This work provides a new narrative for Orsanmichele in the era before the Renaissance. It examines Orsanmichele from the mid-thirteenth century, as the piazza transformed into the city’s grain market. It considers the market’s tandem confraternity, with its stunning Madonnas over three successive loggias. It examines the grain market and confraternity from a social, economic, political, and artistic perspective. It provides extensive data on the Florentine grain trade, sales at the market, and the nexus between traders, political leaders, and the confraternity. The work suggests that developments at Orsanmichele during the medieval period formed the basis for the Renaissance structure.