When young Theodore Roosevelt was appointed police commissioner of New York City, he had the astounding gall to try to shut down the brothels, gambling joints, and after-hours saloons. This is the story of how TR took on Manhattan vice... and vice won. In the 1890s, New York City was America's financial, manufacturing, and entertainment capital, and also its preferred destination for sin, teeming with forty thousand prostitutes, glittery casinos, and all-night dives. Police captains took hefty bribes to see nothing while reformers writhed in frustration. In Island of Vice, Richard Zacks paints a vivid portrait of the lewd underbelly of 1890s New York, and of Theodore Roosevelt, the puritanical, cocksure police commissioner resolved to clean it up. Writing with great wit and zest, Zacks explores how young Roosevelt goes head to head with Tammany Hall, takes midnight rambles with muckraker Jacob Riis, and tries to convince two million New Yorkers to enjoy wholesome family fun. When Roosevelt's crackdown succeeds too well, even his supporters turn on him, and TR discovers that New York loves its sin more than its salvation. With cameos by Stephen Crane, Mark Twain, and a horde of very angry cops, Island of Vice is an unforgettable snapshot of turn-of-the-century New York in all its seedy glory and a brilliant miniature of one of America's most colorful presidents.