Note: Spoilers ahead.
Simon was born to Susanna on Founding-year 1150 on a stormy night, two months early. Due to difficulties with the birth, Doctor Morgenes was called. He delivered the baby, but was unable to save Susanna. With her dying breath, she named the boy Seoman, explaining, "It means . . . 'waiting' . . ."
Rachel, the Mistress of Chambermaids, took Seoman and raised him herself, with the help of the other chambermaids. Since everyone in the service of King John took Westerling names, she called him Simon, which was the closest name to Seoman she could think of.
The Dragonbone ChairEdit
At the beginning of TDC, Simon is a 14-year-old scullery boy at the Hayholt. Because of his tendency to daydream and dawdle, Rachel often calls him a "mooncalf", constantly scolding him for his laziness. He likes to get away from work, spending hours by himself in the Hayholt's extensive network of passages. He eventually manages to become an apprentice to Morgenes. In exchange for an education (Simon particularly loves history), he must do chores and bring various plants and animals for the doctor.
His life changes forever when he stumbles onto a secret dungeon, where Prince Josua has been held captive. With the help of Doctor Morgenes, he helps the prince escape the Hayholt by way of a secret passageway within the doctor's chambers. They are discovered, however, and Simon must then escape through the same door, leaving Morgenes behind to defend them. There is an explosion that kills the doctor and all the guards at the doorway. Simon, in shock, runs through the passageway down into the depths of the Hayholt. He wanders the dark tunnels, lost, for a long time. While there, he has visions of Asu'a and the Sithi, as things were in the final days when they were killed off. Eventually, he finds his way back out above ground, where he witnesses the Norns and the Red Hand present King Elias with the magical sword Jingizu (Sorrow). Terrified, he runs away into the forest.
He wanders the forest alone for weeks, half-starved, delirious, and lost, until one day he stumbles onto a Sithi caught in a trap, about to be murdered by a man. Simon kills the man and frees the Sithi. The Sithi runs away but does shoot a white arrow near Simon. Binabik shows up and tells Simon that the white arrow means the Sithi owes him a debt, and Simon better take good care of it. Binabik then takes Simon under his protection, and they travel together towards Naglimund. They become close friends during this time and Binabik becomes something of a mentor to Simon. During this time, they have many adventures and narrow escapes. They meet the Wise Woman Geloë and gain a new traveling companion, Marya, who claims to be handmaiden to Princess Miriamele. Pursued by nightmarish hounds and a deadly hunter, they make their way through an ancient Sithi city, Da'ai Chikiza. With much difficulty, they finally reach Naglimund.
Once in Naglimund, Simon finds himself an unwilling participant in several councils deciding how to dethrone King Elias. They decide to take a two-fold strategy: 1) to gather allies and wage war against Elias and 2) to gather three mythical swords, as prophesied by the mad priest Nisses many years back. They know that Elias has one sword, Sorrow, and through much study find that Thorn is lost somewhere in the far north. Minneyar (or Memory) is as yet undiscovered. They send a small party (Simon and Binabik included) to retrieve Thorn.
Simon therefore finds himself once again a traveler, and this time into the uncomfortably cold north. On their way, they are attacked by the hellish hounds but rescued by a group of Sithi. After a side trip into Sithi domain, Simon's White Arrow becomes the catalyst for Prince Jiriki (to whom the arrow belongs) to join them on their quest. They do find and retrieve the sword Thorn, but doing so awakens the great Worm (dragon) Igjarjuk. Jiriki tries to slay it, but is nearly killed. In the heat of the battle against the creature, Simon takes up Thorn and stabs the dragon through the eye. Igjarjuk falls into a deep canyon its fate unknown. Its blood falls on Simon's face, burning wherever it runs. He loses consciousness. When he awakens, he is weak and sensitive to his surroundings. He finds that he is on Mintahok, that Binabik and Sludig have been taken prisoners, and that the dragon's blood has left him with a scar and a swath of blanched hair. Jiriki scolds him, because he has now saved the Sitha's life twice.