Winston comes across as a calm and polite person who generally does not seek to interfere in other people's affairs. He is taciturn and diligent in his work. He does not shy away from using firearms, both as a threat and for murder, showing that he can be cold-blooded at times. Winston has a criminal past, which is revealed in dialogue with the blackmailers and Franz. He is also familiar with the use of firearms. Several years prior to the start of the game, Winston lived together with his wife and their son, Jack. At the start of the war with South Borea, pogroms began against South Borneans residing in the country, which included Winston's wife and son. He asked his colleagues to save his family, who asked for assistance from the New Tomorrow, who arranged for Winston's family to be executed and transported to Valverde. However, Winston was unaware that his family had survived, as the courier that was supposed to deliver a letter from his family was accidentally killed in the pogroms. This lead him to believe that his colleagues had betrayed him, so he stole their money and fled. In the opening of the game, Winston arrives at the station and boards the Determination Bringer, where he begins working as a conductor to replace Bart. The player's decisions determine his fate in the possible endings.