The Great-grandaughter of Canadian Veternian and Soldier Harry Colebourn, Lindsay Mattick's picture book follows a young black bear cub named Winnie (Winnipeg) who was bought by a young version of her great grandfather. The story encapsulate the relationship between a man and a bear beginning a journey that leaves an imprint on the annal of wartime history. The story then transitions into the daunting settings of World War 1, as Harry is summoned for duty in Europe; what woiuld happened to this beloved bear.