The subject of Saint Jerome in penitence was of great popularity in fifteenth-century Florence. During this period, confraternities and orders dedicated to the saint became widespread in Italy, some of them practicing the discipline of self-flagellation. Clearly identified by his symbolic cardinal’s hat and lion, the suffering saint is dressed in the utmost simplicity of penitential garb. He is in a stony, desert wilderness, along with a dangerous snake, scorpion, and lizard, associated with the threat of evil, and jaybirds, associated with penitence, beating his already bloody chest with a stone. As he stated in his Letters, he wanted penance for his pride: “Filled with stiff anger against myself, I would make my way alone into the desert; and when I came upon some hollow valley or rough mountain or precipitous cliff, there I would set up my oratory, and make that spot a place of torture for my unhappy flesh”. The painting is now attributed to Domenico di Michelino, whose only surviving documented work is the famous large Dante Reading from the Divine Comedy installed in the Florence Duomo in 1465.