Teddy Roosevelt’s Battle With the Deeply Depraved New York of Yore

In 1895, then-reformer Theodore Roosevelt — fearless and righteous and full of zeal — was appointed New York City police commissioner, assigned to clean up the Big Apple at what many said was its dirtiest, most rotten moment in history.

Author Richard Zacks’ new book, “Island of Vice,” details Roosevelt’s quest, which, depending on your perspective, was either glorious and quixotic or the premise for a dark comedy. In the following essay for MetroFocus, Zacks paints a vivid portrait of the seedy urban underbelly that Roosevelt encountered at the end of the 19th century.

In the 1890s, New York City was a bustling chaotic city with no traffic lights and few traffic rules; horse carriages zigzagged any way up and down any street and a small cadre of two dozen tall “Broadway Squad” officers helped pedestrians to cross the major intersections. Four elevated train lines striped the island, spewing coal dust and granting passengers voyeuristic glimpses into second floor windows. Top-hatted swells strutted along Fifth Avenue while immigrants slept in shifts in overcrowded tenements. At night, armies of beggars and streetwalkers accosted anyone and everyone.

The din of foreign languages astounded even foreigners; the majority of the registered voters in New York in 1890 were foreign-born or first-generation Americans. They and their wives and their offspring mangled the English language. The city packed more Irish than Dublin, more Germans than any city but Berlin… And Syrians and Swedes and Italians and Russians, too.

New York was well-known as the nation’s financial capital with Wall Street and bulbous-nosed J.P. Morgan; as the news capital with the dominant circulation New York World, owned by Joseph Pulitzer; as the arts capital with the Metropolitan Opera; and as the theater capital with hundreds of companies performing programs ranging from highbrow Shakespeare to Bowery vaudeville. New York also ranked as the nation’s largest port, with 144 piers, and even the main manufacturing center, with 12,000 factories employing half a million workers on the island of Manhattan.

In 1884, a Comstock agent bought this hand-tinted erotic photograph of a man with a large... moustache from Elena Del Vasto for $1, then a workingman’s wage for an entire day. Photo courtesy of the Municipal Archives.

But beyond all its commerce and prestige, beyond all its Astor high society and its striving immigrants, it was an open secret that New York City was also the vice capital of the United States. There were 40,000 prostitutes working the streets, charging from 50-cents to $10 a session. Three vast red light districts — the Lower East Side, the Washington Square area and the Tenderloin from 23rd to 42nd Street along Broadway — operated discreetly but openly. Peddlers sold pornographic post cards, and dealers trafficked in raunchy Edison wax cylinders of audio smut. (“She’s a ballet dancer; first she dances on one leg; then on the other; between the two she makes a living.”)

Click on the Images to Enter Sinful  Olde New York:

Gamblers with the right attire could play at Canfield’s elegant casino at 26th Street near Madison Square Garden, under the spinning nude weathervane of the Roman Goddess Diana. They could bet on horses in “pool rooms” located over bars. The dreamy and forlorn, including novelist Stephen Crane, could smoke opium in parlors in  Chinatown. And the owners of the city’s 10,000 saloons routinely ignored the 1 a.m. nightly closing time and also refused to close on Sundays, as dictated by New York State Sabbath and Excise laws.

New York City — then composed mainly of Manhattan, with no Brooklyn, Queens or Staten Island — was a pleasure-seekers’ paradise: a decadent good-time, hard-drinking city.

Click to hear WFUV’s George Bodarky interview author Richard Zacks:


And all of it was made possible by the corrupt, look-the-other-way connivance of the police force and of corrupt Tammany Hall politicians. Police captains shook down brothel madams for big monthly payoffs; corner cops took bribes from bootblacks wanting choice locations and from fruit vendors who wanted to display wares on the sidewalk; they took bribes from cigar stores selling “numbers” (illegal lottery tickets); they demanded payments to let “trucks” i.e., big wagons, park on the streets overnight when street parking was still forbidden.

The captains of the New York City police force in the era before the Mafia were the ones who “organized” crime in their precincts and settled turf disputes.

New York City was certainly a wicked place, full of temptations. Tourists and out-of-town businessmen flocked there. That is, until Teddy Roosevelt stepped in.

Before Roosevelt's term as police commissioner, policemen looked the other way as boys hitched rides on street cars. They also took bribes to look the other way as thousands of vice crimes occurred. Photo courtesy of the New York Public Library Mid-Manhattan Picture Collection.

When Theodore Roosevelt was commissioner, he tried to enforce all the laws and all police conduct rules, to the absolute shock of most New Yorkers. Roosevelt also wanted officers to be courteous to citizens, a concept almost unthinkable at the time.

He tried to shut the saloons on Sunday in strict observance of the Sabbath Excise law, which got him hated by the vast population of beer-drinking, six-day-a-week workingmen. He made special efforts to have fair elections; he helped re-introduce the bigger, more fearsome police night stick in September 1895. He and the board pioneered a pistol shooting range.

Some police historians credit Roosevelt’s practice range as leading to the founding of the first police academy. And the big police club — for better or worse — was standard gear for the New York police for decades after Roosevelt. The Bureau of Elections was soon separated from the police department which reduced the police force’s roll in tabulating the votes.

As for his efforts to combat vice or shut the saloons on Sunday, New York remained sin city for a very long time.


MetroFocus is made possible by Sue and Edgar Wachenheim III, the Sylvia A. and Simon B. Poyta Programming Endowment to Fight Anti-Semitism, The Peter G. Peterson and Joan Ganz Cooney Fund, Bernard and Denise Schwartz, Barbara Hope Zuckerberg, The Ambrose Monell Foundation, Janet Prindle Seidler, Jody and John Arnhold, the Cheryl and Philip Milstein Family, Judy and Josh Weston and the Dr. Robert C. and Tina Sohn Foundation.


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