Joseph Sauvinet, a Frenchman who had become one of the principal businessmen of New Orleans, quickly recognized the value of a resourceful man such as Laffite. Sauvinet set up Jean and his brothers in the smuggling business, with instructions on how to avoid U.S. Customs by offloading their goods downriver below a bend called English Turn, from where the cargo could be transported to Sauvinet's warehouses for resale in New Orleans.
Laffite and his men chose as their base of operations the remote Barataria Bay. It must have seemed a paradise, a place of breathtaking natural beauty and serenity. In addition, Grand Terre was elevated enough to provide protection from all but the worst hurricanes.
Under Jean's stewardship, the privateers captured more than 100 vessels and their cargoes, the most valuable of which were slaves taken in the waters around Havana, which had become the center of the slave trade in the Western Hemisphere.
With the exception of Laffite, who still attired himself as a gentleman, the rest of the Baratarians—there would be probably more than 1,000 of them—dressed like swashbuckling pirates: red-and-black striped blouses, pantaloons, tall boots, and colorful bandannas tied around their heads. Many wore gold earrings, and all carried cutlasses, knives and pistols.
As business grew, the Baratarians became increasingly outrageous. They posted fliers in broad daylight on buildings throughout New Orleans, announcing their booty auctions, held in the swamp halfway between Grand Terre and New Orleans. These were attended by the city's most prominent men, who bought up everything from slaves to pig iron, as well as dresses and jewelry for their wives.
Meanwhile, Laffite began to squirrel away large stores of arms, gunpowder, flints and cannonballs at secret locations. These munitions would prove critically important when the Battle of New Orleans broke out.
The British delegation that came to enlist Laffite in the attack on New Orleans handed over a packet of documents signed by Capt. W. H. Percy, the British senior naval commander in the Gulf of Mexico. Percy threatened to send a fleet to destroy the Baratarians and their stronghold because of their privateering activities against Spanish and British shipping. But if the Baratarians would join with the British, he said 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.
A personal note from Colonel Nicholls to Laffite also requested the use of all the boats and ships of the Baratarians and the enlistment of Baratarian gunners and fighters in the invasion of Louisiana. The privateers' assistance, Nicholls informed Laffite, was crucial. Once New Orleans was secured, the British planned to move the army upriver and "act in concert" with British forces in Canada, as Laffite later recalled, "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 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 would convince his followers to join with the British. Playing for time against the threatened British assault on his stronghold, Laffite told the two envoys he needed two weeks to compose his men and put his personal affairs in order. After that, Laffite promised the Englishmen, he and his men would be "entirely at your disposal."
As he watched the British sail away, Laffite must have considered taking the bribe. He must have also considered the British promise to free his brother Pierre, who had been charged with piracy and was locked in a New Orleans jail facing the hangman's noose. On the other hand, Jean, 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. He had amassed a fortune (though in blatant contravention of its laws) by smuggling on its shores. He promptly sat down with pen and paper and proceeded to double-cross his newfound British friends.