Three Greek letters by the Holy Roman emperor Frederick II Hohenstaufen to the Eastern Roman emperor Ioannes III Batatzes, dating from the year 1250, cast light on the Laskarid involvement in Italian politics outside of the Balkan Peninsula, the traditional sphere of Byzantine influence. In two of the letters, the Holy Roman Emperor informs his son-in-law and ally Ioannes III about the war he is waging against the papal forces in Italy; in the third, Frederick II openly appeals to his Byzantine counterpart not to engage in unionist negotiations with the Holy See. Examining the content of these three letters, I suggest, helps us to redefine the role that the Laskarid polity played in the wider Mediterranean world of the mid-13th century. In this paper, I focus on the Italian case in order to illustrate that the Laskarid Roman Empire was an active political agent that sought to influence the politics of polities well outside its assumed political sphere of interest. The Italian example allows us to understand that the Byzantine Empire of Ioannes III Batatzes and his successors had enough vigor and resilience from the 1240s to the 1280s to project an image of itself as a dominant power invested in determining international affairs throughout Christendom.