Diplomatic interactions between the West and Russia have assumed an evident antagonism in the context of the Ukrainian War. In this context, Brazilian diplomacy has been characterised by a “strategic non-alignment,” as described by current Minister of Foreign Affairs Mauro Vieira, causing disappointment in the West while maintaining pragmatic relations with Russia intact. That said, this chapter aims to investigate “why developments in Ukraine during the 2000s did not affect Brazil’s partnership with Russia.” We argue that Brazil’s non-alignment strategy reflects its foreign policy’s “mixed” character due to a peculiar Western and Global South inheritance. We consider the analysis of Brazil’s positions regarding the conflict in Ukraine a valuable case study on the balancing geopolitics of middle powers navigating the troubled waters of today’s international relations, marked by increased antagonism between the West and the East. Methodologically, the chapter relies on a qualitative and analytical approach to official documents and political discourses of State officials, diplomats, and country representatives. It also integrates secondary sources, including academic literature, media reports, and expert analyses, to ensure a comprehensive understanding of the driving factors behind Brazil’s relationship with Russia, which has remained stable despite dramatic and unpredictable changes in the global political landscape.