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Throughout the history of the exegesis of James 1:9-10a, the imperative καυχάσθω has raised more than a few discussions. What is the relationship of the verb to “the rich man”? Some scholars believe that the imperative is used in a literal sense, whereas others believe καυχάσθω is applied to the rich man ironically. This choice has significant implications for the interpretation of the entire exhortation: what is the intent of the Epistle, to invite the rich man to conversion, or to foretell his impending and unavoidable doom? The zeugma, identified in the two propositions governed by καυχάσθω, argues in favour of an ironic or antithetical interpretation of the imperative. This reading is confirmed by the verses that follow (10b-11) and it is part of a coherent approach to the themes of wealth and boast in the Epistle, which, regarding these topics, shows affinity with its cultural environment. The article proposes to consider the figures of the humble man and the rich one as literary types.