The Gentleman Pirate commanded an armada of fifty ships and over a thousand privateers during the height of his career. His base of operations in Barataria Bay was a small city with its own bars, brothel, warehouses, and a cafe. During his life, he denied that he was a pirate, flying the flag of Cartagena, the main port of Columbia, and raiding Spanish ships, selling the captured contraband to New Orleans merchants (and accounting for the vast majority of the city's trade). Recruited by Andrew Jackson to assist in the defense of New Orleans in the War of 1812, he and his men and their arms were pivotal in the overwhelming victory of the Battle of New Orleans.
However, he never saw acceptance for his integral role in making the city what it is today. Pardoned and granted citizenship for his efforts in the Battle of New Orleans, his camp in Barataria had still been put to the torch and when his men disobeyed his orders and were tried and hung, he lost all hope of being a respectable citizen. However, he was given a second chance to be a part of the city by Vicario, who approached him with the offer of immortality and explained to him that the forces which sought to drive him out of the city were being manipulated by the forces he opposed. It took several long discussions before the decision was made but, in 1821, Lafitte set his Galveston camp to the torch and took the closest members of his crew to accept his new position.
Unlife was unlike anything he could have expected and it took time for the privateer to adjust. During that time, it became swiftly apparent that the picture his sire had painted was incomplete, but he bided his time as he put it all together. Of great help was a former lover named Catherine Sallier, whose husband had shot her and killed himself over their affair. The two remained in contact throughout the years and now he sought her advice and understanding. She helped him come to terms with the changes in his life, but his visits were not unnoticed. During one of his trips there, he was confronted by the Callough Motley, childe of Orlando, who made him an offer. Pointing out that he would always be subordinate to his sire and stressing the violence and decadence of the sect, he was able to convince Jean, over several monthes of discussion, to betray the Sabbat.
Although the Brujah laced their offer with vague promises about a position of power within the city after the Camarilla took it, Lafitte didn't truly believe it. He did, however, reason that the turmoil the conflict would create would give him the opportunity to seize it for himself, given his greater influence there and intimate knowledge of its inhabitants. However, when the assault didn't offer as decisive a win as his new sect had hoped, he opted to wait for a better opportunity and remained openly loyal to Orlando and the Camarilla. He continued to gather influence and economic power to himself, gaining the support of the Camarilla Prince in Houston (helped by the aid he gave Texas during its war for independance).
His betrayel cost him greatly, though. Tremere antitribu helped stir up a massive storm which they threw against Galveston. Caught on his ship, Lafitte was almost destroyed, but more importantly his brother and now childe was lost to the depths of the gulf and much of his ghouled crew was killed. Returning to Lake Charles to recover, he was now utterly alone. Catherine, his brother, and his crew were all gone and he found himself adrift among strangers. Though he gained a new crew, it wasn't the same and he fell into a malaise that lasted until he met Sandra Fuentes. So alike Catherine in manner and personality, he acted rashly and Embraced her, a mistake which he now pays dearly for, forced to face her hatred and the secret of her existence which he keeps from his superiors in Houston.
Meanwhile, his war with the Sabbat has grown repetitious to him, as has the meaningless acquisition of power and wealth. With the end of the millenium, he is facing something of a crisis of age. The only respite he's found has been his sparring with Baptiste Garcia, a man of his own calibre and one whom he respects, despite the fact they've never met.
In life, Jean was a visionary and a diplomat, but the years have taken their toll, sinking him into depression and cynicism. These days, he is gripped by a deep ennui and often spends monthes out at sea on his ship, the 'Corsair', just sailing to calm his weary mind and visiting the places that have been dear to him during his long existence.
Despite his malaise, Jean is still a very dashing figure, possessed of incredible charisma and a roguish charm. His internal conflicts are kept buried, so only those close to him are aware of how deeply troubled he is, and these are few.
Jean is deeply in love with Sandra, moreso now than when he foolishly Embraced her. He is desperately looking for a means to repair the damage he has done, but all efforts have only compounded the mistake. The only means he can think of left at his disposal is imposition of the blood bond, which he is loathe to do.
He is also troubled by the falling out he's had with his 'brother', Paul. He would desperately like to be back on good terms with the man, given their familial ties, but can think of no means to repair their relationship. He has little attachment to the other kindred of New Orleans, never really liking the Serpents or the Samedi, but was somewhat fond of Ange and disliked the humiliation she was put through by his sire. He is disturbed to hear what has become of her in the modern nights.
He is wary of the Camarilla of Louisiana. He doesn't trust Orlando as far as he can throw the man and is all too aware of the ambitions of La Salle and those in his chantry to turn his back on them. He is on much better terms with several of the Camarilla vampires in Houston, however, and considers himself more the subject of its Prince than Orlando, though he doesn't go out of his way to point this out.
He's run into Henri Gilette on a few occasions, when the man has passed through Galveston. He isn't sure of his loyalties and Henri's manner make him wary. They've enjoyed a few nights of reminiscence now and again, but Lafitte has been making inquiries and thinks that the Ravnos is holed up with the Tzimisce of Lafayette and so has become even more suspicious of his business in Galveston. The next time they encounter each other, he intends to interrogate him more thoroughly about his business and be more careful what he shares with him.
Jean has considerable control in several gulf shipping interests, in the U.S., Brazil, Columbia, and Mexico as well as a number of smaller smuggling operations out of those and several smaller countries in the Caribbean. He exerts his influence through a myriad of forms, from stock control to proxy corporations and even a few ghouls (one in Cartagena, one in Port-au-Prince, and one in Houston). He is very careful to keep his use of power to a minimum, usually only making minor adjustments in order to better interfere with Sabbat areas of influence. His strategy, instead, is to win out over the competition merely by being more successful. Two centuries of being in the trade have taught him a lot and he applies his extensive knowledge to every aspect of the business.
As mentioned above, Lafitte has three ghouls, all of whom are of considerable age (the youngest is over a century old). The eldest, Arturo Guevara Yegros, is Lafitte's Columbian lieutenant and has been in his service since his mortal days. The head of a massive shipping dynasty which he controls from the shadows, he and his progeny have weathered the turbulent politics of Columbia since its formation.
Vanessa Cousin is based in Port-au-Prince and serves to coordinate his Caribbean operations. She has changed identities every twenty years for the last century and a half, rebuilding her reputation virtually from scratch each time to avoid leaving too much evidence of her transitions. Not the stereotype of the cold businesswoman, she is actually a friendly and passionate woman who enjoys fully the benefits of her state of existence. While none of her affairs are destined to last long, she throws herself into them completely, a habit which bothers Lafitte on some level (whether it is jealousy or kindred caution is uncertain).
Finally, Kasara Gunturu is the former ghoul of a Ventrue from Houston who served as his Hindu manservant for half a century before his domintor was killed by assassins from Dallas. Lafitte, who had long admired the man for his mind and his education, offered him a place as his man in Houston. Kasara accepted and was sent to business school and proved to have quite the head for business (as Lafitte suspected). He has recently completed law school as well and has become Lafitte's primary agent in the states, though he suffers somewhat among Houston kindred who still think of him as the quaint foreign valet he used to be.