Navigate to Arts & Letters section

A New York Romance

In an excerpt from the new history ‘The Last Pirate of New York,’ a son connects his father’s Bensonhurst, Brooklyn, to the original American gangsters who preceded them

Rich Cohen
June 03, 2019
Illustration: Tablet Magazine
Illustration: Tablet Magazine
Illustration: Tablet Magazine
Illustration: Tablet Magazine

The Jewish people lived in exile. I lived in exile from that exile. The Jews were banished from the Promised Land close to 2,000 years ago. The characteristics of the people, which developed by accretion, resulted from that banishment. Restlessness, melancholy, longing. We were millennia into a bad vacation that would never end. (I’m leaving modern Israel out of this essay.) By the 20th century, the center of that exile, as far as my parents, grandparents, aunts, uncles, and cousins were concerned, was New York City, U.S.A.

My father, born and raised and educated and married in New York to my mother, who was born and raised and educated the same, was banished—it was a corporate transfer, but same difference—from New York in 1963. Five years later I was born on the alien shore of an icy freshwater sea—Lake Forest Hospital, Illinois. All my characteristics were Hebrew at a double remove: provincial and ignorant, troubled by an anxious sense of displacement. Is there a Yiddish word for the suspicion that there’s a party going on and you’re missing it?

My father reminded me of my condition constantly. Let’s say we’d gone to Harry’s delicatessen in our town and I’d ordered a corned beef on rye. Just before I took my first bite, he’d lean over and whisper: “They do that sandwich much better in New York.” Or let’s say we’d gotten tickets to Fiddler on the Roof at the Goodman Theatre downtown. Just after the overture, as Tevya stepped from the wings to talk about Tradition, he’d say, “This is the touring company. The real show is playing in New York.”

I felt I was living in a pseudo world, on the wrong side of a veil, separated from quality and authenticity. Everything I knew was a pale imitation. I made a fetish of New York as a result, as did my sister and brother. (I don’t think it’s a coincidence that we all ended up in the city.) I devoured the streets and stores when we visited my grandparents, or flew in for a wedding or bar mitzvah. We were referred to on such occasions as the Chicago cousins, as if our very existence had been set off by an asterisk.

To me, the holiest part of New York was not even Manhattan—it was Bensonhurst, Brooklyn, where my father grew up and where his stories were set. While my childhood was all manicured lawns and after-school activities and kids with names like Chris and Dennis, his childhood, in stories anyway, was red brick stoops and stickball, street corners, clubs rooms, gangs, clotheslines, and kids with nicknames: Who-Ha, Inky, Ben Worrier, Ben the Book, Zeek the Geek, and Gutter Rat, called that even by his own mother, as in, “Gutter Rat! Dinner!”

At bedtime, when other kids heard stories about the three little bears or the old lady in the shoe, my father told me about the gangster legends of Jewish Brooklyn, Louis Lepke Buchalter and Pittsburgh Phil Straus of the Brownsville gang Murder Inc., or Abe Kid Twist Reles, who turned rat and testified against his own mob. Later, while under police protection, he was thrown out the window of the Half Moon Hotel in Coney Island. The New York tabloids, so much better than The Chicago Sun-Times, dubbed him, “The canary who could sing but could not fly.” When trying to explain the ethnic makeup of his neighborhood, my father would say, “49 percent Jewish, 49 percent Italian, 2 percent other.”

I moved to New York straight out of college and began hanging around places my father talked about. I wanted to know if his stories were true and I also wanted to figure out why I was drawn to them. Everything I have written has, in a sense, been memoir. An early result was my book Tough Jews, the story of those old Jewish gangs and the story of my father and his friends, all members of the Warriors SAC (Social Athletic Club), who had a club room in Who-Ha’s basement on 85th Street between 21st Avenue and Bay Parkway. When you turned out the lights, the Indian painted on the floor glowed.

I continued to obsess not just about Jewish gangsters, but about the gangsters who came before them and served as their models and heroes, and the gangsters who came before that. The result was a 20-year effort to identify the first real New York gangster, whom, I believe, was a man named Albert Hicks, who was hanged on Bedloes Island—now home to the Statue of Liberty!—on Friday, July 13, 1860. Hicks was the last man publicly executed in New York. Twenty thousand people, anchored in sloops and pleasure craft, watched him die, turning the occasion into a raucous festival. Hicks, who had been the most feared man in the infamous New York slums, operated so long ago he was not even called a gangster—he was called a pirate. For me, his story brought to life something even more fundamental: the city as it had been a decade before my ancestors arrived from Russia. In writing The Last Pirate of New York, I tried to recover the topography of that lost city, Eden as it had been shortly after Creation. Everything that’s followed has merely been a kind of elaboration.


Manhattan island lies within an estuary. It’s where the currents converge, where a tidal wash (the East River) meets a cataract (the Hudson River, formerly called the North River), a flood of sweet water that runs down from the mountains. New York Harbor is a network of islands and coves, sea birds and arsenical green marshland, the sort that looks solid until you step on it. The Hudson, turbid and overshadowed by palisades, deepens below Manhattan. In the old days, every road on the island ended at the water, the sun rose at the foot of every street. Even now, when the fog rolls in, the waterfront is a sailor’s dream.

The town grew around the harbor. In the late 1600s, all housing and commerce were crowded in tight communion on the southern shore. It was a fishing village and a trading post, then a bustling military base, a fort on the edge of an unknown continent, then a small town, then a big town, then a small city, then a metropolis. In 1860, New York was among the richest ports in the world. Hundreds of millions of dollars of produce and machinery sat in its warehouses. Its coast was girdled by wharves; more than a hundred piers studded the East River and North River. The population doubled, then doubled again. Huge ships carried immigrant Irish and Germans into the city, a harbinger of the Jews and Poles and Russians and Italians who would follow. The inspection station at Ellis Island was not opened until 1892. In 1860, when this story takes place, emigrants were still landing in Manhattan and being processed through Castle Garden, an antique brownstone beside the Battery, where the Dutch had kept their big guns. As respectable neighborhoods turned into vast immigrant slums, Manhattan approached a mystical number—one million inhabitants.

The order of the day was simple: maraud. The names of these gangs are a hymn of colorful decay: the Whyos, the Chichesters, the Forty Thieves, the Plug Uglies, the Dead Rabbits, the Hudson Dusters.

Such a city is about traffic control: regular ferry service had quickly been established with every important river and sea port in the Northeast. In addition, there was a twice weekly run to Liverpool, England, huge steamships carrying the wealth of the American South, cargoes of cotton that powered Britain’s industrial economy. A black market in slaves flourished in the shadow of the harbor—pirates, violating the ban on the international slave trade, smuggled human beings from the west coast of Africa to New York, where they were sold, transferred and carried to Baltimore, Charleston, Savannah, and New Orleans. There was a booming trade in guns and narcotics. Mott and Pell Streets would soon be riddled with opium dens, sub-basement cellars with velvet couches where hopheads took the curling white smoke deep into their lungs, their stony eyes filling with clouds and clipper ships. Whatever you wanted could be had in the river-front taverns. On Water Street, you walked beneath the bowsprits of dozens of foreign ships, an artificial forest so thick it made a kind of canopy.

Merchants, bartenders and stage performers, bankers, cops and criminals, especially criminals—everyone lived off the sailors who pumped through the city like blood. Most of these criminals, and most of their crimes, were confined to a handful of neighborhoods, the famous slums of New York. The Five Points, Ur-ghetto of urban America, a sprawl of old barns and factories, tenements leaning this way and that. Charles Dickens had written about it:

Here, too are lanes and alleys, paved with mud knee-deep: underground chambers, where they dance and game; the walls bedecked with rough designs of ships, and forts, and flags, and American eagles out of number: ruined houses, open to the street, whence, through wide gaps in the walls, other ruins loom upon the eye, as though the world of vice and misery had nothing else to show: hideous tenements which take their name from robbery and murder; all that is loathsome, drooping, and decayed is her.

As had Davy Crockett:

It appeared as if the cellars were jam full of people; and such fiddling and dancing nobody ever before saw this world … Black and white, white and black, hugemsnug together, happy as lords and ladies, sitting sometimes round in a ring, with a jug of liquor between them, and I do think I saw more drunken folks, men and women, that day than I ever saw before … I thought I would rather risk myself in an Indian fight than venture among these creatures after night.

Most New Yorkers led sensible, hard-working lives. They rented houses and apartments in the center of the island, as far as possible from the raucous waterfront. The rich lived still further uptown, in mansions on suburban Fifth Avenue. Central Park opened to the public in 1858. But the real action, the color and excitement, the fashion, music and night life, was in the slums, the greatest being the Five Points. It was built on the grave of an ancient pond, the Collect, once New York City’s main source of drinking water. Befouled by industry, the Collect was drained in the early 1800s, then covered with streets and buildings, but the fill had not been done properly and the buildings sagged and the basements filled with water. Understandably, the inhabitants of such a neighborhood, beaten and abandoned, championed anyone who seemed to defy the city’s aristocratic powers.

The Five Points bred many of the town’s first street gangs, ethnic armies that went to war with each other and with the world. These were less like modern mob outfits—less like the famous Five Families—than like medieval peasant bands. They had little organization, method or plan. The order of the day was simple: maraud. The names of these gangs are a hymn of colorful decay: the Whyos, the Chichesters, the Forty Thieves, the Plug Uglies, the Dead Rabbits, the Hudson Dusters. The toughest worked in the Sixth Ward, which covered a few dozen acres between Broadway and the Bowery. The grid of numbered streets and lettered avenues was laid out in the early 1800s, but it was still the old New York down here, with bends and hooks and rookeries and lanes. Many streets followed the path of a lost Indian trail or the shore of a vanished lake. Everything was evidence of something that was gone. Cherry Street had once been among the city’s grandest thoroughfares. It’s where George Washington was inaugurated, where John Hancock and DeWitt Clinton lived. It was dotted with parks and stately homes, but cut-rate developers filled the lots with tenements. By 1860, the old mansions had decayed. Many had turned into bordellos or flop houses. In 30 years, the Sixth Ward had gone from leafy elegance to urban nightmare.

The waterfront neighborhoods were even worse. Corlears Hook, a jutting coast that served as a landmark for river navigators (it’s now mostly buried beneath the FDR Drive) had been a red light district since the early 19th century. By 1855, it was the heart of the local crime scene, crowded with dance halls and saloons, including the infamous Tub of Blood bar, home of the Tub of Blood Bunch and the even more infamous Hole-in-the-Wall Saloon, the headquarters of a gang called the Hookers.

The characteristic crime of New York City’s 19th-century waterfront was the “shanghai.” Because conditions aboard sailing vessels were both boring and brutal, some part of every crew fled as soon the ship reached port, leaving whalers and sloops short of manpower. Post a notice, interview seamen—that was the proper way. But desperate captains often hired port agents, disreputable characters to kidnap drunks from waterfront crimps. At these rundown hotels, an agent would comb the lobby bar for a mark. At some point, he would dose the mark’s drink with a mickey—usually laudanum, which was one part opium and many parts canary wine. When the mark stumbled to bed to sleep it off, the agent followed with a blackjack, then delivered the blow that sent the mark into deep unconsciousness. The most storied crimps, such as the Old Fourth Ward Hotel at Catherine and Water Streets, were built on piers with trap doors that led directly from the bedrooms to the river, where a rowboat was waiting. By the time the mark awoke hours or even days later, he was on a ship at sea. The choice was simple: work or swim. In the worst case, such a man would end up on a whaler bound for China—“shanghaied”—which meant he would be away for four or five months, like dropping off the map; his wife might grieve for a time, then marry another. Hundreds of marks were kidnapped in the Fourth Ward in the 1850s and ’60s.

All kinds of criminals operated along the East River. Child crooks, apprentice pickpockets served as lures. Most established gangs had a youth auxiliary for this purpose. The Forty Thieves had the Forty Little Thieves. The Hudson Dusters had the Little Hudson Dusters. Members of child gangs had tough faces, wore ragged coats and patched pants, and were underfed, illiterate, disease-ridden, and mean. They lived three-to-a-bed in tenement flops, stalked the streets, and drank turpentine on a dare. There were con artists, bunko men, crooked dealers in every kind of card game—Faro, Poker, Stud. There were thousands of gang members: some joined because they wanted a family, some because they needed protection. There were pimps and hookers, loan sharks, opium dealers and addicts.

And pirates. An 1850 police report estimated the presence of between 400 and 500 pirates in New York City. To the police, a pirate was any criminal who made his living on the water, attacking and robbing ships beyond the jurisdiction of the landlocked coppers—named for the tin badge on their peaked caps. Most river pirates were boys, twelve to eighteen years old, divided among a dozen or so outfits. The Slaughter Housers worked out of Slaughter House Point; the Patsy Conroys worshipped their martyred founder; the Short Tails were known for their favorite kind of coat; the Swamp Angels, the Hookers, the Border Gang, the Buckoos, and the Daybreak Boys—so called because that’s when they emerged in their flat-bottom boats—hit the sloops in the harbor, then vanished into the sewers.

Then there was that more mysterious category of criminal, a man—always a man—who lived between these worlds, engaged in a mission of his own. Freelancers and solo operators, these thugs were so feared they did not require the protection of any gang. People left them alone because who needed that kind of trouble?


Adapted from The Last Pirate of New York: A Ghost Ship, A Killer, and the Birth of a Gangster Nation, by Rich Cohen. Copyright © 2019 by Rich Cohen. Published by Spiegal & Grau, an imprint of Random House, a division of Penguin Random House LLC.

Rich Cohen is the author of 11 books, most recentlyThe Last Pirate of New York.