In the memories of the journalist Beppe Pegolotti “the ‘Cinciarda’ was a sickly and drunk beggar, the son of a newsagent, with a mild and friendly personality, that the painter had found many times in the inn Da Nello in via dei Servi and who had already been depicted in various poses, sometimes just his head, others in a bust […]. The ‘Cinciarda’, logically, was a nickname, of which, however, the origin was unknown”. Exhibited in the Galleria Firenze in 1945, the painting was presented two years later in the first exhibition of Modern Painters of Reality, set up in Milan at the Galleria dell’Illustrazione Italiana. Crucial work in the artistic path of Annigoni, the Portrait of Cinciarda is placed in a wide repertoire of images of outcasts and marginalised people, depicted with an intense and vivid realism that found in Florence a direct correspondence with the narrative of Vasco Pratolini. Model of Annigoni since the times of his studies at the Accademia in Florence, Cinciarda is depicted in many portraits starting from 1935, up to that of 1942, currently in the Art Collection of the Fondazione Guelpa in Ivrea, which achieves excellent results with its penetrating psychological investigation and physiognomy of the character, of a clearly Flemish derivation. In the painting of the Art Collection of the Fondazione Cassa di Risparmio di Firenze, he is shown as a full figure, wrapped in a large, worn out cloak from which only his hand protrudes, to hold his chin, captured in a moment of waiting and with an inquisitive expression on his face. With the comparison by the critics to Menippo by Diego Velasquez (1639-1640, Madrid, Prado Museum), for the raw truth with which he portrays a humanity that is miserable and destitute, the painting shows obvious suggestions from northern painting, both for the accurate play of light, which reveals the figure from the shadows and accentuates the metallic reflections of the mantel, as well as in the symbolic dimension of the character that becomes an emblem of the fickleness of human destiny. Annigoni remembers “[…] that almost every day he went up the stairs which led to my studio, and after ringing the bell, remained there, waiting, in the same pose in which I depicted him. It was just after the war and this character, so humanly tragic, struck me for the symbolic meanings that he could assume. The end of the war left us shabby: and the ‘Cinciarda’, poor, there at the edge of the stairs, seemed to express all the uncertainty of our future”.