Yaakov’s Gifts to Eisav
21. In Parshas Vayishlach, Yaakov Avinu sends a large gift to Eisav. Some meforshim ask how Yaakov was allowed to send a gift to Eisav – there is an issur of לא תחנם, the Avos kept the whole Torah, and the gifts came right after Yaakov testifies that he kept the 613 mitzvos (רש''י עה''ת ), which include לא תחנם! How did he send Eisav the gifts?
22. Eisav was a Yisroel. Some answer that Eisav had the status of a Yisroel (גמ' קידושין דף י''ח ע''א ). Even if he was a mumar, most poskim hold there is no issur of לא תחנם with a Jewish mumar (above, 9),
23. Peaceful relations. Even if Eisav had the status of a non-Jew, when a Jew is traveling with a non-Jew and is afraid he will harm him (above, 14) or he wants to win his favor (יש''ש חולין פ''ח סי' ק''ג ), he may give a gift. That is why Yaakov said, I will remove his anger – so that he would not harm him (ים שמחה פ' וישלח ). He also said, And I sent to tell my master [this] to find favor in your eyes, i.e., to receive peace in exchange, which is mutar (above, 15).
24. Gaps between the herds. Some explain this is why Yaakov was a bit sparing and did not fill the gaps between the herds when he gave this big gift to his brother, Eisav. It was because Yaakov was being careful about לא תחנם and was being exacting to give only what he estimated was necessary to save himself from Eisav. If he would have given more generously and filled the gaps between the flocks, it would have been a violation of לא תחנם (רבי אלחנן וורסמן, אור אלחנן עמ' רפ''ד ).