This article explores “A Midsummer Masquerade” by O’ Henry in terms of culture-speciёc markers of the author’s individual style and cultural metaphors as potential interpretation gaps. An attempt is made to elicit implicit information on quasi-words and malapropisms, allusions to the Bible, references to historical personages and political events. Approaches to short story translation are considered in light of P. Newmark’s insights into the nature of this genre and his typology of short story speciёc characteristics, which are relevant for translation. The conclusions draw on key points of the general cognitive theory of translation and modern Americans’ comments on the selected fragments. Through showing the potential diversity of interpretation, this research highlights the importance of background cultural knowledge and considers some cases of untranslatability.