Simon Killian suffered his first death on September 21, 1745, in the Battle of Prestonpans. Killian was always a soldier, and eventually it was a role that consumed him, an ideal that he saw without regard to death or loss. War was his glory, all the suffering, he did not see. Killian was the first mentor of British soldier, Everett Bellian. Bellian was first killed at South Africa's Ladysmith during the Boer War. It is likely that Killian also fought in that war.
During World War I, Killian fought with the British. On November 11, 1918, Killian met Duncan MacLeod, who transported wounded soldiers from the battlefield as a medic. Killian was surprised that he was not present at the forefront in the battle. When Killian was ordered to cease all hostilities, when the armistice was signed, he ignored his orders and proceeded with his long-planned offensive. He shot his Sergeant and MacLeod, both witness to the orders to cease fire, and then led his men into a senseless assault. About 300 British and German soldiers where killed in the action. Killian was arrested and tried before a military court. MacLeod testified against him, and the court ultimately sentenced him to death for his actions. With MacLeod's intervention, however, the sentence was commuted to life imprisonment in a psychiatric hospital. Killian spent 70 years incarcerated, and in the end, no one knew where he had come from. During that time, he developed a fascination with spiders. Later he collected dozens, some harmless, some deadly.
After Simon Killian was released from the psychiatric facility, he spent his time in London. But in 1995, he traveled to Seacouver, having learned of MacLeod's presence there. Killian had MacLeod kidnapped, but when he escaped, Simon kidnapped his friend, Amanda - he thought. When he realized that his men had captured Amanda's new friend, Melissa instead, he allowed poisonous spiders to bite her, and then left her in the dojo.
Duncan followed them, Killian let them shoot and imprisoned Duncan in an abandoned Air Force base outside Seacouver. He wanted to have him confined for 70 years in a cell in order to take revenge for his own fate. But after a few hours, one of his people spotted MacLeod at liberty. MacLeod had been freed by Amanda and Joe. When Killian an MacLeod next met, they fought, and Killian was beheaded.