Jack is the oldest son of Gregory Timberfell, a lumberjack who is semi employed at the Combe Lumber camp. The man is well known for being a hardworker but a man who loves his drink. To strangers, he seems a pleasant enough man, though rather standoffish. He lives in a cabin in the woods with his family. His wife and children are rarely seen in town, but for Jack who runs the errands to Bree. The Timberfells are known for living for generations in the Chetwood and since the rise of the Blackwolds, he stubbornly refuses to move even at the risk to his wife and children. Jack's mother passed away a long while back, his step mother is who lives with them and her two daughters by Gregory.

The young man is sometimes seen with bruises on his face or walking with a slight limp, if asked he ran into a limb while chasing a deer or tripped on a root. He always wears an old wool stocking cap, patched and worn, no matter what the weather, something his mother made him a long while ago, purposefully too large so he could grow into it. 

As his father's drinking problem grows worse, Jack spends more time in the woods and town, anything to be away from the fast temper and even quicker fists. The rage directed toward him, sometimes out of his father's frustration over his own failures or that of Jack's mother leaving him seem to be channeled onto the boy more often. 

Recently, one one of Jack's trips to Bree, he saw a poster by Bill Cutting, a man he remembered from the lumber camp. Reading it intrigued him and he stood at the back at the meeting about the Bree Defense. The man was looking for volunteers, lads who wanted to help the surrounding farms and homesteads against brigands. This caught the boy's imagination, that and the promise of coin, food and his own weapon. A chance to be a hero. A chance to get out from under the heavy shadow of his father.