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Between 1492 and 1503, Francesco Todeschini Piccolomini (1439–1503) was the first officially appointed Cardinal Protector of England. This paper focuses on a select few of his activities executed in that capacity for Henry Tudor, King Henry VII. Drawing particularly on two unpublished letters, it underscores the importance for King Henry of having his most trusted supporters translated to significant bishoprics throughout the land, particularly in the northern counties, and explores Queen Elizabeth of York’s patronage of the hospital and church of St Katharine-by-the-Tower in London. It further considers the mechanisms through which artists and humanists could be introduced to the Tudor court, namely via the communication and diplomatic infrastructure of Italian merchant-bankers. This study speculates whether, by the end of his long incumbency of forty-three years at the Sacred College, uncomfortably mindful of the extent of a cardinal’s actual and potential influence in temporal affairs, Piccolomini finally became reluctant to wield the power of the purple.