Paddy Whacked: The Untold Story of the Irish American Gangster (23 page)

With his new lease on life, Diamond 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.
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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 labor 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.

CHAPTER
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Five

5. the dagos vs. the micks

D
ean O’Banion was the boss of all bootleggers on Chicago’s North Side. A combination of gumption, brutality, foresight, and likability got him there. People liked O’Banion because he was friendly, gregarious, and always on. A stout, cheery-faced Irishman with twinkling, blue eyes, he would always doff his fedora upon meeting a lady and would greet men with a slap on the back and a jovial, “Nice to meet ya, swell fellow” (he regularly called strangers “swell fellows”). A former singing waiter in various North Side saloons in his youth, he was sentimental and, at times, kindly to the point of piety. He gave away money, food, and clothing to indigent children. He was a weekly attendee and financial contributor to Holy Name Cathedral, where he had been a choirboy. Among his followers, O’Banion’s generous and upright nature inspired a fierce loyalty. “He was a good man,” said his wife, Viola, after he was gone. “He was fun loving, wanting his friends around him, and he never left home without telling me where he was going.”

Dean O’Banion also killed people, which was another reason his friends and loyalists toed the line. Once, when a small-time gangster named John Duffy called him with a problem, Deanie, as he was sometimes called, immediately offered to help. Duffy, it seemed, had gotten into a violent, drunken quarrel with his wife of eight days; while she was in bed, he shot her twice in the head and left her for dead. After the drink wore off and Duffy realized what he’d done, he panicked and called a fellow hoodlum, who immediately put in a call to his boss, Dean O’Banion.

O’Banion knew Duffy as a none-too-swift gunman out of Philadelphia who had wandered aimlessly into Chicago and offered his services as a tough guy. By helping pull off a few incidental jobs for the North Side gang, he’d become a hanger-on to the O’Banion bunch. Now he had murdered his wife, which was going to attract the cops whether or not the lowly gangster left town. Dean immediately realized that the only way to cut off an investigation at the pass was to take John Duffy for the proverbial one-way ride.

Duffy was told to wait on a particular Chicago street corner. Around eight o’clock, O’Banion and another man drove up in a Studebaker. By this time, Duffy was nearly hysterical. “I need a car to get outta town,” he pleaded. “And I need money. I need at least a grand.”

“Sure,” said O’Banion from behind the wheel. “I’ll give you a grand. I’ll give you more than that. Get in.”

Witnesses saw John Duffy get in the car. The next time anyone saw the small-time hoodlum and wife killer was in a snow bank on a road out of town. His body was found with three bullet holes in the head from a .38-caliber revolver. Another witness had seen three men dumping Duffy’s dead body in the snow bank and initially identified one of the men as Dean O’Banion. But when the witness learned who Dean O’Banion was, he developed a bad case of amnesia.

When O’Banion heard the cops wanted to talk to him about the murder, he told a reporter, “The police don’t have to look for me, I’ll go and look for them. I’ll be in the state’s attorney’s office at 2:30
P
.
M
. Monday afternoon…. I can tell the state’s attorney anything he wants to know about me…. Whatever happened to Duffy is out of my line. I never even saw Duffy. I don’t mix with that kind of riffraff.”