Most physical descriptions of Jean Lafitte seem to agree with that of him found in a letter written by an excited little Louisiana boy named Esau Glassock who had accompanied his father to New Orleans to purchase slaves. Esau wrote his brother that, "I have just seen the notorious Captain Lafitte. He is tall, with pale skin, and he has large black eyes. He is clean shaven except for a beard extending part-way down his cheeks." Additional others said his hands were small and delicate for a pirate; that he was "remarkably handsome" with Gallic features and possessed a "brilliancy of teeth". Says author Jack C. Ramsay, Jr., "When he walked the streets of the city, he exhibited an aire of gentlemanly self-confidence."

His temper was ferocious; most accounts support that; a man who could be kind and serene, but turn panther-like when pushed. When a small group of armed and boisterous Baratarians gathered outside his home threatening mutiny, Lafitte appeared on the porch, pistol in hand, and shot their leader at point-blank range. The mutiny ended.

But, this need for violence to maintain order was rare. To lead, he depended on and honed his innate flexibility; he knew how to adjust to the moment -- to be the gentleman, the rascal, the radical, entrepreneur, the patron of the arts, the lover or the pirate to fit the situation at hand.

Many stories exist, most of them founded on fact, attesting to his chivalry. When a family named Martin found itself in danger caught in a rowboat during a violent storm in the Gulf of Mexico, a vessel manned by Lafitte took them aboard. Mrs. Martin’s diary reads: "Lafitte the Pirate...treated us with all kindness possible (providing us with) a bountiful breakfast (and) even supplying a hat for my husband who had lost his own."

Once after he and his lieutenants divvied up their treasure evenly, two gold coins remained on Lafitte’s desk unclaimed. He turned to the wife of Louis Chighizola and motioned, "Those are for you." But, her husband’s quick hands claimed them. "I’ll hold them for her," Chighizola said. Lafitte’s eyes darkened as he rose from his chair and shot a hand forward, palm up. "Louis," he replied, "Give them to me." His subordinate knew better than to argue. Lafitte then turned to his blacksmith, Thiac. "From these coins, create a thimble of gold and give it the misses." That thimble still exists in the Chighizola family that has remained in Barataria.

A charming story relates the night that the pirates were playing cards in Lafitte’s den. An argument had broken out between Lafitte’s crew and Gambi’s, the latter blaming the others for cheating. "We shall have a third party cut the cards," Lafitte announced and sent Thiac to summon one of the fishermen from the coast up to his house. When the fisherman arrived he looked nervous; he had brought with him his little daughter in hopes that these pirates wouldn’t harm him in front of his child.

Lafitte smiled when he saw the girl and asked her to cut the deck, explaining to her in a gentle voice what that meant. She did, and Lafitte went on to win the play. Gambi stormed out. Before they left, the island chief called the little girl to his lap, thanked her for her help and dropped a $20 gold piece into her palm. She grew up never forgetting the dashing pirate who had been so kind to her.

Women loved Lafitte. That he was aware of his seductive qualities is evidenced in the manner by which he sought -- and won -- female company. A regular at the formal balls in town, usually a guest of some rich merchant or landowner, he tantalized the belles in the room with his courtly demeanor and fine-cut figure, which he primped in the finest cloths and silks of the day. He waltzed as well as the high society crowd. It is said he preferred the company of the quadroons, dark-eyed beauties one-quarter Negro who in Southern society were demanded by wealthy men as mistresses. Lafitte had several and would provide for them well-furnished apartments in town. One of these was a lady named Madeleine Rigaud. Another, whom he visited regularly was Catherine Villars, whose sister Marie lived with and gave children to Pierre Lafitte. Church records indicate that "an illegitimate child" named Pierre was born to Jean and Catherine in 1816.

The second wife of Mrs. Claiborne seems even to have been attracted to him. By chance, both she and the privateer showed up at the same time at the home of a mutual friend, a plantation owner who lived along the Mississippi River. Afraid that his friendship with Lafitte would harm his professional association with the governor, the planter created an alias for his male guest, introducing him as "Monsieur Clement". During dinner, legend has it, Lafitte’s charms oozed to totally captivate the attentions of the governmental wife. Unfounded rumors suggest a tryst afterward.

In no other field of activity is early New Orleans more identified with than that of dueling. As noted in Stuart O. Landry’s Dueling in Old New Orleans: "You had to be careful what you said or how you acted. If you criticized the leading soprano at the opera or inadvertently spilled a little of your mint julep on the cuff of the gentleman standing next to you at the bar, you might be called upon to expiate these delinquencies on the field of honor."

Both Creoles and Americans practiced the sport to avenge their name or sometimes merely to impress their women. Insulted by a statement made by a congressman, Governor Claiborne was once compelled to cross swords, as were many other members of the gentry. Two popular dueling spots were the gardens behind the St. Louis Cathedral after Mass on Sundays or under the weeping willows of a park near Bayou St. John outside of town

One frequent practitioner was Jean Lafitte, adding the term swashbuckler to his romantic image. He excelled in the art of the rapier and never lost a bout, although he was "called out" many times by men testing his skill. One evening, legend has it that, while dining with his lady at what later became the famous restaurant Courtyard of Two Sisters, he fought three separate unrelated duels beneath the magnificent oak that centered the open air inn. Unscathed and unflustered, he finally sat down to eat his dinner.

But, a much bigger battle remained to be fought than a code duello. One that involved thousands of men and would result in thousands of deaths. The War of 1812 had begun with England and Jean Lafitte, never before considering himself a man with a country, would be forced to choose sides.