Paddy Whacked: The Untold Story of the Irish American Gangster (22 page)

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 themselves. 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.

With the Combine in power and Walker running the show, the city sang with an Irish lilt and walked with the cocky strut of a bantam rooster. Thanks in part to the underworld, Paddy had finally arrived. As never before in the city’s history, it was swell to be a mick.

Diamond in the Rough

While there may have been—out of necessity—a semblance of diversity in its operations, the Combine was not a democracy. At night the clubs were thronged and people danced the lindy-hop and got tight, but the daily workings of the machine were brutal and dictatorial. Every speakeasy and bootlegging operation was connected. Like it or not, you sided with the Combine and succumbed to its commercial dictates or you went for the proverbial one-way ride and wound up dead in a ditch.

Independent operators were forbidden. The only exceptions were former members of the Combine who had branched off into ancillary rackets like the racing wire or local neighborhood scams that flew below the radar—the theory being that everything eventually trickled back into the organization. Bootlegging, however, was sacrosanct. From distilling to distributing to sales, anyone who ventured into any aspect of rum running, bootlegging, or the parsing of alcohol had to answer directly to the Combine. A few saloon keepers in, say, New Jersey or Upstate New York thought they could defy the mob because of their distance from Manhattan. They were sadly mistaken. The long arm of the Combine reached from Southern New Jersey all the way to the Canadian border, and everywhere in between.
⁶

Still, there was the occasional challenger.

One man who began to rock the boat as early as the mid-1920s was a former member of the organization. Jack “Legs” Diamond, born and raised in Southwest Philadelphia, took on the Combine as no one had before—and therefore blazed a trail across many a tabloid headline: “The Most Picturesque Racketeer in the Underworld,” the
New York American
called him; “Most Publicized of Public Enemies,” declared the
Post
; “Most Shot-At Man in America,” surmised the
Mirror
. The newspapers loved Diamond because of what he represented: a true renegade who took on the establishment, but in this case the underworld establishment.

In
Legs
, first published in 1975, Pulitzer Prize-winning author William Kennedy captured Diamond’s appeal by presenting his story through the eyes of a fictional criminal defense attorney. Like many journalists and average citizens, the fictional attorney viewed the bootlegger as “not merely the dude of all gangsters, the most active brain in the New York underworld, but as one of the truly new American Irishmen of his day; Horatio Alger out of Finn McCool and Jesse James, shaping the dream that you could grow up in America and shoot your way to glory and riches….

“Why he was a pioneer…He advanced the cause of joyful corruption and vice. He put the drop of the creature on the parched tongues of millions. He filled the pipes that pacify the troubled, loaded the needles that puncture anxiety bubbles. He helped the world kick the gong around, Jack did.”

Mostly, Legs Diamond dodged bullets; he shot people and was shot at. There would be five separate attempts on his life, all bloody near-misses until the last one, an intimate minimalist affair (just three bullets) that left no room for error. Thanks in part to Kennedy’s masterpiece, a Broadway musical based on his life, and other examples of posthumous hagiography, Legs lives on as perhaps the most well known of all Irish American mobsters.

His beginnings were inauspicious. In the Kensington mill district of Philadelphia, where Diamond was born and raised, the Irish had relocated from the filthy river wards in hopes of a higher-level of subsistence. The saga of the Irish in Philly was similar to that in New York, Boston, Chicago, New Orleans, and elsewhere. The anti-Catholic Know-Nothing Movement began in rural Pennsylvania and migrated to the City of Brotherly Love. Church burnings, the destruction of Irish shantytowns, and discrimination in every aspect of city life (particularly housing and employment) were commonplace. Irish Catholic protection gangs sprang up, most notably the Schuylkill Rangers and the Fenians, who clashed with Protestant gangs, predictably so on election day.

Diamond’s parents had come from Ireland, where they first met at a public dance in Kilrush, County Clare and married two years later. In autumn of 1891, with the Old Country mired in its perennial post-famine cycle of food shortages and joblessness, they moved to Philadelphia, where they first settled with relatives of John Diamond. Six years later, in a cramped three-family house of their own at 2350 East Albert Street, their son Jack was born. Two years later they had another boy, Edward.

Diamond’s father was not exactly a distinguished member of the community. A short, frail man who frequently coughed from an unknown lung condition, he bounced from one menial job to another, working as a short-order cook, a helper in a carriage-maker’s shop, and a packer in a coffee-roasting plant. His greatest achievement was becoming a committeeman of the 25th Assembly District, which encompassed the 31st Ward. John Diamond found his calling as a Tammany-style election official, until a dark day in December 1913 when his wife died suddenly from a bacterial infection and high fever. After weeks of mourning, Diamond gathered his meager belongings together and moved his two boys to Brooklyn, where they would stay with relatives.

As motherless teenagers with little adult supervision, the Diamond brothers soon fell into the same kind of trouble they had first experienced in Philly, where they had hung out with a group of young toughs known as the Boiler Gang. Of the two brothers, Eddie was the better fighter. Jack, lean, gangly, and weighing only 145 pounds on a good day, was more concerned about his hair and clothes than about winning fights. He was, however, inventive and daring in his early criminal exploits, which set him apart as a leader.

Jack Diamond’s first arrest came at the age of seventeen, when he got caught breaking into a Brooklyn jewelry store. He was sent to an upstate reformatory, where he was institutionalized for one year. Rehabilitation was not the goal; juvenile reformatories of the early twentieth century were medieval throwbacks to another time, rife with brutal forms of punishment and backward social thinking. Hidden behind red-brick walls and closed off to the public, these underfunded extensions of the penal system would play a role in producing some of the most disturbed and violent gangsters of the era.

Diamond’s criminal record shows that, in the few short months following his release from reform school, he was arrested six times, mostly for burglary. He managed to stay out of jail, and even found time to get married to an attractive Broadway waitress named Florence Williams. They moved into a cheap cold-water flat on the West Side. By all accounts, the marriage was tempestuous; Jack drank while Flo got angry and threw things. She was once heard yelling “I’ll pray for you, Jack. I’ll pray for you, you no good tramp.”

“Take me or leave me,” answered Diamond. “I do what I want.”

The marriage only lasted a few months, which was just as well, since in 1918 Diamond got drafted into the U.S. Army.

Not surprisingly, Diamond’s time in the military was a disaster. His budding antiauthoritarian tendencies were exacerbated to the point where, after less than a year in the service, he tried to go AWOL. Armed with a .45-caliber pistol and carrying a sack of flare guns that he intended to sell, he managed to get by the main gate at Fort Dix but was caught a half-mile down the road. While struggling to get away, he smacked a sergeant with an iron bar and injured two other soldiers. Charged with desertion, along with several other crimes, he was sentenced to Fort Jay and then Governor’s Island in New York Harbor. An attempt to escape landed him a sentence of three to five years of hard labor at the Federal Penitentiary in Fort Leavenworth, Kansas.

“No matter what happens, they’ll never make me serve the full sentence,” said Diamond as they carted him away.

He turned out to be right. In the spring of 1921, newly elected President Warren G. Harding, in a postwar gesture of goodwill, unexpectedly pardoned more than two dozen federal prisoners, including a troublesome though seemingly insignificant former buck private named Jack Diamond.