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His earliest extant performances, in considerable number, are at Cortona, whither he was sent during his novitiate, and here apparently he spent all the opening years of his monastic life.
Whereupon, Fra Domenico da Lecco, a Lombard, having been made General of the Monks of Monte Oliveto, Sodoma went to visit him at Monte Oliveto di Chiusuri, the principal seat of that Order, distant fifteen miles from Siena; and he so contrived with his persuasive words, that he was commissioned to finish the stories of the life of S. Benedict, part of which had been executed on a wall by Luca Signorelli of Cortona.
The Cardinal of Cortona, fearing a popular rising, refused to grant their request. A riot broke out, and the Medici were threatened with expulsion: but by the aid of influential citizens a revolution was averted. The Constable, avoiding Florence and Siena, marched straight on Rome, still watched but unmolested by the armies of the League.
Between Perugia and Cortona lies the large weedy water of Lake Thrasymene, turned into a witching word for ever by Hannibal's recorded victory over Rome.
Her whole behaviour, at the time, cast such a spell on the broken bridge, the little walled town and the trudging friar, that I turned away with the impatient vow and the fond vision of how I would take the journey again and pause to my heart's content at Narni, at Spoleto, at Assisi, at Perugia, at Cortona, at Arezzo.
Having arrived there, he found that most of the rooms in the Palace had been painted, or were still being painted, by a number of masters. To be precise, he saw that there was one room in which a scene had been finished by Piero della Francesca; Luca da Cortona had brought one wall nearly to completion; and Don Pietro della Gatta, Abbot of S. Clemente at Arezzo, had begun some works there.
Signorelli, with his usual originality, chose the moment when Christ broke bread and gave it to His disciples. In that rare picture at Cortona, we see not the betrayed chief but the founder of a new religion. The Cenacolo alone will not enable the student to understand Lionardo.
Nevertheless he executed on stone a Dead Christ with the Madonna, with an ornament also of stone, for Don Ferrante Gonzaga, who sent it to Spain. The whole work together was held to be very beautiful, and Sebastiano was paid five hundred crowns for the painting by Messer Niccolò da Cortona, agent in Rome for the Cardinal of Mantua.
He added that as he was passing through Cortona, he had seen in the capitular church of that city a most beautiful antique marble vase, adorned with sculpture a rare thing at that time, as most of the beautiful works of antiquity have since been brought to light.
In order to arrive at a decision, he asked council of the Florentine orators and four other noble burghers then in Rome, as to whether he could advantageously intrust the city to the Cardinal of Cortona in guardianship over Ippolito and Alessandro, the young bastards of the Medici.