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| “ | Angry foes do not concern me. Anger makes men stupid, and Hosteen Frey was stupid to begin with, if half of what I have heard of him is true. Let him come. | „ |
| ~ Stannis Baratheon to Theon Greyjoy |
Ser Hosteen Frey is the sixth son of Lord Walder Frey and the first child with his third wife Amarei Crakehall. He is married to Bellena Hawick and has a son, Arwood, and through him two grandsons, Androw and Alyn, and two grandaughters, Ryella and Hostella. He is regarded as the fiercest of Walder Frey's brood, inheriting the uncommon robustness of the Crakehalls.
He is part of the Frey force that joins Robb Stark early in the War of the Five Kings. Hosteen is captured by the Lannisters, presumably at the Battle on the Green Fork, and taken to Harrenhal, though ransomed. He is part of the force at Harrenhal with Roose Bolton. While meeting with Roose after the Battle of the Blackwater, the Freys are worried at the Lannisters success against Stannis Baratheon and their alliance with the Tyrells. Hosteen Frey says Robb has lost the war and must make peace with the Lannisters, saying he does not wish to be a prisoner of Tywin Lannister again. Later the Freys receive news that Robb has broken the marriage pact.
The Freys agree to join Robb if his uncle Edmure Tully, Lord of Riverrun, marries one of Walder Frey's daughters Roslin, a half-sister of Hosteen. Meanwhile Jaime Lannister has been captured by Vargo Hoat and is taken to Harrenhal, where he encounters Roose and Hosteen. Lord Bolton lets Jaime go free and after this leaves with the Freys to attend the wedding. Robb, his mother Catelyn, and much of his army are murdered when the Freys and Boltons betray them in what becomes known as the Red Wedding. During the massacre Hosteen stabs Lucas Blackwood dead.
Hosteen and one of his half-brothers, Ser Aenys Frey, command a Frey force of 1400 that goes north with Lord Bolton, who has been made Warden of the North, to assist him against the Ironborn and Stannis Baratheon. Roose orders the Northern lords to attend the wedding of his son Ramsay Bolton to "Arya Stark" (really Jeyne Poole), which is intended to legitimize Bolton rule of the North. It is originally to be held in Barrowton. However after hearing that Stannis has taken Deepwood Motte from the Ironborn, Roose decides to hold the wedding at Winterfell.
The wedding goes ahead in Winterfell. The three Freys that were travelling from White Harbor with its lord Wyman Manderly, Ser Jared Frey, Symond Frey and Rhaegar Frey, had disappeared on the way to Barrowton. Wyman's younger son Wendel Manderly was killed at the Red Wedding but Wyman has apparently made peace with the Iron Throne, arranging for Rhaegar Frey and Little Walder Frey to marry his grandaughters. However he is secretly plotting to restore the Starks to rule of the North. Wyman serves three pies at the wedding to the Boltons and Freys, even eating from each pie himself. It is implied the missing Freys are in the pies. Hosteen says he does not fear the cold and loses an ear to frostbite. However tensions grow in Winterfell due to a series of murders. Hosteen suspects Wyman of the murders in Winterfell and the deaths of the three Freys with him. When Little Walder Frey, the son of Hosteen's full brother Merrett Frey, is found dead Hosteen accuses Wyman. When Wyman insult Little Walder and the Freys Hosteen wounds Manderly and is only prevented from killing him by the intervention of White Harbor men, leading to a fight between them and the Frey men. Seeing the tensions between the Frey and Manderly forces, Roose sends them out to battle Stannis, having received his location in a map sent by Arnolf Karstark.
The Freys leave by the main gate of Winterfell. Meanwhile Theon Greyjoy helps Jeyne Poole escape by jumping with her off the walls of Winterfell. They survive due to the deep snow and are found by Mors Umber, who has joined Stannis. Aenys Frey falls into a pit dug by Mors Umber's troops, breaking his neck. Hosteen loses his horse but survives, command of the Frey force falling to him. Theon relates this news to Stannis and says Hosteen will be angry now, Stannis smiling on hearing this. He says anger makes men stupid and Hosteen was stupid to begin with, nicknaming him Ser Stupid. Stannis implies he has a plan to defeat the Freys. It is possible Stannis' plan is to trick the Freys into charging onto a frozen lake next to the Crofter's village, which will be aided by Hosteen's short-sighted nature and aggressiveness.