Counterfactualism provides historians with the opportunities of delving into personalities and events within the actual timeline from angles that could previously have been overlooked. That is precisely what this essay is going to attempt to show through the use of three case studies. Firstly, the abdication of King Edward VIII in 1936; secondly, the Munich Agreement that Chamberlain signed up to with Hitler over the question of the German Annexation of the Czechoslovakian owned Sudetenland; and thirdly, the appointment of Winston Churchill as Prime Minister in 1940.