Rickard was the first-born son of Edmure Whitehill and Lyanna Whitehill. He had one brother, Meryn Whitehill, and a sister, Meha Whitehill. Whereas Rickard was given preferential treatment, Meryn and Meha were neglected during their early years. This eventually culminated in bandits managing to steal away with the two younger siblings. Whilst Rickard managed to track them down, he arrived too late to stop the rape of his sister and the murder of his brother.
It was after this event that Rickard hardened somewhat. After his father died in the Bolton Uprising, Rickard took control of the house. He fought a losing battle against the bandits of the wolfswood, which seemed to breed scum and filth. As his rage grew, he took to flaying prisoners taken from these battles, his only catharsis in a world which seemed to despise him.
He has five children: Vance, Brandon, Meha (named after his sister), Alys and Damian.
Prior to the First Era
At some point, House Whitehill and House Forrester waged a brutal and bloody war, resulting in the deaths of hundreds, including Rickard's third son, Kyren.
Alys was married to Willem Ashwood, to form a marriage alliance.
House Whitehill sided with the Starks during the Ascent of the Lion, where Rickard killed a minor Reach Lord.
Lord Rickard was able to form an alliance with Lord Bryan Forrester, resulting in a proper peace between their families. Rickard pledged a portion of his forces to the Forresters, in exchange for access to their Ironwood trees.
During this time, Rickard also met with the recently returned Olyvar Bolton, where he became involved in a plot to overthrow House Manderly. He was tasked with building ships to ferry a small retinue of troops into White Harbor.
On a visit to speak with Lord Bolton, Rickard duelled Steffon Hornwood in a trial by combat. Rickard defeated the Lord of Hornwood, and made plans to take control of Hornwood levies. Rickard was also given The Blades, Lord Bolton's elite bodyguards.
Upon his return to Highpoint, Rickard discovered the castle had been taken by traitorous troops. Whilst he was successful in retaking it, he lost a good portion of his garrison and his fourth-born son Damian. The Blades also perished. During this time, the bandits also fired the boats Rickard had been building.
Rickard, returning to The Dreadfort, was tasked with bringing the Mountain Clans into their alliance. In order to quell the growing discontent of his smallfolk, Rickard sent word to Lord Castos of House Ashwood, who agreed to dispose of the bandits in The Wolfswood once and for all.
Towards the end of the era, the boats were rebuilt at last, and Brandon Whitehill hired sellsails to crew them.
Whilst en route to the mountains, Rickard began experiencing severe anxiety, brought on by his fear of failing Bolton.
Rickard and his men crossed Benfrey of House Liddle on the Kingsroad. Rickard traded steel for furs and snowshoes, and heeded Benfrey's advice on travelling the winter roads. Benfrey also gave him directions to the home of the Liddles.
Sometime later, Rickard met with Jason Liddle, who asked for Rickard's assistance in ruling the Liddle clan. During his time there, Rickard killed Aggar, a member of the Elder Council who constantly opposed Jason. He also began forming a plan to defeat the Norreys, enemies of the Liddles, by exposing their leader as a gluttonous thief who has left his people to starve. In order for the plan to work, Elys Liddle is forced to marry the Norrey's younger son.
One evening, during a chance encounter with Elys Liddle, Rickard learned that Jason had poisoned his abusive father.
Before departing to deal with the Norreys, Rickard experienced a vivid and terrifying hallucination of Olyvar Bolton, as his mental illness grew worse.
Upon arriving at the seat of the Norreys, Theon Norrey was extremely distrustful of Whitehill. Rickard planned to take the Norrey captive at the wedding feast, but the plan was discovered and everyone present was captured. The Norry attempted to poison the Liddle, then choke him as an angry mob threatened to break into the hall, but Rickard was able to free himself and beat the Norrey within an inch of his life.
After a fight with Jorah Liddle, Rickard was soon forced to admit to Jason his true reason for having journeyed to the mountain clans. Rickard's growing madness, coupled with the Norrey remnants unwilling to aid them, culminated in Rickard crippling one of the Norrey elders.
- Vance Whitehill (Son, Heir to Highpoint)
- Brandon Whitehill (Son)
- Meha Whitehill (Daughter)
- Kyren Whitehill (Son, deceased)
- Alys Whitehill (Daughter, married to Lord Ashwood)
- Damian Whitehill (Son, deceased)