Now he’s teamed up with historian Katherine Howe for another book and another empire: “Astor: The Rise and Fall of an American Fortune.” John Jacob Astor, son of a German butcher, came to this country in 1784 and ruthlessly amassed his astounding wealth by selling North American beaver pelts — a fur so prized the animal was almost extinct in Europe — and then acquiring large parcels of land in Manhattan. He exploited Indigenous fur traders by introducing alcohol to their tribes and became New York’s biggest slumlord in the 19th century, making him America’s first multimillionaire. His descendants built magnificent mansions and ruled New York for the next 100 years: Caroline Astor — the “Mrs. Astor” — was the undisputed queen of the Gilded Age; the famed Waldorf-Astoria hotel was created by two Astor cousins. When John Jacob Astor IV died on the Titanic in 1912, his oldest son, 20-year-old Vincent, inherited $69 million — about $2 billion now.

Review: Anderson Cooper’s ‘Vanderbilt’

The Astors and Vanderbilts competed for power and prestige over decades; the Vanderbilt fortune was so massive that the Astors were forced to accept the nouveau riche interlopers. Cooper met the last “Mrs. Astor”— another grand dame of New York society — as a young man, but she failed to recognize or acknowledge him when he was working as a waiter at a chic New York restaurant. By then, the Astor fortune was almost gone. Cooper sat down with The Washington Post to discuss money, power, history and the myths of the American Dream. (The interview has been edited for clarity and length.)

Q: Why did you want to write a book about the Astors?

A: I am fascinated by these families. I see it as somebody who grew up looking at the Vanderbilt family from a distance through my mom’s eyes without feeling very much involvement with it. I’m very interested in the pathology of how the fortune is made, the psychology of the person who was so invested in amassing money that they created this fortune, whether it’s Commodore Vanderbilt and certainly John Jacob Astor. And the ripple effect of that mythology over the generations: From afar, they’re called great fortunes and great families, and yet just about every biography that’s ever been written about any Astor male refers to them as morose.

Q: You use the term “pathology.” Why that word?

A: I remember when “Good Will Hunting” came out. I loved that movie, and I’m a big fan of Ben Affleck and Matt Damon. When that movie came out, there were all these articles written about the “two regular guys” who made this movie. I remember thinking at the time, “Regular guys don’t make movies. Regular guys do regular things and have regular lives.” For Commodore Vanderbilt at age 11 to leave school and start working on his dad’s boat and then, by 16, get his mom to give him money so he can buy his own boat and then run his dad out of business and then do all the things that it took for him to amass this empire: There’s a pathology. He sent his wife to the mental asylum. He sent his son who may or may not have been gay to the same asylum. At the end of his life, when he is being fed by a nurse, he’s still obsessing about clawing the rent out of some poor old lady. And that’s a pathology to me.

Q: Do you think that these great dynasties are doomed to a kind of unhappiness, a kind of misery?

A: I don’t think it’s just these great fortunes. Most of the people who have achieved unusual levels of financial success or renown or fame, I don’t think it comes from a good place. I don’t think the things that make people, early on, outliers — focusing on something that other people around them are not focusing on — I don’t think that comes from necessarily a happy place.

Q: Let’s start with the first John Jacob Astor. He was not a good guy. He starts out by ripping off the Indigenous people, then there’s an incredibly successful run as a slumlord. Everybody wants to believe that the American Dream is about good guys doing good and becoming successful. That is not this story.

A: The founding of the Astor fortune was brutal. The plying of alcohol to Indigenous populations wasn’t just an occasional thing; it was part and parcel of the business. The U.S. government actually tried to stop the sale of alcohol, and John Jacob Astor did everything possible to circumvent that. He wasn’t just ruthless with Indigenous populations; he was with the people who worked for him. And the lease structure that John Jacob Astor used and his son continued to great effect: build, cram as many immigrants in as possible, divide up rooms, subdivide rooms, multiple families living in one room, no ventilation, and never fix up the building because it’s going to revert back to the Astors in the end of the lease. So why fix it up? Vincent Astor, 100 years later, stunned people by trying to get out of this slum business.

I think the view that many of the family seemed to have, which justified their actions, was that John Jacob Astor came here with nothing and worked hard and made a fortune. All these other immigrants could do it if they wanted to, but they’re just not willing to work as hard, which is obviously a very limited way to see things.

Q: Let’s talk about income inequality. You make comparisons to the historical Gilded Age and our current Gilded Age — the same fascination with the rich, the same resentments.

A: What I find so fascinating about just being alive in history is we all think we are the first to experience things: “Oh, my God, there’s never been an Elon Musk before or a Jeff Bezos.” [Bezos owns The Washington Post.] Obviously, they’re doing extraordinary things and they’ve created extraordinary companies and all of that. But I know there has been an Elon Musk before and there has been a Jeff Bezos before. It was Cornelius Vanderbilt and it was John Jacob Astor and a whole bunch of other people.

It’s very interesting how we look at these people now: We read about them, we see their yachts, we imagine what their lives are like. I see it differently. I view it through the lens of these past families, and what will the ripple effects be in their lives and their families’ lives? I’m fascinated by the cycles of history — we’ve all been here before, and there has been a version of you here before and there’s been a version of me.

Q: We live in the heightened present of now, the immediate with all its immediate demands. But history can be very instructive, and we can see pattern in all these cycles.

A: To me, it’s comforting to know that we are on a road that has been well-traveled. I have said this about grief, this idea that we are not alone in that we are terrified about the future. Well, everybody was terrified about the future back in John Jacob Astor’s day, and with good reason.

Q: You write about Caroline Astor, who appears as a character in the HBO show “The Gilded Age,” and created “the 400” list — the people she believed were refined and wealthy enough to be part of New York society. She was self-appointed royalty who held tremendous power for decades.

A: It was news to me when I wrote the Vanderbilt book. I had not realized that the people like Caroline Astor and Ward McAllister and the people doing these quadrilles viewed the building of these houses, the creation of society, as a sort of a national American enterprise — doing something for the country to establish America on par with the old countries of Europe. With Ward McAllister, it was just borrowing everything from France — French chef, French food, French paintings, French decor. I actually bought a book of William Vanderbilt’s house, the art collection in his house. I paid like $40 for it online; no one else really wanted it. And they were the ugliest paintings you can possibly imagine. I mean, they are these treacly, awful paintings.

Q: One of the conclusions in the book is that money was the ultimate power, more so than taste, more so than education. It always seems to come down to the money.

A: Money was obviously the price of entry. There was a time when it was these old Dutch families trying to keep hold of New York and set up the barriers to entry. That certainly broke with the Vanderbilts; there were other people who tried to do it and were shunned. But the other revelation, which I had not realized, was the advent of hotels and these public spaces that suddenly allowed the democratization of entry into society. I mean, who thinks about society like New York society now? That just seems dead to me. I’m sure there are society parties, but that idea seems so antiquated and archaic. Now it is all about money and technology.

Q: Issues of class are always going to exist in some form — where you live, where you went to school — but with enough money and enough drive, you can overcome a lot of those things.

A: Absolutely. By the way, a lot of Caroline Astor’s pearls were fake. And her house was probably really dusty and these paintings weren’t actually all that valuable. So, again, when you scratch away …

Q: There’s a lot of theater?

A: I know that firsthand.

Q: In 1912, Vincent Astor inherits his father’s fortune after poor Jack goes down on the Titanic: $69 million at that time, $2 billion today.

A: One of the things that’s stunning about the Astors is just the sheer volume of fresh money that was coming in every year from the rents on these slums. There are a lot of families whose money was made a long time ago; the Vanderbilts stopped making money, they stopped the enterprises and became so top-heavy that it just imploded.

Q: From a business perspective, you could argue that Vincent made a terrible mistake by selling off some of the most valuable real estate in the world.

A: He clearly was not interested in doing what every generation of male Astor had done previously. Look, there are a lot of great books that have been written about various aspects of the Astor family. And we rely on a lot of other books and have footnoted that. What I like about this book is that it’s a broad view from John Jacob Astor to Brooke Astor. And also this idea of the name Astor: What it means and how it came to evolve including the Astor Hotel bar scene. [The hotel — especially in the 1940s — held one of New York’s best known but discreet gay bars.] I tried to track down the actual Astor Bar. There’s a great guy in New York who knows where everything is, and he couldn’t find it.

Q: What is your takeaway from this book?

A: It’s very easy to think of this as a story about a wealthy family and their business. And there’s a lot of that in this. But my takeaway is just sort of the human cost of all of this. As unrelatable as the life the Astors led is, there are all these very human moments and human frailties and how that plays out under the weight of and with the benefit of all this money.

The Rise and Fall of an American Fortune

By Anderson Cooper and Katherine Howe