Leland Stanford Chumley opened one of the best-known and longest-lived Village speakeasies at the quiet, leafy corner of Barrow and Bedford Streets. Chumley came from Chicago with all the right bohemian credentials for the time. He’d been a stagecoach driver, a newspaperman, an artist, a hobo, and was now a Wobbly organizer. The building he bought had been a blacksmith shop and a dairy, and in converting it to the bar restaurant Chumley’s he retained a comfortably rustic and woody atmosphere. He left the two entrances locked and unmarked—the back door at 86 Bedford Street and the front door, with a peephole, in Pamela Court off Barrow. (According to a disputable legend, the term “86’ed,” meaning a quick exit or ejection, was coined at Chumley’s. Patrons needing to beat a hasty retreat—for instance, Wobblies ducking a raid—or unruly guests being too noisy for the courtyard exit would “86 it” out the back door at 86 Bedford.) Wobblies held meetings and printed subversive literature upstairs, while Edna St. Vincent Millay read her poetry downstairs. Chumley’s survived Prohibition as a legitimate establishment without ever putting a sign outside, although its location was perhaps the most open secret in the city. Over the years it acquired a reputation as a literary hangout; the long list of names associated with it besides Vincent’s includes Dreiser, Cather, Cummings, Hemingway, Dos Passos, Bodenheim, Mailer, Maugham, Salinger, Ginsberg, Burroughs. Toward the end of the century, like the Village around it, Chumley’s became a young professionals’ meeting place trading on boho nostalgia.
Another Villager became maybe the most celebrated of all speakeasy proprietors. When twenty-three-year-old Mary Louise Cecilia Guinan, better known as Texas, came to Manhattan in 1907, she headed straight for the Village, where self-created larger-than-life characters like her belonged. Her first residence was a two-dollar-a-week room at 72 Washington Square South, but when she became rich and successful she moved to a duplex at 17 West Eighth Street, filling it with antiques and bric-a-brac and bringing her parents to come live with her there. Brassy, ballsy, wisecracking, and fun loving, Texas Guinan from 1922 on was the mistress of ceremonies at several Times Square clubs, where she was as much a draw as the chorus girls who kick-lined behind her.
Restaurants and legitimate clubs in the Village that did not serve liquor did provide ice and ginger ale “setups,” and patrons were free to bring their own liquor in. Max Gordon, later the founder of the Village Vanguard, ran a dry club called the Village Fair on Sullivan Street; if a patron’s personal bottle ran out while he was in the club, “There was always a guy in a doorway hanging outside Village joints who could get you one.” You placed your order with this shadowy figure and went back inside. Your waitress informed you when he was back and you stepped outside to complete the deal. “The legal niceties were thus observed. The sale was made outside the premises and the joint was in the clear.”
A number of tearooms and speakeasies in the Village catered to gay or lesbian clientele—the Black Rabbit, the Flower Pot, the Jungle, the Bungalow, Trilby’s, the Red Mask. Paul and Joe’s, on Sixth Avenue and West Ninth Street, was originally a tough dive bar trolled by prostitutes, but in the 1920s it evolved into a popular gay destination featuring drag and “pansy” acts. Eve’s Hangout, a basement tearoom on MacDougal Street, was famous for the sign at the entrance MEN ARE ADMITTED BUT NOT WELCOME. Attitudes among the straight bohemians ranged from tolerance to mild disapproval to outright hostility, a reaction shared by most of the rest of the neighborhood. Henry Miller, no slouch himself when it came to sex, writes in Plexus, “The Village had indeed deteriorated. There were nothing but dives and joints, nothing but pederasts, Lesbians, pimps, tarts, fakes and phonies of all description.” He describes how Paul and Joe’s had become “entirely dominated by homos in sailors’ uniforms . . . Coming away from the place we had stumbled over two ‘sailors’ writhing on the floor of the balcony, their pants down and grunting like squealing stuck pigs. Even for Greenwich Village that was going pretty far, it seemed to me.”
The disappearance of the old saloons and the birth of the speakeasy had lasting effects on New York nightlife. It ended the era of men-only drinking establishments. Separate rooms and entrances for the ladies were too much trouble for speakeasy owners, and the coed carousing pioneered in the Village became the norm everywhere. In fact, Prohibition had a generally leveling effect on New York culture. New Yorkers of all strata found themselves thrown together in the speakeasies and clubs, all rebels, all drunk, everyone smoking, everyone flirting, rubbing elbows and other parts with people they never would have met otherwise, dancing wicked dances like the Black Bottom and the Charleston to the wailing Negro jazz band. Before Prohibition, men went to their local saloon or tavern after work and drank nickel beers and ten-cent whiskeys, smoked cigars, talked the news of the day, and went home to their families. Prohibition made drinking sophisticated, cosmopolitan, and “smart.” Barkeeps transformed into mixologists inventing ever more exotic cocktails. Prices skyrocketed, but Wall Street was churning out paper millionaires anyway, and everyone was out every night spending it, whooping it up. Behavior one saw only in Greenwich Village in the 1910s spread throughout the whole city in the Roaring Twenties. Newspaper and magazine columnists cheered the democratizing effects of the new cabaret and nightclub culture, where, as one put it, “Woolworth money is quite as good as Cartier’s.” Of course, a great collective hangover was waiting at the end of the decade but nobody seems to have foreseen it.
THE FEDERAL PROHIBITION UNIT MANDATED WITH STOPPING ALL the illicit drinking in the nation of sots was chronically underfunded and understaffed. The agency fielded a mere fifteen hundred agents expected to watch the nation’s vast borders, police its roads, find and shut down an expanding universe of illicit distilleries and breweries, go undercover into its thousands of speakeasies and clubs, and spy on the daily consumption habits of its one hundred and six million citizens. Many agents’ hearts weren’t in it from the beginning and corruption was rife throughout the unit’s existence. An agent made under two thousand dollars a year in salary; he could make five hundred a day from his local bootlegger just for looking the other way when a shipment went out. In New York City, the hiring of federal agents was just another Tammany patronage trough, and half the federal agents in the city had to be let go under accusations of bribery and extortion. Meanwhile, the police who were supposed to assist the feds were often on the take as well. In one instance, cops swooped down on federal agents who were preparing to bust a bootlegger’s warehouse and arrested the agents as “suspicious characters,” giving the bootlegger time to clear the place out. At the end of the workday many cops went off to throw around some of their ill-gotten gains at their own speakeasies of choice, including the one connected to Police Headquarters via a tunnel under Centre Market Place, where they bent elbows with judges, district attorneys, and other slack upholders of the new law. By the start of 1925 New York had bowed to the obvious and removed the police from Prohibition enforcement, leaving just the badly outgunned and graft-riddled feds.
Encouraged by the lazy enforcement, New York’s Italian, Irish, and Jewish street gangs took to bootlegging, rum-running, and opening speakeasies with abandon. They became, in effect, an entire underground liquor industry. They imported enormous quantities of labeled alcohol from England and Canada (which encouraged, and happily taxed, its boom market for distilleries). Much contraband whoopee entered the city of New York through the Irish-run waterfront of Greenwich Village, Chelsea, and Hell’s Kitchen. Gangsters built their own breweries and distilleries, ran their own trucking and shipping industries, figured out how to launder the cash and evade taxes, opened their own speakeasies, fought off competitors, and paid off everyone they had to. It was all a great learning opportunity for the neighborhood gangs, who grew into the organized crime syndicates that flourished in the 1930s and beyond.
In 1925, as though to flag their contempt for Prohibition, New Yorkers elected an Irishman from the Village to be their mayor. Central casting could not have sent them a better
figurehead for the Roaring Twenties and the Prohibition years than the hard-partying, hardly working, and breezily corrupt Jimmy Walker, aka Beau James, the Night Mayor.
His father, William Walker, came from Kilkenny in 1857 and settled in the Ninth Ward, starting a lumberyard, marrying a neighborhood saloonkeeper’s daughter, and siring four children. James, the third son, was born in the family’s apartment on Leroy Street in 1881. A few years later, the family moved to the handsome town house at 6 St. Luke’s Place, where Jimmy would live for forty years. (Today it looks across the street at James J. Walker Park.) As a prosperous Irishman William Walker came to the attention of Tammany Hall in 1886. At the time, Tammany, the Democratic Party machine, ran virtually every politician, every department, judge, district attorney, and civil servant at all levels of city government. Despite its reputation, Tammany was not completely corrupt, and its effects on the city and state not always deleterious. (Al Smith, though a Tammany man, was a progressive reformer with the common touch and one of New York’s most popular governors.) And though Tammany’s leadership was generally quite crooked and self-serving, some relatively honest men served down at the level of the ward boss or ward heeler, “often a saloonkeeper who functioned as the local provider of patronage, dispenser of cheer and charity, and vote gatherer.” One of their chief functions was to act as greeters of new immigrants in their neighborhoods, helping them fill out citizenship forms and peddlers’ licenses, finding them jobs, negotiating with their landlords. In return, naturally, the grateful new citizens voted solidly Democrat. The ward heeler’s job on Election Day was simply to see that Tammany’s man won, by any means necessary.
Over the decades many a ballot box was stuffed, many Republican ballots were destroyed or lost down a coal chute, and many a dead Democrat was resurrected to do his duty at the poll one more time—or two or three, as needed. In the Irish Village, the building at 47 1/2 Morton Street was known as Little Tammany Hall, “because the voting rolls for the tenement listed far more registered Democrats than the number of people who lived there.” With Tammany’s support, William Walker served four times as alderman, once as state assemblyman, and finally as Manhattan’s superintendent of public buildings, where he sponsored the city’s first recreation piers.
Jimmy grew up affable, popular, bright but lazy, nicknamed Jimmy Talker in grade school. He attended New York Law School because his father wanted it, but what Jimmy wanted was showbiz. He wrote his first hit song in 1905, the sweetly romantic “Will You Love Me in December As You Do in May?” (Later cited by Kerouac in The Town and the City.) He spent the windfall on spiffy new outfits, cranked out several more songs over the next few years, became friends with George M. Cohan and Ira Gershwin, and met his wife, the chorus girl Janet Allen. But though he loved show business the rest of his life and it loved him back, he obeyed his father and went into politics. In the state assembly he came under Al Smith’s wing, and in 1925 Tammany made sure he was elected mayor.
He soon earned his reputation as the most lackadaisical mayor in the city’s history. Instantly bored with his administration duties, habitually late for meetings, he let the Tammany hacks run things while he took off on lengthy and frequent vacations, almost 150 days in his first two years. When critics complained about a raise in his official salary to forty thousand dollars a year he quipped, “That’s cheap! Think what it would cost if I worked full time.” He happily assumed a purely ceremonial role, cutting ribbons, attending dinners, leading parades, handing the keys to the city to almost anyone who dropped by. He took up with a new chorus girl, Betty Compton, and installed her in the top-floor apartment at 146 West Fourth Street, above the Pepper Pot. Janet sat at home while Jimmy and Betty partied all over town. Eventually Betty forced him to choose between them; he left Janet and moved with Betty into a suite in a midtown hotel.
While Jimmy partied and traveled, Tammany ran the city into the ground. Just about everything a municipal government is supposed to be responsible for fell into neglect and rot—health, housing, education, sanitation, police, fire, roads, public transportation, the waterfront, the water itself. The city’s payroll was outrageously bloated with patronage jobs handed out to Tammany hacks and nitwit nephews who were exempted from taking the civil service exam. A survey of one hundred lifeguards at city beaches in the early 1930s, for example, found that fourteen couldn’t swim; another eighteen didn’t even show up for the test. Mothers routinely warned their children to stay away from the beaches’ first-aid stations, because that was where the prostitutes who’d come to service the lifeguards hung around. As the gangsters who ran all aspects of the city’s multimillion-dollar liquor industry warred among themselves in the later 1920s, the city became more violent and dangerous, murder rates climbed, and innocent victims, including children, died in the crossfire. Despite the occasional tough-talking police commissioner or district attorney, law enforcement in the city was simply too riddled with corruption to make a dent.
Through it all Jimmy sailed blithely on. One place you could always find him was at the Broadway musical revues, such as Ziegfeld’s Follies, followed by a duck into one of the better speakeasies or nightclubs. Mayor Walker was as fond of speakeasies and nightclubs as anyone in the city. When the feds periodically leaned on him to make a better show of enforcing the law, his response was at best halfhearted. Pressed by the Prohibition Unit, his police commissioner once proposed a 2 a.m. closing time for nightclubs, which stayed open until 4 a.m. or later. New York was the city that never sleeps decades before Sinatra sang about it. During World War I a previous mayor had enforced a 2 a.m. curfew so young men wouldn’t be too pooped if called upon to defend the city from the Hun, but as soon as the war ended the all-night whoopee started up again. Now club and cabaret owners, many of them personal friends of the mayor, howled. Mayor Walker offered a Solomonic compromise: a 3 a.m. closing time. Undercover federal agents tasked with infiltrating and observing the nightclubs became some of their best patrons. Buying champagne, cocktails, and orchids for their dates in their assiduous efforts to blend in with the crowd, they ran up a federal bar tab of seventy-five thousand bucks in 1928 alone, with no convictions to show for it. Mayor Walker cracked that it seemed a high price to pay “to learn facts which are known to virtually everyone.”
Jimmy was a great fan of another Irish Villager who became a celebrity, controversial in his own way, in the 1920s: Gene Tunney, heavyweight boxing champion of the world. Born James Joseph in 1897 (“Gene” was a nickname that came from a younger brother’s mispronunciation of Jim), he grew up in a cold-water flat above a general store at the corner of Perry and Washington Streets, one of seven kids born to a two-fisted longshoreman who drank at Luke O’Connor’s, one of the bars O’Neill and the bohemians colonized in the 1910s. Gene was quiet, polite, and bookish, considered “something of a prig” by other boys in the neighborhood, “almost a stereotype of the perfect altar boy. He didn’t drink or smoke, and he regarded swearing as crude and sacrilegious.” He took up boxing to defend himself from his brawling father and from bullies who thought him a sissy because he loved to read. Thoughtful and defensive in the ring as well, he was an undefeated amateur when he turned pro at eighteen, then enlisted in the marines during World War I. In 1926, at the age of twenty-nine, “The Fighting Marine” was 79–1 and ready to go up against “The Manassas Mauler,” Jack Dempsey.
Tunney’s celebrity stemmed from his still being a voracious reader of history, science, poetry, literature, and plays (he joined the Shakespeare Society and memorized Hamlet). He liked art and opera and used words of more than one syllable. He called boxing “the art of thinking as expressed in action” and said things like “I think of pugilism as a fencing bout of gloved fists, rather than an act of assault and battery.” The newshounds and their readers, used to prizefighters being grunting pugs and lugs like Dempsey, couldn’t decide if “The Boxing Savant” and “The Bard of Biff” was a pretentious freak, a joke, or a publicity stunt. Then, in Philadelphia’s S
esquicentennial Stadium, before a crowd of a 145,000 that included his proud homeboy Jimmy Walker (and Astors and Vanderbilts and Charlie Chaplin and Tom Mix), plus a radio audience of fifteen million, he scientifically picked Dempsey apart for the championship. Dempsey, who’d been the five-to-one favorite, told his incredulous wife, “Honey, I just forgot to duck.” Mayor Walker led a parade to welcome Tunney home, but Dempsey remained the fans’ favorite. They fought again the following year in the still-discussed “Long Count” bout, when Dempsey, after knocking Tunney to the canvas for the first time in his career, took a long while getting to a neutral corner, delaying the ten-count and giving Tunney precious extra seconds to recover. Tunney got up . . . and won. He went on to enjoy a very successful post-ring career, marrying a socialite, lecturing on Shakespeare at Yale, sparring with Hemingway, and becoming friends with his literary hero George Bernard Shaw, a fight fan.
WITH THE STOCK MARKET CRASH IN 1929 AND THE ONRUSHING Depression the party ended. Walker, the perfect man for leading the conga line in high times, proved perfectly incapable of dealing with the bread lines in hard times. Reformers and Republicans pounced. As new investigations and hearings made painfully clear what everyone had always known anyway—that Mayor Jimmy had presided over and handsomely profited from a Tammany-run government riddled with corruption—Governor Franklin Roosevelt convinced him to resign in September 1932. He finally married Betty and returned to his first love, music, heading up Majestic Records, which put out discs by Louis Prima and others in the 1940s. He died in 1946.
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