This article offers a comprehensive analysis of the historical development of the penal fine as a sanction from the point of view that the changing meaning of money influences the perceived appropriateness of fines as a punishment for every type of offence, or only certain offences. As it is shown here, a series of associations based on the idea of money, its essence and its capabilities had a profound impact on modern European legal culture. The different perception of the significance of money in contrast to freedom explains the rise of imprisonment in the 19th century. The present use of fines to punish less serious crimes and misdemeanours within the criminal law is mainly a direct consequence of the development of money and its characteristics of impersonality and interchangeability since the 19th century.