Abstract: Francesco di Bartolomeo Alfei's expertise as a scribe was raised in a letter of recommendation sent by Leonardo Benvoglienti to the head of the Cathedral Works in Siena in 1458. Chapter Two considers how this career diplomat was privy to such information, and how the two men met (including the possibility that they crossed paths at San Francesco in Siena during attempts to canonise the Beato Bernardino Albizzeschi). The question is raised whether the friendship expressed by the diplomat resulted from the painter being an undercover agent. Leonardo Benvoglienti's diplomatic career in Venice, Montalcino, Rome and Naples is outlined along with a consideration of the language and format of ambassadorial reports and the roles adopted by couriers in delivering their despatches.

Keywords: Sienese diplomacy; ambassadors; ambassadorial reports and couriers; military tactics; espionage and undercover agency; Beato Bernardino Albizzeschi.

One of the earliest records cited by Gaetano Milanesi in connection with Francesco di Bartolomeo Alfei concerns the letter of recommendation written on the artist's behalf by Leonardo Benvoglienti (at that time acting as ‘orator senensis’ in Rome), which was despatched on 14 April 1458. (See Figure 10.) Somewhat curiously, though, Milanesi opined in an appended note that the ‘Francesco di Bartolomeo, dipentore’ – subject of the 1458 letter of recommendation – was the painter ‘Alfei da Montalcino’.

There is continuing discussion as to whether Francesco di Bartolomeo Alfei could claim any close association with Montalcino; attention on occasion being drawn to the reference in the artist's 1465 Lira to ‘Uno pezo di tera prativa ne la corte di Montalcino’. However, none of the documents I have considered indicate anything other than that Francesco di Bartolomeo himself and his father, Bartolomeo di Francesco, were citizens of Siena. Unlike some tax records, where reference was made to a particular individual's origins or birth place, in the case of Francesco di Bartolomeo and other identifiable members of his family, there are references only to Siena; whether in tax records, reports of the Consiglio Generale, ‘copia lettere’ in the Concistoro, or in the artist's own correspondence. There is, however, clear evidence that in later life Francesco di Bartolomeo Alfei assumed a number of official posts both in Montalcino and in its surroundings. It may thus have been on one of these occasions that he acquired the piece of meadowland that was declared in his 1465 tax declaration.