During the real estate boom, few were enjoying the high life more than the real estate developers Toll Brothers (excepting Angelo Mozilo, of course). Now that the market has turned, Andrew Rice revisited the once high-flying firm and its top exec, Bob Toll, to find out what’s next. We asked him a few questions about how he came to the story, and what Bob Toll is really like.

By now, millions of articles have been written about the U.S. housing meltdown. Why did you decide to profile this particular C.E.O. and company?
I think there are two main reasons why Toll Brothers intrigued me—well, not only me, but the industry in general. One is the defined brand identity. There are plenty of builders that are larger than Toll Brothers in terms of sales volume and revenues, but if you say, “I live in a Centex home,” it doesn’t mean much to most people. That’s not meant as an insult to Centex, I could have picked any diversified national homebuilder. But Toll Brothers has done just such an exceptional job at creating a defined niche for itself—and as I say in my story, that could be a blessing through this downturn, or it could be a curse. Which leads to the other reason why Toll Brothers makes for an interesting story: I think there’s a sense among people within the industry that they were extremely smart during the long real estate boom, and there’s a lot of expectation as people watch how they navigate the bust.

You’ve interviewed many real estate moguls over the years. Did Bob Toll seem like a typical housing billionaire?
Bob Toll keeps journalists on their toes. I think that, unlike a lot of real estate people, he seems to enjoy talking to the press, and being the voice of the industry, so to speak. He is smart, funny and well-read. There’s a candid quality to him that is quite endearing to a reporter—candor, of course, is by far our favorite quality—and sometimes he says exceptionally frank things. He has an ability common to many very intelligent public figures: He projects the appearance of openness while very rarely saying anything that’s contrary to his interest.

Was it difficult to get him to open up about his mistakes?
It wasn’t difficult to get Toll to talk about his mistakes. In fact, he seems to glory in them a little. I think there’s a certain aspect of gallows humor to it—everyone in his industry is in the same boat, in most cases to a worse degree than Toll is, so he had little to lose by admitting the obvious, that his company screwed some things up.

On the other hand, Toll tried very hard to make me see those mistakes from his perspective. What seems self-evident in retrospect—that the crash was coming—didn’t look that way to Toll in 2004 and 2005. He was relying on mathematical models that had served him well in the past, and he points out that if he’d quit when his gut instinct told him the traditional boom-bust cycle was about to take hold, he would have missed several years of record profits. For a time there, it seemed like all the old rules of real estate no longer applied. Of course, that was wrong—reality is back with a vengeance now—but Toll says he had to trust his own judgment. After all, he was so right for so long.

You spent some time with him at the Democratic convention in Denver. Why did he go to the convention and what did he do there?
Toll is a lifelong Democrat—his uncle, Herman Toll, was a Democratic congressman who represented Philadelphia—and he is a major donor to the party. But he was at the convention in a supporting role to his wife, Jane, who was a delegate for Barack Obama. I saw Toll a few times over the course of the convention, and he was clearly having a real ball when he was down on the floor, chanting “Eddie! Eddie!” when Pennsylvania Governor Ed Rendell came to the lectern to speak, and kibbitzing with friends from business, politics, and the press. At one point, Andrea Mitchell of NBC News came up to say hi to him—I’m guessing that maybe she knows him because she’s married to Alan Greenspan—and when she asked Toll how he was doing, he grinned and pantomimed putting a pistol to his head and pulling the trigger. I guess when the economy is collapsing around you, it helps to have a sense of humor. Not to mention a billion dollars socked away for retirement.

Was there any particular moment or scene in your reporting that shed any light on where Toll Brothers is headed in the future?
When I interviewed Toll, he happened to ask me where I lived, and when I told him Brooklyn, he started peppering me with questions about a project that was not far from my neighborhood, on the Gowanus Canal. At the top of the market, Toll acquired the rights to develop a large-scale “waterfront” project on formerly industrial land there. To people I know in New York, this sounds mighty improbable: The stretch of the canal nearest to me is lined by a scrap metal yard, a fuel oil depot, and several cement factories; some years back, the local press was captivated by the improbable story of a wayward whale, nicknamed Sludgy, who wandered into the canal. He later died.

The canal is supposed to be cleaner than it used to be, but whenever I walk by it still tends to be covered with a shiny petroleum slick. One of the keys to Toll’s success has always been his eye for good ground, as he calls it, and one of the criticisms of his top-of-the-market strategy is that he seems to have gone far afield in searching for that land—places like West Virginia or the Poconos. I think that one measure of Toll Brothers’ future success will be whether he’s able to make a high-concept project like the Gowanus one work. It seems unlikely to me, but then, that’s how people make fortunes—by taking risks on projects that amateurs like me scoff at. I should also say that his office in New York, headed by David von Spreckelsen, is highly respected by professionals here in the city and seems to have made some other smart moves along the way, so you’d perhaps be unwise to bet against Toll.