The article compares the predispositions and circumstances of Russian annexations of Crimea in the years 1783 and 2014. It illustrates the blatant similarities in the official rhetoric observed on the example of literary works from both eras. Primarily, it concerns Gavrila Derzhavin’s ode Na priobretenije Kryma and Chersonida, a narrative poem by Semyon Bobrov, of which both reflect the so-called Greek plan, a political and cultural programme of Catherine the Great. Contemporary works are represented by Krym kak predčuvstvije, a collection of short stories by Elena Yablonskaya, with poetry reflected including the so-called geopoetics of Igor Sid and his group, as well as other propagandist and nationalist poems by various authors. While in the era of Catherine the Great the focus of the works was on reclaiming Crimea diplomatically and calling up the Russian claims to Ancient and Greek heritage, in our days we see more of a primitive literally propaganda with strong nationalistic elements that relies heavily on communication technology.