Vanessa Kirsch: I think the amount of money is not necessarily the primary decision for our billionaire. He should really be thinking about the strategic influence he can have. Because if you are strategic about it, you can have an incredibly powerful impact with less money. Philanthropy can help invent and develop new programs and projects that work. And then it can help to scale those programs, so that they can be demonstration models that can really change an entrenched system.

Tough: Joel, you run the country’s biggest school system. What if this money was simply added to New York City’s regular education budget for next year? Would you be able to make a difference with it?

Klein: Well, I agree with Vanessa that philanthropists should think strategically, and what you’re suggesting would be about as nonstrategic an investment as you could make. Which is not to say that I wouldn’t like an additional billion dollars next year. But I think our billionaire should think about this entirely differently. There are two things that I would do with this money. One, I would try to set up a national institute for educational policy that does serious research. This is an industry in which there are so many myths, and that’s because there are such large gaps in our knowledge right now. And second, I would make bets on a few selected individuals. Look, we have lots of wonderful examples in America of educational success. The work Steve is doing with Green Dot is a terrific example. But what we don’t have is an entire urban school district  one that’s predominantly made up of minority kids, with lots of English-language learners and lots of poverty  that really works, that works in a way that people say, “O.K., I want to replicate that district.” To get there, you’re going to need a combination of circumstance and individuals. I would look for the most promising individuals and make heavy investments in them. Let’s say you choose Michelle Rhee, the new schools chancellor in D.C. That school system has long been one of the worst-performing in the country, and Michelle wants to really overhaul it. I think our philanthropist could make an eight-year bet on her. It’s the same kind of thing I would have wanted to have happen to us when we started six years ago in New York. To start, I’d give her a couple of million to do some planning. Then I’d ask her to sit down and show me what strategic investments she thinks a philanthropist could make in D.C. that the system itself, for whatever reason, is not going to make. And I would try to make three or four of these strategic bets around the country, on individuals who I thought had the talent, the longevity and the political support to make significant change feasible.

Tough: And are those individuals all superintendents of school systems?

Klein: Yes, superintendents with firm support from the mayor. What you need to create  and what, despite our progress, we haven’t achieved yet in New York  is a school district that people from other cities can come to and say: “This works. All we’ve got to do is replicate this.”

Tough: Steve, Eli Broad, who is one of the biggest philanthropists in the education world, recently decided that he wanted to make an impact on the Los Angeles school system. But rather than doing what Joel is suggesting and making a bet on the superintendent, he made that bet on you and some other charter-school managers. Why?

Image Steve Barr Credit... Henry Leutwyler

Steve Barr: Because I’m a disruptive force. And he’s betting on that force gaining enough momentum that it will ultimately change the system, not just in L.A. but elsewhere, too, in a way that really realigns the education debate. The problem right now in education reform is that there is a tribal mentality. We have nonunion charters spitting out studies saying how good they are versus the unions doing the opposite. If you can find the common ground between those two groups, then you can start to move past that gridlock. In the fall, Green Dot is going to open a new charter school in the South Bronx, and it has the support not only of the mayor and the chancellor but also of the president of the biggest teachers’ union local in the country. That’s what change looks like, and that’s the kind of innovation that I would advise somebody to invest in. I think that’s why people invest in Green Dot. I like that we get good numbers and our test scores and graduation rates are fantastic, but people really invest in us because we’re a disruptive force. Our philanthropist should go out and find 100 people who are where I was a decade ago or where Mike Feinberg of the KIPP network of charter schools was a decade ago and invest in them.