The article is a position paper focusing on the current standoff between two regional powers, the European Union and Russia. Following a series of crises, in particular the annexation of Crimea by the Russian Federation in 2014, the relationship between Russia and many of its neighbours has significantly deteriorated. This shift has led to various geopolitical opinions, often opposite and seemingly irreconcilable. A holistic and historical approach to this new reality leads some to question the validity of the current world order through the prism of the anachronistic concept of Empires. Subsequent to a review of definitions, the author analyses historical characteristics and political factors of the two territories on focus: the European Union and Russia. There are two outcomes of this study: On the one side, the European Union has become an organisation that shares many characteristics of an Empire, but several key elements exclude it from this political construction. On the other side, the geopolitical actions of Russia have shaped the position of the country into a structure that bears many of the artefacts of an Empire with key essential features. The conclusion of this argument states that the European Union is not an Empire by design, despite many resembling features; whilst Russia lives in an anachronistic paradigm of an Empire, without having the means of being one.