Cardinal Reginald Pole served as a papal legate for almost twenty years. He was a leading figure in the Catholic Reform movement, and a prominent political figure both in England and in Europe in his own right. Despite the survival of an unusually vast correspondence and his large literary oeuvre, Pole has remained an elusive figure, often disparaged; his achievements often dismissed; his stature as a leading figure of the century often diminished. How it was that by the middle of the sixteenth century Pole, a lone Englishman, was so pre-eminent in the religious affairs of Europe, especially as he had achieved this prominence in the teeth of the unrelenting hostility of his king and kinsman Henry VIII, who once had been his patron and greatest champion? Pole’s career is also an exemplar of how ignoble dynastic self-interests hampered the noble ambitions of genuine ecclesiastical reformers on both sides of the confessional divide at almost every turn in these early years of the Reformation. This article argues that Pole’s return to England in 1554 as legate a latere has often overshadowed consideration of the other elements of his service, both as a reforming cardinal-deacon, and as a legate a latere in other capacities. While these previous experiences shaped the character of his final legation in England, they also shaped the “Roman” character of the “Catholicism” that was to emerge in the second half of the sixteenth century.