This book is the first scholarly work to explore male homosexual prostitution in interwar Scotland. The male prostitute occupies a contested position within interwar society – depending on the perspective he was representative of a descent into turpitude, of tenacious organised criminality or of exploitation. The book explores connections between male prostitution and criminal gangs prevalent during the interwar period, by detailing the emergence and activities of Glasgow’s notorious ‘Whitehats’, a gang composed of a number of queer male prostitutes and led by William Paton. This book discovers that although Paton’s activities were representative of a career criminal, the young men who joined the ‘Whitehats’ were often driven by poverty and social isolation. This book explores the experiences of Edinburgh police detective William Merrilees and his war on homosexuality in Edinburgh during the 1930s through examining the tactics used to regulate homosexual trade and the implications this held for the men involved. The book not only explores the attitudes, opinions and actions of police officers, politicians and the legal process but also uncovers fragments from the lives of the men involved, through personal reflections and letters. The book explores the anxieties that the trade in homosexual sex provoked, not just for understandings of sexuality but also of gender and nationhood, and offers a comparative perspective of the forms of homosexual trade in Scotland, England and major foreign cities. This book will have broad appeal to academics and students in the field of social, sexual and gender history as well as the social and criminal histories of Scotland and Britain.