Oswald was an otter member of the Juggling Otters in the Traveling Thistledown Troupe, under the leadership of Hypericum Hadduck Hare.
The Juggling Otters performed acrobatic feats and juggled to entertain the Redwall Abbey residents during the feast celebrating Autumn's final day. Oswald and Oriole could juggle almost anything, including apples, sugarplums, and pears while balancing on rounded logs. They especially pleased the Dibbuns when they distributed candied chestnuts they were juggling into the paws of Bungo and Tubspike.