Island of Vice by Richard Zacks

Who is “Ted-dy” Roos-e-velt?

First in war, first in peace.

First to reform the New York Police.

This is how Theodore Roosevelt, then a New York City Police Commissioner, was greeted by a thousand University of Chicago students before giving a speech on George Washington’s birthday. The ironic revelation of this greeting, as noted by Richard Zacks in his new book Island of Vice: Theodore Roosevelt's Doomed Quest to Clean Up Sin-Loving New York, is that at this time Roosevelt was more popular outside New York City than within the city he was cleaning up. Zacks is the author of several books including; The Pirate Coast: Thomas Jefferson, the First Marines, and the Secret Mission of 1805 and The Pirate Hunter.


The premise of his latest book is to tell the story of how Roosevelt fought vice in New York City and lost. His telling of the story reads like a Hollywood thriller that exposes the underbelly of New York City in the late nineteenth century. The judgment on whether Roosevelt lost this fight is open for interpretation and makes for good conversation.

Zacks opens the book with a pull no punches account of the rampant vice in New York City, from a prominently displayed naked statue named Diana, to kids making beer runs to bars for their parents at all hours of the night, to cops taking money for protection or to look the other way. Reverend Charles H. Parkhurst begins to challenge these happenings but is quickly halted by the Tammany Hall Democratic machine. Despite Tammany’s best efforts, information and charges of police corruption begin to surface to the public. With a thus, temporarily, weakened Tammany Hall the Republicans are able to win control of the New York City Mayor’s Office by running reform candidate William L. Strong in 1894.

Enter our hero, Roosevelt fresh from the Civil Service Commission in Washington DC.

Roosevelt literally charges into the fray with the three other Police Commissioners (Avery D. Andrews, Andrew D. Parker and Frederick D. Grant) to tackle the rampant vice and corruption. Zacks is at his best by relaying all of the initiatives that Roosevelt undertakes to combat the undesirable situations, beginning with his overnight tours of the city where he encounters many instances of police officers not performing their duty. Roosevelt then tackles corrupt officers, brothels, and the prevention of voter fraud.

The initiative that receives the most attention in the book is the strict enforcement of the Sunday Excise Law. Roosevelt begins by making sure bars are closed on Sunday which of course begins a series of work-arounds by bar owners to make sure beer keeps flowing through New York City seven days a week. The author has clearly done extensive research into the battle over the Sunday Excise Law and covers all the details with an entertaining style.

While all of these reform measures seem to go well in the beginning, popular opinion within New York City begins to turn against Roosevelt who is relentlessly attacked by politicians, newspapers, and community groups. His unpopularity with the masses lead to his becoming unpopular with Republican leadership who blame his strict enforcement of laws as the cause of lost elections. Meanwhile Roosevelt’s reputation and popularity begin to soar across the country.

Zacks also chronicles the dramatic split of the four Police Commissioners (particularly between Roosevelt and Parker), culminating with several well written courtroom dramas.

Ultimately the writing is on the wall that a new initiative to consolidate New York City with surrounding areas, such as Brooklyn, will result in a new, larger police force with new commissioners. We then see how Grant and Roosevelt begin scrambling to attach themselves to the newly nominated Republican Presidential Candidate for 1896 – William McKinley of Ohio. This scrambling ultimately lands Roosevelt the job he covets in the newly elected McKinley administration and out of New York City.

Zacks then briefly details the rest of Roosevelt’s career and also looks at New York City in the post-Roosevelt era. What we see is not pretty, corruption quickly returns to the police force which begins undoing all that Roosevelt accomplished over the past two years. It is this understanding which leads Zacks to conclude that vice won while Roosevelt lost. I don’t completely agree with this view, while Roosevelt was successful in his crack-down it was ultimately his successors that lost the battle. Meanwhile his stint as Police Commissioner only elevated his name and reputation across the country which aided his further endeavors.

The Island of Vice is a very well researched and ‘Delightful’ account of Roosevelt’s two years as a New York City Police Commissioners and provides many details and stories that I had not previously come across in other Roosevelt biographies. While this book would be very appealing to anyone wanting to learn more about Roosevelt during his pre-presidential days it would also be of interest to those exploring the history of New York City or law enforcement during that era.