Simos was born the privileged son of wealthy hotel owner Charles Castille, the eldest son of the founder of the Galveston branch of the Prejean family. The family had recently been devestated by the Hurricane of 1900, which killed Charles' four youngest siblings and his five children, but Charles was determined to remain in the city and not return to Lafayette as his father and mother had shortly after the disaster.
Life at the Hotel Castille was full of intrigues and secrets. Simos learned the subtle arts of blackmail, manipulation, and money laundering, as well as the numerous and sordid tastes that men and women dreamed of fulfilling but would pay well to see never saw the light of day. He shared this new knowledge with his little sister and the incestuous relationship between the two of them was encouraged, in order to keep them independant of outside influences (even from the family in Lafayette). As they grew up, they began to take an active role in the hotel's functioning and made their father proud.
Charles presided over their secret marriage in 1930 solely in order to quiet pressure from the Lafayette Prejeans to marry the two of them off to the Brasseaux, as they were doing with their own sons and daughters, to ease the growing tensions between the two lines and to ensure their loyalty. This act was the start of a growing separation between the two branches of the family. It also proved to have backfired, as several miscarriages indicated that Amada was unable to bear her brother's children. This devestated Charles, as it spelled the end of his line, but Simos and Amada were not overly concerned. So involved were they with their appetites and intrigues, that it was almost a welcome relief to be able to forgo the usual family duty and focus on their hotel.
As time went on, Charles began to lose his interest in the hotel and his family and Simos and his sister began to take a larger and larger hand in its functioning. Simos saw to most of the financial details while his wife acted as general manager and hostess. The separation of duties, however, was mostly artificial as they shared everything with each other and never made a major decision without consulting the other. The siblings also gained an ally in the main branch of the family when Berenger was sent out to heal the rift and the three found they had a lot in common. In fact, it was Simos and Amada's influence that led him to his current calling.
Things became difficult during the Depression and the war, as money was scarce to pay for the sort of 'refined' services that the pair provided, and so they began to refine their blackmail schemes even further, accumulating a great deal of intelligence on the criminal enterprises and perverse tastes of local politicians, businessmen, and civic leaders. This knowledge proved useful to the New Orleans Lasombra (who gathered it through Berenger) and they began to take advantage of the Castilles regularly. Ironically, this helped to take pressure off of Lafayette to take a more active role in supporting the Archbishop and so the tension between the two branches of the family finally lessened and something of a truce was reached, though mutual trust was scarce.
When the economy began to recover after the war, the golden days of the hotel began. Leveraging their blackmailed 'clients' to bring in new customers and spreading the word through Berenger and their other family contacts throughout the region, the hotel began to boom. Catering to the most decadent and perverse of tourists, they also changed their tactics, only using blackmail and extortion selectively and quietly so as not to spook their wealthier and more powerful clientele or draw the attention of the puritanical post-war authorities. There were several close scrapes, but things were quite good for the pair until the mid-60s, when a scandel erupted, driven by an inevitability that was almost akin to fate. The body of a dead twelve year old girl was traced back to the hotel and linked with a prominent local politician. The evidence was clear that the hotel staff wasn't just aware of the criminal procedings, but was instrumental in attempting to cover it up. Desperate, the siblings dealt with the matter in the only manner they could: they laid the blame on their aging father and let him take the fall.
Charles Castille died in prison in 1971, having served five years of his life sentence. It was an open secret that the entire trial was a scam, but Simos and his sister held the strings of too many judges, politicians, and journalists for anyone to publicly state it, so long as there was the scapegoat. Charles himself didn't seem to fight very hard for acquittal, having long ago lost any passion for life. With the necessary firings and restaffing out of the way, the hotel returned to its normal functioning, except now it had a dark reputation locally and the rich and powerful were much more wary to be seen coming or going. This lead to a new stage of existence for the once luxury resort. Rather than catering to the perversions of the elite, the hotel became a tool for the underworld as a meeting place for the quietly wealthy out-of-towner to meet with the criminal contacts who fed his appetites and partake of the product where anonymity was guaranteed. Drug dealers, slavers, and pimps from overseas would come here to meet with their lower upper class American clients, smuggling their wares in with the help of Berenger and his powerful New Orleans smuggling contacts. The two operations became closely linked throughout the 60s and 70s and flourished in the atmosphere of hedonism and permissability that pervaded the era.
While the change of atmosphere in the 80s made it harder to operate such an immoral enterprise without drawing attention, the influx of money from the prosperous decade helped the hotel begin to drift into a new golden age. The scandels of twenty years before forgotten, the hotel began to again host a more refined clientele. However, during the period, the viewpoint of Simon changed and the dynamic of the couple began to alter accordingly. Always a voyeur, Simon began to take less and less of an interest in running the hotel for its own sake and began to spend all of his time in the control room, watching their guests through the hidden cameras spread throughout the complex. In fact, he expanded this surveillance as cheaper, smaller cameras became available, recording anything which struck his fancy and adding the tapes to his private collection. Feeling somewhat spurned by this, his sister began to play games to rouse his jealousy, becoming less of a detached and manipulative hostess and becoming more active in the actual goings on, as she was in the beginning.
This has been progressing ever since so that now the hotel is less of a business enterprise and is more of a game to feed the twisted desires of its owners. Clients are chosen, not for their money, importance, or discretion, but by how much they appeal to Simon and Amanda's tastes. And further, the game is starting to spill out of the hotel and may soon draw attention as Simon's ire urges him towards random spiteful acts of vengeance against those his wife takes an interest in. Recently, a professional domintor who put her through a particularly vicious BDSM session was pulled out of the water, having been tortured to death (the coroner used the term 'flayed'). Clues are scarce, but the siblings have been having the most passionate sex they've had in years. An even greater threat, however, is a man whose career and marriage were ruined by Simon through the careful use of pictures and who is now giving evidence against the hotel to the DA to get revenge. An investigation is sure to be launched and it is uncertain if the couple was the self-control and subtlty necessary to come through it unscathed.
Simon (he's been using the Americanized version of his name since the 1950s) comes off as a weak, ineffectual playboy. This is a very good act, as he is, in truth, a cruel, ruthless control freak whose voyeurism is merely an outgrowth of his need to be aware of everything which goes on in his domain (his 'castle', as he jokingly calls it). He is possessive to the extreme and has become more so as the years pass, his desire for control fed on his success as a blackmailer and manipulator. While he would never allow himself to seem angry, or say a harsh or threatening word to anyone in person, once his ire is raised he will destroy the object of his anger in the most intimate, total way he can imagine.
Simon is so obsessively in love with his wife that it doesn't even seem like love to the outside world. Those who know him best are convinced that he hates her with the stereotypical passion of a rich married couple who is incapable of seperating due to money, obligations, and appearances. In truth, however, he is fiercely jealous of her, and this is what drives his lust. When they are happy, his sex drive is non-existence. When he is enraged, however, his lust takes on the intensity of a rapist. Oddly, he also respects her rather than holding her in contempt for her 'indescretions', because he is aware of how well he is being played and appreciates her skill at it (and desire to do so).
Simon is incredibly fond of Berenger and this is not a mystery to their mutual acquaintances. The two are like brothers and Berenger regularly visits for business and pleasure. Despite their business relationship, they've never had a serious disagreement, always being able to work out problems together. The closest thing to a sticking point that they have is Simon's mild contempt for the rest of the Lafayette branch. However, this is mostly just a remanent from his father's attitude and he isn't passionate enough about it for it to really matter. In fact, it is almost likely that, were he to become better acquainted with them (something Berenger has been trying for years to encourage), he'd probably get along with them.
Simon was deeply respectful of Vicario and mourned his death, and has served his childe faithfully. Even though Delacroix, at first, found excuses not to deal with he and his sister, whom he found morally repugnant, he has not been able to deny their effectiveness. Even their current lack of attention to the important matter of sect duties is excuseable because of Sandra Fuentes. In her, the Castilles have provided Delacroix with the perfect tool to spy on Lafitte and, eventually, destroy him.
While not what it was at the hotel's height, the web of blackmail, extortion, and the subtle threat of such gives Simon a great deal of control locally and with a few select clients overseas and elsewhere in the United States. Most of this influence is used to keep the authorities away from his activities. Simon's Fame is more infamy from the lingering reputation of the 1960s scandel.