By Autumn 1814, the United States of America, barely 30 years old, was on the verge of dissolving. The treasury was empty, most public buildings in Washington, including the Capitol, the White House (then known as the President's House) and the Library of Congress, had been burned by a victorious and vengeful British Army, in one of the most dramatic incursions of the War of 1812. Festering tensions—arising out of Britain's interference with neutral America's lucrative maritime commerce—had erupted into hostilities in June of 1812. American seaports from the Atlantic to the Gulf of Mexico were blockaded by the British Navy, and the economy was in ruins. The U.S. Army was stymied and stalemated; the Navy, such as it was, had fared little better.
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Then, as leaves began to fall, a mighty British armada appeared off the Louisiana coast with the stated purpose of capturing New Orleans, America's gateway to the great Mississippi River Basin. The misfortune would have split the United States in two. New Orleans was as nearly defenseless as a city could be in those days, with only two understrength Regular Army regiments totaling about 1,100 soldiers and a handful of untrained militia to throw against nearly 20,000 veterans of the British Army and Navy, who were descending upon it as swiftly and surely as a hurricane.
Orders from the secretary of war went out to the legendary Indian fighter Gen. Andrew Jackson, then in nearby Mobile, Alabama. He should go immediately to New Orleans and take charge.
Central to the British design for the capture of Louisiana, which had been admitted to the Union in 1812, was an extraordinary scheme devised by Col. Edward Nicholls to enlist the services of the "pirates of Barataria"—so named for the waters surrounding their barrier island redoubt—who were for the most part not pirates at all but privateers, operating under letters of marque from foreign countries. Under the agreed concessions of maritime law, these official letters, or commissions, allowed privateers to prey on the merchant shipping of any nation at war with the issuing country without—in the event they were captured—being subject to hanging as pirates.
In the Gulf of Mexico, a large gathering of these ruthless men had set up operations on Grand Terre Island, Louisiana, which lies about 40 miles south of New Orleans as the crow flies. The leader of this band was a tall, handsome, magnetic Frenchman named Jean Laffite, who, using his blacksmith shop in New Orleans as a front, came to run a phenomenal smuggling business for the grateful citizens of New Orleans, rich and poor alike, who had been harmed for years by an American embargo on international trade—a measure intended to deprive Europe of raw materials—and by a British blockade designed to stifle American commerce.
It was to the Baratarians that Colonel Nicholls dispatched his emissaries from HMS Sophie to see if they could be enlisted into the British effort against New Orleans. On the morning of September 3, 1814, the Sophie dropped anchor off Grand Terre. Through spyglasses the British observed hundreds of sleepy-eyed, ill-dressed men gathering on a sandy beach. Presently a small boat was launched from the beach, rowed by four men with a fifth man in the bow. From the Sophie, a longboat was likewise launched, carrying its captain, Nicholas Lockyer, and a Captain McWilliams of the Royal Marines. The boats met in the channel, and Lockyer, in his best schoolboy French, asked to be taken to Monsieur Laffite; the response from the man at the prow of the small boat was that Laffite could be found ashore. Once on the beach, the two British officers were led through the suspicious crowd by the man in the bow, along a shaded path, and up the steps of a substantial home with a large wraparound gallery. At that point he genially informed them, "Messieurs, I am Laffite."
Jean Laffite remains among the most enigmatic figures in the American historical experience, right up there with Davy Crockett, Daniel Boone, Kit Carson, Wyatt Earp and Wild Bill Hickok. The youngest of eight children, Laffite was born in Port-au-Prince in the French colony of San Domingo (now Haiti) around 1782. His father had been a skilled leatherworker in Spain, France and Morocco before he opened a prosperous leather shop on the island. Jean's mother died "before I could remember her," he said, and he was raised by his maternal grandmother.
His older brothers, Pierre and Alexandre, would figure prominently in his life. After a rigorous education beginning at age 6, Jean and Pierre, two and a half years his elder, were sent away for advanced schooling on the neighboring islands of St. Croix and Martinique and then to a military academy on St. Kitts.
Alexandre—11 years Jean's senior—returned occasionally from his adventures as a privateer attacking Spanish ships in the Caribbean and regaled his younger brothers with stories of his exploits. They were so captivated by his tales that nothing would do but for them to follow him to sea.
When Jean and Pierre arrived in Louisiana from Haiti in 1807, they came as privateersmen—a barely respectable and an unquestionably dangerous business. Laffite, then in his mid-20s, was described as dark-haired, about six feet tall, with "dark piercing eyes," a furious vertical crease in his brow and a comportment something like a powerful cat. He was also said to be intelligent, convivial and a gambling and drinking man.