Once maaser sheni enters Yerushalaim, it can no longer be redeemed and must be eaten there. While the obligation to eat maaser sheni is biblical in origin, the prohibition against redeeming maaser sheni that has entered Yerushalaim is rabbinic (Makkot 20a). The Chachamim were concerned that if they allowed people to redeem maaser sheni outside Yerushalaim after it had passed through its wall, people might also incorrectly eat maaser sheni that had travelled the same route outside Yerushalaim. The Mishnah records the debate between Beit Shammai and Beit Hillel regarding whether the walls of Yerushalaim can affect maaser sheni prior to its separation. In other words, if one brought tevel (untithed produced) into Yerushalaim does this have any effect on the maaser sheni once it is separated outside Yerushalaim?
The Mishnah brings two opinions regarding the exact case that is debated. The first opinion is that if produce that enters Yerushaliam has reached gmar melecha, i.e. it is tevel and even snacks are forbidden, then everyone agrees that its entering Yerushalaim is significant. This means that everyone views the required terumot and maasrot as if they are already separated.1 Consequently, once the maaser sheni is separated, it must be taken to Yerushalaim and eaten there with the option of redemption no longer available. Beit Shammai and Bet Hillel instead argue about produce that has not reached gmar melacha. Beit Shammai still maintains that the “contained” maaser sheni is affected, while Beit Hillel does not.
R’ Shimon ben Yehuda explains that R’ Yosi understands that everyone agrees in the latter case that the maaser sheni is not affected and the option of redeeming maaser sheni outside Yerushalaim is still available once it is separated. They instead argue when the produce that passed through Yerushalaim had reached gmar melacha. Beit Shammai maintains that we view the maaser sheni as if it is separated. The Bartenura explains that R’ Yosi understands that either Beit Hillel does not agree with this principle at all, or that this case is an exception since the law that the walls of Yerushalaim impacts on maaser sheni is only rabbinic and they are therefore lenient prior to its physical separation.
The Mishnah Rishona asks a strong question. If the maaser sheni is viewed as if it is separated, how can the tevel be removed at all? Maaser sheni cannot be removed from Yerushalaim? The Mishnah Rishona initially answers that even if we view the maaser sheni as being separated, it does not mean that it would prevent the tevel from being removed. The reason is that it is quite possible that the owner might separate maaser sheni from other tevel produce to satisfy the requirement of the tevel in Yerushalaim. In other words, it is possible that this tevel might not every contain maaser sheni. That is why the Mishnah could only discuss that case where the maaser sheni was separated once it had left Yerushalaim. It is only then, once it is separated, that the matter is revealed that the tevel had maaser sheni and the walls affected it.
The Mishnah Rishona ultimate rejects this answer, as the Yerushalmi rules that if produce passes through Yerushalaim after gmar melecha, maaser sheni cannot be separated from elsewhere to satisfy its requirements (see Rambam Maaser Sheni 2:10).2 The second answer he offers therefore is that the Mishnah indeed could have taught that the tevel cannot be removed. Yet it wanted to teach that if it was removed, once the maaser sheni is removed, it nevertheless must be returned.
1The Ritva (Makkot 20a) explains that the rule that we view the matanot as if they are separated is only applied when it leads to a stringency (as in our case). Otherwise, we would not find that a kohen is chayav for eating tevel since is he technically allowed to eat the contained teruma.
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