Petyr Baelish
Ramsay Bolton (seasons 3–6) portrayed by Iwan Rheon. The illegitimate son of Roose Bolton, Ramsay Snow of House Bolton is cruel, sadistic and cunning. He is first introduced to the series when Theon Greyjoy captures Winterfell, and Roose Bolton commands him to retake the fortress, ostensibly to hand it back to the Starks. However, Ramsay's army ransacks the castle and leaves it as a ruin. Ramsay captures Theon, imprisons him at the Dreadfort, and tortures him so severely that Theon forgets his own name, eventually believing himself to be called "Reek". Ramsay even goes so far as to castrate Reek. After capturing Moat Cailin, the Boltons move from the Dreadfort to Winterfell. Roose is named Warden of the North and legitimises Ramsay, making him Ramsay Bolton. Sansa Stark is then married to Ramsay, thanks to an arrangement made by Petyr Baelish in his own attempt to control the North. Ramsay abuses and violates Sansa, raping her on their wedding night. After Sansa and Theon escape Ramsay's capture during Stannis Baratheon's failed attack on Winterfell, Roose chastises Ramsay for his complacency and implies that legitimising him was a mistake. After Roose's wife Walda gives birth to a legitimate heir, Ramsay quickly arranges for his father's assassination. With the Karstarks willing to hide the information, Ramsay stabs Roose through the heart, feeds Roose's wife and son to his hounds, and assumes the title of Lord Bolton. Shortly after, House Umber arrive at Winterfell with two prisoners: Rickon Stark and Osha. Osha is killed when trying to assassinate Ramsay herself. When Jon Snow's wildling army descends on Winterfell to take the castle, Rickon is killed after being used as bait to disrupt Jon's tactics. After a battle, Ramsay is defeated in the field by a combination of the wildling army and the Knights of the Vale, who arrive on the orders of Petyr Baelish and Sansa Stark. He is arrested and chained up in the Winterfell kennels, where Sansa watches him get eaten alive by his own hounds.