Since its independence in 1991, Ukraine’s language regime has evolved in a context of intense cultural heterogeneity. The most crucial element of the language situation in Ukraine concerns cohabitation and intermingling between Ukrainian and Russian language-oriented populations. Ukraine’s competitive state tradition produced a contested language regime. Formed at the crossroads of civilizations, it has been influenced by both East and West. The critical juncture of Ukraine’s independence marked a rupture with its past and generated a new language regime that actively embraced priority for the Ukrainian language. But because of its competitive state tradition, this language regime remained unsettled, solidifying only gradually and non-linearly. Inherited institutions that were both executive dominant and fragmented produced radical shifts when new elites took power. Through these shifts, Ukraine’s language regime has gradually coalesced around a dominant conception, though the tradition of competitiveness remains. Ukraine’s language regime reveals the embedded normative and institutional legacies of its experience under Russian and Soviet rule, as well as the reactive nationalism this imposition provoked. It continues to occupy a crossroads, pulled at once by East and West, paradoxically asserting the very monolingual nationalism perfected in Europe but now cautioned by appeals to minority language rights.