Later, when Kylie had an accident, Benjamin, along with Brady and Olivia, teased her because of it. Then, at Christmastime, Brady and Benjamin helped Jacob, Sierra, and their friends figure out what happened to their Christmas presents.
Benjamin later cheered Brady on while he competed in The Great Engine Games. He then took Brady to the Steamworks after he cracked a cylinder. Later, Benjamin, Olivia, Kylie, Emily, and Brady competed in Jacob's Sodor trivia game as Team Sterling.
Brady and Benjamin later used their snowploughs to clear the lines up to Crovan's Gate. While at Crovan's Gate, Marie came into the station and ran into Benjamin, damaging his snowplough. He tried to tell Brady he was damaged, but Brady did not listen. He did come to his senses, however, when Benjamin broke down on Gordon's Hill.
Benjamin later helped search for Jacob when he went missing.
Benjamin is a kind engine. He is, however, known to tease his twin, Brady, as well as Kylie, one of his closest friends.
Benjamin is based on a Great Northern Railway G3 Stirling Single 4-2-2. Designed by Patrick Stirling in 1870 with 8ft 1in driving wheels and outside cylinders, they were specifically built for high speed expresses between London and York. These locomotives were capable of hauling 280 ton trains at 50 mph, though they could reach 85 mph on lighter services. A total of 53 were built at Doncaster between 1870 and 1895, in three series introduced in 1870, 1884 and 1894 respectively; the last was withdrawn in 1916. The only surviving member of his class (No. 1) is on display at the National Railway Museum. The locomotive in preservation carried a small capacity Sturrock tender, which was given in its first restoration in 1910. Recently, a derelict original Stirling Single tender used as a water and sludge carrier was found in Peterborough and, after restoration, was paired with the locomotive in 2014.