Protestant scholarship has often found Chrysostom’s soteriology wanting, or even Semi-Pelagian. Recent studies, however, suggest that a proper understanding of his soteriology must account for the rhetorical nature of his teachings. This study presents a two-fold argument. Firstly, based on Chrysostom’s didactic teachings, we assert that the theory of recapitulation is an important, if not primary, feature of his soteriology. According to Chrysostom, the Son of God was incarnated in order to fulfil the Law, restore the cosmic order and redeem humanity. In so doing, He enables Christians to transcend their human nature by the Spirit and participate in his life of obedience. Secondly, the richness of Chrysostom’s theory cannot be fully grasped until we pay due attention to the ways he develops and nuances this doctrine in his exemplar portraits. By analysing his rhetorical portrayals of the angels, Adam and Eve, and the ascetics, we conclude that Chrysostom’s vision of the Christian life shares several traits similar to that of the angels. Nevertheless, it is also unique and different in a few significant ways. Namely, it is to be lived out in the body, characterised by the enjoyment of God’s providential care, moderated by ascetic practice and enabled by the Spirit. Ultimately, it is a life that surpasses that of the angels because it is no less than a participation in Christ’s divine and yet human life. As seen from his Pauline portraits, Chrysostom frequently explicates and reinforces these and other aspects of his recapitulation theory in his listeners’ minds by employing the meta-narratives of transcendence and imago Christi in his depiction of the saints.