Simon grew up in Stormwind City with his mother and father, Mr. and Mrs. Alistair Silverheart, and his sister, Lucentia. Both of his parents 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 to becoming a Paladin, and Simon had barely begun his training when his father was killed. The loss of both parents shook Simon to the core and he lost all faith in the Light. Shunning the ways of his family and becoming distant to his sister, Simon when underground and began to practice the ways of the warlock. Soon, he befriended Lucimara, a fellow warlock and best friend to his sister, Lucentia, and the two practiced their dark gift together in the depths of the Slaughtered Lamb pub.
After being involved in a campaign against the undead with The Dark Hand Covenant, 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, dubbing herself leader and bringing Simon along for the ride.