In the Borgherini Chapel in San Pietro in Montorio Sebastiano del Piombo and Michelangelo invent a new pictorial language to express the spiritual ideals of the Amadeiti friars, creating images of great evocative power. It has not been noted hitherto that the Borgherini Chapel contains the first large-scale depiction of the Flagellation: a subject that exemplifies the modern devotion to the cult of the Body of Christ as an emphatic meditation on the sufferings of the Passion, as well as a metaphor for the sins of the Church. A new devotional source sheds light on the iconographic significance of the Flagellation, recalling the Lombard patronage of Bernardino Carvajal and the venerable Arcangela Panigarola, who was closely connected to the Amadeiti friars. Ultimately, the Transfiguration – prophecy of the second coming of Christ and long-awaited reform of the Church – triumphs over the sorrowful Flagellation.