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Winston is Sir Topham Hatt's track inspection vehicle. Winston is as devotedly thoughtful and loyal as a butler. He is willing, helpful, and very patient with Sir Topham Hatt's, frankly, terrible driving skills, often reminding him that it is still "early days" whenever something goes wrong. Winston helps the Fat Controller navigate about the railway without inconveniencing any of the engines while they are going about their work. Being a car on rails, he may look unconventional, but Winston is highly tolerant, considerate, sensitive to others, and is only too happy to do what he can for Sir Topham Hatt, though he can, at times, become rather distracted.

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