After hearing Edward and Salty talk about how the Fat Controller used to travel in an open-topped carriage on his birthday, Winston was determined to find it. Winston was working with Thomas that day and he took the opportunity to look for the coach. After leaving Thomas to look for the carriage twice, Thomas made Winston travel in front of him. This ended in an accident when Thomas does not notice that Winston had slowed down. Thomas then asks Winston what he was looking for and the track inspection vehicle tells him. There, on an old siding, is the carriage. The two then bring the coach to the Sodor Steamworks to be mended and later surprise the Fat Controller with it.
Later, some tracks needed repairs, so Winston took the Fat Controller every day to check on the repairs. After Gordon and Henry laughed at him, Winston got tired of having a bad driver and decided to not remind the Fat Controller to put on the brakes. He had a near-collision with Paxton and Bertie before he ran out of fuel, just before a collision with some trucks. The Fat Controller was cross, but Winston told him that he forgot to put on the brakes. The Fat Controller realized this, and forgave Winston for his adventure. Winston knew he needed a driver after all.
One Christmas, the Fat Controller dressed up as Father Christmas for the celebrations at Ulfstead Castle. The Earl wanted him to drive a sleigh, despite the Fat Controller's views to the contrary. To get out of it, he took Winston to the Steamworks, and Winston was dressed up like a sleigh, which he did not like at all! However, much to Winston's relief, the Earl did not approve, so Winston was spared the embarrassment.
Winston is often seen when The Fat Controller comes to see his engines where there is no road nearby.
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, patient, 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 a Type 4B two seat Wickham Trolley.
Winston is painted red. He has a gold nameplate on either side.
- Matt Wilkinson (UK/US, sixteenth season onwards)
- Jarosław Boberek (Poland, sixteenth season onwards)
- Wataru Hatano (Japan, sixteenth season)
- Helge Winther Larsen (Norway; sixteenth and seventeenth season only)
- Per Skjøldsvik (Norway; Blue Mountain Mystery onwards, excluding the seventeenth season)
- Luis Alfonso Mendoza (Mexico; Blue Mountain Mystery onwards)
- Wooden Railway (Normal and Birthday Decorated)
- Take-n-Play (Normal & Talking)
- Motor Road and Rail (Coming soon; Japan only)
- Wind-up (Japan only)
|North Western Railway|
|Thomas • Edward • Henry • Gordon • James • Percy • Toby • Duck • Donald and Douglas • Oliver • Barry • The Austerity Engine • The Red Engines • Daisy • BoCo • Bear • The Works Diesel • Pip and Emma • Peel Godred Engines|
|Harvey • Emily • Fergus • Arthur • Murdoch • Molly • Neville • Rosie • Whiff • Billy • Stanley • Hank • Flora • Victor • Charlie • Bash and Dash • Ferdinand • Scruff • Belle • Porter • Derek • Diesel 10 • 'Arry and Bert • Salty • Dennis • Den • Dart • Sidney • Paxton • Norman • Flynn • Winston • Stafford|