Chatam Sofer, in his commentary to Masekhet Gittin (22b), amidst his discussion of the laws governing shelichut (the halakhic mechanism whereby certain requirements can be discharged through an agent), asserts that the mitzva of mishloach manot on Purim is not governed by these laws. Generally, when one seeks to perform an action through an agent, this is allowed only if the agent meets certain criteria – specifically, the agent must be a Jewish adult. Gentiles and minors cannot function as an agent for satisfying halakhic requirements, even those requirements which can be fulfilled via agency, because they themselves are not bound by the requirement in question. Chatam Sofer clarifies that this rule applies only to situations which demand formal shelichut – meaning, when one seeks to fulfill a requirement involving an action which fundamentally only he can perform, and shelichut enables him to empower the agent to act on his behalf, as his representative. But when a halakhic requirement does not need to be satisfied by a particular action, one does not need to resort to formal shelichut, and therefore anybody can perform the action. In the case of mishloach manot, Chatam Sofer writes, the Torah does not require personally giving a gift, and in fact the Megilla specifically refers to the obligation with the term “mishloach” – sending. This formulation certainly indicates that one is not required to personally give the gifts, and so, Chatam Sofer rules, this mitzva is not subject to the rules that govern formal shelichut. And thus, he writes, one may send mishloach manot “even through a monkey and all those disqualified [from shelichut].”
Apropos to Chatam Sofer’s ruling – and in the jovial spirit of Purim – Rav Yitzchak Zilberstein tells in this context (in Chashukei Chemed – Megilla, 7a) the humorous story of a rabbi to whom somebody once sent mishloach manot with a child who – like most children on Purim – was in costume. Specifically, this child was dressed as a guerrilla. The rabbi later expressed to the Satmar Rebbe his dismay over this incident, claiming that it is disrespectful to send mishloach manot to a rabbi in this fashion. The Rebbe responded, “This shouldn’t bother you. After all, even if that person had sent you mishloach manot with an actual guerrilla, he would have fulfilled the mitzva!” The Rebbe referred the rabbi to the aforementioned comments of Chatam Sofer, stating explicitly that one fulfills the obligation by sending mishloach manot with anybody – even a monkey… (However, Rav Zilberstein notes that according to those who explain the mishloach manot as intended to enhance the feelings of friendship among Am Yisrael, sending mishloach manot in a manner that the recipient finds insulting perhaps does not fulfill the obligation, as it accomplishes the precise opposite of the intended goal of mishloach manot.)
On a more serious note, there is some discussion among later writers as to whether Chatam Sofer’s comments should be understood to mean that the mishloach manot obligation requires specifically sending food to one’s fellow through a messenger. As we saw yesterday, the term “mishloach” appears to refer to sending through a third party, as opposed to personally giving a gift, and this led some poskim to ask whether Halakha requires sending the food via a messenger. Some inferred this conclusion from Chatam Sofer’s comments, as he noted the implication of the term “mishloach” that the obligation is not to personally give a gift, such that the formal institution of shelichut would be needed if one wished to send it with somebody else. Seemingly, Chatam Sofer understood the obligation of mishloach manot as requiring sending, and not bringing, a gift. However, Rav Eliezer Waldenberg, in Tzitz Eliezer (9:33:4), disputes this reading of Chatam Sofer’s remarks. He asserts that Chatam Sofer inferred from the word “mishloach” that the food may even be given via third party, not that it must be given by a third party, and, as such, one does not need to employ the formal institution of shelichut if he wants to send the food package with a messenger.
(See also Rav Zvi Ryzman’s comprehensive essay on this topic.)