Vice City: How Roosevelt tried-and failed-to clean up NYC

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By Courtney Holbrook

Whether he’s researching the strange methods of 19th-century scientists or on the trail of 17th-century pirates, author, historian and journalist has an eye for the juicy bits in history.

Now, the bestselling author of The Pirate Hunter: The True Story of and three other books has a new tale about and the seedy world of 1890s New York. : Theodore Roosevelt’s Doomed Quest to Clean Up Sin-Loving New York follows Roosevelt in his years as New York’s police commissioner and his struggle to change Lower Manhattan.


What drew you to Roosevelt’s time as police commissioner of New York?

I didn’t start out as a Roosevelt expert; I came to the story through the vice angle. I was researching the 1890s and New York and stumbled upon Roosevelt as police commissioner. I was stunned to discover that it really didn’t go according to the fairy tale version that came out later— you know, he came in as police commissioner and reformed the whole city and stopped crime and cleaned up the police department. It was a much more interesting story than that.

In your mind, did Roosevelt’s time as police commissioner end in failure?

I wouldn’t say outright failure. I would say it was kind of a noble effort. He never backed down. It’s extraordinary—the will and the nerve of the man to continue to keep trying right up until the last moment to rout out all kinds of corruption, to try to clean up the saloons and the brothels and the rest of it. But you know, the city was just overwhelmingly oriented towards vice. And the fact that he succeeded pretty well for around eight or 10 months is just extraordinary.

Q: Roosevelt started out well as police commissioner; he cleaned up the lazy and bribe-happy police. What do you think was the turning point?

A: I think the turning point was the November election where the Republicans in New York lost to the Democrats and blamed it on Roosevelt’s tactics as police commissioner. He succeeded up until that point. He shut down the Sunday saloons—the fact that he did that was just astounding in New York City. It was the most entrenched custom. Saloons couldn’t legally be opened on Sundays, so everyone just went to the side door of the saloon on Sundays, the working man’s one day off a week.

If the Republicans had wound up winning that election in November, Roosevelt could have proved to his own party and to the world that New York City indeed wanted to be reformed and they wanted Roosevelt’s principles. But they lost.

Q: Was Roosevelt’s decision to reform the city a product of ambition or morality?

A: I think the morality motive was really strong. I think he really thought it would be a better life for everybody if Sundays were spent picnicking with the family instead of the husband and father going off to the saloon and getting drunk.

Q: Can you talk about your writing process for this book?

A: It was difficult figuring out how to structure it, because I wanted to create the city of vice before I brought Roosevelt in. So I had to create a narrative line that really moved forward and then introduce Roosevelt. I just had trouble figuring out those riddles a lot of the time.

What I like to do is research. New York in the 1890s had something like 20 very vigorous newspapers. The number is actually higher, but there are about 20 that you can get easily at the New York Public Library. It became addictive, because every newspaper had slightly different versions and slightly different quotes and different wise-guy phrasings. I got addicted to looking at seven versions of every event I was trying to research. It was a way to try to put off writing. I got the project in 2006 and it took about five years. I probably researched for four years, and wrote for one.

Q: What will you be presenting at your talk at the ?

A: I’m excited to give these talks, because it allows me to go and pull 50 photographs from the 1890s. I just love New York City scenes, like the streetcars with the horses pulling them and the men in hats and the women in the corseted dresses to the ground. It’s time travel and they’re just really great images. I also have some really great naughty and slightly risqué images that I just couldn’t resist putting in.


Richard Zacks will speak about Island of Vice at the Tenement Museum, 103 Orchard St. (betw. Delancey & Broome Sts.),, March 20 at 6:30 p.m.



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