Q. How could Yaakov who kept the whole Torah send a gift to Eisav, is that not prohibited because of Lo Techanem?
A. See question 234 in regards to sending gifts to customers or business acquaintances as the holiday season approaches we wrote: The Talmud (Avoda Zarah 20a) instructs that there are different interpretations to the biblical proscription of “Lo Techonem” (Devarim 7:2) one is; “not to give them free gifts”. Who exactly qualifies as “them” and what is a “free gift”, is open to Halachik discussion. Shulchan Aruch (Y.D. 151: 11) rules: It is prohibited to give a free gift to an idol worshiper you do not know. Taz (ibid. 8) explains that if you know him, it is not considered a “free gift”, as you would expect a favor in return. As such, gifts to customers or business acquaintances, even if they were to qualify as idol worshipers are not prohibited. (However, Horav Shlomo Miller’s Shlit”a opinion is indeed to avoid sending gifts that would reach a Gentile on the day of the celebration. It is better to shun the prior day also).
Additionally, Yaakov's gifts to Eisav were given as an act of survival, since he feared for his life and therefore allowed.
Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit'a
Important Numbers
