Renaissance lot books, sometimes called books of fortune or books of sorts, first attracted scholarly attention in the mid-1800s and have since then been discussed in general terms with reference to pagan and Christian divination and medieval astrological prophecy. Although most studies focus on the sixteenth-century printed lot books, an examination of the only hand-painted example known today, the beautifully illustrated “Libro delle Sorti” by Lorenzo “Spirito” Gualtieri (c. 1426–96) dated 2 January 1482 that is located in the Biblioteca Nazionale Marciana in Venice, can be studied to better understand the quattrocento culture from which these volumes emerged. Lorenzo Spirito’s lot book is an excellent case study for how these types of books resulted from a conflation of different ways of answering difficult questions pertinent during this tumultuous time when feudal-era condottieri were transforming themselves into the noble Renaissance courtiers of Perugia.