While out hunting hare with three companions, James heard a great crashing through the brash. He and his friends took cover just as Jardon Pyke, Ralph and Rancis came into the clearing. The latter two were riding tandem and James watched as the one-eyed man disarmed the smaller man and knocked the larger to the ground. Whistling a signal, he and his fellows made their presence known and arrested the trio for trespassing. The following day an envoy from House Jasper, on behalf of House Elesham arrived. Jardon was released from the stocks where he was being held when his allegiance was made known. James was chastised by his grandfather for being imperceptive.

James participated in the tournament melee at Snownook in 285 AC. Jardon Pyke and James sought each other out in the opening moments and traded blows. When another knight intervened and knocked James to the ground Jardon seized the moment, choking out Ser James with his axe handle in a manner reminiscent of a stockade. Late that day James watched as his grandfather faced down Ser Cortnay in the championship joust. When Hoster Woodhull was killed by Cortnay’s lance, James charged Cortnay with murder. Lord Ronnel Jasper presided over a trial the following morning. After James presented the centuries-long feud between the Eleshams and Woodhulls as motive and the steel-cored tournament lance as evidence Cortnay called for a trial-by-combat. Ronnel ordered a trial of seven at the ‘bridge of the Andals’ to occur in one week. James, accompanied by six other warriors (Ser Brynden Tully, Ser Roland Coldwater, Rancis, Dolins, Ser Maelys, and a mystery knight), championed the Woodhull cause. The Father ruled in favor of James when he guided his sword to cut down Ser Cortnay, ending the trial.

In February 286 AC Woodhull was visited by a party from House Jasper (Theodore Jasper, Ser Darron, and Ser Dolins). They sought the support of House Woodhull in preparation for an anticipated conflict with House Lynderly. Ser James was hesitant to promise soldiers, citing simmering tension with House Elesham and, accordingly, a need to keep his soldiers on Paps. A marriage pact was proposed in which he would marry Ella Elesham and his daughter Asha would marry Lord Elmo Elesham when they came of age. James agreed. The following day James, the Jasparians, Iggy, and the visiting Blackfish went to treat with House Elesham and finalize the agreement. At the clearing Darron and Teddy fled upon hearing the sounds of soldiers marching from the direction of First Light (the seat of House Elesham). Dolins had been waylaid en route, investigating a strange sent, leaving just Iggy and the Blackfish with James. Elesham aggression led to a brief skirmish which the Blackfish fled but Ser James was wounded by Ser Argyle and taken captive. He was last seen escorted to a secure room at First Light.