As a boy, Jack was sent by his father, Duke Hartshorne, to study to be a knight under his onetime rival Duke Ghlomus, in an effort to ameliorate their old rivalry. Also known as Jack the Dragonslayer, having slain his first dragon as a squire of twelve, Jack became a knight in the Order of the White Wolf, a Mahorelan knightly order under the protection of Duke Ghlomus. When the Duke and several of the Order’s senior knights betrayed the Order to a rival during the onset of the Duke’s Wars, Jack left in disgust to pursue his own career. After a brief stint as a mercenary, he joined the Crimson Plume, a band of professional dragonslayers. Jack soon wearied of the life, finding the business of professional dragonslaying to involve far more currying noble favor than actual adventure seeking. About this time, he crossed paths again with his childhood friend Red Tom, on the run from certain merchants and princes from whom he had stolen. The two left together, in search of treasure and adventure, and Jack dropped the title ‘Sir’ in favor of a sobriquet more befitting his new life: Perilous Jack. As is customary of dragonslayers in general, Perilous Jack is proud, boastful, and impulsive to a fault.
Initiated by his father at a young age into The Cloak, a secretive cabal of dark mages, Simon spent more of his early life in the company of demons and goblins than in the company of men. Simon never relished the dark ways of The Cloak, nor did he share their desire for world domination, and so in his late teens, he struck out on his own, taking many of The Cloak’s magical treasures with him. Inevitably, mages and assassins followed, seeking to reclaim their stolen goods and punish the transgressor, but they met a greater challenge than they expected, for Simon had made powerful friends in his journey to freedom – the warrior Perilous Jack, master thief Red Tom, and the priestess Serra the True. Together, the foursome defeated the assassins of The Cloak and cemented forever the bonds of friendship that would carry them through countless adventures. Thanks to his sheltered upbringing, Dark Simon is painfully shy, particularly around Serra the True and other women, a condition only exacerbated by his short stature and somewhat flabby physique.
Serra the True
Of the four members of Perilous Jack and Associates, Serra has had perhaps the most varied career. Orphaned at the age of nine by the Great Fire that destroyed the Southern Ward of Piamos in 967, she has made her way alone in the world since. She has worked in a traveling circus as a singer, dancer, musician, acrobat, fortuneteller, clown, and lion tamer; then as a tavern wench, a clothing model for a high society seamstress, a deck hand, a caravan guard, a shop girl to a prominent herbalist, and as a healer. Shortly after taking up the latter profession, she experienced a profound vision of Yisod, the Goddess of the Moon, while wandering through a meadow in summer, an event that changed her life. She became a priestess of Yisod, in whose capacity she has labored as a healer and an adventuring righter of wrongs ever since. Serra is as outspoken and fierce as Simon is shy and retiring, never hesitating to express her indignation at a wrong. This, coupled with her great physical beauty and scrupulous honesty, can make Serra the True at once a maddeningly desirable – and simply maddening – companion.
Before he was sent away by his father to be a knight, young Jack’s truest friend was Red Tom, the son of Duke Hartshorne’s Weapons Master. The two boys were inveterate rogues together, spending every free moment exploring the Duke’s castle and grounds, stalking imaginary monsters, stealing anything and everything of value, and hoarding the booty in their private ‘dragon’s lair’ in a forgotten corner of the dungeons. After Jack left, Tom found his position in the castle greatly reduced and himself not well liked, prompting him to run away one night, taking some of the choicer items in the ‘hoard’ and in his father’s workshop with him. He hasn’t stopped running yet. A consummate burglar, tomb raider, and pickpocket, a career gambler, and possibly one of the greatest swordsmen who has ever lived, Red Tom continues to eke out a living at the margins of civilization, preferring to stalk and strike from the shadows and walk lonely paths than join in the great endeavors of man. Lean from years of meager living, hard of body and sharp of mind, he lives always by his wits, his rakish good looks, a sharp tongue, and an even sharper blade.