In his first appearance, Oliver was helping to clear room for new railway lines at the quarry. Later, the foreman assigned Oliver to move some rocks, but Jack wanted to do it and instead toppled over a hill. Jack learned his lesson and after that he allowed Oliver to continue with his jobs. Once, Oliver uncovered a complete dinosaur skeleton while digging a swimming pool. The following day, Oliver was on the front page of the Sodor Times with the headline "Digger Digs Dino!"