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I asked a question on here regarding being able to purchase a car on hol hamoed and one of the answers given mentioned that if you are afraid to lose the deal then it's permitted.

It seems that most melachos are permitted once Chesron Mamon exists. How does one qualify something is Chesron Mamon and why exactly did the rabbis permit melachos in such scenarios? We don't violate melachos on Shabbat due to Chesron Mamon...

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One way to understand this is that the restrictions are Rabbinic (Tosfos, Maggid Mishna to the Rambam Shvisas Yom Tov 7:1 and others), and they built-in this exception. Rabbinic decrees often have such trap doors in order to ensure that they are manageable by the people.

Another is that while the prohibition is Biblical (Rashi and many more), the exact nature of the prohibition is left by the Torah for the Rabbis to decide.

Here is a nice summary of the various sources.

More listing of sources here.

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    Rambam in all likelihood holds Deoraita (like Kiddushei Khesef) – Double AA Mar 31 '15 at 19:33
  • @DoubleAA, Shevisas Yom Tov 7:1. Not sure how you can read a Biblical prohibition into that language. – Yishai Mar 31 '15 at 19:41
  • @Yishai It seems pretty clearly biblical to me. Recall the rather forced series of Drashot in the Gemara in Chagiga. Think like hebrewbooks.org/rambam.aspx?mfid=82874&rid=2854 Divrei Sofrim is a particularly charged term in the Rambam. – Double AA Mar 31 '15 at 19:45
  • @DoubleAA, huh? Re. the Gemara, he could hold that is Asmachta. After all, other Rishonim explicitly do. Not sure how Kiddushei Khesef is relevant. What does Chol HaMoed have to do with Kinyan? Anyway, I don't see anything that justifies "in all likelihood" and "pretty clearly" (And I'm sure you are aware of the Nosei Kelim that disagree with you). – Yishai Mar 31 '15 at 19:57
  • Of course he could hold it's an Asmachta. I'm saying all the indicators point to his usage of Divrei Sofrim to be a comment on the directness of the derivation (as he uses it by Kiddushei Kesef (see Kesef Mishna that I linked to)), not to indicate rabbinic standing. See too the Rambam's comments to Keilim 17:12. – Double AA Mar 31 '15 at 20:27
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Perhaps one may suggest the following. Simply speaking, chesron mammon is an actual loss of money, as opposed to losing out on potential gain, as the gemaras in Moed Katan (2b, 3a, see there) seem to imply.

The Torah only forbade work that has a halachic name of "melacha" (the 39 of shabos etc.) with the exclusion of techumim, crossing the line of permitted travelling distance. Therefore, automatically, everything else is permitted. The sages felt that it was degrading to the holiday to perform anything that involves excessive bother (Moed Katan 2a, see there).

However, the rabbis said that where there is a loss of money, anything that isn't too strenuous may be performed, for those instances don't express total degradation of the holiday: rather, it is understood that the action is due to the loss of money.

In a similar vein, the Ksav Sofer permits smoking on a holiday, but only on the second day of the holiday, for on the first day it would be degrading to the holiday, but the second day, after not haven smoked the previous day, the buildup of discomfort would be tremendous and smoking is no longer a display of degradation.

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Don't forget that hesron kiss or davar haaved (חסרון כיס) is not only measured by the acquirer's situation, but the situation of the vendor is also taken into consideration to permit the transaction. In other words, to buy something is allowed if this helps the salesman with parnassa of the mo'ed.

Source: Mishna moed katan 3-4. see in Bartenura; פרק ג - משנה ד

אֵין כּוֹתְבִין שִׁטְרֵי חוֹב בַּמּוֹעֵד. וְאִם אֵינוֹ מַאֲמִינוֹ אוֹ שֶׁאֵין לוֹ מַה יֹּאכַל, הֲרֵי זֶה יִכְתֹּב. אֵין כּוֹתְבִין סְפָרִים, תְּפִלִּין {יז} וּמְזוּזוֹת, בַּמּוֹעֵד, וְאֵין מַגִּיהִין אוֹת אַחַת, אֲפִלּוּ בְּסֵפֶר (הָעֲזָרָה) עֶזְרָא. רַבִּי יְהוּדָה אוֹמֵר, כּוֹתֵב אָדָם תְּפִלִּין וּמְזוּזוֹת לְעַצְמוֹ, וְטוֹוֶה עַל יְרֵכוֹ {יט} תְּכֵלֶת לְצִיצִיתוֹ: ‏

ר"ע מברטנורה אֵין כּוֹתְבִין שִׁטְרֵי חוֹב בַּמּוֹעֵד. הוֹאִיל וְיָכֹל לְכָתְבוֹ לְאַחַר הַמּוֹעֵד {טז}: וְאִם אֵינוֹ מַאֲמִינוֹ. וְאֵינוֹ רוֹצֶה לְהַלְווֹתוֹ בְּלֹא שְׁטָר, וְלֹוֶה צָרִיךְ לְמָעוֹת, כּוֹתְבִין: אוֹ שֶׁאֵין לוֹ לַסּוֹפֵר מַה יֹּאכַל, הֲרֵי זֶה יִכְתֹּב וְיִטֹּל שְׂכָרוֹ, דִּשְׂכַר פְּעֻלָּה לְמִי שֶׁאֵין לוֹ מַה יֹּאכַל שָׁרֵי: וַאֲפִלּוּ בְּסֵפֶר הָעֲזָרָה. סֵפֶר תּוֹרָה שֶׁכֹּהֵן גָּדוֹל קוֹרֵא בּוֹ בְּיוֹם הַכִּפּוּרִים, וְאַף עַל גַּב דְּצָרִיךְ לָרַבִּים {יח}: לְעַצְמוֹ. לְקַיֵּם הַמִּצְוָה. אֲבָל לֹא לִמְכֹּר אוֹ לְהַשְׂכִּיר: וְטוֹוֶה עַל יְרֵכוֹ תְּכֵלֶת. שֶׁנּוֹתֵן הַחוּט עַל יְרֵכוֹ וּמְשַׁפְשֵׁף בְּיָדוֹ וְהוּא נִטְוֶה מֵאֵלָיו. אֲבָל לֹא בְּיָדוֹ בֵּין אֶצְבְּעוֹתָיו, וְלֹא בַּפֶּלֶךְ כְּדֶרֶךְ שֶׁהוּא עוֹשֶׂה בְּחֹל. וַהֲלָכָה, טוֹוֶה אָדָם תְּכֵלֶת לְבִגְדּוֹ בֵּין בְּפֶלֶךְ בֵּין בְּאֶבֶן {כ}: (ר"ע מברטנורה). ‏

עיקר תוי"ט {טז} דְּהָכָא מִסְּתָמָא לֵיכָּא לְמֵיחַשׁ שֶׁמָּא יֹאמַר לֹא כָּךְ הָיָה כְּמוֹ בְּמַתָּנָה, כֵּיוָן שֶׁהִלְוָהוּ לֹא יִהְיֶה לֹוֶה רָשָׁע וְלֹא יְשַׁלֵּם: {יז} תְּפִלִּין כוּ'. כָּתַב סְמַ"ג בְּשֵׁם הַיְרוּשַׁלְמִי, בַּמֶּה דְּבָרִים אֲמוּרִים, לְהַנִּיחַ, פֵּרוּשׁ לְאַחַר הַמּוֹעֵד, אֲבָל לַהֲנִיחָן בַּמּוֹעֵד אֲפִלּוּ לְהָנִיחַ לַאֲחֵרִים יָכֹל לְכָתְבָן. וּבֵית יוֹסֵף נִדְחַק בְּפֵרוּשׁוֹ לְמַאן דִּסְבִירָא לֵיהּ דְּלֹא מַנַח תְּפִלִּין בַּמּוֹעֵד: {יח} יֵשׁ לְפָרֵשׁ בְּיוֹם הַכִּפּוּרִים צְרִיכִים לוֹ רַבִּים, אֲבָל לֹא עַכְשָׁיו, הָא אִם צָרִיךְ לִקְרוֹת בּוֹ מַגִּיהִין בּוֹ וּכְדַעַת א"ח. אֲבָל הַמַּגִּיד כָּתַב דִּבְסֵפֶר תּוֹרָה אֵין לְהַגִּיהַּ, דְּלֹא הִתִּירוּ אֶלָּא תְּפִלִּין דְּאֶפְשָׁר לְכָתְבָן כֻּלּוֹ בַּמּוֹעֵד, מַה שֶּׁאֵין כֵּן סֵפֶר תּוֹרָה שֶׁאִי אֶפְשָׁר לַעֲשׂוֹתָהּ כֻּלָּהּ בְּחֹל הַמּוֹעֵד. וְגִרְסַת הַסֵּפֶר בְּאָלֶ"ף, וּפֵרֵשׁ רַשִׁ"י סֵפֶר תּוֹרָה שֶׁל עֶזְרָא: {יט} עַל יְרֵכוֹ. אֲבָל בִּתְפִלִּין אִי אֶפְשָׁר עַל יְדֵי שִׁנּוּי, שֶׁצָּרִיךְ כְּתִיבָה תַּמָּה. תּוֹסָפוֹת: {כ} שֶׁתּוֹלֶה בַּחוּט כְּדֵי שֶׁיּוּכַל לְשָׁזְרוֹ יָפֶה. רַשִׁ"י: (עיקר תוי"ט). ‏

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