A stocky man of five-and-fourty, Randyll holds presence wherever he goes. He is of average height, with thick black hair. On his face lies a thin jagged scar, a relic of time spent warring against the squids during the Second Greyjoy Rebellion.
A string of incompetent and sickly lords had left House Oakheart a ruin of its former self; the glory of their history lost in the last few decades. Hightower. Tyrell. Tarly. Florent. Rowan. The great Houses of the Reach now ridiculed Old Oak like bullies mocking a child. Randyll's father, Osmund Oakheart, was no exception to the line of incapable leaders. He was powerless and spineless, with nothing to show for his life but the rolls of fat that occupied his stomach. Osmund let the other noble families of Westeros laugh at him behind his back, and did nothing to dispel the rumours that followed him around like a plague.
It was a surprise to the whispering lord and ladies, when, Osmund married a beautiful exotic lady of the east. The day Talea of Myr graced the Oakhearts with her sultry presence at court, was the eve of a new dawn.
Talea seduced the grotesque man easily, worming her way into his heavy bed without lifting a finger. They became betrothed and married under the light of the Seven, and Talea grew pregnant within the year. Randyll and Orys Oakheart were born as twins, and the Lady of Myr smiled as she held them in her arms. Not only for the love she bore for the babes, but because the desires and ambitions in her heart were coming to fruition.
In the next two years, another set of twins were born. Young Gwayne Oakheart and Taena Oakheart were just as attractive as their mother, sharing the same blonde-hair and bright set of green eyes.
The Oakheart four grew up under the guidance of Talea, their father mysteriously suffering a deadly fall two years after the birth of his last children. Rumours spread like wildfire that the manipulative Myrish women had done the deed herself, but no conclusive proof was given.
Each of Osmund and Talea's children were bred and taught for a specific purpose; Randyll would become the heir, Orys would become the commander, Taena the beauty and Gwayne the warrior.
Talea focused all her mind on shaping Randyll to become a formidable lord, one who the smallfolk and other nobles would cower in his presence. Randyll grew up with her ideals and her notions, believing in the goal to bring House Oakheart into wealth, victory, power and glory.
He later married Cassana of Tarth and produced several children, Daeron Oakheart, his second son, being the most notable. She died from a swift fever two years before the First Epoch.
Randyll is a vain, cold and calculating man with a heavy flavour for politics and power. He is also highly intelligent. He holds no love for his smallfolk and vassals and they do not love him back, although he does indeed command their loyalty through fear and respect.
When the Ascent of the Lion began, Lord Randyll Oakheart simply did not pick any side and remained neutral. He held no loyalties towards the Tyrells or the Hightowers, and neither the Lannisters nor Baratheons looked appealing as rulers of the Iron Throne. Only when the victor was certain would he declare for the winning side.
He rallied his banners and fortified Old Oak and the lands owned by him, watching the events in the Reach with wary and calculating eyes. But his son, Daeron had other plans. To spite his un-loving father, he lied to and convinced Oakheart's men to participate in the Battle of the Kingswood as loyalist forces to Harys Baratheon.
The Stag lost, and the future of Randyll's house became uncertain and precarious. His second son had impulsively sided against the Lannisters, and now the lions were seeking vengeance. Randyll bent the knee to King Damon and pledged his allegiance, refusing to acknowledge Daeron or his white-cloak.
Randyll did not make a single move during the first year of the Lannister's reign, waiting before he began his plan to bring the Oakhearts back to rightful glory.
He was now a vassal of the Hightowers, something he wasn't very pleased about. Gylen Hightower and him had been rivals for some time, and now the Lord Hightower was Paramount of the Reach. Although he disliked him, Randyll would need to consolidate an alliance with him quickly for the safety of his rule and house.
Looking for more influence in the Reach, Randyll began putting machinations and plots into motion to gain power. He contacted Lord Gylen Hightower and negotiated a marriage between himself and Gylen's sister, Lady Gera Hightower; he travelled south to Oldtown to meet his betrothed.
"How dare he threaten me with his insolent words, whilst rumours spread that he plays with fire and worships the red demon. I never paid loyalty to the Tyrells, and the Hightowers will be no different." - Randyll Oakheart talking about Gylen Hightower
"House Oakheart is an apple tree to maintain and cultivate, mine to prune and pick as I wish to do so. Some of the fruits will be rich, impeccable and pleasing. Others will be too sour, too ripe and rot in the sunlight. A bad apple. I will not grant bad apples in my tree..in this house." - Randyll Oakheart
Daeron Oakheart, son
Cassana Tarth, wife - deceased
Orys Oakheart, brother
Osmund Oakheart, father - deceased
Talea Oakheart, mother - deceased
Gwayne Oakheart, brother - deceased
Taena Oakheart, sister
Lancel Flowers, bastard son
Loras Oakheart, eldest son and heir
Ryam Oakheart, son
Lynesse Oakheart, daughter