This article examines the linguistic, stylistic, and cultural challenges involved in translating historical and political narratives, with particular reference to Lee Kuan Yew’s From Third World to First: The Singapore Story (1965–2000). Using a qualitative descriptive and comparative approach, the study explores how translators navigate issues of political terminology, rhetorical style, and period authenticity. The analysis identifies three core areas of difficulty: the translation of ideologically charged terms, the reproduction of persuasive rhetorical structures, and the retention of historical context for culturally diverse audiences. English–Russian examples illustrate how dynamic and communicative equivalence can help preserve both meaning and emotional force. The findings underscore the translator’s role as a cultural mediator who must balance fidelity to the source text with accessibility for the target readership. The study concludes that successful translation of historical and political texts requires not only linguistic competence but also historical awareness and intercultural sensitivity.

Translation studies, historical narratives, political discourse, stylistic equivalence

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