Simon grew up in Stormwind City with his parents, Alistair and Valeria Whiteheart, and his sister, Lucentia. Both Alistair and Valeria were Paladins of the Holy Light, colleagues of Uther Lightbringer, and raised their children in the ways of the Light. When Simon was at a young age, his mother died under mysterious circumstances, and he was forever shaken. A few years later, his father, Alistair, had migrated to the continent of Kalimdor on a pilgrimage to spread faith in the Light to other cultures. While there, he was ambushed by a villainous rogue named Krall and murdered in cold blood.
Lucentia had already embarked on the path of the Light and was a junior Paladin of the Order, but Simon had barely begun his training alongside Arthur the Faithful and Katharine the Pure when his father was killed. The loss of both parents shook Simon to the core and he lost all faith in the Light. He reasoned that with the ability to resurrect the recently dead, any Paladin or other healer class could have, and should have, been able to revive Alistair. Simon simply would not accept that his father, nor his mother, had to die. Shunning the ways of his family and becoming distant to his sister, Simon went underground and began to practice the ways of the warlock. Bitter and alone, he managed to maintain a tenuous friendship with the warlock Lucimara, the daughter of his father's best friend, Adalbert Renhold, and best friend to his sister, Lucentia.
After being involved in a campaign against the undead with The Dark Hand Covenant and the Silver Sun, Lucimara came into the possession of a dark grimoire formerly belonging to Embron Silkwood, an undead mage of The Blackheart Templar. Having aided in the defeat of the Templar, Lucimara read through the grimoire, learning its secrets for herself. She soon decided to start the Templar fresh and create her own shadow faction of the same name, dubbing herself leader and bringing Simon along for the ride.