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This study examines two types of -ing subjects in English: the Late Modern English pattern the deceiving him was easy and constructions such as by trying to make her mother happy proved unlucky for Paul, which are becoming frequent among American undergraduates. It is argued that the presence of the and by in both structures is prompted by the desire to provide explicit grammatical marking for clauses that, because of their role as pre-verbal subjects, are cognitively very complex. The paper discusses the ongoing grammaticalization of by Xing sequences and outlines the historical developments leading to the emergence of the pattern with an introductory the, for which it proposes an analysis in terms of Lass’s (1990, 1997) concept of exaptation.