Lord Woolsack is an aid of the Boy in the military campaign of Stronghold, and was one of the few people loyal to the King after his capture.
Lord Woolsack is a careful and rather passive man, who rather thinks through every single step than just act foolhardily. He is often in conflict with Sir Longarm, who tends to make decisions swiftly.
After the Boy's father was killed by Duc "The Wolf" Volpe in an ambush and the kingdom was taken over by The Wolf and his dukes, Woolsack fled into a forest at the far west of the Cornwall peninsula with the prince and Sir Longarm.
Woolsack trusts the Boy to create a wooden fort against the rampaging wolves in the county in order to secure enough food for the few remaining troops loyal to the King. He gains the trust of Sir Longarm and gives the Boy more tasks, seeing that he accomplishes his tasks successfully. After the wolves were eradicated, Sir Longarm wanted to weaken Duc de Puce's position by killing his patrols to cover his activities along the border, while not notifying Woolsack.
However, some of the Rat's soldiers escaped and notified the Rat about their activities. The Rat then launched a massive siege on the Boy, which he repelled, but this shocked Lord Woolsack, who suggested a retreat. However, Sir Longarm ordered the Boy to press on and confront the Rat's armies. Woolsack's passive decision making cost him the trust of his comrades, and Sir Longarm promoted the Boy as the commander of the rebel forces.
After de Puce was defeated and Duc Beauregard fled, Lord Woolsack rose an army and attempted to open up a second front to divide the Wolf's forces. The Wolf and Duc Truffe launched a two-pronged counterattack and the Pig confronted Woolsack, capturing him in battle and brutally torturing him.