There were shadows to the Italian Renaissance. Just as art and philosophy were flourishing, so too were darker practices, from murder-for-hire to prostitution. However, despite popular parallels between families like the Borgia and the Medici and the Mafia, there has been little systematic examination of the presence of organised crime in the era. In this short and lively essay, Mark Galeotti rereads and occasionally reinterprets the rich secondary literature to introduce a cast of corrupt princes, bandit chieftains, professional assassins, human traffickers, thugs and conmen and suggest that there were signs of the early beginnings of organised criminality in the towns and cities of late medieval and Renaissance Italy. An historian and political scientist, Mark Galeotti is Professor of Global Affairs at New York University's SCPS Center for Global Affairs.