This chapter discusses the early life of A.K. Chesterton and the experiences prior to 1933 that shaped his ideological relationship with fascism, ultra-nationalism, anti-Semitism and racism. In order to trace the origins of Chesterton’s hostility towards immigration and decolonization, the first part of this chapter considers his upbringing in South Africa, and the manner in which this informed his conceptions of race and national identity. Thereafter, it considers his involvement in the First World War and his experiences as a member of the ‘Front Generation’ – the young soldiers whose traumatic experiences of violence and upheaval in the First World War led them to engage in the radical politics of the interwar period. This section also examines the lineage of anti-Semitism that can be identified between A.K. Chesterton and his elder cousins, the famed author G.K. Chesterton and his brother Cecil Chesterton. Finally, this chapter concludes by discussing the immediate circumstances that drove Chesterton to join Sir Oswald Mosley’s British Union of Fascists in 1932, and how his interest in fascism was shaped by his colonial background.