14b----------------------------------------14b

1) WHEN THE INTENDED RECIPIENT OF A GIFT DIES
QUESTION: The Gemara cites a dispute between two Beraisos with regard to a case in which a person sent money with a Shali'ach to give to his friend, who died before the Shali'ach reached him. The sender said to the Shali'ach, "Give this money to my friend," and the intended recipient died before the money reached him. One Beraisa says that the money is returned to the sender, and the other Beraisa says that it is given to the heirs of the intended recipient.
Rav Aba bar Mamal suggests that both Beraisos agree that saying "Holech" ("bring [this gift to so-and-so]") is not like saying "Zechi" ("make an acquisition [on this gift on behalf of so-and-so]"). The Beraisa which says that the money is given to the heirs of the recipient refers to a case in which the benefactor was a Shechiv Mera (on his deathbed).
RASHI (DH b'Shechiv Mera) explains that since the words of a Shechiv Mera are "k'Chesuvin uche'Mesurin Dami" -- as if they are written in a contract and given over, and when a Shechiv Mera says "Holech" it is as though he says "Zechi," the recipient acquired the money before he died (that is, he acquired it at the time the money was given to the Shali'ach). Hence, the money goes to his heirs. Rashi reiterates a number of times in the Sugya that when a Shechiv Mera says "Holech" it is as though he says "Zechi."
Why does Rashi not explain simply that when a Shechiv Mera gives a command, it is as if it his words are already given over ("k'Chesuvin uche'Mesurin Dami")? Why does Rashi add that when he says "Holech" it is like "Zechi"? The law of "Divrei Shechiv Mera k'Chesuvin uche'Mesurin Dami" is unrelated to the principle of "Holech k'Zechi"; even if the Shechiv Mera says merely, "I want my money to be given to so-and-so," and he does not say "Holech" ("bring" or "give" it to him), his words nevertheless are "k'Chesuvin uche'Mesurin Dami" and we must honor his request and give the money to the recipient!
ANSWER: Rashi is bothered by a number of questions. If the Kinyan takes place because of the words of the Shechiv Mera, it should make no difference whether or not the recipient was alive when the benefactor (the Shechiv Mera) gave over the money to the Shali'ach. What matters is that the recipient was alive when the benefactor said that he wants the money to be given to the recipient, since it is his Amirah, his words, which make the Kinyan. Accordingly, why does the Gemara say (in the words of Rav Zevid) that the recipient acquires the gift if he was alive "at the time the money was given to the Shali'ach"? The Gemara should say that the recipient acquires the gift if he was alive "at the time the benefactor said to give him the money." (MAHARSHA)
Moreover, the Halachah is that although the words of a Shechiv Mera are considered written and given over ("k'Chesuvin uche'Mesurin Dami"), they only take effect after the death of the Shechiv Mera, and not retroactively (Bava Basra 137a). If the Kinyan here works through this special mechanism of "Divrei Shechiv Mera," why is the money given to the heirs of the recipient when the recipient died before the Shechiv Mera died? The recipient did not acquire the money while he was alive, and the money should go back to the sender (or to the sender's heirs), as TOSFOS asks! (RASHASH, KARNEI RE'EM, MAHARAM SHIF)
To answer these questions, Rashi explains that since the Halachah is that the words of a Shechiv Mera are "k'Chesuvin uche'Mesurin Dami" after the Shechiv Mera dies (because of the certainty that the Shechiv Mera wanted the money to be delivered to the recipient), when the Shechiv Mera adds "Holech" we may assume that he adds that word in order to be Makneh the money to the recipient even earlier -- before he dies (unlike an ordinary statement of "Holech" which is not like "Zechi"). Therefore, the moment at which the Shali'ach receives the gift he is Zocheh on behalf of the recipient.
If, as Rashi writes, the Shechiv Mera's "Holech" is like "Zechi," why does Rashi write later (15a, DH v'Yesh Omrim) that the sender may change his mind before the Shali'ach delivers the money and not give the money to the intended recipient? The recipient was already Koneh the money through the Zechiyah of the Shali'ach! (See also MORDECHAI.)
The answer is that the only reason why "Holech" is like "Zechi" in this case is that the gift of a Shechiv Mera ("Matnas Shechiv Mera") is a stronger form of Matanah gift than an ordinary Matanah. Therefore, we assume that he wants the recipient to be Koneh through his word "Holech" being like "Zechi." Although a Shechiv Mera's words are "k'Chesuvin uche'Mesurin Dami," nevertheless a Shechiv Mera can change his mind before he dies. Therefore, the power of "Holech" is no greater than the normal words of a Shechiv Mera, and we assume that the Shechiv Mera wants to give the gift retroactively from that point on the condition that he does not change his mind before he dies. (MAHARAM SHIF; see RASHASH.)