1) A SUKAH IN THE FIELD WHERE ONE WORKS
QUESTION: The Beraisa states that the watchmen of orchards and gardens are exempt from the Mitzvah of Sukah. The Gemara asks that they should not be exempt; they should be required to build a Sukah in the field where they sleep.
Abaye answers that the principle of "Teshvu k'Ein Taduru" teaches that one is required to live in a Sukah only in the manner in which he lives in a house. Since it is the manner of watchmen not to live in a house (but to sleep in the field), they do not need to live in a Sukah during the festival.
Rava answers that the watchman is exempt from the Mitzvah of Sukah because if he stays in a Sukah, thieves will take advantage of his inability to guard the entire field from within the Sukah and they will steal the crops.
The Gemara earlier quotes a Beraisa that says that travelers are exempt from the Mitzvah of Sukah while they are in transit. The Gemara there, however, does not ask why they are exempt, as it asks here with regard to the watchmen of fields. Why does the Gemara not ask this question there?
In addition, the Beraisa that mentions the watchmen of fields and orchards also says that the watchmen of a city are exempt from the Mitzvah of Sukah, and yet the Gemara does not ask that they should be required to build a Sukah in their place. The Gemara asks only about watchmen of fields and orchards (as the Gemara implies when it asks, "v'lei'Avdi Sukah Hasam" -- i.e. "there, in the orchard"; see Rashi DH Pirtzah).
It is clear that when the Gemara asks its question about the watchmen of fields, it is not aware of the principle of "Teshvu k'Ein Taduru." The fact that Abaye introduces that principle in response to the Gemara's question indicates that the Gemara was not familiar with this principle until now. Accordingly, why does it not ask that the other people -- travelers and watchmen of cities -- should be required to build a Sukah wherever they are?
ANSWER: The RITVA asks another question. According to Rava, why should one be exempt just because of a fear that thieves will come and steal some fruit? A potential loss of money (or the inability to do one's job properly) does not exempt one from the Mitzvah of Sukah. Since Rava, who argues with Abaye, does not apply the principle of "Teshvu k'Ein Taduru" in this case, the watchman should be obligated to dwell in a Sukah despite the risk that some fruit might be stolen.
The RITVA explains that Rava agrees that there is a requirement of "Teshvu k'Ein Taduru." However, he does not apply it in this case in the same way that Abaye does. Abaye maintains that "Teshvu k'Ein Taduru" suffices to exempt people such as watchmen from living in a Sukah. A person who lives in any place where people usually live without furniture (such as a watchman who lives in a field) is exempt from the Mitzvah of Sukah, because dwelling in a place without furniture is not the type of "Taduru," residence, that the Torah commands for the Mitzvah of Sukah (Rashi). (Alternatively, according to the Ritva, Abaye maintains that when one is in a place where a person normally eats or sleeps outside of his house (such as in a field), he does not have to live in a Sukah.)
Rava does not agree with this application of "Teshvu k'Ein Taduru." Even if a person lives in a place with no furniture, he is obligated to live in a Sukah during Sukos, because that is his normal way of living, his way of "k'Ein Taduru." Rava agrees, however, that if one stands to lose money as a result of living in a Sukah, or there is some other difficulty posed by living in a Sukah in that place, then he is exempt because of "Teshvu k'Ein Taduru." He would not live in a house under such conditions.
Why does the Gemara not ask this question with regard to travelers and the watchmen of a city? They, too, should be required to build a Sukah in their place and live in it during Sukos. Why does the Gemara ask this question only with regard to watchmen of fields and orchards?
The answer is that the Gemara earlier was aware of the principle of "Teshvu k'Ein Taduru," which exempts travelers and city watchmen from the Mitzvah of Sukah. However, at that point the Gemara assumed that "Teshvu k'Ein Taduru" teaches that during the time that a person normally does not live in a house, he does not have to live in a Sukah; a guard who works during the day is exempt from the Mitzvah of Sukah during the day, but since he normally sleeps in his house at night, he must sleep in a Sukah at night during Sukos. However, in the case of orchard watchmen who guard the orchards both during the day and during the night, at no time does the watchman stay in his home; he is a professional, full-time watchman whose job is to stay in the field at all times (Rashi). Consequently, his residence in the field is akin to an ordinary person's residence in a house, since that is how he lives throughout the year. Hence, the Gemara asks that he should be obligated to live in a Sukah during Sukos because of "Teshvu k'Ein Taduru."
Abaye answers that "Teshvu k'Ein Taduru" does not mean that one must live in a Sukah during Sukos the way he lives in a place the rest of the year. Rather, it means that one must live in a Sukah during Sukos the way an ordinary person lives during the rest of the year.
Rava answers that since the watchman may suffer a financial loss by living in a way that is different from the way he normally lives (in the open field), "Teshvu k'Ein Taduru" does not apply. If, however, he will incur no loss by living in a Sukah, then he is obligated to live in a Sukah in the field because of "Teshvu k'Ein Taduru" (even though ordinary people do not live in the fields). This is in contrast to the view of Abaye.
This approach still does not explain why the Gemara does not ask that city watchmen should be required to build a Sukah. They, like orchard watchmen, live at their watch-posts throughout the year, day and night. Why does the Gemara not ask this question in that case?
In the text of the Gemara of the RABEINU CHANANEL, RIF, RITVA, and ROSH, as well as in the manuscripts cited by the DIKDUKEI SOFRIM, the words "ba'Yom uva'Lailah" -- "[city watchmen who work] during the day and during the night" -- do not appear in the case of travelers nor in the case of city watchmen. The first time the Gemara mentions "during the day and during the night" is in the case of the orchard watchmen. Travelers and city watchmen do not remain in their places during both the day and night. Accordingly, there is no basis to ask that travelers and city watchmen should be obligated to dwell in Sukos. (It seems that the difference between orchard watchmen and city watchmen is that no city watchman risks his life to work at night and sleep outside of the safety of the city walls.) (M. KORNFELD)
2) HALACHAH: A PICNIC DURING SUKOS
OPINIONS: The Beraisa says that "Holchei Derachim" (travelers) are exempt from the Mitzvah of Sukah. RASHI explains that they are exempt because of the principle of "Teshvu k'Ein Taduru" -- one is obligated to live in a Sukah during Sukos in the same manner that he lives in his house during the rest of the year. Since, during the rest of the year, a person does not stay in his house at all times but he departs on business and pleasure trips (at which times he does not live in his house), during Sukos he does not have to stay in his Sukah all the time, but he may go on a trip without a Sukah.
This ruling is cited as the Halachah by the SHULCHAN ARUCH (OC 640:8). The MISHNAH BERURAH (640:40) adds that if one can find a Sukah without difficulty during his trip, then he is required to dwell in that Sukah. Also, if he travels only during the day but not during the night, he is obligated to sleep in a Sukah at night.
The Acharonim, however, disagree about the extent of his obligation to sleep in a Sukah at night. The LEVUSH rules that he is obligated only if he can find, in the town in which he lodges, a Sukah that is already built, but if there is no Sukah (such as in a town with no Jews) he is not obligated to build his own Sukah. In contrast, the MAGEN AVRAHAM rules that he is obligated to build his own Sukah wherever he lodges. The Mishnah Berurah (in BI'UR HALACHAH) and others side with the Levush, because one is not obligated to spend half the night building a Sukah in order to sleep in it for the remainder of that night. Rather, one is required only to make an effort to find a Sukah that is already built.
In practice, is one who departs on a trip during Sukos exempt from eating and sleeping in a Sukah? Similarly, is one permitted to eat outside of a Sukah during a picnic outing?
(a) RAV MOSHE FEINSTEIN zt'l (Igros Moshe OC 3:93) writes that when the Gemara says (and the Shulchan Aruch rules) that travelers are exempt from the Mitzvah of Sukah, it refers only to those who travel for the sake of business. One who travels for pleasure, on the other hand, is not exempt from the Mitzvah of Sukah. Accordingly, one who goes on a picnic outing during Sukos is obligated to eat in a Sukah, and if he does not eat in a Sukah he transgresses a Mitzvas Aseh. Even though it is the normal manner for people to leave their homes to eat outside during the rest of the year, the principle of "Teshvu k'Ein Taduru" does not permit one to leave the Sukah to eat outside during Sukos.
Rav Moshe Feinstein supports this opinion from Rava's teaching that one who is "Mitzta'er" is exempt from the Mitzvah of Sukah. This means that if one experiences more distress while inside a Sukah than he would experience in the house (or anywhere outside of the Sukah), he is exempt. "Teshvu k'Ein Taduru" teaches that just as a person leaves his house during the year when it is uncomfortable for him there, so, too, he is not obligated to dwell in his Sukah during Sukos when it is uncomfortable for him there. If it is true that one who goes on a picnic outing is exempt from the Mitzvah of Sukah, then Rava should not have focused on the negative element (one who is uncomfortable in the Sukah is exempt), but on the positive element -- one who enjoys being outside of the Sukah more than he enjoys being inside is exempt.
Rav Moshe Feinstein also cites the Gemara in Menachos (41a) that states that a person should not attempt to exempt himself from a Mitzvas Aseh (such as by wearing a garment that does not have four corners so that he does not have to fulfill the Mitzvah of Tzitzis). On the contrary, a person should make effort to put himself in a situation in which he is obligated to perform a Mitzvas Aseh, as the Gemara in Sotah (14a) relates with regard to Moshe Rabeinu, who requested permission to enter Eretz Yisrael in order to be able to fulfill the special Mitzvos Aseh that are observed there (Sotah 14a).
He concludes that one should not go out for a pleasure trip during Sukos to a place where there is no Sukah.
(b) RAV YOSEF SHALOM ELYASHIV shlit'a (quoted in HE'OROS B'MASECHES SUKAH) disagrees with the above view. He says that it is the normal manner for people to go out for pleasure trips from their homes just as they go out for business trips. Since this is the manner in which one lives in his home during the year (that is, he leaves his home occasionally for a trip), he may live in the Sukah during Sukos in this manner as well. Hence, one should be permitted to leave his Sukah to go out on a pleasure trip.
How does Rav Elyashiv understand the Gemara in Menachos that says that one should not attempt to exempt himself from a Mitzvas Aseh? Rav Elyashiv explains that in the case of a pleasure trip during Sukos, one is not exempting himself from the Mitzvah; he still has his Sukah. He simply is living in it the way he lives in his house during the rest of the year. When one leaves his Sukah to go on a pleasure trip, he does not forfeit the Mitzvah of Sukah. Rather, he is living in the Sukah the same way he lives in his house. (When Rashi says that "Holchei Derachim" are those who go on business trips, he does not mean to limit the exemption to those who go out on business. He mentions "business" merely as an example of why one would travel during Sukos.)
Perhaps the difference of opinion in this matter may be explained as follows. There are two different types of pleasure outings. When a person travels in order to tour or visit certain places, his trip is similar to a business trip in that he has a specific destination and objective. "Teshvu k'Ein Taduru" exempts him from the Sukah during the trip. If he finds himself near a Sukah during his trip, he must eat there (as the Mishnah Berurah writes), because that is what he would do during a trip at any other time of the year -- if he would find a house in which he could eat, he would enter the house and eat there.
A second type of pleasure outing is a trip that one takes merely to be outside, with no particular destination. He may not exempt himself from the Sukah simply because he enjoys the outdoors and wants to eat in the outside air. Such a case would be considered an attempt to exempt oneself from a Mitzvas Aseh, because even if there would be a Sukah nearby when he picnics, he would not want to enter it to eat. Moreover, since he specifically wants to eat outdoors, he not only does the type of act that does not need a Sukah (such as touring), but he also does an act that shows that he does not want a Sukah. By going on a picnic during Sukos, he shows that he specifically wants to eat outside of the Sukah, and this is considered an insult to the Sukah. Such a person is instructed to enjoy the outdoors during the rest of the year, but not during Sukos. The intent of the tourist, on the other hand, is to travel in order to see the sites, but not to avoid sitting in a Sukah.
The ruling of Rav Elyashiv (the preeminent Posek in Eretz Yisrael) refers to the average Israeli, who travels in order to reach a destination. The ruling of Rav Moshe Feinstein (the preeminent Posek in America), on the other hand, addresses the Western phenomenon of picnicking in order to experience the pleasure of being outdoors. Such an intent implies that one specifically seeks to get out of the Sukah, and thus it is prohibited. (M. KORNFELD)

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