Arlan of Pennytree

"Squire to Ser Arlan of Pennytree who knighted him in his sixteenth year."

- Ser Arlan is mentioned in Ser Duncan the Tall's entry in The Book of Brothers

Ser Arlan of Pennytree was the mentor of Duncan the Tall.

Season 8
Ser Brienne of Tarth reads The Book of Brothers and completes the entry of the late Lord Commander Jaime Lannister. She flicks over the entry of Ser Duncan the Tall, which mentions the he was a squire to Ser Arlan, who knighted him in his sixteenth year.

In the books
In the A Song of Ice and Fire novels, Ser Arlan was a hedge knight who was born in the village of Pennytree. As a child, he was taken to King's Landing by his grandfather and showed him the last dragon, who died later that same year.

As an adult, Arlan defeated Ser Damon Lannister in a tourney at Lannisport. In 193 AC, Arlan fought in a melee at King's Landing where he unhorsed the lord of House Stokeworth and the Bastard of Harrenhal. He was defeated by Prince Baelor Targaryen in a tourney at Storm's End in 199 AC, with Arlan claiming to have broken seven lances against Baelor, with Baelor claiming that it was only four.

Arlan's nephew Roger served as his squire during the Blackfyre Rebellion, with the two fighting for Lord Hayford. They fought in the Battle of the Redgrass Field, in which Roger and Arlan fought alongside Lord Hayford when he was killed by Lord Gormon Peake. Arlan later found Dunk in the slums of Flea Bottom and took him as his squire. They served the lord of House Dondarrion in the conflict with the Vulture King.

Arlan died of a chill as he and Dunk were traveling to a tourney at Ashford, with Dunk inheriting his horses Thunder, Chestnut and Sweetfoot.

His personal sigil was a silver winged chalice on a brown field.