The ongoing war in Ukraine underscores the importance of understanding the strategic culture of states whose assertive behavior challenges the international order. In this context understanding Russian strategic culture, particularly as articulated through presidential communication, contributes to deep exploration of geopolitical dynamics and challenging nature of European integration. This paper examines the evolution of Russian strategic culture through the analysis of Russian presidential speeches from 1999 to 2023, showing how they underpin Russia's impetus to maintain influence over its perceived historical territories and assert its great power status. Using a mixed-methods approach to the analysis of the selected Russian presidential speeches, this study demonstrates how the respective communications perpetuate the discourse of Russia's claim to spheres of influence and its idiosyncratic role in global affairs, showing the recurrence, evolution, and intertwining of themes such as national pride, security, and anti-Westernism over time, while also identifying shifts in Russia's strategic priorities, particularly towards its immediate neighborhood. By foregrounding the role of presidential communication, this paper provides an in-depth analysis of Russia's strategic culture discourse patterns, including the state’s perception of European integration through the prism of a growing anti-Westernism that not only leads to the destabilization of its neighbors, but also challenges the very boundaries of the European integration project, raising questions about the future of regional polity-formation in Europe.