This paper aims to analyze the evolution of the leading commercial insurance company Česká pojišťovna on the Czech insurance market in the years 1947–2021. Its evolution was closely linked to the processes of building socialism in the 1950s and the federalization of Czechoslovakia at the end of the 1960s. The paper uses qualitative research methods, methods of description and comparison, as well as local micro-historical analyses shall be applied. The main features of insurance products in the period of the totalitarian regime are characterized. Both the economic transformation in the 1990s and globalization in the last decades have had a radical effect on the further development of the analyzed company Česká pojišťovna. In the period after 1989, the development is marked by a focus on changes in the shareholder structure of the analyzed insurance company, and the development of its market share is shown. As a result of demonopolization, new companies could emerge, creating a competitive environment. The leading commercial insurance company Česká pojišťovna’s market share gradually began to decline.