Focusing on Benedetto da Maiano's pulpit in Santa Croce, this paper attempts to investigate the intriguing interrelations between art and preaching by analyzing the manner in which the nature and content of preaching helped shape the pulpit. In Santa Croce, the pulpit is a permanent preaching pulpit used for the seasonal cycles of Advent and Lent; it was specifically intended as a platform for popular preaching to the laity. Located in the lower nave, rather than near the altar, it is not a freestanding structure but part of the pier. The pulpit is examined in terms of its sources (visual and especially textual), its physical context within the church, its historical and cultural context (in particular as related to the sermons of San Bernardino and his followers), and the political and religious climate after the Ottoman conquest of Constantinople. The Franciscan cycle of this pulpit is associated with the veneration of Saint Francis in the 15th century, the conception of Francis as alter Christus, and crusade ideology.