Author of the masterpieces Animal Farm and Nineteen Eighty-Four, George Orwell, the nom de plume of Eric Arthur Blair, experienced, explored and explained some of the defining political, economic and social traumas of his time – predicaments that have, and will always be, part of Man’s infatuation with power and power politics. Orwell’s experiences of colonial exploitation in Burma, extreme poverty in Paris, London and the industrial North, and the horrors of ideological deceit and betrayal during the Spanish Civil War fashioned his literary persona, his political canon and influenced his vision of a future dystopia. This book explores Orwell’s journey to dystopia, using his major texts as milestones, and also examines the author as a divided self and as a chronicler of his age on a fateful journey to dystopia. Furthermore, it investigates his responses to the use of what he calls ‘force and/or fraud’ in the politics of his time, seeking a new understanding of the tensions and contradictions that characterise his writing. The analyses explain how authoritarian systems and totalitarian regimes manipulate power and employ pretence in order to divide the self and force individuals and society into obedience. The book argues that new insight into Orwell’s political views is gained by investigating Niccolò Machiavelli’s The Prince, where Machiavelli uses the phrase ‘force or fraud’ to encourage totalitarian tactics in running a State. Milestones on the Road to Dystopia: Interpreting George Orwell’s Self-Division in an Era of ‘Force and Fraud’ presents new insights that interpret the close relationship between self-division, paradox and the use of a pseudonym, demonstrating how they help in understanding Orwell’s character, works and the nature of totalitarian politics. Analysing self-division, both as an Orwellian trait and as a totalitarian strategy, and finding a connection with Machiavelli, against the milieu of Orwell’s development as a writer, is an intricate and interrelated topic that has not previously received critical attention, either in its individual parts or as an integrated study. This book establishes an essential template with which to analyse Orwell’s self-division apropos his growing fears of totalitarian power politics, and offers distinct analytical acumens that allow for an updated understanding of Orwell and of his relevance to political thought and the question of ‘common decency’ in twenty-first century literature and politics.