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In 1620 Orazio Capponi ordered that an afterlife portrait of Cardinal Carlo Borromeo (1538–84) be enshrined within a reliquary monument for the family chapel at Santa Felicita. The Capponi family maintained strong devotions for the Virgin, having commissioned Jacopo Pontormo to decorate the private chapel at the Capponi alle Rovinate palace with a Madonna and Christ tondo. In their parish church, Santa Felicita, Pontormo’s Annunciation fresco enframes Cardinal Borromeo’s portrait. Approaching the family chapel at Santa Felicita as an extension of domestic space, the paper examines how the afterlife portrait of Cardinal Borromeo, in conjunction with the Annunciation fresco, mediated the family's experience of the life stages, and, in particular, old age, death, and the afterlife, affirming the role of relics, portraiture, and religious narrative as the Capponi family’s means for repositioning their bid for immortality in a post-Tridentine context.