Fra Angelico’s painting, The Conversion of St. Augustine, offers a great insight into the spirituality of the Doctor of Grace. At the forefront of the painting, commanding the immediate attention of the viewer, is the figure of St. Augustine sitting and weeping. The painting portrays the moment of St. Augustine’s conversion as it is described in his Confessions (book VIII, chapter 12).
In the garden of his friend’s house in Milan, after long struggles with “old attachments” that kept him from embracing the life of continence, Augustine gave way to the “storm” of tears that had been welling up inside of him, expressing his great remorse for his sinfulness, which proved to be invincible to his own strength. He wept because he felt he was the “captive” of his “sins,” and while crying, he kept repeating, “How long shall I go on saying ‘tomorrow, tomorrow’? Why not now? Why not make an end of my ugly sins at this moment?”