While searching for legal opinions that could grant the annulment of his marriage to Catherine of Aragon, King Henry VIII of England sent his ambassadors to Italy, where they encountered a range of intellectuals both supporting and opposing his petition to the Pope. Among the most notable supporters of Henry's divorce were Francesco Zorzi, a Franciscan Observant, and Rabbi Eliyyah Menaḥem ben Abba Mari Ḥalfan, an esteemed Jewish scholar involved in the messianic movement of Shlomo Molko and David Reubeni. What is particularly striking about their common conclusions is that Zorzi and Ḥalfan both lived in Venice and were excellent connoisseurs of Kabbalah as well as prominent religious and political figures in their respective communities. This paper seeks to re-assess the writings of these two intellectuals during the period of the royal divorce (and, potentially, their libraries) to explore the Kabbalistic, intellectual, and even political influences that may have shaped their stance on the matter.