Abstract: This chapter shows how shortly after initiating the confraternity project in Siena, Francesco di Bartolomeo Alfei was drawn into serving the military machine of the Republic of Siena, in the guise of ‘esploratore’ (surveyor). His contract, recorded by the office of the Balia (the government tribunal) in December 1455, involved mapping the city and surroundings of Orbetello, under siege by Jacopo Piccinino. This, along with other survey work commissioned around the same time in the face of hostile action by the Orsini of Pitigliano laying siege to Castello Ottieri and, at a later date, following Florentine manoeuvrings in the Val di Chiana, not only compromised the artist's commitments inside Siena but also impacted his way of life until he was well into his seventies.

Keywords: the office of the Balia; Sienese military machine; mercenaries; the Ottieri; Jacopo Piccinino; the Orsini of Pitigliano.

Whether or not it was Meo di Lorenzo who set Francesco di Bartolomeo Alfei on the path to the shadier side of Sienese diplomacy and politics is open to question. However, there can be little doubt that having such an individual as a father-in-law must have been useful when it came to seeking out government employment. Indeed, an hypothesis raised and considered here is that it was through the conduit of the office of the Biccherna that Francesco di Bartolomeo Alfei embarked upon an alternative career as an ‘esploratore’.

The December 1455 Balia record shows that Francesco di Bartolomeo Alfei had received payment for ten days work on a view on paper of the city of Orbetello with the Argentario headland in the background. Given the distance between Siena and the Maremma, and the number of days it had apparently taken the artist to complete this image, it seems likely that Francesco di Bartolomeo Alfei remained on site to complete the work. As a result, he may well have found himself involved at this early stage in his career as a kind of surveyor gaining information on the ground about potential dissidents and in particular those favouring the cause of Count Jacopo Piccinino, the mercenary soldier who had swept down from the north. There can be little doubt, either, that the 1455 mapping was intended to serve the Republic of Siena during engagements not just with one old enemy, but also with other hostile forces in their southern territories.