Paddy Whacked: The Untold Story of the Irish American Gangster (9 page)

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.

The common belief that the Irish were drawn to New Orleans by the city’s inherent Catholicism is only partially true. Mostly, they came because they were tricked into it. Throughout the late 1840s and early 1850s, Louisiana cotton merchants recruited Irish immigrants in Liverpool, where many had first disembarked to flee the famine. Taking advantage of the immigrants’ ignorance of American geography, the brokers sold them tickets to New Orleans with the assurance that it was only a few days journey to New York, Boston, Albany, or wherever else might have been their desired destination. The Irish arrived by ship in a land of alligators, swamp rats, strange fruits and vegetation, incessant subtropical sun, and humidity. Some never recovered from the initial shock.

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

The employer’s enthusiasm was based on avarice and greed. In the antebellum South, slaves cost money. The slave owners considered their Negroes too valuable to risk at such dangerous work (especially their top-of-the-line house Negroes). Better to get an Irishman, who had no choice but to accept the rough and dirty work. If an Irishman died on the job, he could be replaced at no cost, since starving Paddies were arriving by the boatload on a near daily basis.

The biggest project of the era was the New Basin Canal, a navigational outlet conceived by merchants and promoters to link Lake Pontchartrain with the Mighty Mississippi. Irish labor from all over the country was recruited. Over a four-year period, hundreds, if not thousands, of Paddies slipped into the cypress swamp and dug on a straight line toward the lake. Given the rampant cholera, malaria, and yellow fever, everyone knew the mortality rate would be high. The precise cost in terms of human lives can never be known, for even contemporaries argued over the number of diggers who died. One account stated that 3,000 Irishmen were buried along the canal, while another quoted a figure closer to 30,000. A popular song of the era put the number somewhere in between:

Ten thousand micks, they swung their picks,

To dig the New Canal

But the choleray was stronger ’n they,

An’ twice it killed them awl.

The work conditions were disease-ridden and abysmal, and the living environment for the workers wasn’t much better. At the height of the post-famine “invasion,” destitute immigrants moved into shacks abandoned by Negroes in an extremely poor section of what was known as the Third Municipality. The city at the time was divided into three municipalities, each with its own council (board of aldermen) and executive officer (called a recorder but, in effect, a police court judge). The First Municipality was the Latin Creole district, the Second Municipality or uptown area was regarded as the American and progressive quarter, and the Poor Third was for immigrants—mostly German and Irish.

The crowded, unsanitary living conditions were a nightmare. In the spring of 1847 the
Times Picayune
reported that “a small house in Dauphine Street contains about fifty immigrants, worn down by starvation and disease to mere skeletons…some of them…eating straw that they gathered in the street.” Newly arrived passengers on the plague ships were described as “food for fever,” which certainly rang true in 1853, when one of many yellow fever epidemics devastated the city. Yellow fever is a deadly virus transmitted through mosquitoes; once bitten, the victim carries a parasite in his red blood cells that causes fever, jaundice, physical debilitation, hemorrhaging, and possibly death.

The disease originated in the swamps among the working men and then spread. There was no cure. Before the sweltering summer of 1853 had come to an end, twelve thousand people died, of whom one-third were Irish. Among working men, seven out of ten fell to the sting of yellow jack.
²

Disease led to hunger, hunger to despair. Those lucky enough to survive were left emotionally and spiritually scarred. The famine refugees acquired some of the characteristics of a hunted animal. One of the many who had been reduced to begging on Canal Street expressed his plight to a reporter: “What’ll I do!? I have no place to go and no means but what I beg.”

Out of this bitch’s brew of slave labor, disease, and squalor arose the city’s criminal underworld. New Orleans had always been a wild and licentious place, a haven for pirates, international adventurers, riverboat gamblers, professional snake oil salesmen, and the like. The great Irish rabble merely put their own spin on things.

The earliest record of gang activity in the city can be traced back as far as 1834, when a back-of-town gang called the Corkonions waged a bloody war with another Hibernian gang known as the United Irishmen. Like the early Five Points gangs in New York, the Corkonions and United Irishmen were offshoots of Ireland’s rural terror societies, which in recent years had given rise to the Young Ireland Movement, a determined effort to free Ireland from the yoke of British rule. In the Old Country, these gangs were engaged in a war of resistance. In New Orleans, their activities usually revolved around labor-related issues. The war between the Corkonions and the United Irishmen had been fomented by a sugar refinery company that wanted a canal dug and encouraged underbidding between gangs of Irish diggers. In February 1834, the gangs turned on each other, resulting in four deaths and numerous arrests after the City Guard was called in to quell the riot.

By the 1850s, Irishmen had themselves become labor contractors, and the labor riots were mostly a thing of the past. Gang activity was now more commercial, and it was generally centralized in one area: the highly colorful Gallatin Street district of gambling dens, concert-saloons, dance houses, and abundant bordellos.

The district is long gone now, with little or no trace of its ribald past, but from the early 1840s to the mid-1870s, Gallatin Street thrived on vice and sin of every variety, with nary a legitimate business in sight. In the words of author Herbert Asbury, the district “was completely filled with barrelhouses where for five cents a man could get not a meager tumblerful of liquor, but all he could drink; dance houses which were also bordellos and gin mills; and sailors’ boarding houses from which seaman were occasionally shanghaied…. From dawn to dusk the district slept off its debauches behind closed shutters; from dusk to dawn the dives roared full blast, and Gallatin Street was crowded with countrymen, sailors, and steamboat men seeking women and diversion. And they in their turn were sought by a horde of harlots, sneak thieves, garroters who openly carried their deadly strangling cords, and footpads with slung shots looped about their wrists. There was crime and depravity in every inch of Gallatin Street; the stranger who entered it at Ursuline Avenue with money in his pocket and came out at Barracks with his wealth intact and his skull uncracked had performed a feat which bordered on the miraculous.”

The most notorious gang on Gallatin Street went by the name the Live Oak Boys, so called because they carried what the New Orleans
True Delta
described as “elaborately carved oaken cudgels.” These cudgels, no doubt, were in fact shillelaghs, the weapon of choice for the rural resistance societies back in the Old Country.

The Live Oaks were formed in 1858 by Red Bill Wilson, a well-known criminal figure in the district who carried a knife concealed in his bushy, red beard. The gang was not a large, politically oriented organization like those found in New York, but rather a loose collection of rowdies with no recognized leaders. Among the gang’s members were a tough bunch of fighters, including Bill Swan, Jack Lyons, Jimmy O’Brien, his brother Hugh O’Brien, and Hugh’s sons, Matt and Hugh, Jr.

It was the O’Brien family who achieved the greatest infamy and brought the Live Oak Boys into the realm of legend. In 1867, Jimmy O’Brien was the first to enter the annals of New Orleans criminal lore when, after a night of drinking and thieving with fellow Live Oak Henry Thompson, he sought to rob Thompson in his sleep. Thompson awoke to find O’Brien rifling through his pockets. When he struggled, Jimmy calmly pushed a knife deep into Thompson’s heart and continued his search. Jimmy O’Brien might have gotten away with this murder if he hadn’t been seen by a Negro and a small boy. Their testimony at trial was enough to seal O’Brien’s fate; he was convicted and sent to the penitentiary for twenty years. He died in prison.

Next up was Jimmy’s brother Hugh, who stole a rowboat and set out from the Dumaine Street wharf with dreams of becoming a pirate. He was killed when he tried to rob a fisherman on the Mississippi River.

Hugh left behind his two sons, Matt and Hugh, Jr., who were then nineteen and twenty-one years old, respectively. Unlike the thousands of Irish immigrants who slaved away in the swamps every day, the O’Brien brothers and the rest of their crew were known for never having performed a stroke of honest work. Their nights were devoted to carousing and brawling in Gallatin Street dives, their days to sleeping, lounging, and planning new crimes. They were especially feared and disliked by the dance-hall proprietors; a night rarely passed when they didn’t raid one or more of the district’s resorts. Usually, when the Live Oaks came charging into a dance house brandishing their oaken shillelaghs and looking for a fight, the bouncers, bartenders, musicians, and customers rushed out the back door. The gangsters were left to wreck and rob the place at their leisure.