| “ | 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 character of A Song of Ice and Fire. He's already dead before the begin of the main series. He was a knight (possibly a hedge knight) and an infamous outlaw of the equally infamous Kingswood Brotherhood. He was thought to be insane, but was also a deadly swordsman. Even if there's little information about this man, he's regarded to be a completely evil person.
History
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. House Toyne had fallen into disgrace after altercations with the Targaryens. Under Simon's leadership, the Kingswood Brotherhood achieved no small measure of infamy as they kidnapped various nobles and evaded capture. These outlaws were difficult to find, as they were helped and sheltered by the smallfolk in the Kingswood, in the crownlands and the stormlands. At some point they became such a nuisance that the king sent a detachment of soldiers led by notable members of the Kingsguard to destroy them. The outlaws even attacked Princess Elia Martell's escort and wounded the Lord Commander, Ser Gerold Hightower.
Ser Jaime Lannister, who was a squire of 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, cruelty and chivalry all jumbled up together, but he did not know the meaning of fear. Among this man's victims is included Ser Victor Tyrell of Highgarden, cousin of Lord Mace Tyrell.
The Smiling Knight met his fate in a clash with the Kingsguard, sent by the king to destroy the outlaws. During the combat, the Smiling Knight briefly crossed swords with the squire Jaime, but Jaime held him off. Ser Arthur Dayne next fought an extended exchange with him until the Smiling Knight's sword broke. Dayne paused the fight and allowed the outlaw to take a fresh sword. The Smiling Knight did so, but remarked that it was Dayne's famous sword Dawn that he truly desired. Dayne replied "Then you shall have it, ser." In their second exchange, the Smiling Knight was slain. The Kingswood Brotherhood was destroyed and their leader Simon Toyne was slain by Ser Barristan Selmy. Jaime regards the battle against the Smiling Knight and his fellow outlaws as one of his fondest memories of his life.