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The Mountain of my boyhood. Half as big but twice as mad.
~ Jaime Lannister's thoughts about the Smiling Knight.

The Smiling Knight is a minor antagonist in the A Song of Ice and Fire novel series. He was a robber knight, an outlaw, and a notorious member of the equally infamous Kingswood Brotherhood. As his alias suggests, he has a permanent, disturbing smile on his face. The Smiling Knight was thought to be a lunatic, but he was also a deadly and formidable swordsman.

Biography[]

Smiling Knight TheMico

The Smiling Knight was a member of the outlaw band known as the Kingswood Brotherhood, led by the stormlander Simon Toyne. The band operated during the rule of King Aerys II Targaryen, in which, under Toyne's leadership, they achieved no small measure of infamy as they kidnapped various nobles and held ransom before evading capture. The Smiling Knight and his fellow outlaws were difficult to find, as they were helped and sheltered in the Kingswood by the smallfolk, who looked to them for protection of their rights. At some point, the Brotherhood became such a nuisance that the Mad King sent a detachment of soldiers led by several of his Kingsguard to deal with them.

Ser Jaime Lannister, who squired for Lord Summer Crakehall along with Merrett Frey, recounts that the Smiling Knight was his generation's Ser Gregor Clegane in terms of men's eagerness to best him in combat. Apparently, the Smiling Knight was a complete madman, as cruelty and chivalry were all jumbled together, but he did not know the meaning of fear. Ser Victor Tyrell of Highgarden, Lord Mace Tyrell's cousin, became a victim of the Smiling Knight.

As the Kingswood Brotherhood clashed with the Kingsguard, the Smiling Knight briefly crossed swords with Jaime, but the latter held him off. Ser Arthur Dayne, the Sword of the Morning and the deadliest of the Kingsguard, then fought an extended exchange with the Smiling Knight until the latter's sword broke. Arthur paused the duel to allow the outlaw to take another sword. The Smiling Knight did so, but remarked that Dawn, Arthur Dayne's sword, is what he truly desired. In response, Ser Arthur replies, "Then you shall have it, ser." In their second duel, the Smiling Knight was slain.

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