- "I spend most of my day praying I don't run into anything. Besides that, I'm usually pretty chipper!"
- ―Winston, Perhaps He's Got a Corset
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 patroling 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!
When the Fat Controller gave orders to Paxton to return to The Blue Mountain Quarry, he rode in Winston, who reprimanded him for eating a croissant and getting crumbs all over his nice leather seats.
When Henry complained about Kurt to Stanley and Hiro, the Fat Controller drove in in Winston, crashing his faithful inspection car into a pile of crates! Winston was a bit frustrated, but cheered up when he thought Stanley was trying to flatter him by calling him "Sir."
Winston is polite, patient, and curious. He enjoys the Fat Controller's company but does not enjoy being thrust backwards and forwards so often. He tolerates it nonetheless, and acts as thoughtful as a butler. Occasionally, he will epress his frustration outloud, but is usually shut off by the Fat Controller. Winston loves the chance to explore and find out things for himself whenever he can!
Winston also detests when the Fat Controller gets crumbs in his nice leather seats!
- Season 2: Blunderbuss, Swan Dive, Aura of Menace, Henry and Kurt, Self-Fulfilling Prophecy
- Season 3: Perhaps He's Got a Corset, Samson, BoCo, and the Man in the Hills (cameo), Culdee Fell, Ice Breaker (cameo)
- Web Clips: The Fat Controller, the Stationmaster, and the Raiboat - Meet the Characters! (does not speak), Timothy, Bill, Ben, and Marion - Meet the Characters! (cameo)