Ramsay Bolton

Before he was anyone, Ramsay was an inconvenient secret. Roose Bolton, out hunting his lands, came across a miller's wife and decided to claim a right generations out of practice: the first night with a newly married woman. He hanged the miller for not reporting the marriage and took the woman under the same tree the man's body hung from.

A year later the woman arrived at the Dreadfort with a baby in her arms. Roose nearly did away with both of them, but something in the child's eyes stopped him — they were his own. He bought her silence with a mill, a pig, some hens, and a yearly purse of copper stars, on one condition: she was never to tell the boy who his father was.

The promise didn't hold. Twelve years later the mother came back asking for help — the boy had grown up wild and no one could control him. Roose sent a servant nicknamed Reek to look after him, meaning it as a punishment for both. He was wrong, or right in a different way: the servant and the bastard became inseparable, and it was never clear which of the two led the other astray.

By then Ramsay already knew whose son he was, and the resentment came with the name. When Domeric, Roose's legitimate heir, tried to treat him like a brother, Ramsay answered by poisoning him — or so his own father assumes, without much doubt. House Dustin, related to Domeric's mother, never forgave it. Two years before the War of the Five Kings broke out, Roose brought Ramsay to live at the Dreadfort and named him his heir.

With Roose away in the south, Ramsay was left in command of the Dreadfort and wasted no time putting his father's absence to use. When House Hornwood lost both its lord and its heir, he attacked, seized the widowed Lady Donella, and forced her to marry him. After raping her, he made her sign a document naming him Lord of Hornwood, then locked her in a tower with no food — she starved to death, having eaten parts of her own fingers.

The North began to fear him in his own right, not just as his father's shadow. Ser Rodrik Cassel, who governed Winterfell in the Starks' absence, tried to stop him, but Ramsay escaped death by letting the servant who'd been at his side since childhood — Reek — die in his place. Ramsay took the man's name and place, and was brought to Winterfell as a prisoner disguised as a common servant.

When Theon Greyjoy took the castle, Ramsay offered him loyalty in exchange for his freedom and became his right hand in hunting down the fugitive Bran and Rickon Stark. They never found them. It was Ramsay's idea to solve the problem another way: kill two farm boys and pass them off as Ned Stark's sons.

The northern lords, enraged by the boys' supposed deaths, marched on Winterfell to retake it. Ramsay offered to fetch reinforcements from the Dreadfort — and did come back, but at the head of an army of his own. His men greeted the northern forces as allies; when Ser Rodrik offered his hand, Ramsay cut it off and ordered the slaughter. He rode up to Winterfell's gates carrying the bodies of Ser Rodrik and the other lords, took off his helm before Theon, and revealed who he was. The castle fell and was sacked without distinguishing ironborn from northmen.

At the Dreadfort, Theon stopped being just another prisoner. Ramsay began flaying him piece by piece, unhurried, and sent Robb Stark a strip of his skin as proof that Bran and Rickon's deaths had already been avenged.

The Red Wedding redrew the map of the North overnight, and House Bolton collected its share for helping arrange it: Roose was named Warden of the North, and Ramsay was given a wife who carried the name Arya Stark — a marriage that, on paper, opened the door to calling himself Lord of Winterfell. King Tommen Baratheon also signed the decree that made him, for good, a Bolton.

With the war in a different phase, Ramsay decided Theon should be Reek again, fully. He forbade him to wash, left him caked in filth, flayed the skin off several of his fingers and toes — leaving the wounds open for days before cutting the fingers off — and broke a number of his teeth. Everything suggests he had him castrated as well.

In the middle of all that cruelty, Ramsay was also governing: he named two Frey boys, Little Walder and Big Walder, as his squires, and prepared the last move he needed to finish off the North — Moat Cailin, still held by the ironborn. He sent Theon as an emissary to negotiate its surrender, promising food and freedom in exchange.

The ironborn surrendered. Ramsay had every one of them flayed and displayed their skinless bodies along the causeway leading to the fort, as a warning to anyone passing. Roose disliked the spectacle — he told his son he'd need more discretion if he ever wanted to actually rule — but did nothing to stop him.

When Roose learned that Stannis Baratheon had taken Deepwood Motte, he decided Ramsay's wedding would be held at Winterfell. It served two purposes: strengthening Ramsay's claim to the title Lord of Winterfell, and goading Stannis into attacking. Roose told Theon something else besides: that Ramsay would kill any son of his own the moment he had one.

The bride who married Ramsay wasn't Arya Stark. She was Jeyne Poole, the daughter of Winterfell's former steward, passing herself off as Arya — something only Ramsay, Roose, and Theon knew. Ramsay raped her on their wedding night and the nights after, forcing Theon to watch, and sometimes to take part.

Word of the wedding reached the Wall. Jon Snow, now Lord Commander, and Melisandre sent Mance Rayder to rescue the woman they believed was Jon's sister. Jeyne and Theon managed to escape Winterfell; Mance wasn't as fortunate and ended up Ramsay's prisoner.

Ramsay answered with a raven to Jon: he claimed to hold Mance, to have defeated the northern army and Stannis himself, and to have taken his sword. He demanded his wife back, along with Selyse Florent, Shireen Baratheon, Melisandre, and Val — and his Reek. If Jon didn't hand them over, he threatened to come for him.

The books and the show part ways here. In the novels, the last certain thing about Ramsay is that letter to Jon Snow — after that there's no more word of him, and the records list him as alive, with no telling what became of him from there.

The television adaptation, on the other hand, does close his story: there, he died in the year 303.