Geoffrey Chaucer lived and wrote his poetry during a period of unprecedented political instability in late medieval England. Parliamentary crises, baronial rebellion, popular revolt, disastrous foreign war, weak government, authoritarian rule and, finally, outright deposition made the years between c.1370 and c.1400 both momentous and dangerous times to witness. Chaucer was not immune to these events and his career as a servant of the crown can be seen to have suffered. Yet, political commentary – overt or indirect – is curiously absent from his work. Scholars have traditionally explained this in terms of his keen and calculated sense of self-preservation, but I suggest that Chaucer was displaying an ambiguous and detached political stance that was commonplace amongst his contemporaries. Scholarly attention on the polarised nature of the late fourteenth-century polity ignores the fact that most people looked on the political conflicts of these years with deep anxiety, mixed with a determination to remain steadfastly neutral. In this, Chaucer – the man and his work – was wholly representative of his age.