Plot hole: James appears in every episode before his introduction in "Thomas and the Breakdown Train." Also, James is supposed to be black, because at the end of the episode, James is told he will get a different coat of paint. (He is also black in the book).
Continuity mistake: The engine sheds change design throughout season 1.
Answer: Butch the breakdown truck must have pulled Gordon's tender all the way up the rails so the breakdown train can reach it and also Butch helped to get Gordon close to the winch.