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Sir Simon, from Ultima VI
Early on, a Sir Simon the Slayer was listed as part of a project known as the "Great Work," in which Lord British, then king of Sosaria, commissioned a series of exploratory travels to provide detailed maps of his realm. He explored and mapped the desolate settlement of Death Gulch, a city among the eastern islands of Sosaria known for its criminality and vice. 
In Ultima IV, Sir Simon could be found along with Lady Tessa in the armoury of the village of Paws. He had been entrusted by Zircon early with securing the Mystic Armour, and had hidden it in the oak grove in Empath Abbey. He awaited an Avatar, ready to divulge the secret location of the armour when one appeared. When the Stranger approached him, already eight parts an Avatar, Sir Simon revealed the armour's location. 
During the time of Ultima V, Sir Simon ruled over Bordermarch, a small island fortress whose inhabitants were dedicated to fighting the tyranny of Lord Blackthorn. When the Avatar visited him, Sir Simon was able to tell the hero of the Crown Jewels, and the importance of retrieving them from the Underworld. He elaborated on the powers of Lord British's Crown, telling of how it could shield its wearer from magical spells, and mentioned also the Sceptre of Lord British, which could dispel any barrier, even those within the realm of the Shadowlords. He advised the Avatar that his wife Lady Tessa knew of Lord British's Amulet. 
Sir Simon was forced to flee Bordermarch's island after it sank beneath the ocean during a massive earthquake, following the events at the end of Ultima V. Along with Tessa, he went on to administer Serpent's Hold in Ultima VI.
Ultima V: Lazarus Edit
In Ultima V: Lazarus, it is told that Sir Simon became the Lord Mayor of Trinsic shortly after the Quest of the Avatar. He remained in that office until Lord Blackthorn's Oppression began, when he defied Blackthorn and refused to follow his laws. Blackthorn besieged Trinsic, and eventually conquered it. Sir Simon had to flee to his fortress of Bordermarch.
- There is a barony within the Society for Creative Anarchonism known as Bordermarch, which was founded by a Sir Simon of the Amber Isle and a Lady Tessa of the Gardens. This fief is in the greater kingdom of Ansteorra - where Richard Garriott has been known to participate in the persona of Shamino Salle' Dacil in the barony of Bryn Gwlad. It is probable that the Ultima character is based upon this Sir Simon, given Garriott's penchant for giving his friends in the SCA in-game cameos.
- ↑ Garriott, Robert. Ultima III Clue Book: Secrets of Sosaria. Origin Systems, Inc: 1983. Page 25.
- ↑ Zircon. Underworld Dragon's Ultima IV Transcript. Ultima IV. "mystic."
- ↑ Sir Simon. Underworld Dragon's Ultima IV Transcript. Ultima IV. "mystic."
- ↑ Sir Simon. Underworld Dragon's Ultima V Transcript. Ultima V. "ability, amulet, crown, scepter."
- ↑ The Barony of Bryn Gwlad. History Barony Bordermarch. Retrieved: 2010-10-08.