Theodore Roosevelt’s fruitless quest to clean up New York’s ‘Island of Vice’ in the 1890s

Roosevelt as police commissioner (Courtesy New York Public Library)
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Brian Sholis

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As last week’s newspaper stories about alleged Manhattan madams Anna Gristina and Jaynie Mae Baker remind us, mankind’s primal urges will inevitably find fulfillment in a city as large as New York, no matter the laws on the books.

Among its other virtues, Richard Zacks’ new book Island of Vice: Theodore Roosevelt’s Doomed Quest to Clean Up Sin-Loving New York emphasizes how easy such gratification was in the 1890s, just before the modern, five-borough New York City was created. (Zacks appears tonight at the Tenement Museum to discuss the book.) Prostitutes were at one point working out of numbers 6, 8, 10, 12, 14, and 16 Delancey Street. The sale of alcohol was outlawed on Sundays, yet nearly every bar or saloon had side and rear entrances, and curtains in the front windows to block prying eyes. Casinos catered to both low- and high-end customers, from factory workers to members of the Vanderbilt family. And the police profited from nearly all of this illicit business, as patrolmen and captains alike pocketed cash to look the other way. Big Bill Devery, when appointed captain of the notorious Eleventh Precinct on today’s Lower East Side, charged madams a $500 “initiation fee” and $50 in monthly protection money.

In May of 1895, Theodore Roosevelt, after a six-year sojourn as a civil-service reformer in Washington, D.C., returned to his hometown to take up a post as police commissioner. William L. Strong, elected mayor the previous autumn on a “fusion” ticket comprising Republicans and disaffected Democrats tired of Tammany Hall graft, had offered him the job. In his new role, Roosevelt would oversee—alongside three colleagues who agreed to elect him president of their group—police department operations.

The cops’ venality offered him plenty of opportunity for reform, and Roosevelt wasted little time. Like Roosevelt’s biographers, Zacks portrays his central character as impatient, hectoring, and dynamic, speed-walking between appointments and buttonholing those who could give him what he wanted. Zacks charts how the new commissioner managed in less than a month to force the resignations of Police Chief Thomas Byrnes and roughneck inspector Alexander “Clubber” Williams, popular emblems of the old order. With his patrician upbringing and perfect diction, many saw Roosevelt’s reforms as an attempt “to end the era of tough underducated men dominating the force.”

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Part of the explanation for Roosevelt’s efforts, Zacks seems to suggest, was his disgust for the political patronage systems so entrenched in Gilded Age America. Roosevelt’s political career in Washington had been floundering, in part, because fighting for civil-service reform—the institution of rules about hiring government workers on merit, rather than political preference—was such an uphill battle. Vice concerned him, but he believed he needed a more competent force in order to fight it, and finding reasons to dismiss Tammany recruits was the quickest way to reach that goal.

Some of Zacks’s most entertaining passages chronicle Roosevelt’s after-midnight prowls along city streets, searching, often alongside a reporter for one of the city’s many dailies, for cops sleeping or drinking on the job. (In the below image he is caricatured in the New York World.He would nearly pick a fight with those he found, then gleefully inform them just who they were arguing with and demand they appear at police headquarters early the next morning. Such episodes are retold with zest, and the book is unfailingly entertaining. Drawing upon courtroom and committee room minutes, as well as newspaper reports and his subjects’ voluminous correspondence, Zacks has crafted a popular narrative history of a pretty high order.

It enters a crowded field. There are not only many lengthy biographies of T.R., like the one by Edmund Morris, whose third and final volume, Colonel Roosevelt, arrived in late 2010, but also a steady flow of narrower studies, such as Hot Time in the Old Town (2010), about Roosevelt and the summer 1896 heat wave, or Honor in the Dust (2012), on Roosevelt’s place in American imperial expansion. Island of Vice dovetails with perennially popular studies of Gilded Age excess and crime, such as Karen Abbott’s Sin in the Second City (2007). It’s easy to see how such a book was published, sitting as it does at a busy intersection on the map of publishers’ desires: the Roosevelts, New York City, sex, and crime.

What broader developments Zacks hopes to explain, or what lessons he wishes readers to draw, are somewhat harder to discern. Readers familiar with the period might crave more analysis of, say, the sometimes contradictory goals of municipal, state, and national politics, which are hinted at in the actions of Roosevelt, Senator Thomas C. Platt, New York’s Republican Party kingmaker, and Ohio’s William McKinley, who would be elected president in 1896. Such a story could be emphasized through the political education we witness Roosevelt receiving by mail from his longtime friend Henry Cabot Lodge, a Republican senator from Massachusetts. Other stories, such as how the city’s tremendous population growth, and how the dislocations of urban (often immigrant) life fueled the vice industry, remain submerged beneath the frothy surface of bawdy anecdotes.

While the book has little overarching argument, the narrative it does put forth has a definite shape, and Roosevelt’s early successes met increasing resistance beginning in late 1895. Despite his popularity with moralizing reformers who lived upstate or elsewhere in the country, Roosevelt’s opponents went on the offensive. These included members of the defeated Tammany machine, business owners (such as brewers) missing profits they had become accustomed to, and a community of working-class German immigrants who wanted to celebrate in traditional ways on their only day off work. Roosevelt’s domineering personality also began to engender conflict at 300 Mulberry Street, with fellow commissioner Andrew D. Parker proving himself a formidably canny opponent.

As momentum slowed, those who had been knocked off balance by Roosevelt’s early attacks regained their footing.

“Over and over, New Yorkers chafed at the purity crusade,” Zacks writes. “It was as though the spirit of the city—some inarticulate force of hundreds of thousands of European immigrants mixed with locals, all of it long marinated in Dutch tolerance—refused.” Roosevelt, increasingly frustrated, turned his eyes to national politics, and, with Cabot’s help, was appointed Assistant Secretary of the U.S. Navy. He was headed back to Washington.

New York reverted quickly to its previous—some might argue timeless—ways. Devery, once captain of the Eleventh Ward, was made police chief in 1898 by a new, Tammany-dominated Police Board. He set up shop on a Chelsea street corner, gladhanding past midnight with “Tammany politicians, underworld pals such as Frank Farrell, bagman Glennon, various police captains, ordinary citizens. He carried two fat rolls of cash in rubber bands.” His presence on 28th Street and Eighth Avenue demonstrated—depending upon one’s vantage point—that power flowed downward from his hands or that corruption once again rose all the way to the top.

Richard Zacks speaks about 'Island of Vice' on Tuesday, March 20, at 6:30 p.m. at the Tenement Museum. The event is free, but an RSVP is required. For more information, click here.