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Abstract: The essay analyses the little known story of ]uan de Figueroa, the first ambassador appointed to Rome by Philip II in 1558. Pope Paul IV refused to receive the representative of the Habsburg sovereign, charging him with heresy and excommunicating him for having been guilty of behavior detrimental to ecclesiastic authority. A delicate political-diplomatic issue opened: Figueroa departed the pontihcal territories without having taken possession of his office, awaiting a solution to the controversy. A few months later, just as the Pope's position softened, the ambassador died. New documents, accompanied by a reevaluation of others already known, demonstrate that the situation was more complicated than traditionally believed. The repudiation of Figueroa was actually caused by factional conflicts occurring at the court of Philip II and by maneuverings on the part of unofficial representatives of the catholic king in Rome (Cardinal Pedro Pacheco and Francisco Vargas) in agreement with the cardinal—nephew, Carlo Carafa.