Paddy Whacked: The Untold Story of the Irish American Gangster (8 page)

Sullivan was born in Five Points on July 23, 1863 and lived with his mother, six siblings, a stepfather, and three boarders in a run-down tenement apartment at 25 Baxter Street, just south of Paradise Square. His mother and father were immigrants from Landsdowne, County Kerry who, upon their arrival, were among the very poorest of the Five Points poor. Sullivan’s stepfather was a ne’er-do-well who contributed little to the survival of the family, leaving Tim, the oldest, as the man of the house.

Young Tim became quite an entrepreneur. He worked as a newspaper delivery boy and had by his early teen years developed a network of contacts among the city’s other newsboys and periodicals dealers. He formed his first business enterprise by giving orphans and runaways just starting out as newsboys their first stack of papers free, both to help the struggling street urchins and to win their loyalty. It worked. “Every new newspaper that came out, I obtained employment on, on account of my connection with the newsdealers all over the city of New York,” Sullivan recalled years later. He took most of what he earned home to his mother but still had enough left over to expand his business interests. His saloon on Chrystie Street was the first of four that he opened in and around the Sixth Ward; one of them, across from the Tombs Police Court, became a center of political activity in a sprawling district that included the city’s primary center of vice, the Bowery.

Sullivan was a towering, bigheaded, and gregarious Irishman with a loquacious manner. He was sentimental and generous. In 1886 he established a fund for delivering shoes to the ward’s sizable homeless population. From that point on, noted the
New York Herald
, the “young element” in the district “hailed him as their chief.” By the age of 23, as a result of his popularity in the ward, Sullivan was put forth as a candidate for the state assembly. Despite his youth and inexperience, he won by a landslide. On the night of his victory, a large crowd gathered at his campaign headquarters on the Bowery and chanted loudly, “Hurrah for Big Tim! Hurrah for the Big Fella!”

Within a few short years, Sullivan was the most powerful politician in lower Manhattan. Although an avowed teetotaler with not so much as an arrest for loitering on his record, his power was based largely on his mastery of the art of the shakedown. Local merchants, gambling bosses, pimps, liquor vendors, saloon keepers, and gangsters were required to buy tickets to Big Tim’s clambakes, chowder suppers, and summer outings at College Point. Like John Morrissey before him, he acquired great influence within the halls of Tammany for his ability to deliver votes, which was based on the principle of the repeater, or as the Big Fella called them, “guys with whiskers.” In a speech delivered on behalf of a recently elected alderman, he explained his technique of altering a hoodlum’s appearance so that he could vote multiple times undetected:

When they vote with their whiskers on, you take ’em to a barber and scrape off the chin-fringe. Then you vote ’em again with the side-lilacs and mustache. Then to the barber again, off comes the sides, and you vote ’em a third time with just a mustache. If that ain’t enough, and the box can stand a few more ballots, clean off the mustache, and vote ’em plain face. That makes every one of ’em good for four votes.

By the onset of the Gay Nineties, Sullivan had replaced Morrissey in the hearts and minds of Tammany stalwarts as the new Irish vice lord. Only Big Tim was a newer, improved version with few of the flaws; he had a clean criminal record, he didn’t drink, and he had no desire to be loved, coddled, or even accepted by the WASP elite. Through guile, charity, personal magnetism, and a willful manipulation of the ward’s rougher elements, Sullivan was in the process of establishing a domain of power that would render the WASP elite irrelevant.

However, there was a new challenge on the horizon that was much more immediate than social ostracism or judgement by the uptown swells. And that had to do with a new generation of immigrants arriving in America’s big cities. For decades, the Irish had occupied the lower rungs of the immigrant ladder virtually unencumbered. They had begun the process of institutionalizing a system by which they would climb that ladder, a process based in part on the symbiotic relationship between the gangster and the politician. By 1890, the results of this process were only beginning to be seen; through patronage, the Irish had begun to dominate civil service jobs in the fire department, police department, and elsewhere in the city. They had begun to rise.

Of the newer immigrants now arriving, the most ambitious were the Italians; they were also, by far, the greatest in number, with tens of thousands arriving in many of the same cities and locales where the Irish had already paved the way. Like the Irish before them, these immigrants came with little more than the clothes on their backs. What some of these immigrants did bring, however, was their own criminal tradition of commerce and respect rooted in the villages of Sicily. This tradition was known to some as the
onorata societa
(the honored society), to others as
la mano nera
(the Black Hand), and to others simply as
la mafia
.

Like the American gangs founded by a generation of Irish famine immigrants and their offspring, the mafia was based at least in part on intimidation, the threat of violence, and even murder. The Sicilian version in America would come to be known as
cosa nostra
(our thing) and would be comprised of
gli amici
(the friends), who had to be Italian-born and
gli amici degli amici
(the friends of friends), extended business associates who could be non-Italian. The mafiosi even had their own version of racketeering, which in Sicilian was called
pizzu
. Defined literally,
pizzu
meant the beak of a small bird, such as a canary or a lark. Back in Sicily, when the mafia don referred to
fari vagnari a pizzu
(wetting the beak), he was talking about the same system of tribute that already existed throughout the Irish American underworld.

The manner by which this arcane Sicilian tradition infiltrated, ascended, and operated alongside the world of the Irish mobster would come to define the American underworld over the next century. But first there would be inevitable power struggles. Merciless, bloody, rooted in a street-level explication of brute capitalism in its purest form, this war of the underworld would play itself out in many domains. But the saga’s earliest and most defining confrontation would take place in a unique and colorful locale, way down south amidst the festering swamps of Southern Louisiana, in a port city world-renowned for its licentiousness and crime—the city of New Orleans.

CHAPTER
#
Two

2. a perfect hell on the earth

L
ate on the night of October 15, 1890, Police Superintendent David C. Hennessy stepped out into the damp New Orleans night and pointed himself toward home. He was accompanied by another man, William J. “Billy” O’Connor, a retired policeman, friend, and captain of the Boylan Protective Police, a private detective agency closely aligned with the New Orleans police department. Earlier that night, Hennessy and O’Connor had adjourned a meeting of the Police Board at old City Hall. Afterward, the two men stopped by Hennessy’s office in the Central Police Station, located at South Basin and Common Streets on the outer fringe of the French Quarter. By the time the two men left the station, it was near 11
P
.
M
. O’Connor suggested to the chief that he accompany him at least part of the way home; he knew there had been threats against Hennessy’s life by the city’s criminal element. Hennessy, a proud man, said nothing, which was his way of saying “okay.”

“We’re about to get a soaking,” said Bill O’Connor, looking out from under an awning at the steady drizzle. Earlier that day it had rained so hard that male pedestrians were inclined to take off their shoes and roll up their pants before crossing the muddy streets from one wood-planked sidewalk to another.

“We best go along Rampart,” suggested Hennessy. “The sidewalks on Basin Street are very bad.”

Holding umbrellas overhead, the two men walked through the dense mist. An uncharacteristic quiet hung over the Vieux Carré. Even in the off-season, the French Quarter normally bustled with daytime merchants and hustlers. The night brought about a different kind of activity—and not just the prostitutes and drunkards who lingered in the shadows. According to many denizens of the Quarter, the area was haunted by the ghost of Jean Lafitte, the notorious French pirate, and other spirits conjured up by Marie Laveau, the recently deceased voodoo priestess. Some people believed that if you listened closely, you could even hear the screams of those killed during the great fire of March 1788, when a lighted candle from the altar of a Catholic chapel burned down this section of the city, paving the way for the construction of the French Quarter.

On this night, there were no screams. No sound at all. Even the ghosts seemed to be in hiding, perhaps in anticipation of the trouble that this dark, misty night seemed to portend.

Hennessy and O’Connor approached the corner of Rampart and Poydras streets and came upon the gas lit exterior of Dominick Virget’s Oyster House. The Chief suggested they stop for a snack.

“Why not?” agreed O’Connor.

The two men ducked out of the rain and took a seat in the back of the room. Each ordered and consumed a half dozen oysters on the half shell. Hennessy, thirty-two years of age, was a conservative, young man and a teetotaler; he washed his oysters down with a glass of milk.

By the time they finished and headed back out into the night, the rain had let up a bit. The two men continued walking along Rampart Street until Hennessy said to his friend, “There’s no need to come any further with me now, Bill. You go on your way.”

They shook hands and went their separate ways—O’Connor splashing across the street in the direction of the Mississippi River, Hennessy in the opposite direction toward his home at 275 Girod Street.

The area where Hennessy lived was not the best. Rooming houses, dilapidated cottages, and shanty housing for poor blacks, Irish, and Italians lined the streets. The only reason Hennessy, a man of stature and notoriety in the community, lived in such modest surroundings was because his mother insisted. She had lived in the same house for some time and grown attached to the area.

A lesser man might have been frightened or at least concerned walking along the neighborhood’s dark, deserted streets late at night, but David C. Hennessy was no ordinary citizen. In his years as a lawman in New Orleans, he had established a reputation as a fearless crime fighter. He was especially well-known as the man who had single-handedly taken on the Sicilian stiletto and vendetta societies, also known as the mafia, which had only just begun to emerge as a mysterious new criminal threat with tentacles that stretched throughout the city.

As Hennessy approached his house, a figure emerged out of the drizzle. It was a teenage boy, who looked at Hennessy, whistled loudly, and then continued on down the block: strange, but no big deal. Hennessy thought little of it. He walked up the steps to his porch and slipped a key into the front door.

Just then, a fusillade of gunfire erupted, rumbling through the night like rolling thunder. Hennessy barely had time to turn before he was hit by a full volley: three heavy slugs ripped into his abdominal area, puncturing his stomach and intestines; one entered his chest, piercing the membrane around his heart; a fifth smashed his left elbow; a sixth broke his right leg; shotgun pellets riddled his entire body—torso, arms, legs.

Chief Hennessy writhed in agony. He heard the sound of his assailants scurrying away. Barely conscious and bleeding like a sieve, he drew his pistol and stumbled after the gunmen. As they approached the corner of Basin Street, Hennessy raised his gun and fired two shots through the thick gun smoke that hung over the street like cloud cover. As the men scattered, Hennessy got a decent view of the shooters; there were many, possibly five or six. In his haste, Hennessy tripped on the steps of a secondhand goods store and fell to the ground; he forced himself to his feet and staggered twenty yards to Basin Street, where he fired another shot. He saw figures running in the smoke and fog and tried to follow, but his strength was dwindling fast. In front of a frame house at 189 Basin Street, he called out, “Billy, Billy!” and crumpled to the ground.

Bill O’Connor was walking on Girod Street when he first heard the rumbling fusillade of gunfire. He immediately turned and ran toward the noise, becoming momentarily disoriented in the darkness and fog. As he approached Basin Street, he saw gun flashes and heard more shots. While dashing toward the commotion, he came upon a patrolman.

“Which way did they run?” O’Connor shouted.

“Uptown, I think,” answered the cop.

They both ran toward Basin Street, just in time to hear Hennessy call out, “Billy, Billy!”

O’Connor and the patrolman found Hennessy lying in the cobblestoned street, blood oozing from multiple wounds.

“They gave it to me good,” said the chief, “and I gave it back the best I could.” This statement seemed to take the last of Hennessy’s strength. He gurgled with pain.

O’Connor held the chief in his arms. “Who, Dave? Who gave it to you?”

Hennessy motioned for O’Connor to lean in closer. O’Connor bent down, and the chief whispered, “Dagos.”

Dagos
. O’Connor knew what the word meant. Italians. Mobsters. Mafiosi. O’Connor hurried to a nearby grocery store and telephoned for an ambulance. Hennessy was rushed to Charity Hospital, but it was obvious there wasn’t much hope. By noon the following day, the chief was history.

News of the assassination wafted through the streets of New Orleans like a malodorous breeze. David Hennessy had been a popular man in the Crescent City. Throughout his law enforcement career, he frequently made the newspapers and was especially lionized by the city’s Irish population, who embraced him as one of their own. He was young and square-jawed, with a graceful, confident manner—attributes that would come to be known by a later generation of Americans as “Kennedyesque.” And like the dashing, young president for whom that term was coined some seventy years later, David C. Hennessy was gunned down in the prime of his life by an assassin’s bullet.