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In 1445 the Compagnia della Misericordia, a confraternity of Borgo San Sepolcro, commissioned Piero to paint a polyptych for them, within three years. According to the taste of the time, the polyptych was to be painted with precious colours and have a solid gold background. Piero did not respect the time limits set down in the contract, for he was busy working on other, more important projects. The polyptych was only finished almost twenty years later.
The oldest parts are the two panels with St Sebastian and St John the Baptist, to the left of the main panel. No other figure of Piero's, more than this St Sebastian, shows such close connection with Masaccio's nudes, even in his rather graceless but realistic pose. A little later Piero painted the panels of the tympanum, with the Crucifixion in the centre, and St Benedict, the Angel and the Madonna of the Annunciation, and St Francis in the sides. Towards 1450 Piero finished the figures of St Andrew and St Bernardino.
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