as George, because he doesn’t have as much money, although he is a rich man. So a few Wall Streeters take a serious interest in giving sizable bucks away.

How could wealthy Wall Street donors do a better job in their philanthropy?
What a lot of rich people do is dump it on their colleges. They give Harvard another desperately needed $100 million for its endowment. They do it because it’s easy, and it’s uncontroversial. I don’t think a lot of intellectual energy goes into giving by most Wall Street moneymakers. Warren Buffett is the perfect example of that. He never gave any of it away, and then he shoveled half of it into Bill Gates’ lap to let Gates worry about it. He is typical in that respect—but only in that respect.

What do you make of the concept of venture philanthropy—that is, of holding gift recipients to the same standards as, say, a venture-financed company?
I don’t buy into any of that. I try to develop confidence in the organizations I give money to in advance. I’m on the board of many of them, so it’s easy in those cases. Otherwise, I can make my opinion based on public reports. I don’t pretend to understand them in depth. Other people—and especially foundations—require a lot of paperwork from the organizations they donate money to. You can learn more about what a charity is doing by talking to a few people it works with than by going in and wasting the time of management.

So what else are you focused on other than conservation?
Education. But I don’t give any money to colleges. I think the whole college and university system is bloated beyond recognition and is a great drain on the resources of this country at this point. I give to the New York Public Library. That’s an organization used by people who want to learn and who aren’t going there to get a degree or something like that. They are not there to get credentials.

I have also started to give money aggressively for scholarships to Roman Catholic schools. And I’m not even Roman Catholic—I’m an atheist. But I think Roman Catholic schools give a better education to their students than public schools do. The whole Roman Catholic structure around the country has been shrinking—at one time they educated 5 million kids, and now it’s down to 2.5 million. That’s appalling. I am, in a small way, trying to reverse that in the city of New York.

Why not give to even more pressing problems, such as poverty or AIDS, which is killing millions of people each year?
The most pressing issues are the most pressing because they have not been solvable. Hundreds of billions in foreign aid has been put into Africa without making much of a difference. I would rather put my money where it can have some meaningful impact. I don’t like to throw money at programs that really haven’t worked. The great George Soros is said to have spent $5 billion to $6 billion in charity. The work he did before the Iron Curtain fell is famous and was extraordinarily productive, but I don’t know what he’s done with much of that money since then.

Well, then, what about poverty in your own backyard, such as the work the Robin Hood Foundation is doing to fight poverty in New York City?
It’s easy for rich white people to throw money at disadvantaged black people—whether it’s here or in Africa—and feel good about it. I call that solving the white man’s burden. Let me be straight: I do not disapprove, in any way, of aiding black people in need. What I am critical of is unfocused and lavish spending on blacks as blacks. Robin Hood is a private welfare program, and I have no interest in that. More to the point, there isn’t nearly as much poverty in New York as a lot of the figures indicate. So that sort of unfocused spending does not interest me.

But Robin Hood is raising so much money—$71 million at its last gala—that you can’t possibly criticize its fundraising acumen.
Not at all. Although I hate those kinds of dinners and don’t go to them, if other people like to go to them, God bless them. If people can have a little fun in this mundane world of charity, God bless them.

Is Wall Street giving back enough?
I find the term giving back an offensive one. In the process of making their money, Wall Street professionals have been profoundly productive. You surely have read about collateralized debt obligations and structured investment vehicles and other forms of securitized debt, and how people don’t know what they’re worth, and how Wall Street has done something terribly wrong in packaging and selling them this way. But these guys have diffused the risk in the entire economy. Instead of banks closing down, as they would have 50 years ago, you now have risks spread all around the world. People who make money in this country are being more productive in making it than in giving it away. I find it inconceivable that Bill Gates can create the benefits in giving away his fortune that he has created with Windows and the PC-based information economy.

Can we take it that you’re a Republican, then?
I am a Republican, although I am ashamed to admit it at this point.

Okay, let’s rephrase that other question: Should Wall Streeters be giving more than they do?
It depends how old they are. Until their middle fifties, they should spend their time making money. Once they reach their mid-fifties, however, many highly productive entrepreneurs have really shot their wad. It was true in the Gilded Age. I think Carnegie and Mellon both sort of retired at 40. People who are bright enough to make bright fortunes usually have bright ideas when they’re young. Up until they’re about 50, then, they should be making money.

There is all this talk about philanthropy that ignores the effort needed to make the money in order to give it away. That said, I don’t think most people in their fifties, sixties, and seventies are giving away nearly as much as they should. I have confronted some of my rich friends with this, and they admit it but don’t do anything about it. There is a paralysis. They want to do something as creative in giving it away as they did in making it. But that’s highly unlikely, and deep down they resent that. So what happens is that they die, there’s a foundation, their heirs take a generous cut for themselves, and then they give the rest of it away to organizations that the person who made the money wouldn’t have dreamed of giving it to while they were alive.