During the prologue to the Iraq War of 2003, George W. Bush repeatedly employed the example of Japan to advocate why Iraq could be remade as a democratic state within the Western alliance. If a nation as divergent and unique as Japan could be agreeably transformed, he reasoned, any nation could. The bulk of the pre-war assumptions of George W. Bush have long since been derided but this particular premise remains broadly held. Even today, when failure is plain to see, there is still a general sense that Iraq will ultimately emerge as another 'Japan'. Remembering Santayana, inspired in its title by the adage of the Spanish-born philosopher, George Santayana, that "those who don't remember the past are condemned to repeat it," sets out why this assumption by George W. Bush was, and remains, fundamentally wrong. It revisits the history of interaction between the West and Japan, identifies the problems which misconceptions have spawned and sets out a course for a future in which lessons are learnt rather than mistakes remade.