Oliver is a tugboat from another harbor with two smokestacks and a blue cap. Called by what he is, Oliver is a deceiving, scheming character, who was brought "on trial" to work in the harbour. However, when Theodore tried to show him around, Oliver took no notice of his advice and ended up embarrassing himself when he moved the wrong cargo. This lead to endless teasing from the cargo, and made Oliver angry, thinking that Theodore made them laugh at him. He began causing trouble between Theodore and the other tugboats by telling lies, but was eventually found out by the Dispatcher and sent packing. He came to the Big Harbor to help with some extra work. He was disliked by George and Owan and especially loved to bump and bully Theodore, not matter how hard Theodore tried to be friends with him. Finally, the Dispatcher sent Oliver back home for his bullying. However, in spite of this, he still charters from The Big Harbour to his harbour acting as a "spare" tugboat for heavier work, much to the annoyance of the Big Harbour Tugboats!

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