Sir Winston originated from a running joke made by popular Youtube Let's Player named Sips who did LPs of Orcs Must Die 1 and 2. In the second level of Orcs Must Die a paladin guardian is standing in the back of the level and Sips decided to name him "Winston" for whatever reason. Once he was able to place his own paladin guardians he started to call them "Sons of Winston" and gave them unique names. This persisted when he played through OMD2. Robot Entertainment decided that since Sips's videos brought so many fans to the series that they would base a character off Sips's LPs.