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
Late 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.
The shock of Chief Hennessy’s murder gripped the city and indeed the nation. The fact that he had been killed by the mafia, as reported in the New Orleans Times Picayune, the New York Times, and elsewhere around the United States, was a red flag in the face of God-fearing, law-abiding citizens throughout the land. In recent years, sensationalistic tales of the mafia had enflamed the anti-immigrant sentiment that bubbled below the surface of the American republic since before the famine ships arrived from Ireland. Only now the new “scum of Europe” were a strange, olive-skinned breed from the Mediterranean believed to be shrouded in secrecy and a tradition of criminality.
Among lawmen who had made a name for themselves as experts and pursuers of this new criminal scourge, none was more vaunted than David Hennessy. His exploits had brought him national attention. He was a hero.
Of course, as with most heroes, the image put forth was only half the picture. In the months following Hennessy’s death, interesting facts would begin to emerge about his career and his involvement with the city’s criminal underworld. For those who cared to know the truth, a more complex reality took shape. Hennessy, it seemed, was not a plaster saint after all; his life had been marked by tragedy and violence. He was the son of a cop—a cop who had himself been murdered under mysterious circumstances. Years ago, Hennessy had even quit the New Orleans police force in near disgrace only to be politically reappointed. And most surprising of all, contrary to his reputation as a crusader against the mafia, he had recently gotten embroiled in a violent rivalry between two Italian crime factions in the city. For mercenary reasons, the chief had aligned himself with one family against the other, which may have led directly to his death.
The fact that Hennessy’s true legacy was messy should have been surprising to no one. Being a policeman in the city of New Orleans meant that, unless you had your head in the sand, you developed an intrinsic understanding of—if not a working relationship with—the city’s criminal class. It had been that way ever since the early population of Nouvelle-Orléans was deliberately fleshed out with thieves, vagabonds, and prostitutes released from French dungeons. (Who else would want to live in the middle of a swamp?) From the beginning, the city’s institutions were founded on a kind of interpretive morality that would buttress the careers of untold pirates, slippery politicians, gamblers, madams, gangsters, shady entrepreneurs, and ambitious policemen at all levels of the force looking to consolidate power and supplement their meager incomes.
David Hennessy may have been a shining light to some, but he was still a product of his environment; his mentality and ambition were a manifestation of the city’s unique moral universe. His mastery of the bureaucracy and his penchant for self-promotion were second-to-none. That he achieved national stature was no small accomplishment for someone so far from the commercial nerve centers of the Northeast. A self-made man, he had risen from the muck of a star-crossed diaspora. The circumstances of his ascension—and his demise—were rooted deep in the narrative of the city’s Irish underclass.
Shamrocks, Shillelaghs, and Yellow Fever
Of all the strange and hellish locales in which the scattered Irish peasantry found themselves in the wake of famine and exile, none was more alien than the swamps of Southern Louisiana. Constructed on a spit of land between the Mississippi River and Lake Pontchartrain, the city of New Orleans was actually below sea level. The natural environment was fetid, with sweltering summers and extreme humidity; the surrounding area was prone to hurricanes, flooding, and infestations of exotic, disease-carrying insects.
Also in abundant supply in New Orleans was work. Since the city was erected in swamp land, its very survival was dependant on an elaborate system of canals and levees, many of which were only in the planning stages. Somebody had to dig those ditches. Paying an average $1.25 per day, the work was of the backbreaking, pick-and-shovel variety, with a staggering mortality rate. For this reason, the immigrants were initially welcomed in the city. The Times Picayune summed up the feelings of many potential employers when it editorialized about the arriving ships filled with “Irish, green as shamrocks…. What a valuable acquisition they will prove in carrying out[the city’s] internal improvement.”1
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