“You got a problem,” Owney would have told Big Bill. “Gangsters been picking off your trucks like sitting ducks and what are you gonna do about it.”
“That’s why I called you here.”
“You gotta organize the shooters and the cherry-pickers, not to mention the bulls and the pols.”
“You’re right. I need the hijackings to stop. I need a place to make my own brew right here in the big city, protected by the Tiger and the coppers. And I need outlets—speakeasies, nightclubs, you name it.”
“You need a lot, my friend.”
“Are you with me you Liverpool mick bastard?”
“Give me one good reason why.”
“I can make you rich.”
Here, a rare and knowing smile would have creased Owney’s lips: “Pal, you and me, we’re like two peas in a pod.”
Thus was born what would be known forever after as the New York Irish Mob.
When New York Was Really Irish
Under the aegis of Big Bill Dwyer, Owney Madden went about organizing the underworld. Since money was no object, he started with the most costly proposition: the opening of a massive brewery right in the middle of the city. This way, the Combine, as the expanding Madden-Dwyer partnership would become known, would not have to worry about highway robbers; they could control the flow of booze from the source to the marketplace.
In early 1924, the Phoenix Cereal Beverage Company opened for business at Twenty-sixth Street and Tenth Avenue, not far from where Dwyer and Madden had both been raised. A huge red-brick building that took up the entire block, the Phoenix had formerly been home to Clausen & Flanagan Brewery, which had tried to sell near beer, a diluted product with minimal alcohol content that was legal under the Volstead Act. Nobody wanted near beer; they wanted the real thing, which the Phoenix brewery churned out in high volume.
Using a government patent that had been secured by the brewery’s previous owners, the Phoenix operated under the guise of government authorization while producing an illegal product called Madden’s No. 1. You could buy Madden’s No. 1 by the barrel or by the bottle, with a label that had a sketch rendering of the brewery and surrounding area—Hell’s Kitchen in all its glory. Apparently, nobody felt the need to hide anything. The bootleggers took care of Tammany. Tammany, in return, took care of the Prohibition agents and made well-placed contributions to the Policeman’s Benevolent Association for protection. The Combine hummed like a well-oiled machine.
Madden, the former Gopher boss, formed a number of key alliances that made it all happen. He had a friend from his brief foray in the taxi business named Larry Fay. A scrawny, horse-faced Irish American from Long Island, Fay became a major player in the underworld after hitting a legendary hundred-to-one shot at Belmont Race Track. With the proceeds, Fay bought into the taxi business. He owned a large fleet of cabs and had hired a number of West Side hoodlums—including Owney Madden—to stamp out the competition. At Madden’s behest, Fay was brought into the Combine. His primary role was to establish a number of popular nightclubs that would become the primary outlets for Madden’s No. 1, along with bootleg rum, scotch, vodka, and champagne smuggled into the country via Big Bill’s mastery of Rum Row.
As a club impresario and man-about-town, Larry Fay fancied himself a bon vivant. To compensate for his homely visage, he developed an abiding passion for fancy duds. When he returned from a trip to Europe in 1923, he allegedly brought with him trunks filled with Bond Street creations that were made for him by London’s most fashionable tailors. His personal style tended toward loud neckties and gaudy suits, under which he almost always wore a bullet-proof vest. He took great pride in his flashy fashion sense; a newspaper reporter who once referred to him in print as the “Beau Brummel of Broadway” received a case of liquor and an invitation to eat and drink on the cuff for six months at one of his clubs.
The first of Fay’s storied establishments was Fay’s Follies, a nightclub he’d opened all on his own in 1921. His most celebrated club came three years later when, with Madden and Dwyer as silent partners, he opened El Fay at 107 West Fifty-fourth Street, which quickly became famous as the home of Texas Guinan, a bawdy and highly popular cabaret singer and entertainer who was the precursor to Mae West.
The success of El Fay helped turn smart-talking Larry Fay into a Broadway archetype, the sort of character immortalized in the writings of Damon Runyon, most notably in the Runyon-inspired play and movie, Guys and Dolls. Fay had the magic touch. As Prohibition progressed and the money rolled in, he married the Roaring Twenties version of a trophy wife, a beautiful Broadway showgirl named Evelyn Crowell. He went on to open many other clubs besides El Fay and was one of multiple partners in the Silver Slipper, the Rendezvous, Les Ambassadeurs, and, of course, the Cotton Club, where Duke Ellington and his Orchestra resided as the house band, introducing some of the most complex and enduring compositions in the history of jazz music.4
Nightclubs and speakeasies such as these were the most obvious byproduct of the booze-fueled Roaring Twenties, but the most important element that kept the Combine running smoothly was something no one was supposed to see: the protection racket. Protection was purchased for a price—cold, hard cash usually stuffed into envelopes and surreptitiously exchanged between grubby hands under a desk or table, in a dark alleyway, or through contributions to a special police widow’s fund. Protection usually started at the top and worked its way down. The Combine delivered the money directly to the ward boss or district leader, whose office dispersed the funds to the necessary judges and precinct captains, who in turn slipped the designated denomination to a lieutenant or shift commander, who then greased the palm of the appropriate patrolman. A judicious offer of an occasional bottle or case of booze to said lieutenant or captain was also recommended, since the boys in blue were known to have among the wettest wickets in town. In return, the Phoenix Cereal Beverage Company operated unmolested by law enforcement and Combine-controlled speakeasies, nightclubs, and dance halls stayed open for business. The booze flowed freely.
More than anyone else, the man who greased the wheel for Madden and Dwyer and made the Combine into a formidable operation was a white-haired, grandfatherly Irish American named James J. Hines, powerful leader of the 11th Assembly District on Manhattan’s Upper West Side. A protégé of the late Big Tim Sullivan, Hines was the Big Fella’s natural successor as the System’s primary conduit between Tammany Hall and underworld forces. During the years of Prohibition, Hines would become the ultimate man behind the man, an iron-willed district leader and devoted family man who went to church every Sunday, then on Monday broke bread with the most notorious mobsters of his day. While serving as political fixer and bag man for the mob, he also played a significant role in the election of mayors, senators, and at least two presidents.
There was nothing in the appearance or demeanor of Jimmy Hines that would lead you to believe he was an acolyte of the underworld. On a good day he resembled the actor Spencer Tracy, with reddish-brown hair that had gone snowy white and a face that could be alternately kind and craggy. Although he was born on 116th Street and Eighth Avenue in a part of the city that would become known as White Harlem, he sometimes spoke with a trace of the Old Country in his voice, an affectation that was intended to underscore his historical connection to Tammany’s Hibernian roots.
He began his career as a blacksmith, a trade he inherited from his father, who was also an occasional election captain in the 11th Assembly District. When his father became ill, Jimmy, just seventeen at the time, took over his father’s blacksmith business and also his duties as political canvasser in the district. Hines was exposed early to a system in which ward politics relied heavily upon the services of gangsters to win elections.
In 1907 Hines threw his own hat into the ring by running for alderman. He won easily. Three years later, he challenged the popular incumbent district leader. During a campaign that was described as a reign of terror because of the violent tactics of both Hines and his oppon
ent, Hines emerged victorious. Soon after the election, he formed the Monongahela Democratic Club, an outgrowth of the James J. Hines Association, from which he practiced the typical Irish version of Tammany politics—turkeys for the needy on Thanksgiving, donations to Catholic charities, and the dispensing of favors for votes. His Democratic club also became the basis for his patronage and boodling operations. With his brother Philip, Jimmy started a trucking company that, despite its limited work history, managed to be awarded many lucrative contracts on city and state construction projects. Hines also rented out the top floor of his political clubhouse for commercial gambling purposes to a young, up-and-coming Jewish gangster named Arnold Rothstein.
Despite Hines’ power and growing popularity at the district level, which assured his reelection for the next twenty-five years, he appeared to have a scant future in citywide elective office. An unimpressive public speaker with none of the galvanizing personality characteristics of Big Tim Sullivan or Chicago’s Bathhouse John Coughlin, Hines, to use a well-worn phrase, spoke softly and carried a big stick. He was the sort of man who, in a crowded room, liked to whisper behind a hand or in a person’s ear, making his wishes known with a simple nod or gesture. If anything, he displayed his power by maintaining an air of mystery and inscrutability—unless you got on his bad side, in which case friends suddenly became enemies, municipal inquiries fell on deaf ears, and doors slammed in your face with merciless authority.
Madden and Dwyer met Hines often, either at Big Bill’s Times Square office or at the Monongahela Club, where the district boss presided like a tribal chieftain. Constituents of all ages and denominations were free to enter Jimmy Hines’ club, with complaints, suggestions, and requests. If they saw Owney “the Killer” Madden seated with their district leader, so much the better. In the World According to Tammany, having a gangster at the elbow of the ward boss was not a bad thing; it enhanced the boss’s reputation and made good political sense. Politics, after all, was the raw meat that fed the beast. George Washington Plunkitt, the bard of Tammany and an early inspiration for Hines’s career, said it best: “As a rule, [a district leader] has no business or occupation other than politics. He plays politics every day and night in the year, and his headquarters bears the inscription, ‘Never Closed.’”
Money was funneled into the coffers of Alderman Hines by the leading lights of the Combine, and that became the source of his power. Hines was the money man who took care of the cops, judges, prosecutors, and bail bondsmen; he made the world go ’round.
With Dwyer, Madden, Fay, and Hines coalescing all the elements of what would eventually become known as organized crime in New York, it would not be inaccurate to say that, in these early years of Prohibition, the town was run by the Irish Mob. The high seas, the streets, the police department, and the city’s political universe were all controlled by the Combine. But it was at every level of the underworld that one could see the shadow of the shamrock. There was Vannie Higgins, second only to Big Bill among rum runners and bootleggers. Higgins was the mob boss of Brooklyn, with speedboats and his own airplane, from which he controlled the flow of booze throughout Long Island. Irish Americans also predominated the strong-arm rackets. A young gunman from Philadelphia named Jack “Legs” Diamond was making a name for himself as a bodyguard for Arnold Rothstein and as an inveterate bootlegger. Also, an Irish-born orphan and teenager named Vincent Coll was fast becoming the era’s most feared hired gunman. Along with his brother Peter, he was employed by Jewish gangsters, Italian mafiosi, and Irish alike.
Then there was the NYPD, which had been an Irish patronage racket for at least four decades. Before Prohibition, only saloons that wished to operate beyond licensed hours had been required to pay tribute to New York’s Finest. Now any place that served liquor had to come up with the green. Inspectors, captains, and vice cops were raking in money; even an ordinary patrolman who worked in a prominent bootlegging neighborhood like Hell’s Kitchen, where many booze storage warehouses were located, could turn a nice dollar. Tough waterfront precincts, once seen largely as punishment precincts, were now highly desirable because that’s where the smuggled booze came ashore.
Finally, there was Tammany Hall, which was even more Irish than the police department. The Celtic clan system that had been transplanted from pre-famine Ireland and reinvented in New York, Chicago, and elsewhere around the United States had finally reached its apotheosis in the Big Apple. Of the city’s thirty-six wards, more than half were run by bosses of Irish descent, with numerous other district leaders, precinct captains, and election officials who were part of a tradition that stretched back to the earliest and most poverty-stricken days of Irish immigration. In terms of actual numbers, the Irish were a much smaller percentage of the overall population than they were in the 1860s, 1870s, and 1880s, but their power had grown. Years of dedication and allegiance to the democratic party system had paid off in an era of ascendancy—made all the more giddy by an infusion of Prohibition cash that dwarfed the proceeds of earlier vice rackets like organized gambling and prostitution.
Even with so many sons and daughters of Erin involved in the daily workings of the Combine, it was never meant to be exclusively an Irish operation. Madden, Dwyer, and the others had the foresight to realize that the underworld in New York could never operate as a hermetically sealed ethnic universe. Back in the days when the Dead Rabbits, Plug Uglies, or Kerryonians were first establishing a foothold in the Five Points, certain gangs had been Irish-only, but Prohibition was different. Prohibition was about capitalism, not ethnic solidarity. You could have an Irish American brain trust, but if you hoped to control the system and dominate the market, you had to create working relationships with every group. The genius of Tammany Hall had always been its ability to incorporate WASP, Jewish, Polish, and Italian representatives, giving everyone their piece of the pie. Using the Tammany approach, the Combine expanded to incorporate many non-Irish gangster pioneers: Jews like Rothstein, Meyer Lansky, Waxey Gordon, and Dutch Schultz (born Arthur Flegenheimer, a German Jew); African Americans like Bumpy Johnson and Madam Stephanie St. Clair in Harlem; Italians such as Lucky Luciano, Joe Bonnano, and Francesco Castiglia, born in Naples and raised in East Harlem.
The Combine enlisted the services of these men at the highest levels. In fact, when Big Bill Dwyer was finally arrested, charged, and convicted on bootlegging charges in 1925–1926, it was Francesco Castiglia who stepped in and took over the daily runnings of Big Bill’s operation. That’s when Castiglia changed his name to Frank Costello, a Hibernian name that was perhaps more acceptable to the Combine’s less ethnically enlightened Irish distributors. Castiglia/Costello oversaw the operations of the Combine without a hitch until Big Bill was released early for good behavior (after serving thirteen months of a two-year sentence) and returned to the city to pick up right where he left off.
The ethnic diversity that kept the Combine running smoothly permeated the era. Police Commissioner Grover Whelan estimated there were 32,000 speakeasies in New York, and most were remarkably democratic in their clientele. As long as you could pay up and were savvy enough to know where the hot new establishments were located, you could gain entrance. All classes and many races mixed. Prohibition brought about a kind of ethnic interaction that might not have happened otherwise, with Greeks, Irish, Swedes, Italians, WASPs, and Jews socializing and doing business like never before: an antiestablishment, brotherhood of man bound together by their hatred of the Volstead Act.5
The Combine may have had ethnic variety in its operations and customer base, but it nonetheless gave off an aura that manifested seven tough decades of Irish upward mobility. After fighting and clawing their way through the worst kinds of poverty and discrimination, the Irish in New York—and many other big U.S. cities—had finally arrived at a place of social desirability. The Irish American bootlegger, in particular, with his tough-guy demeanor, quick patter, and devil-may-care attitude toward the law came to signify the way many American men wanted to see them
selves. The street slang, clothing styles, and attitudes of the Irish hoodlum became popular in the way that rap and hip hop would many decades later; this trend was an opportunity for middle-class Americans, if there was such a thing in the 1920s, to adopt the look and style of the outlaw underclass.
It would be a few years before the phenomenon was codified and made explicit in the movies of Jimmy Cagney, but the desire for a drink and the surreptitious, exciting world of the illicit speakeasy had already defined a generation. The mixture of glamour and danger that fueled this world was immortalized forever by F. Scott Fitzgerald in The Great Gatsby. In the novel, as in real life, the bootlegger was viewed as a daring figure who took chances to deliver a service to the public. He may have been dangerous and may even have been a killer, but he was also devilishly attractive. The public face for this character, to most people, was an Irish one.
The city’s love affair with this Irish gadfly persona reached a new pinnacle in 1926, when Jimmy Walker, a smart-talking former Tin Pan Alley songwriter, was elected mayor. Walker was not a bootlegger, but he was an Irish Catholic politician who liked to drink and hang out in Broadway nightclubs, where he shook hands and imbibed with such underworld leading lights as Owney Madden, Larry Fay, and Arnold Rothstein. Beau James, as Walker was known in some circles, was a product of the Tammany Machine, a Greenwich Village boyo who knew how the game was played and wasn’t about to rock the boat. He professed his desire to see Prohibition repealed and appointed a police commissioner who wouldn’t be too hard on the mobsters. By most indications, the general public approved.
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