Osha was a woman of the Free Folk (or “wildling”), in service to House Stark of Winterfell. Osha successfully escorted Rickon Stark to Last Hearth to seek refuge with House Umber but they were eventually betrayed by Smalljon Umber.
Osha is a wildling spear wife, one of the “Free Folk” who live north of the Wall. Like other wildling’s, she worships the Old Gods of the Forest. Due to the rising threat of the White Walkers and their undead wights, Osha fled south of the Wall with a group of other wildling’s, hoping to go “as far south as south goes”. They bypass the wall by taking a boat across the Bay of Seals, to the east of the Wall.
Osha joins Stiv and Wallen to form a band of wildling’s. They fled south and abandoned their service to Mance Rayder. The group cross the Wall and travel into the Wolfs wood north of Winterfell. They chance upon Bran Stark and try to steal his horse. Robb Stark intervenes, killing Wallen and taking Osha prisoner. Stiv holds Bran at knifepoint, but is shot in the back by Theon Greyjoy. Osha surrenders to Robb and is taken to Winterfell.
Osha is put to work as a servant. Theon is irritated when she refused to call him “My lord,” especially when she correctly pointed out that his father is still alive so he is not entitled to the honorific title yet. Maester Luwin sends Theon away and asks Osha why she was south of the Wall. She replies that there were things sleeping under the ice which are not sleeping any more. Luwin is skeptical of her claims.
Osha goes to Winterfell’s gods wood to pray to the Old Gods of the Forest, and finds Bran there. She tells him that north of the Wall, the old gods are the only gods. She also says that Robb is leading his army in the wrong direction. The true enemy lay to the north, beyond the Wall, not the south. When Hodor passed by naked, Osha remarks he must have giants’ blood in him, and tells Bran that giants – and worse – exist north of the Wall.
After Bran dreams that he saw his father Ned in the catacombs of Winterfell. Osha carries Bran into the tombs to check. Once inside, they are surprised by Shaggy dog and find Rickon there too: having experienced the same dream as his elder brother. When they emerge from the tomb Luwin tells the boys that their father has been killed.
Osha continues to discuss Bran Stark’s strange dreams with him. He denies having had any more but nevertheless insists on being taken to the pool in the Gods wood. She correctly predicts that the Red Comet signifies the return of Dragons to the world, those of Daenerys Targaryen. Bran tells Osha that he has dreamt of seeing a Three-Eyed Raven but she offers no explanation. He also confides that he has experienced a dream about the sea coming to Winterfell and drowning its residents, including Ser Rodrik Cassel. Ironically, Rodrik leaves Winterfell to relieve a siege of nearby Torrhen’s Square by unknown forces.
The siege was in reality a feint orchestrated by Theon Greyjoy to draw away Winterfell’s defenders. Theon infiltrates and seizes the castle, forcing Bran to surrender and yield Winterfell to him. Later, Osha offers to fight for Theon but he refuses, suspecting treachery. Osha is also present with Bran and Rickon when Theon personally executes Ser Rodrik, in public. She then tells Bran that his dream has come true.
Later that night, Osha seduces Theon, claiming that she wants her freedom. After he falls asleep, she escapes with Bran, Rickon, and Hodor, killing the guard Drennan as they make their exit. They walk to a shepherd’s farm in the Stark lands, considering approaching the farmer for shelter and food. Theon tracks them to the farm using hounds, but then loses their scent. He returns to Winterfell with the charred corpses of two boys, claiming they are Bran and Rickon. He makes no mention of Osha and Hodor.
The escapees actually doubled back, using a stream to mask their scent and were hiding under Theon’s nose in the crypts of Winterfell. After Theon sister, Yara, arrives at Winterfell, Luwin spots Osha smuggling bread into the catacombs and follows her. She explains their escape and Luwin tells her that the bodies must be those of the orphan farmhands. She promises not to tell the boys, agreeing that they have suffered enough.
Later, Roose Bolton’s bastard son, Ramsay, launches a siege of Winterfell. Theon’s men betrayed him in return for safe passage to the Iron Islands. However, Ramsay reneged on his promise and has them flayed alive. He then takes Theon prisoner, killing many of its inhabitants and destroying much of the castle.
Since they were hiding under the catacombs, Osha, Bran, Rickon and Hodor manage to evade capture. Before leaving Winterfell for the north, Osha encounters a dying Luwin and uses a dagger upon his request to give him the “gift of mercy”. Luwin instructs Osha to escort Bran and Rickon to the Wall so that they can find their half-brother, Jon Snow. Osha agrees and leaves Winterfell with Hodor, Bran, Rickon and their dire wolves.
Fleeing from Winterfell, Bran’s group encounter Jojen and Meera Reed. Jojen approaches their camp unarmed but Osha sneaks up on him with a sharpened stake. However, she is surprised by Meera, who sneaks up behind her, and holds a knife to her throat. Bran insists that everyone calm down. Jojen claims that he received green sight visions which told him where to find Bran, and that he would need their help. The group continues to travel north to Castle Black, as Maester Luwin instructs, hopefully to find Jon Snow.
Fuelled by the long animosity of the Northerners and Free Folk towards each other, Osha and Meera get into an argument about which of them can skin a rabbit better, which turns to who is doing the hunting. Bran again tells them to make peace. Jojen then starts shaking violently in his sleep, and Meera holds down his tongue with a cord so he doesn’t bite himself. She explains that the visions take their toll. Osha dislikes this, thinking it is black magic. On waking, Jojen says that he saw Jon Snow – and that he isn’t at Castle Black, but on the north side of the Wall, and surrounded by enemies.
Osha’s pent-up frustration comes to a head, and she says she doesn’t want Jojen influencing Bran with black magic anymore. Bran explains that because Jojen’s vision said Jon Snow isn’t even at Castle Black, they shouldn’t head there anymore. Instead, Bran and Jojen believe that the Three-Eyed Raven in his dreams is leading him Beyond the Wall, so they should head directly north to the structure, instead of turning to head to Castle Black. Bran says that he believes that maybe the gods meant for him to find the Three-Eyed Raven, meant for him to have these visions, and ultimately, his fall from the tower that crippled him happened for a reason.
Osha is outraged and says she will never go back north of the Wall again. Osha then explains to them the reason she fled south of the Wall. She once had a husband named Bruni, a good man who loved her. One day he disappeared, and everyone said he’d simply left her, but she knew him better than that. One night he did return to their hut – as an undead wight, with skin pale as a dead man’s and his eyes bluer than clear sky. Bruni began to choke her. Somehow she managed to get hold of a knife, and rammed it deep into his heart, but he didn’t even seem to notice. Osha ultimately managed to get away by burning down their hut with Bruni inside it. She didn’t ask the gods for that, she says, but their message was clear: north of the Wall is no place for living men to be anymore.
Eventually, Osha and her masters reach The Gift, a region south of the Wall which was considered to be beyond the borders of the Seven Kingdoms. The Gift had been gifted to the Night’s Watch thousands of years ago by Brandon the Builder, from which the Watch draws support for its material needs. While the region was fertile, it was uninhabited due to frequent wildling attacks which had forced the Small folk to migrate south over the centuries. Bran’s discussion of this history and Rickon’s remarks about wildling’s drinking blood causes Osha some discomfort.
That evening, the party takes shelter at an abandoned mill to escape a thunderstorm. Later, the group observe a band of wildling’s chasing down a lone Northman. During the ensuing incident, Bran used his abilities as a warg to possess Hodor, who becomes frightful of the storm, to which Osha attempts to calm him. Bran latter wargs into Summer and Shaggy dog and fight off the wildling’s. This party of wildling’s included the boys’ half-brother, Jon Snow, who earlier had been taken captive by the Free Folk. Using his warg abilities, Bran helps Snow to escape from his captors and return to the Night’s Watch.
Later that night, Bran arranges for Osha to bring Rickon to the holdfast of Greatjon Umber, the Lord of Last Hearth and the head of House Umber, as well as a loyal ally of the Starks. While Rickon is upset to be separated from his brother, Osha realises this was for his own good and cooperates with the plan. This arrangement also suites Osha because she is unwilling to travel with Bran and company due to the threat posed by the White Walkers. During their journey to Greatjon Umber, Rickon and Osha are accompanied by the former’s dire wolf Shaggy dog. Meanwhile, Bran, Hodor, Jojen Reed, and Meera Reed head beyond the Wall.
Osha and Rickon are betrayed by the Umbers when the new Lord of Last Hearth, Smalljon Umber, wants to protect his lands from the wildling’s that have been given safe passage through the Wall by Jon Snow. Lord Umber still makes it clear that he hates the Boltons and that he will not pledge allegiance to them. However, to gain Ramsay Bolton’s support, he offers him Osha and Rickon Stark. At first, Ramsay does not wholly believe the boy to be truly Rickon. When the Smalljon presents him with the head of Rickon’s dire wolf, Shaggy dog, Ramsay sarcastically welcomes Rickon home.
Ramsay later has Osha brought to him, and asks her about her involvement with Rickon and House Stark. Osha pretends to have been a slave and says that she carried around Rickon to find a buyer for him. She also tries to seduce Ramsay, but it is only a ruse to get him distracted and kill him with the knife that is on the table next to him.
As Osha lies on his lap, Ramsay reveals that Theon had told him how she helped the Stark boys escape. Osha rushes for the knife, but Ramsay takes another one out from his holster and stabs her in the neck. A surprised Osha falls to the floor and quickly bleeds to death while clutching her wound, as Ramsay cleans the blade and watches in amusement, returning to peeling and eating his apple with the knife he laid on the table before.