Paddy Whacked: The Untold Story of the Irish American Gangster (19 page)

Among Eastman’s many minions was a fresh-faced, physically unimposing Jewish boy named Arnold Rothstein. Through Monk Eastman, Rothstein was introduced to Sullivan at his political headquarters on the Bowery.

“You’re a fine-looking young Jew boy,” said Big Tim.

“Thank you Mister Sullivan,” responded Arnold.

“They’ll be no ‘mister’ here,” said the boss. “Call me Tim.”

Barely sixteen years old, Rothstein worshipped the Tammany leader who seemed so magnanimous in his dispensation of favors. A talented billiards player and gambler with a good head for numbers, Rothstein became a regular at Sullivan’s Hesper Club headquarters. He was particularly useful as a translator for the district’s many Jewish immigrants who had just arrived from Poland and Austria. In later years, after Rothstein amassed a fortune through gambling profits, bookmaking, and loan-sharking, he would become a dominant financier of the underworld. He never hesitated to cite Big Tim Sullivan as his mentor, the man who made it all possible.

Given The Big Fella’s stature for so many years, his decline and death was sad and ignominious. His decline started in 1912, when Sullivan was diagnosed with tertiary syphilis, an unfortunate disease for a man who often bragged over the years that he was clean as a whistle in his personal habits. He started to become forgetful and, at times, delusional; he was losing his mind. In the summer of 1913, he was institutionalized for a few weeks at a sanitarium, then moved to a house on Eastchester Road in the Bronx. It was necessary to assign several guards to watch over him. Occasionally Big Tim eluded his guards and frequented his old haunts along Broadway and the Bowery. Patrons would see a pajama-clad man in the corner of a saloon and say, “My God, that man looks like Tim Sullivan. Could it be? Is that Tim Sullivan?” And then,
poof
, in the bat of an eye, the man would be gone.

Finally, on a September night, Big Tim disappeared after exhausting his guards by playing cards with them all night. Later, the body of a fifty-year-old man was found on the rails near the Westchester freight yards. How it got there, nobody knew. An engineer on duty claimed that the man was already dead before he was run over by a train. The corpse lay in the morgue for a few days before it was identified as Timothy Daniel Sullivan.

Big Tim’s funeral was attended by everybody who was anybody—three U.S. senators, a delegation of twenty members of the House of Representatives, justices of the New York Supreme Court, the Police Commissioner, the boss of Tammany Hall, not to mention assorted shoulder hitters, homeless people, and mobsters. They were sorry to see him go, but they might have been even sadder to learn that old Dry Dollar Sullivan would not be around to truly enjoy the fruits of his labors. In the following decade, Prohibition would transform the underworld, bringing in untold riches—and Big Tim, the man who helped lay the foundation, never even made it to Opening Day.

King of the Rum Runners

The Eighteenth Amendment, which prohibited the manufacture, sale, or consumption of alcoholic beverages, was ratified by the U.S. Congress on January 19, 1919. One year later, the laws that would regulate enforcement of the amendment went into effect. The laws became known as the Volstead Act, so named after Andrew Volstead, the Minnesota congressman who first introduced the legislation in the House of Representatives. The Volstead Act laid out the nitty-gritty details of Prohibition; it also spelled out the exceptions, requiring a government permit, which included sacramental wine, medicaments containing alcohol, hard liquor if prescribed by a physician (but not to exceed a pint per patient within any ten-day period), alcoholized patent medicines unfit for beverage, flavoring extracts, and syrups. The penalties for violations of the Act ranged from a five-hundred dollar fine for a first offense to a two-thousand dollar fine and five years of imprisonment for repeat offenders.

To the country’s immigrants and their offspring—be they Irish, German, Scandinavian, Greek, Polish, Jewish, or Italian—the Volstead Act appeared to be part of a larger assault on life and liberty that began with the earliest formations of the Know-Nothing Movement and emerged, years later, as the Anti-Saloon League. If American born citizens who decried Prohibition tended to view it as a puritanical regression founded on the country’s Protestant origins, the immigrants saw it as that and something more—a political movement that, behind the cloak of cultural purity and good Christian values, was determined to seize the levers of power and exterminate dissent through governmental mandate.

It took a while for the full effects of Prohibition to become known. Contrary to historical revisionism, the forces of organized crime did not immediately swoop down on an unsuspecting public. There was, initially, no system in place for importing illegal alcohol, manufacturing product, or distributing it through speakeasies and so on. That all came later, after it became abundantly clear that many Americans were determined to circumvent the law by distilling their own booze at home.

In the early months of Prohibition, U.S. cities abounded in shops that sold malt, hops, yeast, bottles, bottle-capping machines, rubber hosing, alcohol gauges, and other paraphernalia for home brewing. Economists estimated that the sums expended for brewing and distilling materials absorbed an inordinate portion of the country’s household budgets. More alarming than the expense was the degree to which average Americans were willing to cross the line and engage in criminal activity. It was a new twist on family values, best exemplified in a popular rhyme of the era:

Mother’s in the kitchen

Washing out the jugs;

Sister’s in the pantry

Bottling the suds;

Father’s in the cellar

Mixing up the hops;

Johnny’s on the front porch

Watching for the cops.

The problem with home brewing was that the end product was usually horrible. If the corks didn’t pop out of the bottle prematurely or the bottles didn’t explode before their contents matured sufficiently to drink, the result was often a mud-brown liquid, stinking sourly of mash and tasting like drain cleaner. As for the effect, one amateur brewer was quoted as saying “After I’ve had a couple glasses, I’m terribly sleepy. Sometimes my eyes don’t seem to focus, and my head aches. I’m not intoxicated, exactly, but merely feel as if I’ve been drawn through a knothole.” Bathtub gin wasn’t much better. Made with raw alcohol, water, glycerin, and juniper oil in a bathtub, its rancid taste was easily disguised in a fruity cocktail, but it often caused gastritis, heartburn, diarrhea, and other symptoms of acute alcohol poisoning.

Slowly but surely, the difficulties of manufacturing a palatable product at home made it clear to black market entrepreneurs that people were willing to venture forth and pay for the Real McCoy, whether it was legal or not.

Irishmen and Irish Americans were in a unique position to meet this demand. Many people of Irish descent saw the temperance movement and Prohibition as a direct assault on their very existence. The efforts of the Anti-Saloon League seemed to be aimed squarely at that aspect of Irish culture, which had for centuries revolved around the concept of the saloon as the central gathering place of the community, a place where political alliances were formed, stories passed on, friendships born, and old grudges either resolved or exacerbated. Furthermore, generations of Irish immigrants had made their living through the liquor business, which had been devastated by passage of the Volstead Act. Given this dual assault on life and liberty, many Irishman saw it as their cultural duty to violate both the spirit and the letter of Prohibition, especially when it became apparent that many citizens—from immigrants to upper crust WASPs—had no intention of abiding by what they perceived to be a silly and unenforceable law.

New York was by far the wettest city in the country, with a huge population of rich, poor, and working class who wanted to imbibe and were willing to pay for it. For those in the underworld who wanted to capitalize on the demand, the challenge was to devise a system for importing a top quality product, storing it, and delivering it to the consumer.

An early pioneer in this regard was a bespectacled, ruddy faced Irish American named William Vincent Dwyer. Born on Manhattan’s Tenth Avenue at a time when the area was ruled by two prominent gangs, the Gophers and the Hudson Dusters, Dwyer first made a name for himself as a dock walloper and stevedore with the International Longshoremen’s Association (ILA), a union that would prove to be a breeding ground for some of the toughest strong-arm men in the underworld. As a local bookmaker, Dwyer met and made friends with many underworld figures. He was neither a gang member nor a tough guy, but he was comfortable in the presence of violent men. More importantly, he knew how to cultivate muscle and use it to his advantage.

With his broad facial features and lumbering manner, Dwyer could have passed as a country farmer, but beneath the rather dull exterior was a true man of vision. Big Bill (as he would come to be known) saw from the beginning that the key to bootlegging was to develop a system whereby booze could be smuggled into the country free of harassment from Prohibition agents, the Coast Guard, and local police officials. Using money he had amassed as a supplier for a number of early garage-level bootlegging enterprises, Dwyer assembled a staff of businessmen and former gang members. He began to purchase what would eventually be a fleet of steel-plated speedboats equipped with machine guns, along with several seagoing rum ships. On shore, Dwyer’s organization purchased and maintained warehouses, trucks, garages, cutting plants, and wholesale outlets.

From two midtown Manhattan offices, one in the Loew’s State Building in Times Square, the other in the East River National Bank building on Forty-first Street, Dwyer threw his net far and wide. First, he established relationships with liquor suppliers in England, Canada, the Caribbean, and elsewhere. Then he devised a system for meeting liquor shipments at sea, off-loading the product, and running it ashore to islands and coastal cities, where it would be transferred by trucks to storage facilities in the New York area. From there, Dwyer shipped booze via Teamster convoys to many localities around the country, including Florida, New Orleans, Cincinnati, St. Louis, and Kansas City. In just a few short years, Big Bill Dwyer became the largest single distributor of illegal booze in the entire United States.

Using his uncanny ability to persuade otherwise upstanding citizens to join his operation, Dwyer established himself as overlord of Rum Row, a corridor of the outer-Atlantic where the transshipment of booze was a daily occurrence. His supremacy hinged on one major factor: He had the U.S. Coast Guard in his pocket. It was through a petty officer named Olsen that Big Bill found dozens of pliable coast guardsmen. Olsen would bring ashore fellow shipmates whom he felt might be open to a bribe. At Dwyer’s expense, the guardsman would be treated to a night of revelry under the lights of Broadway; a sumptuous dinner, theatre tickets, a girl, and a hotel suite usually did the trick. By the time the bribe was tendered the following day, the guardsman was more than willing. An enlisted man, after all, only earned a grand total of $126 a month; a warrant officer at sea, $153. Dwyer might have offered ten times that much, if the guardsman was able to bring additional officers into the fold.

“Guardies” and other military men liked to drink, as did the police and even a few Prohibition agents. Big Bill understood this. His ability to bring coast guardsmen, coppers, and federal agents into the operation underscored a fact that would remain true throughout Prohibition’s bloody thirteen-year run: None of it would have been possible without the acquiescence of a significant portion of America’s law enforcement community.

Dwyer saw himself as a businessman, not a gangster. As the money flowed in, he diversified. He purchased hotels, race tracks, restaurants, nightclubs, and two Miami Beach gambling casinos. He established the New York and American Hockey clubs, virtually introducing professional ice hockey to the United States. He entertained regally at his suburban estate in Belle Harbor, Long Island, which he shared with his wife and five children.

No matter how wealthy Big Bill became, however, he could not resolve one vexing problem. He may have controlled Rum Row, and he had warehouses under armed guard to store his booze, but he was vulnerable when it came to the transportation of liquor via truck from one locale to another. In the early years of Prohibition, gangsters who had once been under the thumb of the political bosses started to become uppity. The profits from illegal booze were too good to pass up. Thus, America’s backroads became lawless no-go zones as renegade gangs began hijacking liquor shipments, stealing the booze, and outletting it themselves.

To Dwyer, the problem was clear. Somebody had to organize the underworld. Big Bill realized he could not do this himself; he was not a tough guy or a gangster. He needed a major underworld partner that he could trust. An opportunity presented itself in early 1924 when two of Dwyer’s shipments were hijacked in Upstate New York. The first incident was a warehouse robbery in which sixteen thousand dollars worth of booze was pilfered, the other a truck hijacking in White Plains in which Dwyer lost twenty-five thousand dollars worth of product. Dwyer put pressure on local cops to do something about it. As a result, a gang of five men were arrested for both robberies. Among this group of men was a name Dwyer recognized.