When Pope Paul IV was elected in 1555, he began to institute radical change in the treatment of Jews, starting in his port city of Ancona where New Christians had settled and with papal permission reverted to Judaism. In the summer of 1555, the pope’s emissary arrested new Christians who had become Jews, confiscated their property, publicly tortured them, and during the next year strangled and burned about 25 of them. The prominent Jew Dona Gracia and local Christian merchants tried to intervene to save them with no success. To punish the pope, Sephardic Jews began a boycott of Ancona. The boycott failed with strong opposition by Jews. Similarly, in Germany in 1933 after Nazi rule began there were spontaneous boycotts against Germany around the world, and, with a rise in violence against Jews, Jews and Christians began to organize boycotts against Germany. These boycotts also failed, also with strong opposition by Jews. We will compare the two boycotts, and perhaps look at the larger issues of boycotts in our own time.