Wilber is a man of about 40 who takes his knightly vows, and all other things, seriously. A humorless man, stern and decisive. He has spent his life in service of his father’s house, House Osgrey, and their liege, House Rowan. In 283 AC he encountered a delegation from House Jasper whilst traveling through The Reach. He, Bert, and Wendall were serving as outriders for a supply caravan from High Garden to Storm’s End and were ambushed by Jardon, Carsen, and Nestor Royce in the night. Wounded by a bolt and bloodied he and his fellows surrendered and were taken captive.

After being interrogated Wilber and his follows were held captive by Ser Carson while Jardon rode forth in an effort to capture the caravan. Wilber was released as a part of the terms of truce while the caravan fell into the hands of the rebels.

Wilber next encountered members of the Jasper household in June of 284 AC. He was seeing Berta Rowan safely to Uplands to wed the young heir of House Mullendore when they were threatened by Carsen. A brief melee ensued in which the aggressors yielded (Jardon was backing Carsen in his effort). He commented that he was pleased to see that he could best the Jasparians in a fair fight.

Wilber, much to his chagrin, was tasked with escorting his cousin Jeyne Oakheart to wed Jardon Pyke. The pair arrived at Snownook on the final day of 285 AC and were welcomed on the beach by Calaila and Maester Thaddeus. Wilber requested a septon to perform the ceremony on Jeyne’s behalf. A brief time later he arrived in Snownook’s hall and exchanged harsh words with Carsen, going so far as to call him craven, but ultimately stormed off.

The next afternoon, a short time before the wedding ceremony, he asked Jardon to delay the bedding ritual given Jeyne’s pregnancy. Jardon intimated that he may be willing to do so for a price and asked 25gd but stipulated that the bedding would be acted out for appearances. Wilber countered with 5gd which were accepted on the stipulation that Wilber perform a favor to be named later. Wilber declined and cited Jardon’s dishonor as the reason. Wilber was present for the ceremony but left in a Myrish goodbye – which is to say he left without farewells or fanfare.