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It was said that Jean dressed as a gentleman and had a gentleman’s manners to match, but that neither he nor Pierre (and certainly not their older brother Dominique You, who still dressed like a pirate) were actually treated as such in the rarefied society of nineteenth-century New Orleans. Though they were accepted as daytime equals and nighttime drinking and gambling partners because of their bearing, wealth, demeanor, and prowess with the dueling sword and pistol, the male upper crust of the city excluded them from their extravagant social events, let alone their parlors to meet their wives and daughters.

J
ust how the Laffites became involved so quickly and prominently in the massive smuggling enterprise then engulfing New Orleans is a matter of historical controversy. The most plausible explanation comes from New Orleans historian and LSU professor Jane Lucas De Grummond,*
 
41
who tells us that in the summer of 1805 Jean sailed into the city after a privateering cruise with 12,600 English pounds that he needed to dispose of (without anyone asking a lot of questions). Brother Dominique You (who had been in the city awhile) found the answer in the person of Joseph Sauvinet, a Frenchman who had become one of the principal businessmen of New Orleans. As head of the largest accounting and banking house in the city, Sauvinet had divined the enormous profits to be made from smuggling and just as quickly recognized the value of a man such as Jean Laffite—not to mention the value of his 12,600 British pounds (about $860,000 today).

Sauvinet set up Jean and his brothers in the smuggling business, with instructions on how to avoid U.S. Customs by off-loading their goods and booty downriver below a bend called English Turn, from where it could be transported to Sauvinet’s warehouses for resale in New Orleans. According to De Grummond, this “was the beginning of a contraband commercial venture that was to involve nearly everyone in New Orleans.”

Using some of their share of the captured English pounds, the Laffites then began acquiring a small fleet of privateers with which, over the next half dozen years, they terrorized Spanish shipping in the Gulf of Mexico. Under the rules of the French letters of marque, prizes seized were to be taken to French ports, where a court would award the privateers a percentage of money based on the value of the prize itself (minus copious administrative fees and costs). But as the first decade of the nineteenth century wound down, fewer and fewer of these ports were available owing to a long string of French defeats in those island waters, and finally, after Guadeloupe and Martinique fell to the British, there were none left at all.

Naturally this became a pressing problem for the privateers, since the bulk of their haul often consisted of the captured ship itself, and because America was not then at war with Spain (or, for that matter, with France or England), it was illegal to dispose of the craft within the United States. A base of operations, as it were, was required to take these valuable prizes and somehow turn them into cash. The privateers found their base on the remotest part of the Louisiana coast, at a place called Barataria Bay.

T
here are parts of Barataria today as dark and unsullied as they were two hundred years ago; it is a place somehow set adrift in time. The bay is hemmed in on the Gulf of Mexico by Grand Isle and Grand Terre (the latter is about six miles long and three miles wide), as well as by several smaller barrier islands, but its name is not just a play on that term; rather, it seems to have been aptly named by some prescient early Frenchman after the mythical island of Barataria in Cervantes’s
Don Quixote,
which translates, roughly, into “a place of deception.”

The bay,*
 
42
dotted with many small marshy islands, is about twenty miles wide at its widest point near the coast and tapers out northward to a length of about thirty miles. Among its virtues was that it provided a safe haven from the harsh winter northers as well as all but the fiercest summer hurricanes that blow out of the gulf.

For the privateers of those times seeking a secure harbor, it must have been a paradise, a place of breathtaking natural beauty and serenity. Wondrous varieties of oysters, shrimp, crab, and fish teemed in the blue-green waters right up to shore. Ducks, geese, woodcock, snipe, and other waterfowl were in abundant profusion. Deer roamed the surrounding forests, as well as squirrel, rabbits, and turtle (and frogs, for those so inclined) in the marshes. The island upon which the early Baratarians had settled—Grand Terre (named after a similar isle near Guadaloupe)—was elevated enough to provide protection from all but the worst hurricanes and was covered with canopies of Spanish moss–draped live oaks, palms, pines, and, close on the beaches, a low, scrubby, and gnarled pearlike tree that, judging from its defiantly bent appearance in later photographs, must have custom-designed itself against the strong winds that blew in across the gulf.

There are two other reasons Barataria was an ideal place for a smuggling operation. To the north, behind the barrier islands, the bay was isolated by cypress swamps—their tall branches filled with the nests of eagles and waterbirds—and surrounded by a thousand square miles of nearly impassable quagmires and marshes in which resided dangerous alligators and bears, rattlesnakes and water moccasins, as well as the ever-present anopheles mosquito that carried the deadly “yellow jack.” All this made Barataria secure enough from prying official eyes, or so the privateers thought. Second, through a serpentine waterway of rivers, lakes, canals, and bayous, Grand Terre was connected directly to New Orleans, so that smuggled goods could be brought unimpeded into the city in blunt-bowed pirogues, the customary means of inland travel then in south Louisiana.

About halfway between Grand Terre and New Orleans is a raised piece of land in the swamps, which, judging from the huge mounds of clam- and oyster shells, was in centuries past used by Indians for ceremonial purposes, including, many believed, ritual sacrifice—owing to the large numbers of human bones also found there. Known as the Temple, it now became utilized by the privateers as a sort of midway sales and auction spot at which as many as five hundred wealthy New Orleanians at a time would arrive by boat on designated days to buy captured slaves and other smuggled goods and merchandise.

The slave trade was central to the Baratarians’ economy. Spanish ships carrying Africans were usually easy marks for the heavily armed privateers, and it was not extraordinary for them to have on hand several hundred or more of these miserable people, whom they kept on Grand Terre in slave pens called “barracoons” to await purchase by the ever-expanding number of sugar plantation owners.*
 
43

Other merchandise was kept in warehouses, and soon there would be more than forty of these on Grand Terre containing the wealth of Spain, Mexico, South America, and the West Indies: fine silks, Moroccan rugs and leather, elaborately carved furniture—beds, chairs, tables—ornate silver flatware, china, crystal, tapestries, lace, clothing, lamps, and kegs of whisky, rum, and wine. Almost everything imaginable that could be seized on the ocean was sold to the acquisitive citizens of New Orleans, for whom these things were unattainable as a result of the Embargo Act and, close on its heels, the British blockade—and at a healthy discount to boot.

A
s we have seen, Jean Laffite was not an inconsequential man, but, like so much else about him, exactly how he became the leader of the Baratarians remains murky. History records that there were then two types of Baratarians. First was a band of Grand Isle and Grand Terre islanders who for many years had engaged themselves in fairly minor smuggling undertakings in between their usual fishing and hunting activities. Then, after the British conquest of the French-held Caribbean islands, there sailed into Barataria Bay a new sort—the homeless privateers. Soon the two groups began squabbling, and often fights broke out, some of them deadly.

At the same time the more successful privateers realized they needed an agent, as it were, to represent them in New Orleans, promoting sales of their booty, negotiating prices, arranging auctions, and keeping the law out of their way. Jean Laffite, a privateer himself, came highly recommended, since he also mingled and mixed with the richest and most powerful men in the city. This worked out well for several years; then the two Baratarian factions started feuding again, and it became apparent that what they really needed was a genuine leader. Laffite had experience with both factions—and they with him—so much so that they managed to drop their differences long enough to ask him if he would come down to Grand Terre and become the headman, or
bos.

Laffite agreed, and among the first of the differences he settled was a dispute between himself and a villainous Italian captain named Vincent Gambie over the latter’s attack on an American sailing vessel. A confrontation ensued during which one of Captain Gambie’s men, armed with a pistol, moved threateningly toward Laffite, who—without so much as a “Stop or I’ll shoot!”—shot him through the heart. Recalling the incident many years later, brother Dominique You stated, “That put the fear of God in them.”

The ascendency of the Laffites marked the beginning of a heyday for the Baratarians, which would last several more years. Under Jean’s stewardship the privateers captured more than one hundred prizes with all their cargoes, the most valuable of which were slaves taken in the waters around Havana, which had become the center of the trade in the Western Hemisphere. Being in charge of such rough customers was not always easy. In addition to Gambie, there was another fiery Italian captain named Louis Chighizola, known as “Nez Coupe” because he had lost half of his nose in a swordfight.

With the exception of Laffite, who still attired himself as a gentleman, the rest of the Baratarians—and by this time there were probably more than a thousand of them—dressed just like the swashbuckling pirates from the old stories: bright red and black striped blouses, pantaloons, tall boots, and colorful bandanas tied around their heads. Many wore gold earrings, and all carried cutlasses, knives, and pistols.

As business grew, the activities of the Baratarians became more and more outrageous. Flyers were posted in broad daylight on buildings throughout New Orleans announcing the booty auctions, cataloguing the items to be sold. These were attended by the most prominent men in the city, who bought up everything from slaves to pig iron to dresses and jewelry for their wives. Everybody knew smuggling was illegal, but for the Creoles, poor and upper crust alike, it had been a way of life under both the Spanish and the French regimes for as long as anyone could remember. Occasionally, some of the Baratarians ran afoul of the law, yet Laffite’s connections included not only powerful members of the state legislature but also the most outstanding lawyer in Louisiana, Edward Livingston.

Under Laffite, Barataria took on a remarkable new look. In addition to the large home he built for himself, other houses of the thatched-palm-roof “cottage” variety began to spring up on Grand Terre as the money poured in. At any given time dozens of ships lay at anchor inshore, and not infrequently Baratarians could be seen strolling defiantly upon the streets of New Orleans in various stages of sobriety. Laffite had ordered the construction of a fort at the west end of Grand Terre and armed it with cannon from plundered ships. After the fall of the French in the Caribbean, Laffite arranged for the privateers to operate quasi-legally under the flag and letters of marque of Cartagena, a large city-state in what is now Colombia that had recently declared independence from Spain and was at war with that country. In addition, Laffite began to squirrel away large stores of arms, gunpowder, flints, and cannonballs at various secret locations in the wilds of Barataria—for use against exactly what is not clear—but these munitions would prove a godsend when the Battle of New Orleans broke out.

Six

N
ot everyone was pleased with the cozy arrangements between Laffite’s Baratarians and the citizens of New Orleans, especially William C. C. Claiborne, the new governor of Louisiana, which had recently been admitted as the eighteenth state of the Union. Claiborne’s complaints against the “pirates of Barataria” soon became abundant. First, they were violating U.S. tariff regulations right under his nose—no inconsequential matter either, since, without a federal income tax, the government in Washington depended for most of the nation’s revenues on duties collected on imported goods. The fact that the U.S. Treasury was about to go broke did not help things at all.

Then there was the African slave issue. Not only had the importation of slaves become illegal by federal law, but there were apparently further consequences of the Baratarian smuggling of this human cargo that distressed Governor Claiborne. Several years earlier a slave rebellion had erupted on the plantations north of New Orleans; after murdering a number of whites, the slaves marched on the city itself but were finally broken up by militia units. To Southern whites the notion of a slave uprising was their most dreaded fear, and the fact that it was blacks from Haiti who had instigated the earlier rebellion caused the governor and others to conclude that slaves from the Caribbean islands were rebellious by nature and thus not to be trusted—
these
were precisely the kinds of bondsmen the Laffites were importing to Louisiana.

Not only that, but Jean, Pierre, and a couple of dozen Baratarians had recently been apprehended at night by a company of U.S. Army regulars while attempting to smuggle about $4,000 worth of cinnamon into New Orleans. After posting bail, the Laffites skipped town for Grand Terre, from where they taunted the authorities. Claiborne issued a proclamation damning the activities of the Baratarians and specifically naming Jean Laffite as the principal troublemaker. The governor personally offered, “in the name of the state,” a $500 reward for the capture and delivery of Jean Laffite.

No one could accuse Laffite of not having a sense of humor—let alone audacity—because he immediately responded by having handbills plastered all over New Orleans promising a $5,000 reward for the capture and delivery to
him
of Governor Claiborne!

Numerous writs of arrest were also brought against the Laffites by federal authorities, but U.S. marshals, fearful for their lives, refused to go into Baratarian territory to serve them, and the court records are filled with marshals’ notations about the Laffites: “Not found in New Orleans.” Even the U.S. government surveyor declined to practice his business in the Baratarians’ lair, writing his boss in Washington, “They are an outlaw set [and] I am fearful they will give me some trouble.” In fact, the surveyor went on, the Baratarians had actually arrested several customs agents and sentenced one of them “to ten years at hard labor with a 56-pound weight hung to his leg.” As if that wasn’t enough, a number of American merchants in New Orleans began to complain to Claiborne that since most of the smugglers’ goods were being acquired by their French Creole rivals, their own businesses were suffering.

Try as he would to rid himself of this lawlessness, the governor was continually whipsawed. After an encounter between customs agents and the Baratarians left one agent dead and two others “greviously wounded,” Claiborne went to the Louisiana legislature to seek action. The legislators—preponderantly of French extraction—considered the governor’s request for money and men to destroy the Baratarian stronghold and “took it under advisement,” where, as the New Orleans historian Stanley A. Clisby aptly put it, “it remains to this day.”

T
ime, however, was running out for the Baratarians. In his frustration Governor Claiborne finally appealed directly to President Madison, who ordered the secretary of war and the secretary of the navy to do something. They in turn told Commodore Daniel T. Patterson of the navy and Colonel George T. Ross, commanding the 44th U.S. Infantry, to come up with a plan to rid the country of these “banditi” who were attacking ships on the high seas belonging to “nations not at war with the United States.”

Accordingly, the
Carolina,
a schooner-of-war armed with fourteen guns, was moved to New Orleans for the express purpose of breaking up the operations at Grand Terre. The fact that she was still there when the British attack broke out, and the crucial role she played in repelling it, remains one of the delicious ironies in a war filled with irony.

In the meantime, further trouble came the Laffites’ way. In the late summer of 1814, just as Jackson was concluding the Treaty of Fort Jackson with the Indians, a federal grand jury in New Orleans indicted Pierre Laffite for aiding and abetting piracy, a hanging offense. Pierre had recently suffered a stroke (which left him somewhat cross-eyed), and he had taken to spending time in the city with his wife and family, which was where the authorities caught up with him. He was thrown into the calaboose—the filthy, lice-ridden, old Spanish jail—without bail and chained to the wall, in case he entertained the notion of escape.

This development weighed heavily on Jean, for he had every reason to be concerned for his brother’s health in those conditions. No amount of legal maneuvering by lawyer Edward Livingston could spring Pierre from “the depths of a dungeon,” as Laffite described it, and for all Jean knew Pierre’s next steps might be to the gallows. These matters were on Jean’s mind when he received the delegation from His Britannic Majesty’s military services at Grand Terre on that sultry day in early September 1814.

A
fter recovering from the surprise that their tall, swarthy guide was none other than the infamous Laffite himself, the British captains got down to business. Initially, this consisted of handing over to Laffite a packet of documents produced by their superiors that included an advance copy of Colonel Nicholls’s “proclamation,” which was about to be distributed to the citizens of Louisiana. Next were two documents of the carrot-and-stick variety, signed by Captain W. H. Percy, British senior naval commander in the Gulf of Mexico. On the one hand, Percy threatened to send a fleet to destroy the Baratarians and their stronghold because of their privateering activities against Spanish and British shipping. On the other, if the Baratarians would join with the British, they would receive “lands within His Majesty’s colonies in America” and the opportunity to become British subjects with a full pardon for any previous crimes.*
 
44

Finally there was a personal note from Colonel Nicholls to Laffite as “Commandant at Barataria,” in which the Irishman explained himself by announcing, “I have arrived in the Floridas for the purpose of annoying the only enemy Great Britain has in the world. . . .” What the British wanted, the letter went on to say, was use of all the boats and ships of the Baratarians and the enlistment of the Baratarian gunners and fighters in the invasion of Louisiana. Nicholls also promised Laffite, personally, that he would be made a captain in His Majesty’s Royal Navy.

This was quite a bit to digest, but at the same time it seems to have made Jean hungry, too, for as Judge Walker tells us, after glancing over the papers Jean ordered an elaborate feast to be laid out for His Majesty’s envoys, consisting of “the best wines of old Spain, the richest fruits of the West Indies, and every variety of fish and game, spread out before them and served on the richest carved silver plate.” Apparently a good time was had by all, for when they were done eating, “they all smoked cigars of the finest Cuban flavor.”

The drift of the conversation, according to Walker, then came around to the declaration that Laffite and his minions were crucial to guiding the British invasion force up through the swamps, and that once New Orleans was secured the army would move upriver and “act in concert” with the British forces in Canada, thereby, as Laffite put it, “to shove the Americans into the Atlantic Ocean.” The British officers indicated that His Majesty’s forces also intended to set free all the slaves they could find and enlist their help in subduing the presumptuous Americans.

The two Englishmen next offered Laffite their pièce de résistance: a bribe of 30,000 British pounds (more than $2 million today) if he could convince his followers to join with the British against the United States. If this seems like a lot of money—and it was—the British would nevertheless have consided it well spent, since it was understood that the Baratarians’ knowledge of those tangled, trackless marshes and bayous leading up to New Orleans would be nearly priceless. To attack the city by appearing on its outskirts right out of the swamps would for all purposes amount to a British coup de main in which the money was a pittance compared to the enormous amount of booty they expected to confiscate from New Orleans warehouses after so many years of embargo and blockade.

As Laffite was pondering this generous offer, however, trouble began to brew. Upon seeing the red-coated British marine and blue-jacketed British naval captain, the run-of-the-mill Baratarians suspected that something nasty was afoot. Not a few of them were Americans and, despite their troubles with the law (which they mostly considered a nuisance), they wished no part of a British scheme to conquer America. Accordingly, a disturbance broke out, with the Baratarians demanding to know the meaning of the Britons’ presence; some grumbled that His Majesty’s emissaries should be hanged as spies.

After considerable remonstration, Laffite managed to get his people calmed down long enough to spirit the Englishmen back to their gig and send them on their way, but, playing for time against the threatened British assault on his stronghold, he told the two envoys he needed “a fortnight” (fourteen days) to compose his men and put his personal affairs in order. After that, according to papers later filed with the U.S. Federal Court in New Orleans, Laffite promised the Englishmen that he and his men would be “entirely at your disposal.”

What was going on in Jean Laffite’s mind as he watched the Britishers sail happily away is uncertain. He must have considered the bribe, for it would have been far out of character for a man of his makeup to turn down that kind of money without a thought. Then there was the fact of his brother Pierre languishing in the wretched jail, contemplating the hangman’s noose—the British having also promised that, upon their victory, Pierre would be set free.

On the other hand, Laffite, though a Frenchman by birth, apparently considered himself something of a patriot where America was concerned. After all, the country had been good to him—at least until recently—as he had amassed a considerable fortune (though in blatant contravention of its laws) by being a smuggler on her shores. Also, under the British offer, he would have had to give up all his ships to take advantage of the promised “lands within His Majesty’s colonies in America,” and farming was not exactly Laffite’s goal in life. The slave-freeing business must have bothered him too; after all, being a slaver himself, Laffite would not likely cotton to any notion of arming slaves.

What exactly he might have thought about all or any of this appears to have had little more moment than a passing shadow, because Laffite promptly sat down with pen and paper and proceeded to double-cross his newfound British friends.

T
he British—at least Colonel Nicholls and his people—seemed to live in a fool’s paradise so far as the makeup of the American people was concerned. First, they had convinced themselves that a vast body of Indians from Florida would join them in the descent upon New Orleans, but they were, of course, disabused of that particular scheme by Andrew Jackson’s attack on Pensacola, which sent the Indians scattering into parts unknown. Likewise, they believed that the French and Spanish Louisiana Creoles hated America enough to rise up and join with them to separate from the United States.

More far-fetched was the British conviction—embodied in Nicholls’s proclamation of August 29—that even the Anglo-Americans living west of the Appalachians were so disaffected with the government in Washington that they would gladly acquiesce to a British invasion of their soil. (In a stunning display of geographical misunderstanding, Nicholls had appealed in his proclamation to the “Inhabitants of Kentucky, you have too long borne with grievous impositions . . . ,” failing entirely to include the then populous state of Tennessee, as well as the territories of Alabama and Mississippi.) As the historian Wilburt S. Brown aptly pointed out, these British soldier-diplomats “seemed to have become victims of their own propaganda.”

No matter what anybody would say about it later, Laffite’s letter to the U.S. authorities (even if somewhat tainted by a logically self-serving pardon request) was a bold, loyal, audacious, and public-spirited declaration of patriotism. Addressing himself to his powerful friend Jean Blanque, Laffite revealed the entire British scheme, as well as their smarmy offers and bribes to him, in such a way as to express a clear and present warning of the danger. He also informed Blanque that he was stringing the British along and asked for instructions from the authorities at New Orleans. A huge British fleet containing an entire army was at the moment gathering for an attack on the city, Laffite said, and he asked Blanque to do whatever he would with the information but obviously assumed Blanque would take it to the governor. When he was finished, Laffite put his letter into a packet and sent it by a special courier who reached Jean Blanque in New Orleans in less than a day, a remarkable feat in itself, since the trip from Grand Terre normally took three.

Jean Blanque did exactly what Laffite had expected him to do: he rushed those critial communications to Governor Claiborne. As a wealthy and respected lawyer, banker, and member of the Louisiana legislature (as well as an investor in Laffite’s privateering enterprise), Blanque carried considerable weight, especially since Laffite had included all the documents the British had given him, imperial seals and all.

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