There is no universal content or format for creating effective political messages, but there are elements that can give guideline to the formation of a political message. In a fast-paced world filled with information, there are limited possibilities to reach out to citizens, even during the election campaign period. Modern electoral and political trends further complicate the process of attracting voters due to the growing information space, two-way communication channels such as social networks, which is why political stakeholders are directing more and more importance, time, and resources towards developing high-quality and effective political messages that will successfully reach citizens who will accept them and become voters. This paper is a substantive analysis of the political messages of the winning candidate in the city of Šibenik in three election cycles 2013-2021 researched what kind of messages political stakeholders communicate during the election campaign. Methodologically, the research was designed as a qualitative content analysis. The collected empirical material is represented by selected texts of the daily newspaper Slobodna Dalmacija, the weekly newspapers Šibenski list and Šibenski tjednik, which were published during the official campaign in three cycles of 2013, 2017 and 2021. The content analysis dealt with several elements of political communication, such as election messages, election ads and media content characteristic of good pre-election campaigns with the aim of determining strategies for the development of an effective political message. During the analysis, the functional theory of political campaigns proved to be the basis whose elements are dominantly present in the political messages of the winning candidate, while other elements analyzed from the theoretical frameworks of communication and political science were found to be present in a smaller proportion. Data analysis, along with its methodological limitations, gives guidelines on how the political message must be conceived and communicated with regard to the content, tone, period of the message, political environment, cultural and social environment, and ideological-programmatic positions of the political stakeholder.