Darrol was born the younger of two sons (and six daughters). He ascended to his lordship before his 20th name day after his elder brother, the Lord of Skymark, died in a hunting accident. In the decades that followed all but one of his sisters was married off (and all but one eventually died). His sister Gylda has been a trusted companion throughout Darrol’s life. Although he gave up tournament competition, Darrol remained a gifted warrior and commander. The bards have written a song or two about his escapades in the fourth and fifth Blackfyre Rebellions.

Much like his father before him, Darrol was blessed with a large brood. His wife Elaina birthed and raised their five sons. Following the wisdom of having ‘an heir and a spare’ Darrol chose to keep his two eldest sons (Donnel and Mikkel) at home while sending his younger three sons (Erol, Alyn, and Perin) away when they reached the age of majority, to: the Citadel, the Night’s Watch, and Snownook, respectively.

He was present in the Tower of the Hand when Jon Arryn appointed House Jasper as Marshall of the FIngers and the Isles on the day Robert Baratheon wed Cersei Lannister. He was the sole representative of House Pryor and appeared calm, conveying little during the ceremony.

Along with Gylda and Elaina, Darrol received the envoy from House Jasper that returned Perin’s remains to Pebble in April of 285 AC. He was cold toward them, warmed only slightly be well chosen words from Calaila and Dolins. Though anger, pain, and grief were still present, they accepted that Perin may well have been murdered by one of his creditors. Darrol was emphatic that the next communication from House Jasper must contain news that his son’s assassin has been captured and is en route to Pebble so that he may dispense justice. An invitation to House Jasper’s upcoming tournament was declined.

Darrol was next encountered by Teddy Jasper at the Spring Tourney of 288 AC. Darrol approached him just after losing in his bout and demanded to know what had happened to his son’s killer. Teddy initially tried to assuage his anger with false words, but upon further pressing Teddy caved, and lied. He told Darrol that he had put his “best man” on it and that he should speak with Ser Darron Brewlan. Darron was the standing Champion of the Sun and so Darrol returned to the knight’s paddock to wait for him. However, Teddy was able to head him off and told Lord Pryor that his youngest son was murdered for gambling debts. Teddy cast the blame upon a criminal syndicate from the Reach and named The Duke and Terry. This satisfied Lord Pryor in the moment but he made it clear that he considers the matter unresolved until Teddy delivers their heads.

Lord Pryor was named the Marshall Of The Fingers & The Isles, replacing Lord Jasper, by Nestor Royce in July of 288 AC. Three months later he hosted a Tourney on Pebble celebrating the decision. Though it was a week long affair, storms delayed the arrival of House Jasper until the final day. Upon his arrival, Teddy Jasper and his mother were brought to an audience in Darrol’s private box overlooking the tourney grounds. Darrol was wroth that Perin’s killer had still not been found years later and reminded Teddy of the debt owed on that score. Teddy insisted that House Jasper would see justice done just as soon as Terry could be found. Before sending him away Darrol made clear that House Jasper would have no support from House Pryor (or the other houses of the region) until then.