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Abstract: This paper presents a body of research aimed at forming a clearer picture of the merchant Costantino Spada. Until now little was known about him beyond his name and the fact that he was instrumental in helping to establish the career of Caravaggio. The discovery of previously unpublished documents has made it possible to narrow down the location of the dealer’s shop to the area behind Palazzo Madama, and has enabled a new understanding of the social and commercial network within which he operated. These discoveries have helped to identify, or in certain cases to hypothesize, Spada’s relations, previous to the arrival of Caravaggio in Rome, with the principle patrons of the artist, including cardinal Del Monte, the brothers Vincenzo and Benedetto Giustiniani, and the Mattei and the Aldobrandini families, and also to understand his dealings with other influential figures of the time, like the Sienese aristocrat, Patrizio Patrizi, and the cardinal from Bergamo, Gian Girolamo Albani. This new information presents a figure of undeniable importance, with whom Caravaggio enjoyed a close friendship which lasted at least until 1599, as revealed in a recently discovered document regarding the painter. The knowledge of this friendship has led to the conjecture that Spada acted as facilitator for the commission that Caravaggio received from the heirs of Ermete Cavalletti to paint the Madonna of Loreto for the church of Sant’Agostino: these documents concerning the merchant have confirmed his close family ties with one of the principle occupants of the convent of Saint Augustine, the monk Giovanni Battista Gori.