7. Master Luwin

Maester Luwin was a sweet old man, loyal to the Starks, and basically served as Bran and Rickon's father figure in Winterfell especially after Ned's death. He saved Osha by suggesting keeping her as a prisoner, and helped Osha hide Bran and Rickon from Theon when he was trying to kill them.

Time of death: Season 2, episode 10, "Valar Morghulis"

Cause of death: Osha gave him a quick death after he suffered a stab wound when Ramsey's men took over Winterfell.

Sadness ranking: 8. He was probably the Starks' most trusted ally, and his death was slow and heartbreaking.