Long before the foundations of New Orleans were laid, the river existed as a legend and a rumor. It was the monster to the west, just beyond the next hill, stand of trees, prairie, horizon. It was the mother of all waters, the torrent that flowed out of the garden to touch the desolate earth. It flowed through the Indian imagination as it flows through the American mind, through music and literature, carrying the shipwreck and the bloated body of the fool who went missing after a party on the levee. The river starts as a stream in Minnesota and picks up volume as it heads south, meandering through the country—“It seems safe to say that it is also the crookedest river in the world,” Mark Twain writes in Life on the Mississippi, “since in one part of its journey it uses up one thousand three hundred miles to cover the same ground that the crow would fly over in six hundred and seventy-five”—before shattering into a network of bayous, swamps, and estuaries below New Orleans. This is the delta, and it’s a mess. For generations, sailors could not find a reliable channel to follow into the river, as the mouth of the Mississippi constantly silted up with debris from the north. “The river annually empties four hundred and six million tons of mud into the Gulf of Mexico,” writes Twain. “This mud, solidified, would make a mass a mile square and two hundred and forty-one feet high.” Simply put, the country is vomiting its innards into the Gulf. 

The mouth of the Mississippi appeared on Spanish maps years before it had been seen by a white man. I’m thinking of a particular map: Tabula Terra Nova, drawn in the early 1500s. This is one of the first renderings of the world as it would come to be known: two hemispheres—Occident, Orient. America is a shapeless mass, the Tropic of Capricorn cleaving the New World in two. Due west of Ethiopia, adrift in Oceanus Occidentalis, the southern hemisphere is crowded with the names of settlements. But a generation after Columbus, North America is punctuated by few landmarks, the river among them. It emerges from beyond the left border of the map and branches as it touches the sea. It was drawn before the voyages of Ponce de León, meaning it had not been seen by the mapmaker, or by anyone who might have spoken to the mapmaker. 

The Mississippi was navigated by white men in 1519. So here’s the first tall ship, with its sails and steel-plated men, cruising the archipelago of grass islands. The ship was captained by Alonso Álvarez de Pineda, famous in Seville, an explorer who returned home with miraculous tales of the New World. He traveled twenty miles up the Mississippi that first trip. He said he had seen a city on a hill beside the river, and in that city little men, pygmies, covered in golden ornament. Pineda, killed by Indians on a later voyage, left behind the first accurate map of America’s Gulf Coast—a scrawl, like something written on a cocktail napkin after the second drink.

Luis de Moscoso was the first European to see the future site of New Orleans, a strip of land between the Mississippi and the great salt estuary later named for the French minister of the marine Louis Phélypeaux, count of Pontchartrain. He was a member of de Soto’s last expedition. This trip was later recalled as a delirium, a terror: the men marching in armored ranks through the swamp, the sun beating down, the stink of the marsh, the ­misery of the waste places. They searched out the natives, killed whomever they met, then took notes on each killing. (As John Wayne says in Red River, “I’ll read over him in the morning.”) In March 1541, the party, which began with six hundred men and two hundred horses, was attacked by Chickasaw Indians. Horses slaughtered, Spaniards killed. Those who escaped did so by running. De Soto died on a raft in the river, which is perfect, a consecration, his flesh devoured by catfish with black eyes and long whiskers. Moscoso led what was left of the party south. It was from this vantage point—on rafts in the river—that Moscoso and a dozen others saw the swell of land that would become New Orleans. It was the summer of 1543.

The site was not visited again for over a hundred years, and then by Robert de La Salle. The French explorer traveled the length of the Mississippi, planting a cross near what is now Jackson Square in 1682. The city foundations were laid in 1719 by Jean-Baptiste Le Moyne de Bienville, a diplomat charged with establishing a town near the mouth of the Mississippi, which was to give Paris control of the interior. In his diary, Bienville said the site was selected for its natural advantages. At ten feet above sea level, it seemed unlikely to flood. In this, the founder set the general pattern of municipal leadership: totally confident and completely wrong. The waters inundated the city, then just wooden stakes and foundation holes, less than a year after the cornerstone had been laid. The outline of the town was already visible: a parallelogram, which is just a drunken square, four thousand feet along the river, its ass protruding one thousand eight hundred feet into the swamp country that continued to Lake Pontchartrain.

This was divided into sixty-six three-hundred-square-foot lots, which, covered in houses, hotels, stores, and such, would eventually be known as the French Quarter. A parade ground was set aside on the riverfront: Jackson Square. The early years of the city were just disaster after disaster: hurricanes, floods, Indian attacks, outbreaks. In 1735, the city was set upon by wild dogs. Yellow fever and cholera rampaged through the beginning of the last century. In 1905, the windows of the French Quarter were shuttered, the streets filled with funeral processions, the horse-drawn hearse carrying victims of yellow jack to the Saint Louis Cemeteries beyond the ramparts. According to historians, the jazz funeral is probably a remnant of that plague year, when burials were so frequent that turning the dour processions into a ­parade was a means of survival, the march to the ground being a dirge ­because death is terrible and great, the march back to town being a parade because life is greater still.

As soon as there were streets, they were lined with whorehouses. The early inhabitants were a ragged crew of gamblers, vagabonds, criminals, and drunks. The first women were prostitutes sent to pacify the ne’er-do-wells. In 1724, Bienville enacted the infamous Code Noir, which called for the expulsion of all Protestants and Jews, but this order was largely ignored. In fact, if you were a Jew in North America in the eighteenth century, you would have had a hard time finding a better place. In 1788, the city, then ­under Spanish rule, burned down and was rebuilt, which is why the French Quarter looks less French than Spanish. Only two original French buildings survive. One of these, at 632 Dumaine Street, is markedly different from the others—blank-faced with few windows, oblong, closed off, shuttered, ­lonely, strange. The French ­retook control in 1803, holding it just long enough to sell the entire territory to the United States. New Orleans was a small city, ten thousand or so people crowded into streets lined with beaneries, each an imitation of a grander ­establishment in the French capitals of the West Indies, such as Santo Domingo, which themselves were filled with imitations of Paris. 

The United States took over on December 20, 1803. William Claiborne was Louisiana’s first American governor—that’s why his name is on everything. As the years went by, New Orleans, which experts believed would be normalized by an influx of Americans, only became more exotic. By the mid-1800s, its population was a hodgepodge: there were descendants of the French who first settled on the land; there were descendants of the Spanish who had ruled a generation later; there were descendants of the French who moved in when Quebec fell to the British (because they came from Acadia in Canada, they came to be known as Cajuns); there were Americans who came in the wake of the Louisiana Purchase, farmers and rivermen from Kentucky; there were French nationals who came when the slaves rose in Santo Domingo, driving out colonial property owners; there were others who emigrated from this or that island when the wrong nation came to ­power—French speakers from Cuba, Dutch from Curaçao. New Orleans was a big drain, pulling in the debris of the river and ocean trade, with great forests and lumber mills to the north and the Gulf of Mexico to the south, Cuba, Jamaica, the Spanish Main. 

Once upon a time, men in New Orleans carried charts that classified the product of every conceivable coupling:

black + white = mulatto

mulatto + white = quadroon

quadroon + white = octoroon

octoroon + white = quinteroon

mulatto + black = griffe

Indian + white = mestizo

And so on . . .

By the mid-1800s, the city was known for its quadroon balls, opulent affairs where local dandies went stag to dance halls on St. Philip Street and watched through opera glasses as young women of mixed race, the offspring, usually, of a white father and a half-black mother, were marched across the floor in extravagant gowns. When the moment was right, a man selected a quadroon. Dolled her up. Established her in luxury in a house in a section of the city set aside for the purpose. Loved her. Impregnated her. A Duke from Saxe-Weimar, Germany, who attended a ball described the quadroons as “almost entirely white: from their skin no one would detect their origin; nay many of them have as fair a complexion as many of the haughty creole females.” A quadroon, once established, was referred to as a placée. She took her man’s name, as did her children. In this way, the wealthy men of New Orleans could lead a double life, one above ground with a white wife and white children, the other subterranean with quadroon placées and octoroon children. The practice continued till the Civil War, in the wake of which racial distinctions hardened. No more balls. No more secret families. Most of the quadroons (who, after generations of intermarriage, were more white than most white people in the city) went north, where they vanished into the fabric of America.

The city owed its importance to the river. The Mississippi was the first American superhighway, Huckleberry Finn the first American road novel. The wealth of the farms and forests, the factories and mills, everything west of the Alleghenies—all of it floated down the river. New Orleans was the city at the end of the run, where the produce was counted, tagged, stacked, and shipped. The life of the city was the waterfront, the docks, the boats. The first were pirogues or canoes, fashioned, Indian-style, from tree trunks. These were followed by keelboats, mackinaws, flatboats, scows, the grandest of them three hundred feet long and as tall as a house. There were barges known as arks; broadhorns, or Kentucky flats; and ferries, called sleds, with roofs and passenger cabins. Before steam power, the challenge was getting back upriver—to Cairo, to Saint Louis. After the flatboats were unloaded in New Orleans, they were broken into pieces and sold as scrap wood. For years, the sidewalks of the French Quarter were made from the debris of the riverboats. The crews then walked home—a trip through wild country that took months. When he was young, Abraham Lincoln made the trip from Illinois to New Orleans by raft. It was in the course of this journey that he first saw slaves, sold in the French Quarter markets. 

It was a rough life on the river, a story by Robert Louis Stevenson or Jack London. The crews slept on the decks of the boats, months in the open, watching the shore—punishing in its sameness—drift by at two or three miles an hour. The men were unshaven and dirty; they washed in the river but were ­never clean. They were bare-chested all summer or donned brogans studded with spikes. In the winter, when the temperature dropped below freezing, they wore fur so fresh it had claws. There was always a card game going, men hunched over a deck, betting by firelight: faro, poker, blackjack, seven-up. They subsisted on bread and meat set before them in communal pans twice a day. They were drunk all the time. They referred to their whiskey as “good old Nongela,” as it was distilled on the banks of the Monongahela River. These men were tall and short, fat and thin, fair skinned and swarthy, the same sorts who once filled the galleys of Roman ships. It was a male ­society, where the rivermen constantly fought to establish position. Each boat had a champion, a man who bloodied all the others. He wore a red turkey feather in his hat, which told the world, I’m the baddest motherfucker on the Mississippi. At night, when the ships tied up at the landings, crews intermingled. When the holder of a red feather came across another red-feather holder, a circle formed and a battle commenced. The names of the great fighters live on: Mike Fink, the toughest man on the Ohio; Bill Sedley, who whipped everyone on the Mississippi then went mad in New Orleans, killing two people in a dive bar before fleeing into the Indian Territory.

It’s a culture lampooned in Huckleberry Finn when two flatboat toughs circle each other while sharing their bona fides. In this passage you have, in nascent form, the best of the blues and hip-hop, as well as the trash talk of Muhammad Ali:

Whoo-oop! I’m the old original iron-jawed, brass-mounted, copper­-bellied corpse-maker from the wilds of Arkansaw!—Look at me! I’m the man they call Sudden Death and General Desolation! Sired by a hurricane, dam’d by an earthquake, half-brother to the cholera, nearly related to the small-pox on the mother’s side! Look at me! I take nineteen alligators and a bar’l of whiskey for breakfast when I’m in robust health, and a bushel of rattlesnakes and a dead body when I’m ailing! I split the everlasting rocks with my glance, and I squench the thunder when I speak! Whoo-oop! Stand back and give me room according to my strength! Blood’s my natural drink, and the wails of the dying is music to my ear! Cast your eye on me, gentlemen!—and lay low and hold your breath, for I’m bout to turn myself loose!

For men on the river, every trip ended in New Orleans. That is where they were paid and spent what they were paid. It was the goal, the place they would finally drive out the boredom of all those weeks on the water. It was the adventures accumulated in the course of all those sprees that turned New Orleans into a party town. All those tchotchkes (the nipple-shaped shot glass), T-shirts (what drinking problem? i get drunk and fall down. no problem.), and stories (“and the funny thing is, I don’t even remember driving home, but there was the car, in the middle of the lawn”) started on the keelboats, where the deckhands shouted as the spires came into view. Even in the 1800s, rivermen referred to New Orleans as the City of Sin. The culture of the docks spilled into the streets and became one aspect of the town. The violent mood in the dives, the Mardi Gras of stoned outsiders filling the squares and driving the locals indoors, the way the town can seem like two towns—the one seen by the drunken conventioneer who gets in a fight on Bourbon Street; the other seen by the native, secret and protected—was established during the first river boom, when the keelboats crowded the water bank to bank, and the deckhands took their restless ennui as a cause to raise hell in the Vieux Carré.

Any river city whose wealth is concentrated and dispersed on ships is going to be lousy with pirates. New Orleans attracted them from its earliest days. The geography invites it. A dozen miles outside of town, the land gives way to swamp, bayou, bay. Lake Pontchartrain, north of the French Quarter, dumps into Lake Borgne, which dumps into the Mississippi Sound, which is protected from the Gulf of Mexico by barrier islands. If you designed a seascape for piracy, this would be it. There were big islands—Grand Terre, Grand Island—in the sound, but also lonely outcroppings where the sea grass waved and the earth vanished if you stepped on it. There were islands covered with dwarf oaks and Spanish moss, a screen from outsiders. There were groves in the water, trunks rising from the waves. There were low-lying islands that disappeared in flood tide. There were inlets and swamps and landmarks that served as rendezvous points for pirates, the most notorious being the temple, a mountain of clam shells that had dominated a barrier outcrop as long as even the oldest Indian could remember. There were ­channels between islands, some deep enough to float a ship, some so shallow only a raft could get through. If being chased by a British man-of-war, a pirogue-riding pirate could vanish into a narrow, weed-bedecked channel, then emerge into a lost bay. The entire area was a tangle: reefs, storms, sea surges, tides, roots, alligators, shells, catfish, and turtles as old as the world. Turn around twice and you’re lost forever. 

Old Spanish maps identify it as Barataria. The origins of the name are mysterious. Some say it comes from part two of Don Quixote, in which Sancho Panza is appointed governor of an island called Barataria, a name that rings mock heroic in the original. It echoes the Spanish word barato, which means “cheap.” In other words, Barataria is Bargainland, a Filene’s Basement for the pirate set, where all items have just fallen off the back of a truck. The bayous were a smuggler’s paradise, where good deals could always be found. Over time, Barataria became the subconscious of the city, New Orleans reflected in a dark mirror, a refuge for all those who’d been driven out or had chosen to live beyond the law. Thieves hid stolen goods there, fugitives vanished into the weeds. There was a permanent population of runaway slaves. It was a warehouse where the criminal inventory was stored. (Blackbeard took refuge in Barataria in 1718, drifted and dreamed as bounty hunters searched in vain.) It grew alongside the city. The bigger the warehouses on Tchoupitoulas, the better the business in the bay. 

By the 1800s, Barataria was attracting buccaneers. It was everything a ­pirate wanted: far away yet close at hand, convenient, within reach of shipping lanes that carried the wealth of the New World. The men who lived there were not pirates in the traditional sense—they were privateers. In strong boxes they carried letters of marquesses, documents that deputized them into foreign navies, giving them the right to prey on ships flagged by enemy nations. In the age of Napoleon, everyone was at war with someone, making these letters easy to come by. The most notorious privateers were Frenchmen chased out of Santo Domingo or Cuba, sailors who preyed on Spanish ­galleons. Such men—many burned with hatred for Spain—could secure letters from a half dozen countries, but most sailed under the flag of Colombia, where Simón Bolívar was in revolt. 

Barataria boomed in 1808 when the American Congress banned the importation of African slaves. From then on, all slaves would be bred (terrible verb) domestically. This was done partly to curb the nation’s addiction to slavery and partly to protect America from foreign ideologies, the notions of freedom and revolt that might, accidentally, in the way of cholera, be ­imported from a state like Haiti. But there were many in the South who preferred African-raised slaves for reasons that strike us as obscene: because they were more docile, stronger, darker; because, uncorrupted by America, they worked harder. 

It’s not unlike what happened in America during Prohibition. Here was a group of criminals—gangsters in one case, buccaneers in the other—who were disorganized, small time, in it for a quick score. And here was a business, legitimate and thriving one minute, then, with the stroke of a pen, turned over to crooks. Anyone who partook in the African slave trade was now an outlaw. In this way, an above-board business became the provenance of ­pirates. Men who might have otherwise reformed or faded away—many of the gangsters of New York were on their way out, too, before Prohibition—now had a big-time industry to run. Soon after the law’s passage, privateers began preying on slow, fat-bellied ships heading for Cuba. They attacked, then carried the human cargo back to Bargainland. This meant ­serious money: sable coats, silk eye patches, a diamond stud for each ear. The result was more pirates, more pirate ships, more pirate guns, more pirate violence. It was a gang war like the gang war between Al Capone and Bugs Moran. Who will control the North Side? Who will control Barataria? It was hurting business. Planters and merchants were afraid to go to the bayous to make a purchase. This was a moment that demanded a leader, a strongman who could bring order to the pirate islands.