As Charles the Bold's relations with the papacy were inevitably somewhat more sui generis than those with the purely temporal Italian rulers of Naples, Venice, Milan and the other states discussed in the previous chapter, they will be dealt with separately here.

The duke's relations with Rome were affected both by the papacy's universal role and, in the half-century before the Reformation, by its increasingly Italian characteristics. During the reigns of the two pontiffs in question — Paul II (1464–1471) and Sixtus IV (1471–1484) — the universal role of the Holy See affected Charles very closely in certain areas. Papal taxation and appointments, for example, could have diplomatic repercussions; the pope's power to grant or refuse dispensations from the canonical prohibition on marriages within certain degrees of consanguinity might make or mar marital diplomacy; and the pope's duty to intervene between warring rulers in the interests of peace and for the furtherance of the crusade was a political fact that could not be ignored. In other senses, though, the duke's relations with Rome were much more directly connected with Italy. The numerous legates who visited his court, whether as peacemakers or as tax-collectors, were nearly all Italian. The pope's standing as the temporal ruler of the Papal States had a bearing on the papacy's attitude towards its neighbours in Italy, and hence on its attitude to Charles himself, as a result of his relations with those neighbours. The degree of influence that certain Italian rulers had in Rome was a factor to which Charles gave serious thought before making alliances in the peninsula, and his attempts to render Paul II and Sixtus IV more pliable led him to attempt to assemble a pro-Burgundian party at the curia. Finally, the value of undertaking a general survey of his relations with the Holy See is emphasised by the consideration that, in this respect, he has been less well served by historians than his predecessor, Philip the Good, or his contemporary, Louis XI; this should be borne in mind when reading what follows, because more research is clearly still needed.