61. Roose Bolton

Roose Bolton was the ord of the Dreadfort, and up until the Red Wedding, loyal to House Stark. When the War of the Five Kings went unfavorably for the Starks, he betrayed them and took part in the Red Wedding with the Lannisters and the Freys, and he was appointed the new Warden of the North. He arranged Ramsay's marriage to Sansa Stark, in an attempt to secure their taking of Winterfell.

Time of death: Season 6, episode 2, "Home"

Cause of death: Ramsay Bolton stabbed him after Roose threatened to name his unborn son successor.

Sadness ranking: 3. He was the only person who could keep Ramsay in line and looked down on his sadistic ways, but he did a lot of terrible things, starting with betraying the Starks and giving Ramsay some power.