“Island of Vice”: Teddy Roosevelt vs. booze and sex in old New York

A new history of TR's stint as the Big Apple's police commissioner illustrates the folly of moral crusades

Topics: Biography, Books, Editor's Picks, History, What to Read,

"Island of Vice": Teddy Roosevelt vs. booze and sex in old New York

“Sing, heavenly muse, the sad dejection of our poor policemen,” read the Homeric opener to a story on the front page of the New York World in 1895. “We have a real Police Commissioner. His name is Theodore Roosevelt. His teeth are big and white; his eyes are small and piercing … his heart is full of reform.” Roosevelt, a few years ahead of his entrance into national politics, had his work cut out for him. New York was, as author Richard Zacks puts it in “Island of Vice: Theodore Roosevelt’s Doomed Quest to Clean Up Sin-Loving New York,” the “vice capital of the United States,” with 8,000 saloons and over 30,000 prostitutes.

“Island of Vice” is Zacks’ account of Roosevelt’s tenure on New York’s police commission during the mid-1890s. As such, it faces a dilemma. The hero of the story is, obviously, TR, that quintessential American, with his boundless energy and can-do spirit, his faith in traditional values and the moral use of violence, his omnivorous mind, his machismo and his naivete. The antagonist is sin-loving New York, Roosevelt’s hometown but above all the decadent and narcissistic big city that salt-of-the-earth Americans love to hate. Yet the book’s main attraction isn’t the glimpse it offers of a larval president or the chance to revel in rural/suburban rectitude. Anyone who settles in with “Island of Vice” will be reading it for the vice.

Few subjects are more amusing than tales of mischief and malfeasance executed by colorful characters with the antique flamboyance of an earlier era. Zacks, who knows this, extravagantly butters his book with figures like the brawling tavern-keeper Mike Callahan, who demonstrated his commitment to 24/7 service by tossing the keys to his establishment’s front door into the East River. (He would not need them again for 25 years.) It’s delightful to learn that the current site of the NYU campus was once a neighborhood known as Frenchtown, notorious for importing European filles de joie willing to engage in oral sex — a service that, by all reports, few of their American colleagues offered. Or that a “tight house” on Bayard Street featured women who wore formfitting bodystockings and danced with soldiers. (A private show without the tights was referred to as a “dance of nature.”)

Roosevelt, a Republican, came into office on a wave of political discontent with the once-supreme Democratic Party machine known as Tammany Hall. Police corruption scandals and a very energetic Presbyterian minister named Charles H. Parkhurst had rubbed the city’s nose in its own cesspit. Parkhurst formed a society of moral crusaders, including a team of detectives who took the reverend on a tour of New York’s fleshpots, everything from opium dens to dirt-floored “stale beer” joints (serving dregs collected from other bars) to a whorehouse where the reverend and an oversensitive congregant watched naked women play a game of leapfrog. Then they moved on to Frenchtown, where they witnessed some girl-on-girl action that Parkhurst declared “the most brutal, most horrible exhibition that I ever saw in my life.”

Although Parkhurst’s nocturnal research raised an eyebrow or two, like all such reformers he needed proof of New Yorkers’ easy access to vice in order to refute police claims that they had such crimes under control. In a way, they did. The police chose to let assorted rascals flourish unchecked not because they took a worldly view toward “victimless” crimes, but because they were extracting payoffs to look the other way. From shoeshine boys who “owned” certain street corners to shopkeepers whose sidewalk displays violated city ordinances, New York presented a (literal) wealth of shakedown opportunities for the boys in blue. Catching thieves and murderers was more of a sideline.

This nasty state of affairs was the result of the pervasive cronyism and political patronage of Tammany Hall. Roosevelt, appointed with three other commissioners by a rich and idiosyncratically independent mayor, had the job of cleaning it up. Initially popular, he went on legendary “midnight rambles” with his friend, the journalist Jacob Riis, looking for patrol officers who slept or drank on the job, hassled innocent civilians or fraternized with streetwalkers. When it came to slapping down bullying or negligent officers, the public stood behind TR.

That’s not to say Roosevelt didn’t meet with considerable resistance. The figure Zacks offers up as his antithesis is William “Big Bill” Devery. Devery was a thoroughly crooked yet strangely endearing precinct captain who, as the New York Times noted in his obituary, “was always on trial for something or other and always being acquitted” — the latter due entirely to his political connections. Devery, a product of Hell’s Kitchen, epitomized the kind of cop Roosevelt wanted to see ejected from the force. The force and its various allies fought back every step of the way.

Roosevelt also feuded bitterly, and self-destructively, with his fellow commissioners and other city officials. He angered the leaders of his own party’s machine by alienating sizable portions of New York’s population. This he achieved by deciding to strictly enforce “excise” laws preventing bars from serving alcohol on Sundays. Previously, the law had seemed to exist solely for the financial benefit of the police, and in truth very few citizens besides Puritans like Parkhurst really wanted to see a Sabbath-day prohibition put into effect. But Roosevelt mulishly insisted that “while the law is on the statute book it must be strictly enforced.” He refused to back down, even when, among others, the entire German community (who viewed Sunday outings at the biergarten as a wholesome family activity) rose up against him and his party and helped vote Tammany Hall back into power.

Some of the most entertaining parts of “Island of Vice” describe the ingenuity of saloonkeepers in circumventing the excise laws. Because a “hotel” that also served food was entitled to sell booze on Sundays, many bars converted their second floors to “rooms” — cubicles where drinks could be ordered — or required that each beer be accompanied by a sandwich. It wasn’t necessary that the sandwich actually be eaten and often the same dessicated specimen would be passed from customer to customer. A joke circulated about a dive where drinking had to be temporarily suspended (with much cursing) because “somebody ate the sandwich.” An unanticipated side effect of these bogus “hotels” was that females of the type Roosevelt described as “semi-respectable” ended up drinking in dangerous proximity to private “rooms” where they might easily lose what remained of their virtue.

The most lustrous resource for anyone writing about Gilded Age New York are the archives of the city’s multiple newspapers. Saucy, scathing and flagrantly partisan, they are irresistibly quotable, and Zacks does not resist. The Pulitzer-owned New York World was the nation’s largest-circulation paper and an implacable Roosevelt critic. Insisting that “RUM RULED THE CITY” despite the police commissioner’s best efforts, it told of a Sunday when “the Tenderloin [neighborhood] glistened with its brilliant evil; the eastside wallowed in beer.” Complaining of the “ponderous” ankles of an actress whose performance in “Ten Minutes in the Latin Quarter; or, a Study in the Nude” had provoked a scandal, another paper demanded that “she ought not to be allowed to reappear upon the stage unless submerged in bloomers and shoulder-of-mutton sleeves.” Bemoaning the “dry” Sundays of the Roosevelt regimen, yet another broadsheet wrote “New York is rapidly becoming a jay and hayseed village such as had the supreme felicity of giving birth to Dr. Parkhurst.”

Roosevelt himself seldom drank and was devoted to his wife and children, but one of his flaws was an impatient inability to see how anyone else might experience life differently. He stubbornly squandered his political capital on a battle that seems entirely pointless and quixotic to contemporary eyes. His skirmishes with other officials over issues like budgetary allotments and promotion protocol are bureaucratic matters that Zacks tries, and often fails, to make interesting. The reader returns with pleasure to the Leigh Sisters and their famous “umbrella dance” and longs to hear more of the pool hall and betting parlor on Bleecker St. that catered exclusively to women.

There’s grist for a few good movies between the covers of “Island of Vice,” but none that would feature a Hollywood ending. Because it’s hard to side with Roosevelt in this fight, the book offers more ambiguous pleasures. Between risque anecdotes and vintage dirty jokes, it provides a vigorous depiction of large-scale municipal politics in all its sticky, sweaty glory, and an ever-useful reminder that there are limits to even the most dynamic leader’s ability to dictate personal morality. Sin-loving New Yorkers wouldn’t have it any other way.

Laura Miller

Laura Miller is a senior writer for Salon. She is the author of "The Magician's Book: A Skeptic's Adventures in Narnia" and has a Web site, magiciansbook.com.

More Related Stories

Featured Slide Shows

  • Share on Twitter
  • Share on Facebook
  • 1 of 11
  • Close
  • Fullscreen
  • Thumbnails

    Ten spectacular graphic novels from 2014

    Beautiful Darkness by Fabien Vehlmann & Kerascoët
    Kerascoët's lovely, delicate pen-and-watercolor art -- all intricate botanicals, big eyes and flowing hair -- gives this fairy story a deceptively pretty finish. You find out quickly, however, that these are the heartless and heedless fairies of folk legend, not the sentimental sprites beloved by the Victorians and Disney fans. A host of tiny hominid creatures must learn to survive in the forest after fleeing their former home -- a little girl who lies dead in the woods. The main character, Aurora, tries to organize the group into a community, but most of her cohort is too capricious, lazy and selfish to participate for long. There's no real moral to this story, which is refreshing in itself, beyond the perpetual lessons that life is hard and you have to be careful whom you trust. Never has ugly truth been given a prettier face.

    Ten spectacular graphic novels from 2014

    Climate Changed: A Personal Journey Through the Science by Philippe Squarzoni
    Squarzoni is a French cartoonist who makes nonfiction graphic novels about contemporary issues and politics. While finishing up a book about France under Jacques Chirac, he realized that when it came to environmental policy, he didn't know what he was talking about. "Climate Changed" is the result of his efforts to understand what has been happening to the planet, a striking combination of memoir and data that ruminates on a notoriously elusive, difficult and even imponderable subject. Panels of talking heads dispensing information (or Squarzoni discussing the issues with his partner) are juxtaposed with detailed and meticulous yet lyrical scenes from the author's childhood, the countryside where he takes a holiday and a visit to New York. He uses his own unreachable past as a way to grasp the imminent transformation of the Earth. The result is both enlightening and unexpectedly moving.

    Ten spectacular graphic novels from 2014

    Here by Richard McGuire
    A six-page version of this innovative work by a regular contributor to the New Yorker first appeared in RAW magazine 25 years ago. Each two-page spread depicts a single place, sometimes occupied by a corner of a room, over the course of 4 billion years. The oldest image is a blur of pink and purple gases; others depict hazmat-suited explorers from 300 years in the future. Inset images show the changing decor and inhabitants of the house throughout its existence: family photos, quarrels, kids in Halloween costumes, a woman reading a book, a cat walking across the floor. The cumulative effect is serene and ravishing, an intimation of the immensity of time and the wonder embodied in the humblest things.

    Ten spectacular graphic novels from 2014

    Kill My Mother by Jules Feiffer
    The legendary Pulitzer Prize-winning cartoonist delivers his debut graphic novel at 85, a deliriously over-the-top blend of classic movie noir and melodrama that roams from chiaroscuro Bay City to Hollywood to a USO gig in the Pacific theater of World War II. There's a burnt-out drunk of a private eye, but the story is soon commandeered by a multigenerational collection of ferocious women, including a mysterious chanteuse who never speaks, a radio comedy writer who makes a childhood friend the butt of a hit series and a ruthless dame intent on making her whiny coward of a husband into a star. There are disguises, musical numbers and plenty of gunfights, but the drawing is the main attraction. Nobody convey's bodies in motion more thrillingly than Feiffer, whether they're dancing, running or duking it out. The kid has promise.

    Ten spectacular graphic novels from 2014

    The Motherless Oven by Rob Davis
    This is a weird one, but in the nervy surreal way that word-playful novels like "A Clockwork Orange" or "Ulysses" are weird. The main character, a teenage schoolboy named Scarper Lee, lives in a world where it rains knives and people make their own parents, contraptions that can be anything from a tiny figurine stashable in a pocket to biomorphic boiler-like entities that seem to have escaped from Dr. Seuss' nightmares. Their homes are crammed with gadgets they call gods and instead of TV they watch a hulu-hoop-size wheel of repeating images that changes with the day of the week. They also know their own "death day," and Scarper's is coming up fast. Maybe that's why he runs off with the new girl at school, a real troublemaker, and the obscurely dysfunctional Castro, whose mother is a cageful of talking parakeets. A solid towline of teenage angst holds this manically inventive vision together, and proves that some graphic novels can rival the text-only kind at their own game.

    Ten spectacular graphic novels from 2014

    NOBROW 9: It's Oh So Quiet
    For each issue, the anthology magazine put out by this adventurous U.K.-based publisher of independent graphic design, illustration and comics gives 45 artists a four-color palette and a theme. In the ninth issue, the theme is silence, and the results are magnificent and full of surprises. The comics, each told in images only, range from atmospheric to trippy to jokey to melancholy to epic to creepy. But the two-page illustrations are even more powerful, even if it's not always easy to see how they pertain to the overall concept of silence. Well, except perhaps for the fact that so many of them left me utterly dumbstruck with visual delight.

    Ten spectacular graphic novels from 2014

    Over Easy by Mimi Pond
    When Pond was a broke art student in the 1970s, she took a job at a neighborhood breakfast spot in Oakland, a place with good food, splendid coffee and an endlessly entertaining crew of short-order cooks, waitresses, dishwashers and regular customers. This graphic memoir, influenced by the work of Pond's friend, Alison Bechdel, captures the funky ethos of the time, when hippies, punks and disco aficionados mingled in a Bay Area at the height of its eccentricity. The staff of the Imperial Cafe were forever swapping wisecracks and hopping in and out of each other's beds, which makes them more or less like every restaurant team in history. There's an intoxicating esprit de corps to a well-run everyday joint like the Imperial Cafe, and never has the delight in being part of it been more winningly portrayed.

    Ten spectacular graphic novels from 2014

    The Shadow Hero by Gene Luen Yang and Sonny Liew
    You don't have to be a superhero fan to be utterly charmed by Yang and Liew's revival of a little-known character created in the 1940s by the cartoonist Chu Hing. This version of the Green Turtle, however, is rich in characterization, comedy and luscious period detail from the Chinatown of "San Incendio" (a ringer for San Francisco). Hank, son of a mild-mannered grocer, would like to follow in his father's footsteps, but his restless mother (the book's best character and drawn with masterful nuance by Liew) has other ideas after her thrilling encounter with a superhero. Yang's story effortlessly folds pathos into humor without stooping to either slapstick or cheap "darkness." This is that rare tribute that far surpasses the thing it celebrates.

    Ten spectacular graphic novels from 2014

    Shoplifter by Michael Cho
    Corinna Park, former English major, works, unhappily, in a Toronto advertising agency. When the dissatisfaction of the past five years begins to oppress her, she lets off steam by pilfering magazines from a local convenience store. Cho's moody character study is as much about city life as it is about Corinna. He depicts her falling asleep in front of the TV in her condo, brooding on the subway, roaming the crowded streets after a budding romance goes awry. Like a great short story, this is a simple tale of a young woman figuring out how to get her life back, but if feels as if it contains so much of contemporary existence -- its comforts, its loneliness, its self-deceptions -- suspended in wintery amber.

    Ten spectacular graphic novels from 2014

    Through the Woods by Emily Carroll
    This collection of archetypal horror, fairy and ghost stories, all about young girls, comes lushly decked in Carroll's inky black, snowy white and blood-scarlet art. A young bride hears her predecessor's bones singing from under the floorboards, two friends make the mistake of pretending to summon the spirits of the dead, a family of orphaned siblings disappears one by one into the winter nights. Carroll's color-saturated images can be jagged, ornate and gruesome, but she also knows how to chill with absence, shadows and a single staring eye. Literary readers who cherish the work of Kelly Link or the late Angela Carter's collection, "The Bloody Chamber," will adore the violent beauty on these pages.

  • Recent Slide Shows



Comment Preview

Your name will appear as username ( settings | log out )

You may use these HTML tags and attributes: <a href=""> <b> <em> <strong> <i> <blockquote>