Olyvar Bolton was the second born child of Lord Walton Bolton and Lady Bethany Bolton. His elder brother Eldrick was heir to the Dreadfort and from an early age had proven to be his father's favorite son. Olyvar, born after the two daughters Kyra and Barbrey, is the twin of Bethany Bolton (named after their mother). As the two babies of the family, it was their mother who they spent most of their time with. As the male twin and second born son Olyvar underwent training in stewardship rather than rulership.
At the age of ten and six, Olyvar's father had a spat with King Harys at a feast in King's Landing, and returned home to raise arms against him. Edmure Stark crushed the rebellion, and slew all of the Boltons except for Olyvar and Bethany, who hid in one of the many secret passages within the Dreadfort.
Bethany and Olyvar hid in the Dreadfort's catacombs, hiding from those that stayed behind in the castle after the war. Olyvar would occasionally sneak out to steal from the kitchens, using doors and stairways that no-one but the family knew about. It was on one of these hunts for food when Olyvar overheard two soldiers talking about he and Bethany.
Learning that they were believed to be dead, Olyvar led Bethany away from The Dreadfort and south, on the roads.
After moving place to place, never stopping for long for fear of being caught or found out, Olyvar and Bethany found themselves in White Harbour where Olyvar worked as a dock hand.
Olyvar continued to work as a dock hand until one day when he saw Lord Jojen Stark and Ser Thaddius Lannister disembarking from their ship. With them was Thaddius' squire, who was sent on an errand. Olyvar eventually rescued the squire from danger of his own orchestration, and delivered him to the Lannister and Lord Stark, who (perhaps out of guilt for his brother's massacre, or perhaps out of fear that Olyvar would reveal the nature of his relationship with Ser Thaddius) returned to him the Dreadfort and all his house's lands and titles.
After the restoration of his House, Olyvar began to renovate the Dreadfort (which had sustained significant damage during the Uprising and following years of neglect) and reward the people who stayed loyal to his house. After incurring a slight by Androw Manderly at the Feast of the Purple Lion, the two houses developed a rivalry, each suspecting and seeking to prove the other guilty of the Prince's death.
Olyvar was summoned to King's Landing after the feast and congratulated for the restoration of his titles, then interrogated regarding the events surrounding the Prince's death (whose body he returned to the capital). Queen Danae Targaryen and King Damon Lannister spoke with him, offering their support of House Bolton in place of House Stark should the circumstances allow for usurpation.
Bethany Bolton was wed to Jojen Stark and Olyvar returned to the Dreadfort where he began to plot with Lord Rickard Whitehill to take on House Manderly of White Harbour. Unsure of what to do with Lyanna due to their differences in ages and Olyvar's clear avoidance of anything sexual, Olyvar tasked Lyanna with rebuilding The Dreadfort. During her time there much of the cloth and linens were changed. Banners looked fresh and hallways looked clean. She even had a painting of the Bolton family commissioned. Lord Olyvar Bolton, with his now pregnant wife Lady Lyanna Bolton.
Olyvar had Lord Whitehill build Ironwood boats that would be used to house a small retinue of men that would later be used in the sacking of White Harbour. Lyanna later died in childbirth, a birth induced by an apparent trauma involving some stairs.
Warne Bolton was born. Olyvar closed off The Dreadfort to any visitors during the first couple of weeks since Lyanna's passing.
Soon after Lyanna's death, Olyvar got wind of Talisa Stark's return to The North. As she rode through Bolton lands, he sent out his men to ensure she would have a days rest at The Dreadfort. After finding out all he could from her on the whereabouts of Symeon Stark and whatever other discoveries he could about the events of the Feast of the Purple Lion he sent Talisa on her way with an armed escort until she left Bolton lands.
In his efforts to continue to build relations with his bannermen, Olyvar organised a visit from Lord Barth Overton and his family. However, during a conversation with Lord Overton, Olyvar allowed his anger to get the better of him and killed him. Upon his return to the Dreadfort Olyvar described being attacked by a beast with wings, soon after a 'messenger' brought news that it had been spotted in the Hornwood. The new Lord Barth Overton, named after his father raised his arms and marched on the Hornwood. Starting a fire that would eventually burn down the majority of the Hornwood.
Following the fire Olyvar watched the lands of Hornwood burn and turn on itself as he sent out men, posing as Hornwood smallfolk, who spread the word that bandits had attacked their lands. After the rumours picked up some traction Olyvar arranged for some actual attacks on towns and supply lines within House Hornwood's land, further pushing the narrative that House Manderly cared not for their vassals.
In the interests of maintaining appearances, Olyvar attended a feast stopping at Winterfell to see his sister, Bethany, on the way back. There the reunited siblings spent every moment together, until a messenger came for Olyvar carrying word from the Crown. Symeon Stark had been captured and there was to be a trial in King's Landing. By order of the King, Olyvar was to be a judge at the trial, and so he rode South.
The Trial of Symeon Stark concluded, the judges found Symeon guilty in the matter of the death of Prince Thaddius Lannister. After the trial and before Symeon's execution, Olyvar and Damon Lannister met once again. Olyvar gained further support from the crown in regard to his ambitions in the North.
After the execution fo Symeon Stark, Olyvar sailed North back to The Dreadfort.
"This is a cold, quiet man." - thoughts of Eyron
"A word master." - Steffon Hornwood
"...the godswood was not a place he liked to go, and were it another man beneath its eaves he might have ordered him to his feet so that he might address his king to his face, but the Bolton unnerved him, too." - Thoughts of Damon Lannister
Walton Bolton, father (deceased)
Bethany Bolton, mother (deceased)
Eldrick Bolton, brother (deceased)
Kyra Bolton, sister (deceased)
Barbrey Bolton, sister (deceased)
Bethany Bolton, sister