Type 4B two seat Wickham Trolley
D Wickham and Co
Winston is the Fat Controller's inspection car.
In Adventures on Rails, he was brought to replace the Fat Controller's New Car after it was accidently crushed by James. He immediatly found out about the Fat Controllers poor driving skills after he accidently took his brakes and sent him flying along the Main Line up to the Steamworks. He is usually driven by the Fat Controller if not by his Driver.
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.
Winston is painted red. He has a gold nameplate on either side.
Adventures on Rails
- Season 17 - Sir Topham Hatt's New Car, The Three Little Engines Part 1, Best Dressed Engine, and Three Cheers for Thomas!
- Season 18 - Percy's Big Mistake
- Season 19 - Middle Engines, Incoming!, and Stepney's Visit (non-speaking role)
- Season 20 - Den and Dart Save the Day (non-speaking role) and Diesel Dream
- Season 1 - Winston and the Signal, Harvey Goes Fishing (does not speak), Winston and Elizabeth, Dave the Diesel (does not speak), and The Christmas Tree
- Season 2 - Frozen Points, Fergus the Generator, Stanley and the Flood, Miniature Engines, and Independence (cameo)
- Season 3 - Percy and the Diesels, Hector the Ballast Hopper (does not speak), CoBo (does not speak), and Pompous Popularity
- Season 4 - Flora and the Troublesome Coach, The Wrong Sort of Coal, Broken Down Crane, and James and Flynn (cameo).
- Season 5 - Sodor Snowstorm, Silver Steam, Stanley's Branch Line,
- Season 6 - The New Diesel Fuel
- Season 7 - Young and Old, Love for the Sea, and Salty and the Small Engines (does not speak)
The Many Adventures on the Island of Sodor
- Season 1 - James and the Railway Inspector, Bertie Rides the Rails, and Franklin the Forklift (does not speak)
- Season 2 - Bill and Ben's Big Mistake (cameo), Daisy Does it All (cameo), and Edward’s Escapade
The Adventures on Sodor
- Season 1 - Percy's Oil Spill (cameo), Harvey's Goods Train, The Lost Breakdown Train (does not speak), and Bill and Ben (does not speak)
- Season 2 - Jealous James (does not speak)
- Railway Show Engines - Vinnie's Vicious Deed (does not speak) and Accidental Ashima (cameo)