23. Rodrik Cassel

Ser Rodrik Cassel was the master-at-arms at Winterfell, and loyal servant to House Stark. He trained many soldiers including Robb Stark, Jon Snow, and the man who killed him, Theon Greyjoy. In season one, Rodrik escorted Catelyn to King's Landing and the Vale.

Time of death: Season 2, episode 6, "The Old Gods and the New"

Cause of death: Beheaded in terrible fashion by Theon Greyjoy during the Fall of Winterfell.

Sadness ranking: 6.5. Rodrik was loyal to the Starks through and through. His death was especially sad because it was gruesome and Theon performed the execution on a whim in front of Bran and Rickon, who were close to him.