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The reigning cultural and legal standard of family relations in late medieval Florence, if not indeed for Italy as a whole, was patrilineal, agnatic, and public (legitimate). That standard was enshrined in law and celebrated in culture. Economic and biological realities, however, prevented some people from achieving a model existence in their lives. This essay follows a “trouble case” in which one Florentine attempted in his dying moments to transmit his property to his illegitimate son. The son’s claims were countered by his aunts. The canonist Domenico da San Gimignano reviewed the case for the court and argued in favor of the son’s claims, following a line of legal reasoning reluctant to penalize a child. His opinion indicates where and how, through consensual acts of some public weight, there was some flexibility in that reigning scheme of family relations.