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The Smiling Knight

The Smiling Knight's History

During the time of the Kingswood Brotherhood, the Smiling Knight killed Ser Victor Tyrell - cousin of Lord Mace Tyrell of Highgarden. While rescuing Lady Jeyne Swann from the Brotherhood, Ser Barristan Selmy of the Kingsguard defeated the Smiling Knight and slew Simon Toyne.

Ultimately the Smiling Knight was killed in a clash with the Kingsguard. During the combat, he briefly crossed swords with Jaime Lannister, but the squire held off the Smiling Knight. Ser Arthur Dayne next fought an extended exchange with him until the Smiling Knight's sword broke. Arthur paused the fight and allowed the outlaw to take a fresh sword. The Smiling Knight did so, but remarked that it was Arthur's famous sword Dawn that he truly desired. Arthur replied "Then you shall have it, ser." In their second exchange, the Smiling Knight was slain by the Sword of the Morning.

Ser Jaime Lannister recalls that the Smiling Knight was his generation's Ser Gregor Clegane in terms of men's eagerness to best him in combat. According to Jaime, the Smiling Knight was "a madman, cruelty and chivalry all jumbled up together, but he did not know the meaning of fear."