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Abstract: Caravaggio’s time in the hospital of Santa Maria della Consolazione in Rome, during his apprenticeship to Cavalier d’Arpino, is here re-examined and reconstructed through a comparison of information found in a recently published document relating the words of a barber’s apprentice, Pietro Paolo Pellegrini, and a passage of the Scritti, (the writings), of Carlo Cesare Malvasia, who gives an interesting version of Caravaggio’s stay in hospital and of his separation from Cavalier d’Arpino. The study of these two documents, one oral and the other literary, and of the information contained in them, gives rise to new conjectures regarding the souring of relations between Caravaggio and the Cesari brothers at the time of his admittance to hospital after a wound to the leg caused by a kick from a horse. The words of Malvasia shed new light on the portrait of the prior of the hospital, the Sicilian Luciano Bianchi, which the Lombard painted in payment for his medical treatment, and which, according to the biographer, was sold in Rome and much appreciated by Giuseppe Cesari, although he was unaware of the author. The collection of the prior, which is unknown to us, is hypothetically reconstructed on the basis of the tastes and fashions of contemporary collectors in Rome with connections to the medical profession.