Richard Zacks mines through firsthand historical accounts to present a period of New York City's past so salacious that it makes the once-seedy Times Square look like its current sanitized incarnation in Island of Vice.

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Historical figures abound in Zacks' (The Pirate Coast, 2005, etc.), rigorous work, none more compelling than police commissioner Theodore Roosevelt, who had just enough hubris—and chutzpah—to think he could corral the carnality.   

Do you think Roosevelt was taken aback by the vice he encountered?

That’s what’s funny—even though he was born in New York, he really didn’t know a lot of the sections of New York City. He grew up so privileged that you can argue that he knew the Dakotas better than he knew Delancey Street. He really was surprised by a lot of it, and he also was pretty squeamish about vice.

He had trouble talking about prostitution, he used a lot of circumlocution to talk about the problem, ad he was also coming off the alcoholic death of his brother Elliott a year before, and here he was thrown into a situation where he had to crack down on saloons, so it just added extra drama to the whole quest.

This was personal for him.

Yes, I think to a large extent it was, so I gave a chapter over in the book to the story of Elliott, Eleanor Roosevelt’s father who died the summer before of alcoholism, and so then Roosevelt comes in, and he wants to take corruption out of the police force and one of the biggest parts of the corruption is that they look the other way and let the saloons stay open on Sundays.

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So, Roosevelt decides in his wisdom that he’s going to shut all the saloons in New York on Sundays. They’ve been quietly operating through the side doors for decades and policemen made a few dollars, and New Yorkers got to drink and Roosevelt had the nerve to try to shut it all down—and it all blew up in his face enormously. But it was just an exciting quest and he was pretty fearless about it.

Do you see any similarities between Commissioner Roosevelt and New York’s current mayor, Michael Bloomberg—he’s a billionaire who’s taken on some unpopular fights.

I recently write an op-ed in the New York Times when Bloomberg announced he would crack down on alcohol sales, a memo got leaked, apparently it was one of the many plans but it was really a pretty hardcore crackdown. Now he’s backing off, but yes, there are some parallels.

The biggest difference is that Roosevelt was so fiercely in your face about everything. He just wagged his finger and he kept saying over and over “I’m only enforcing the law. I’m only doing what I’m supposed to do,” and it was mind-boggling because no one had ever tried to do this. The city had three major brothel districts, there were over 30,000 prostitutes, there were 10,000 saloons, most of them operating illegally, after hours. There were open gambling joints, there were casinos, and Roosevelt was just going to shut it all down. He was going to stop police corruption and wipe out vice. And you’re either in awe, or you can’t believe the man could actually try that. It’s one of those things the reader will decide is either Don Quixote or a great reformer.

You wrote that the job did as much for Roosevelt as he did for the job. What do you mean by that?

I think he developed an incredible reputation as a law and order performer. I don’t think the rest of the country realized quite how unpopular he was in New York City. They were just thrilled by the efforts he made. He also gave hundreds of speeches, so he went from being a civil service commissioner who gave a handful of speeches to reformers to a guy who was going out night after night, and sometimes it was pretty raucous, people would jeer at him and he learned how to handle that.

He learned to handle intense newspaper criticism, and he also learned not to back down. He kept his fearlessness throughout the whole thing. He was treated like this insane reformer who is so over the top that you can’t imagine that he’d ever surface again. Which is kind of wonderful, because we all know that within four years he’d be president of the United States.  

How did you research the book?

I always go to primary sources whenever I can, I don’t like reading the secondary sources with all the filters. It just cracks me up that each generation of historians are usually so predictable in their prejudices, so I always try to go back to the original.

For me, I was really lucky, I found a 4,000-page trial transcript of a police captain who was up for not shutting down 50 brothels in the area which is now NYU [New York University]. Newspaper accounts or even governmental reports, they filter, they use euphemisms and cut things out. But at the trial, they just hired a stenographer to write it all down.

This one artist had a studio over looking 13th Street, and there was a hotel there where all the street walkers went to, and they asked him, “What did you see?” And he said, “Fornication. Three windows at a time.” There’s also a street walker who is older who is angry that some of the younger girls have some cops as boyfriends, and they get to walk on Fifth Avenue, and she’s forced to walk on the side streets. So I had 4,000 pages of that.

What surprised you the most in your research?

I have to say—and I’m a guy who wrote a book called History Laid Bare—the extent of vice in New York City. I have the addresses of over 300 brothels, 30,000 prostitutes! For a guy who has written about vice in ancient Rome, I was staggered. Basically, in this city, if you wanted to have a good time that way, you could go to a casino, you could go to a brothel—you could go from the high end to the low end. And New York had a veneer of respectability, so it was like two cities in one.

Where did all the vice go?

Roosevelt tried his best, but ironically what happened was that the Raines Law comes in, and 1,000 saloons converted to 24-hour hotels that could serve drinks, and they needed 10 bedrooms. And the bedrooms allowed street walkers, but also women who were starting to get in the work place, starting to change their views on morality.

The joke is that the reason prostitution was no longer as big, was because of the amateur competition—because of women who weren’t prostitutes who started to have premarital sex. In the 1890s, the bar scene was almost exclusively male. So if you had a women there at 10 or 11 o’clock at night, she was there probably as a prostitute, or else she was a drunk. There was no pickup scene whatsoever. If a man wanted to have sex that night, he needed to pay for it basically. It was just such a different mentality, and gradually morals changed and there wasn’t this huge need for prostitution. By the 1930s, the brothel districts of the city had pretty much disappeared.