This paper discusses the diplomatic career of a Jesuit whose political acumen and militant understanding of mission went to loggerheads with imperial, papal, and even Jesuit interests in northeastern Europe. Antonio Possevino (1533-1611) was a priest, writer, and administrator who served as the superior of the Jesuit mission in Sweden and the pope’s extraordinary legate to Muscovy, the Polish-Lithuanian Commonwealth, and the Holy Roman Empire between 1577 and 1587. Like any high-ranking Jesuit, Possevino had dreams of global evangelization, but the means he envisaged for attaining them were predominantly political and military. During his diplomatic career he became so enmeshed in local politics that he was accused of partiality to the Polish-Lithuanian king, whose envoy he effectively became on several occasions. At the request of the imperial court, who perceived him as hostile to their interests, and despite Possevino’s efforts to prove his impartiality, his superiors dismissed him from his diplomatic activities. Exiled in Italy, far from high-level politics, Possevino remained involved with northeastern Europe, but only behind the scenes or under the cover of a pseudonym. His story illustrates the multiple identities and uneasy but inevitable mixture of politics and religion in early modern Catholic diplomacy.