Huldrych Zwingli faced criticism from nearly every angle in the sixteenth century when it came to the hotly contested doctrine of original sin. Some Romans Catholics, like Domingo de Soto, saw him as “digging up the grave of Pelagius once again and giving his corpse new breath” (De natura et gratia, 1549); some Lutherans like Melanchthon viewed him as maintaining original sin “in name” but “stripped it of the thing [sin] itself” (Commentarii in epistolam Pauli ad Romanos, 1532); and even some of the Reformed saw fit to argue that Zwingli’s early view of original sin had been corrected (See: Martin Bucer, Metaphrases Et Enarrationes, 1536). Zwingli’s views have been subject to caricature, criticism, and even in recent years, reclamation (Crisp, 2016). In this paper, I will reconsider Zwingli’s shifting doctrine of original sin through the angle of his exegesis of Romans 5 and unfolding debates that were ongoing on this controversial passage. Careful attention will also be paid to the question of original guilt in the context of the Anabaptist movement in Zurich. More specifically, I will examine the indebtedness of his exegesis to the works of Origen and Erasmus in his Annotationes in Romanos (1539) to help better clarify the shape of his theology and propose a better way of categorizing his distinct and controversial perspective of original sin.