The present text examines Antonio Pollaiuolo’s two designs for the unrealized bronze equestrian monument to the Milanese duke Francesco Sforza and the unique, unexplored insight they provide into its complex history, evolution, patronage, iconography, and political significance at the Sforza court during the last three decades of the fifteenth century. Pollaiuolo’s drawings represent the nexus of an extensive series of equestrian images of Francesco, which served to legitimize his rule and that of his successors. By examining the drawings with the broader context of Francesco’s portraiture, the present text demonstrates they represent the Sforza duke (a notion that has recently been challenged in the scholarship), at varying ages and levels of idealization. A close analysis of the variations in pose, physiognomy, iconography, and level of detail in the two drawings suggests that they illustrate differing ideological conceptions of the monument produced several years apart – one in the early 1470s for Galeazzo Maria and the other in the early 1480s for Ludovico – reflecting the latter’s manipulation of his father’s image to suit his propagandistic needs. Exploring the close connections between visual and literary propaganda at the Milanese court, the text will suggest that Pollaiuolo’s earlier design may relate to the Sforziade, the biography of the duke completed in 1473 by the court humanist Francesco Filelfo, who may have played a key role in planning the monument.