Winston was a red engine who arrived on Sodor in 1922 to help Sir Topham Hatt I run the North West Railway. During World War II, though, he left in order to help with the war effort. Unfortunatley, Winston was destroyed in an ammunition explosion caused by an ammunitions van which was set on fire in 1944. Even so, he was a hero for having pulled the van out of the way at Norbridge.
Winston was brought to Sodor before Henry, Alfred and 87546, running the main line with Adam. With the arrival of Henry, Alfred and 87546, Winston mainly handled mine trains from the Mid Sodor Railway on the Arlesburgh branch, working with Lily. In 1923, Winston, Edward, Alfred, Henry and Thomas were called together to the sheds to welcome a brand-new LNER A0 Pacific type express engine named Gordon. A few nights later, Winston took the Breakdown Train to Maron to clear up an accident caused by Alfred knocking some sleepers loose and derailing Gordon. A rainy day in the year before, Winston was asked to and try and push Henry out of the tunnel, but with no success. A week later, Winston witnessed Colin's accident, and went for help. Later, Winston had to give Thomas some water when he ran out, and scolded him to be more careful next time. In 1934, Winston received the grim task of taking Colin, Lily, Adam, Roger and Clive to the scrapper's torch at Crock's Scrap Yard (except, Lily wasn't there). Winston continued servicing on the railway for another 10 years after that.
The "Iron Hero"
When World War II began, the United Kingdom asked The Fat Director for an engine to help with the extra war time traffic and Winston volunteered. Winston befriended Mary, Alice's sister and Colin Stiles, a 16 years old porter at Norbridge station. On May 30th, 1944, a week out from the Normandy Landings in Northern France, Winston was pushing Mary into Norbridge station when the latter's injector failed. Winston went back to collect his ammunition train, but when he passed the station again, a frantic Colin Stiles flagged him downed. Winston stopped, annoyed, only to realize that his train was on fire. Winston's fireman uncoupled the first van, where the fire was, from the rest of the train. Winston set off, telling his driver, James Clarke, to jump clear. But he refused, claiming that someone has to get Winston clear. Back at Norbridge station, Stiles and the fireman were just discussing about the matter when an explosion ripped the air. Winston's driver had been killed and Winston was destroyed. A monument was placed in honor of Winston and his driver. The engines of Sodor were only informed of what happened forty years later.
Winston was a friendly, helpful, and really reliable engine. He was ready to help out a friend in need, very conscious of railway schedule running, and could avoid delays as much as he possible. This personality cost his own life, but saved many.
Winston was based on the L&YR Class 28 with modifications very much like James. He was built sometime between 1909 and 1912.
Winston was painted bright red all over, with golden dome and stripes and deep blue borders, very much like James, though he didn't carry a number and had red wheels instead of black.
- Season 3 - Bad Water (does not speak), Suspicions and Bygones (mentioned)
- Season 4 - Iron Hero
- Season 5 - Little Western Legacy
- Season 1 STMY - The Missing Engine (cameo) and Consequences
- Season 2 STMY - Arrogance (does not speak) and Mistrust (cameo)
- Winston was characterized by a reskinned 2006 model of Si3D James available on NWR3D. For appearances in flashbacks in STMY, he is a reskin of WildNorWester RWS James model; of which WildNorWester himself made.
- His whistle is a high pitched version of James'.
- His 2006 model uses Sixteen the Steelworks Engine's faces in the railway series.
- Winston is based on the Red Engine that appeared in the RWS version of "The Sad Story of Henry".
- Winston's fate is based on that of the engine that was destroyed by an ammunitions explosion in June 1944 at Soham.
- Wildnorwester was planning to make a Mini-Series about Winston of how he first arrived on Sodor and how he left Sodor to help with the war-time traffic on the mainland. However, Wildnorwester dropped the plans for the Mini-Series.
- His faces appear to be the same as Caden's and Frank's.