Paddy Whacked

by T. J. English

  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.

  With his new lease on life, Di
amond returned to New York and immediately plugged into the city’s thriving Prohibition underworld. He and his brother Eddie fell in with a crew based on the Lower East Side that included a young burglar and narcotics dealer named Lucky Luciano. For a time, they worked in the organization of Vannie Higgins, the bootlegger boss of Brooklyn and Long Island. Diamond was arrested on an almost weekly basis, but was provided legal representation by the Combine and rarely spent more than a few days in jail. He began to partake of the city’s vibrant nightlife, especially the dance halls. Some believe that he acquired the nickname “Legs” because of his talents on the dance floor, while others claim he had the name from adolescence, and it referred either to his running abilities or simply the fact that he had long, gangly legs. As with the origins of most underworld monikers, it is difficult to separate the fact from fiction.7

  Sometime in early 1922, Lucky Luciano took Diamond to Lindy’s, a Broadway diner and famous hangout for actors, writers, and sporting men. It was there that Luciano introduced Jack to Arnold Rothstein: “Jack, meet The Big Bankroll. Mister Rothstein—Legs Diamond.”

  Legs knew all about Rothstein, who had been weaned at the knee of the late, great Big Tim Sullivan. Arnold had come a long way since his days as Dry Dollar’s Yiddish translator and gofer at the Hesper political clubhouse on the Lower East Side. Known variously as the Big Bankroll, Mister Big, and The Brain, Rothstein was considered a financial wizard with billions of dollars at his disposal. Among other things, he was rumored to have been the money man behind the fixing of the 1919 World Series, known as the Black Sox Scandal, though his role was never proved.

  The Brain looked Legs up and down and said “You look like a mick.”

  Said Legs, “Could be. Or I could be a yid. Take your pick.”

  “Hey kid, you lookin’ for work?”

  “Hell yeah,” said Diamond.

  “Good. Go say hello to Fatty Walsh. You’ll be workin’ with him.”

  Tom “Fatty” Walsh, Rothstein’s chief bodyguard, was seated at an adjoining booth. Legs nodded hello to the chubby Walsh. From that point on, he was part of Rothstein’s entourage.

  Legs quickly proved his value to Rothstein; he enforced the will of the underworld financier and reaped the benefit. He was on the payroll but free to commit crimes with his gang, which he did frequently, most notably as a robber of minks, jewels, and cars. All that was expected in return was that he unstintingly protect Rothstein. His value in this regard was made abundantly clear when he played a major role in breaking up a plot against The Big Bankroll. A Chicago gangster named Eugene “Red” McLaughlin had come to town with the idea of kidnapping Rothstein and holding him for $100,000 ransom. The Chicago mobster approached Legs Diamond, thinking he might be willing to take part in the job. Legs played along, even going so far as traveling to Chicago to finalize the plot with McLaughlin. Then Chicago newspapers reported that McLaughlin, shot and weighted down with boulders, was found dead in a ditch in Cook County’s Sanitary Canal.

  Diamond’s role in foiling this kidnapping scheme made him golden in Rothstein’s estimation. He was promoted to a level higher than Fatty Walsh. This development, apparently, gave Jack Diamond delusions of grandeur. He began to see himself on a level with The Brain—both socially, through his manner of dress and almost nightly touring of the city’s speakeasies, dance halls, and clubs, and professionally, through his dangerous idea to move in on the operations of the Combine.

  A motivating factor for Legs was his jealousy of Owney Madden, who had also started as a lowly street thug, but was now codirector of the largest bootlegging enterprise in the United States. Feeling that he deserved a piece of Madden’s action, Legs—taking a page from Owney’s own play book—began hijacking Combine booze shipments throughout the New York-New Jersey area. He even enlisted the tacit cooperation of Brooklyn mob boss Vannie Higgins by leading him to believe they could create a Combine of their own just as powerful as the Madden-Dwyer operation. Diamond assured Higgins that he had been promised backing from none other than Arnold Rothstein, which was partly true.

  At gunpoint, Legs, his brother Eddie, and their gang began picking off booze shipments on a semi-regular basis. They excelled particularly at hijacking the trucks of Big Bill Dwyer and Owney Madden. It was a dangerous game to say the least. When word got back to Dwyer and Madden, they were livid, especially since Legs was trying to pull others, namely Higgins and Rothstein, into his disloyal scheme. In his Times Square office, Dwyer, normally in control, was said to have yelled at the top of his lungs that Legs Diamond was “nothing more than a river pirate come to New York City” and promised “that no good son of a bitch will get his, if it’s the last thing I do.”

  On a cool October afternoon in 1924, Legs was driving his newly purchased Dodge sedan up Fifth Avenue on his way to the Bronx to meet Dutch Schultz, another Combine-affiliated gangster whom Diamond was trying to lure into his camp. Legs never made it to the Bronx that day. At 110th Street in Manhattan, a hulking black limousine pulled alongside his car. The long barrel of a shotgun poked out from a back window on the passenger side and opened fire. Two blasts aimed squarely at Legs sprayed the side of the car. Diamond ducked and floored the accelerator simultaneously, sending his Dodge careening down the street. Once he regained control of the car, he headed straight to nearby Mount Sinai Hospital, where he stumbled out of the car and through the emergency entrance. He had shotgun pellets embedded in the side of his head and in his foot. When police arrived at the hospital, they found Legs with his head and foot wrapped in gauze. Pen and notepads poised, they asked about the shooting. Diamond gave his version of the standard gangster response.

  “I dunno a thing about it,” he said. “Why would anyone wanna shoot me? They must of got the wrong guy.”

  Legs survived the attack and moved his operations to Greene County, in Upstate New York, where he would continue for years to pose a challenge—if not an outright threat—to the otherwise hegemonic operations of the Combine.

  The fact that Diamond’s rivals were able to run such a sprawling operation with only the occasional intra-ethnic menace from renegades like him was a testament to the organizational skills of the New York Irish Mob. Legs worked alone because the Combine had early and successfully incorporated all potential dissident factions. There was nowhere for a rival to turn for support. Lone wolf Irishmen like Legs would be an annoyance throughout the duration of the Combine’s existence, but the biggest and most dangerous potential threat—the Mafia in New York—had already been co-opted.

  By making Frank Costello and Lucky Luciano ranking members of the Combine, the Irish Mob had forestalled a possible inter-ethnic showdown in New York. Luciano, in particular, was brought into the fold for one specific reason: to handle the old Mustache Pete’s of the Maranzano and Massaria families who formed the foundations of Cosa Nostra in the New York area. Luciano went about playing both sides against the middle until the two families went at each other in the famously bloody Castellamarese War later in the decade, but for years Lucky successfully kept the old guard Sicilians from encroaching on the Combine’s rum running and bootleg territory.

  This ethnic accommodation forged in New York in the early years of Prohibition proved to be an anomaly. Elsewhere around the United States, the bootlegging business was a more wide open affair; bloodshed was increasingly the most common by-product of a market regulated not by tariffs and taxes, but by intimidation, gunfire, and what few piddling arrests federal Prohibition agents were able to make. In the streets, the law of supply and demand prevailed: There was money to be made, and whoever had the muscle and the skills to seize control would rule the roost.

  At the root of this fierce competition was a smoldering ethnic rivalry that had been bubbling within the country’s criminal underworld for at least thirty years. Ever since the first wave of Sicilian immigrants began arriving in American cities, Italian and Irish gang forces had been headed for some kind of showdown. This rivalry had reared its head before, in la
bor battles, political skirmishes, and, most notably, in the interaction between corrupt Irish cops and early adherents of the Mafia, or the Sicilian Black Hand, down in New Orleans.

  The idea that Irish and Italians in America would be at loggerheads was cruelly ironic. In many ways, the two immigrant groups were like cousins who trod many of the same paths. Sharing the same religion, both groups felt the sting of discrimination and bigotry in the New World. They also shared a similar peasant heritage that contained a strong tradition of social interaction through song, drink, storytelling, and the give-and-take of political negotiation. In their attempts to get ahead, Irish and Italian immigrants often worked side by side, lived in the same neighborhoods, and inter-married as much or more than any two ethnic groups in the history of the United States.

  And yet, this very closeness guaranteed a level of competition that was inflamed by the wide open nature of underworld crime during the Prohibition era. In many cities large and small, war was declared between bootlegging consortiums looking to corner the market. Nearly every ethnicity in America got involved, but Irish and Italians, because they were more successfully entrenched in the fabric of big city life than more newly arrived groups, tended to be the overseers of these underworld organizations.

  The history of Prohibition is rife with ethnic mob wars in cities like Cleveland, St. Louis, Kansas City, Boston, Philadelphia, and Baltimore, but nowhere was the Irish-Italian rivalry more pronounced than in the city of Chicago. In Chicago, there was no organizing Combine like the one Dwyer, Madden, and Hines created in New York—at least not one that maintained peace for any length of time. Hostility and brute force were the primary tools of negotiation in the former Mud City, where King Mike McDonald had once ruled a gambling empire, and Hinky Dink and Bathhouse John presided over the vice rackets. The days of the First Ward Ball, when all of the city’s criminals came together under one tent, had given way to a more violent form of underworld interaction. Throughout the middle years of the Roaring Twenties, Gangland Chicago would come to define the rapacious, violent nature of Prohibition. And it would bring to a head, once and for all, a rivalry between Irish gangsters and Italian mafiosi that would determine the course of organized crime in America for generations to come.