Winston came to the railway during the events of the discovery of Luke hiding out at the Blue Mountain Quarry. He is often seen with the Fat Controller patrolling the line and accompanies him when he gives his engines their agenda. On one particular occasion, he ran away to avoid the Fat Controller's careless driving, but after a hectic excursion, he learned that he's better off with the Fat Controller in the driver's seat!
Winston is as devotedly thoughtful and loyal as a butler. He is willing, helpful, and very patient with the Fat Controller'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 the Fat Controller, though he can, at times, become rather distracted.
Winston is painted red. He has a gold nameplate on either side.
- Season 1 - Percy's Oil Spill (cameo), Harvey's Goods Train, Waterworks (cameo), Bill and Ben (does not speak), and Scruff the Scrapper
- Season 2 - Jealous James (does not speak), Sidney Gets Lost, and Timothy and the Aquarium (cameo)
|North Western Railway|
|Thomas • Edward • Henry • Gordon • James • Percy • Toby • Duck • Donald and Douglas • Oliver • Bill and Ben • Daisy • BoCo • Bear • Neil • Harvey • Emily • Fergus • Arthur • Murdoch • Molly • Neville • Rosie • Whiff • Stanley • Hank • Flora • Victor • Charlie • Bash and Dash • Ferdinand • Scruff • Belle • Porter • Timothy • Marion • Logan • Glynn • Ryan • Geoffrey • Diesel • Mavis • Derek • Diesel 10 • 'Arry and Bert • Salty • Dennis • Den • Dart • Sidney • Paxton • Norman • Philip • Flynn • Winston • Stafford • Dustin|