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This article addresses versions of the legend of Trajan occuring between the late seventh-century Whitby’s Anonymous and the fifteenth century. As it is a legend which treats the salvation of a persecutor of Christianity, it is not strange that it arouses some skepticism, and thus initially generated arguments that tried to deny or confirm it. Subsequently the legend, already accepted, was used to support other types of arguments advanced by an array of impressive authorities, including John the Deacon, Jacobus de Voragine, Albert the Great, Thomas Aquinas, and Dante and the commentaries on the Divine Comedy. The various arguments related to the legend of Trajan are the subject of this study.