This paper will consider the early generations of Jesuits in Florence, Siena, and Montepulciano. Starting with Paschase Broët and Simão Rodrigues, who were sent by Pope Paul III to reform the Benedictine monastery in Siena, the Jesuits eventually founded colleges in fi ve cities of the Grand Duchy of Tuscany. Although these schools claimed to educate hundreds by the end of the sixteenth century, historians know little about those students (or their teachers). I have created a database with the information I have gleaned from a variety of sources about the education, life, and careers of several dozen Tuscan Jesuits. While this is a small sampling, it allows for some cautious conclusions about the success of the colleges, particularly in comparison to a similar database I have created for seminaries in the same region.