As parliamentarian during the Bosnian war, witness at the International Criminal Tribunal for the former Yugoslavia, and finally as politician with considerable executive power in the role of High Representative, the length and multifaceted nature of Paddy Ashdown’s interaction with Bosnia and Herzegovina is atypical. This rarity provides a unique opportunity to examine the factors that influence a politician’s views and understanding of a foreign country and examine how and why they oscillate and develop over time. By first identifying the preconceptions and misjudgements which Ashdown entered the realm of the Bosnian war with in 1992, this paper examines the aforementioned stages in Ashdown’s interactions with the country and subsequently provides a political evolution of his views from 1991 to 2006.