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An averagely tall man of average build with no remarkable physical traits whatsoever other than a slightly above average height. Balancing on the medium of everything, he isn't thick, but not quite thin, nor is he built, though he looks as if he could handle a considerable amount of physical exertion. His broad shoulders compensate for his six feet two inches height, and his frame generally warrants little attention from any passers-by. His dark green eyes are deep-set, with a line or two underneath to emphasize a fatigue not common to his age. Minute creases between his brows brings a sort of harshness or deviance into his every expression no matter how charming or amicable. Permanent stubbles on his face and over his lips play off of this worn-out businessman look, topped off with a purposefully unkempt haircut. Overall, the untidiness in his appearance is compensated by clothing, ranging from well-cut Armani suits to casual t-shirt and jeans ensembles. The general effect is that no matter how simple or extravagant he happens to look, the man exudes an air of affluence and modesty.

The first-born child of a relatively young family, Simon was no stranger to the idea of helping oneself. His parents were not exactly fit to be caretakers, and their incapability rendered him independent as soon as he learned how to walk. All through his early childhood, the boy learned to do everything by himself. First eating and dressing, and eventually to hiding himself from the numerous and frequent visitors in the house. The highlights in his life would be the occasional trips to his grandparents'. His parents would leave him to spend days there, where enjoying the coddling of the older couple. When his baby brother came home from the hospital, Simon fashioned himself as the guardian of this tiny baby, protecting him as much as he could manage at six years old.


With the presence of the younger boy, he became more aware of what was going on around them. School was a waste of time at that age, but he did manage to hear what the other parents had to say about his family twisted through the mouths of his classmates. He frequently entertained the idea of leaving home, but the responsibility he felt for his baby brother rendered these fantasies invalid. Finally, on his brother's fourth birthday, Simon took the birthday boy out to play with no intentions of returning. They were an hour away from midnight when his father found the two of them stranded at the bus station. Beaten to a pulp first and chastised with the most colourful words after, his father sent him away to the grandparents' permanently, separating the siblings from one another.


The kindness of his grandfather and grandmother helped him through this rough patch with his parents until he no longer wished to go home. Out of ease, he dropped his father's surname and picked up his mother's maiden name from his grandfather, severing all ties to his old family. The only links he had with the household were infrequent letters to his brother, and Christmas cards when the holidays came around. As he finally entered middle school with average grades, these letters stopped as well, due to the lack of response from his brother who never seemed to have received them. It was no surprise that when his parents died in an unfortunate accident, Simon accepted the fact readily, and was a little glad that his brother had gone into the care of the next of kin.


Upon entering high school, his allowance was no longer sufficient. The conditions of the area high school weren't exactly conducive to an academic career, nor did it promote honest work as something profitable. Simon began holding drugs for other people, pinching as much as he could without being found out, then dealing it back to the same people. His friendly nature and feigned generosity made it easy for him to find friends, and cheat them out of things until it seemed as if they owed him. After the death of his grandfather, he dropped out of school, and took it upon himself to organize this amalgam of friends who were all (more or less) exceptional in some way. With some power to spare, he began acquainting himself with more powerful characters in the city. At twenty-one, he was working as the right hand man of the most powerful gang leader in the city. The man taught him everything he ought to know about how to manage things from the topmost level, and how to keep the rest of the men compliant. But Simon wasn't one to keep people at a distance like his boss, rather he worked closely with his subordinates, garnishing respect, trust, and credibility in this collection of outlaws.


After two years of service to the leader of the gang, his ambitions got the better of him. Soon, someone in the gang let slip the half-truth that his boss was only successful due to Simon's success. The rumour then became common knowledge, and everyone who was anyone knew that it was Simon who had the most power. His mentor wasn't very fond of hearing this, and planned a hit on the enterprising young man. As according to his plan, the knowledge of the hit solidified the idea that he was the most powerful, and made his boss out to be a backstabber. When other underworld authorities (whom in name had more power than he did) reported this to him, all that Simon needed to do was to feign a sense of betrayal to make the illusion authentic. Upon expressing their loyalties to him, it became the first act of the new godfather of the city to kill his former employer via a respected hitman named Jack Cavanagh.


During the first year under his command, his gang eliminated its lesser rivals and made its more powerful rivals compliant. He soon gathered around him a circle of very loyal and able men, aiding him in his business and ensuring his safety. In effect, the godfather has begun to build an empire around him, assimilating these uncoordinated gangs into a methodized criminal organization.

Simon is a very driven person who is more psychologically sound than his life allows. He has a severe want for independence, to prove his strength and resist all weakness. The need for acceptance has made him a people person and a very easy going one at that. He always keeps his friends close and never forgets anyone on the way up, nor does he neglects to repay any small debt. It has also made him quite caring, taking many obligations onto himself and sincerely lending help whenever he is able. His manipulativeness plays in when he needs something, and this kind of behaviour is viewed by others as ambition, an admirable quality. Disallowing others to repay him outright, the man makes it so that most of those around him feel indebted to him, another way of keeping people controlled but friendly. As proven by his childhood antics with his brother, he is a problem solver oriented to his own gain under the guise of bettering the lives of others. In the process of achieving something, he might become overly calculating, and try to circumvent any problem that might appear. He can be ruthless when dealing with said problems, but convince himself and others that it is for the best.


As a leader, he is disciplined and altruistic, and will work as hard as he can to benefit those who helped him on the way up. He does his best to be the leader that people want him to be without seeming weak, and is the authoritative person that a mass needs in order to function. When dealing with threats, Simon can be very protective of his own, and will exact revenge when someone harms one of his protégés. His disregard for his own health when helping his own is often balanced out with his disregard for a person's well being when dealing with his adversaries. The reckless irresponsibility of a child that he keeps controlled ekes out when toying with the life of someone dispensable, exerting the need for violent control to keep the situation in order. The opposing desires of pleasing others and not wanting to appear controlled by their will makes some of his choices questionable and ambiguous. In the end, most of these choices turn out for the best, and gather more people around him in view of their success. But when these decisions do fail, those who become his enemies can't be swayed to change their minds.


His overall behaviour and aims aside, upon meeting him, he can be a very pleasant person. Someone who's good humoured and easy to get along with. His appearance and words lend a down-to-earth feeling, making his power not so overbearing. The apparent eagerness to work with people rather than control people also lends a credibility of dedication, making him out to be someone who cherishes honesty and loyalty. He is wise enough to dish out his intelligence to people accordingly, and will match people in their wit but not surpassing them. He only allows his arrogance to peek through in casual conversation when he believes he is upholding righteousness or justice. Due to the respect that is given to him as par for the course, he never distances people when he doesn't have to. Personally a man who appreciates the finer things in life, but will work to share that appreciation with everyone under his domain.