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Ramsay was in prison at Winterfell disguised as Reek. When Theon captures Winterfell, they release him and he "helps" Theon. It is ramsay's idea to take Bran and Rickon's clothes with them on their search and then kill the miller boys to pretend they are Bran and Rickon. After Asha comes to visit Theon and leaves him only 10 men, Ramay/Reek suggests that he could raise a couple of hundred men to help Theon defend Winterfell. Theon agrees (Theon is not very bright). When Rodrik comes back with his host and is about to retake Winterfell, Ramsay and his men come along pretending to be on Rodrik's side, then they butcher Rodrik and his men. Theon welcomes him in thinking he is on Theon's side, but Ramsay is on his own side, and he kills all of Theon's men and everyone else at Winterfell and burns Winterfell (Bran, Rickon, Osha, Hodor, Meera and Jojen are all hidden in the crypts at this point). Ramsay also takes Theon as his new "Reek" and begins torturing him (though we don't see that until book 5). Ramsay leaves Winterfell abandoned and goes back to his Dreadfort.
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