In this paper, I examine the unpublished First World War diaries of Giovanni Pirelli – heir to the helm of the Pirelli tyre company – for their account of how the war and fall of Fascism may have catalysed his dissociation from his family, his class, and his ideological foundation. In the post-war period, Pirelli traced the source of his rejection of his inheritance to his experiences during the Russian retreat, but in the moment, the expression of this kind of transformation is fragmentary and complex. Scholars often look to war diaries and letters for their testimony to the state of the individual in combat. Through close reading, I trace how Pirelli’s writings negotiate his immense privilege and his attempt to construct a moral identity in the midst of war. I consider how they demonstrate his break with his wartime ideals and Fascism and how they anticipate his later transition from industrial heir to socialist activist. My examination of these diaries reveals the ambiguities inherent in this transformation of Fascist and bourgeois subjectivity.