The Mishnah (22a) warned that a Jew should not allow himself to be alone with a pagan, since they are suspected of killing without compunction. On yesterday’s daf (=page) the Gemara quotes a baraita that warns a Jew who is traveling among pagans to be careful in their presence, and to refrain from giving clear information about his ultimate destination. The model for this behavior is the Patriarch Ya’akov who tells his brother, Eisav, that he planned to continue to Se’ir (see Bereshit 33:14) when, in fact, he did not plan to continue past Sukkot (see Bereshit 33:17).
To support this teaching, the Gemara tells two stories of Jews who found themselves in these types of situations. Rabbi Akiva’s students were traveling to Keziv and found themselves amongst a band of robbers. Telling the robbers that they were planning on going to Acco – which was further south – they left the road at Keziv, leading the robbers to praise them and their teacher for their care in traveling. The Gemara on today’s daf tells of Rav Menashe who was traveling to Be Torta and told the thieves who he met that his destination was Pumbedita. When he left the road at Be Torta the thieves ridiculed him, calling him the student of Yehudah Rama’ah – Yehudah the trickster. In response, Rav Menashe declared a ban on the thieves, who were unsuccessful in their endeavors for years until they begged his forgiveness. The Gemara concludes by pointing out the difference between robbers in Israel who showed respect and admiration for those who protected themselves, and thieves in Babylon who could only insult those who they could not take advantage of.
The Midrash, as well as many of the later commentaries, asks how Ya’akov, who is seen as a man of truth, could be the archetype of the man who uses subterfuge to save himself. The suggested approach is to say that Ya’akov did not lie, since he ultimately planned to reach Se’ir (see Ovadiah 1:21) at the End of Days. The Iyun Ya’akov derives from this that even when acting with deceit in order to protect oneself, one should try to avoid a baldface lie. He suggests that the statements of Rabbi Akiva’s students as well as Rav Menashe should be understood in this light, even though a person is permitted to lie in order to protect the peace (see Yevamot 65a).