This article argues that translation is always close reading par excellence. Thestarting point is the author’s translation of F. Scott Fitzgerald’s short story collectionAll the Sad Young Men (1926) into Swedish, Alla sorgsna unga män (2014).Focusing less on particular translation methods and theories, this article insteadlooks at how the translation process forces emphasis on, and interpretation of,synchronic and diachronic dilemmas. Translation thus becomes a method foranalyzing literary style and context differently than from a native language perspective.The article is structured in two main sections, looking at some examplesof the synchronic and diachronic difficulties involved in the translation process.The synchronic section argues that Fitzgerald’s use of punctuation, and especially1-em and 2-em dashes, are highly original to his literary style. This section alsoclaims that Fitzgerald’s style is dependent on the advanced use of polysyndeton,allusion, auditive aesthetics, metonymy, and personification. The diachronic sectiondiscusses a few interesting contextual cases that illuminate how Fitzgeraldinterweaves contemporary events into the universal themes of his work, creatingnot only the local and temporal color of the jazz age, but also involving readersin what Partington refers to as the “smugness effect”: a collusion between authorand reader. In summary, using the translation process as an analytical tool revealselements of literary style and contextual writing in Fitzgerald’s prose that mightotherwise have gone unnoticed.