Abstract: Previous assessments of Francesco di Bartolomeo Alfei (including the aborted commission to fresco the chapel of the Fraternita di Santa Maria degli Angeli e Compagnia di San Francesco in Siena and disputed claims about the ‘Maestro dell’Osservanza’ and the altarpiece of the Birth of the Virgin in Asciano) provide the background to an analysis of the politics of his journeyman painting, applying the symbols of Sienese power in subject communes. This chapter outlines the artist's early involvement in government affairs from the mid 1450s onwards; from service in Rigomagno to the east of the Via Francigena near the unsettled borderlands of the Val di Chiana, to Monte Orgiali in the south towards the Maremma and the old stronghold of the Aldobrandeschi.

Keywords: visual propaganda; Sienese territory; political alliances; the Aldobrandeschi; journeyman painting; surveillance and intelligence.

The earliest record of a petition by Francesco di Bartolomeo Alfei for government employment that was published by Gaetano Milanesi dated to 10 April 1466. Describing himself there as ‘dipentore vostro cittadino’, Francesco di Bartolomeo informed the ‘Signori’ and ‘Capitano di popolo’ of his understanding that the majority of Sienese possessions in the ‘contado’, and particularly those in the Maremma, lacked painted signs containing the Sienese coat of arms on their entrance gates. The artist asked that, in return for painting four or six such signs in the Maremma region (or wherever directed in other parts of the territory by Sienese officials), he should be offered the post of ‘vicario’ of Monte Orgiali (to the east of Grosseto) for the period of one year, starting the following July. He also asked that in painting such signs, officials in the individual communes should be obliged to provide him with the scaffolding and materials for the plaster (‘calcina’) and any other necessary items (‘altre cose bisognevoli’). Francesco di Bartolomeo would in consequence be required only to offer his own expertise and provide the necessary colours (‘per modo che lui v’abbi a mettere se non el magisterio et colori di suo’). Alfei added that, if assigned to that post, he should not be expected to attend to his official duties whilst engaged in any painting work. Presumably, his allotted salary as ‘vicario’ (no doubt with board and lodging included) would in the meantime continue.